Are you a maker or a manager?

I’m a maker. Moment is a maker company with 40 people of which 39 are making.

In a maker culture the biggest leadership challenges are…

1. Deciding what to work on.
2. Mentally switching between multiple topics.

In the early days, what a team works on is relatively simple…what is going to work to bring a new customer?

Everything a team is working on is in support of getting a new customer. If you spend a $1 in engineering it’s because you believe that $1 will turn into new customers through what you ship. If you spend $1 on new computers it’s because you believe those computers will turn out work faster which gets you another customer. A dollar is a dollar and you are trying to guess at which dollar spent will result in another customer.

Sometimes those customers are investors who fund your business and sometimes those customers are people paying for what you offer. Regardless, getting good at deciding what to work on just takes practice. Every team learns to solve this in their own way.

Learning how to mentally switch topics is much harder. Not everyone is wired for it, especially if you are a maker. Managers don’t really go deep enough into any topics to have this issue. But if you are trying to make, then covering a broad range of topics can be debilitating.

Here is what helps me.

Why Covering Multiple Topics Is Hard

It’s important to briefly understand why this is hard.

First, people are not taught how to cover multiple topics. Traditionally companies are organized functionally and therefore like minded, skill specific people are grouped together. People are taught the functional responsibilities of their role. Over time people get comfortable with this definition and therefore learning new domains becomes less interesting.

Second, speed compounds the issue. Small teams need to move quickly. Which means people can get overwhelmed if they are trying to both learn new subjects and execute the domains they already know. They end up gravitating to what they know and ignoring the stuff they don’t.

Third, you have to be vulnerable. Admitting what you don’t know, asking for help, and getting better takes more self reflection. Not everyone is interested in this.

Fourth, it takes discipline. Consistency in your personal approach and team process matters in learning how to master this skill. Not everyone thinks about the discipline of their work.

Deciding On Team Structure

Team structure is the first way to define the problem.

If you structure the company functionally…sales, marketing, engineering, etc then covering multiple topics comes down to one person. Functional teams are highly dependent on what the other teams do, therefore you need at least one person who is exceptional at switching topics and making sure the separate groups are connected.

If you structure the company with cross functional teams then you have to teach breadth to a larger group of people. You will go slower in the short term in developing these skills. In the long term you will go faster as you have multiple leaders who can take groups of people into whole new markets.

At Moment we organized into cross functional teams. Each team has a lead, 3-7 people, and the resources they need to deliver their own goals. This means we have to teach multiple people how to cover multiple topics effectively. Personally I believe in coaching as the long term gains outweigh the short term ones.

If you don’t have time to coach people, then being functionally organized reduces the problem to a single person inside the company.

Define Your Feedback Process

How do you prefer to review work and give feedback?

If you can see work, understand the issue immediately, and provide succinct feedback then you can build your schedule around a series of short feedback sessions. What you say has to be correct and you can’t come back later and change it. Otherwise your team will get fed up.

The number of people in the world who can do this is very small. In my fifteen years I’ve met one.

If you see work and your first answer isn’t right, then you need a schedule that gives you time to think, reply, and correct your own reply. You’ll want to create a schedule that groups similar subjects and creates as much thinking time as possible. The weekly schedule at the back of 7 Habits Of Highly Effective People is one way of doing this.

Personally I have to think before responding. I need time to look at the whole context before providing feedback. Therefore to give myself time to think and still run a company I group my schedule.

• Team meetings and 1:1 sessions are the same 2 hours every day.
• Phone call availability is the two hours around my team sessions.
• Email is only at the beginning or end of the day.

This gives me at least half of a day, every day to really think about 2-3 topics. If the topic is big then i get one per day. If the topics are smaller, then can get in 5-6 topics in a day.

What has helped the most is working off-hours from the team. That means early mornings or weekends. I can’t resist Slack so not being online helps me to better concentrate.

Set A Communication Style

How you communicate further dictates your schedule and ability to switch topics effectively.

If you prefer to provide verbal feedback you need to be online when your team can talk. You have to develop how your team does phone calls or you will quickly get a meeting culture. And lastly, you have to learn how to be very succinct.

The mistake people make is to assume that a long conversation is an effective conversation. The reality is people can only remember a few things that you say. It may make you feel good to say a lot but the ratio of what you said to what is executed on can be way off.

If you prefer to provide written feedback then you need to develop a consistent method that everyone can use. You have to teach that method to your team so everyone creates a habit in using the same process when giving feedback on the work.

Personally I prefer written feedback. I use briefs to create, commenting on briefs to edit, and then Slack to give real time feedback. I try to focus on information hierarchy so that written docs are both easy to skim and organized for finding information you need. I also find written feedback lets you go deeper on topics and gives you a chance to write and re-write that feedback.

Where this breaks down is Slack. My need to reply quickly trumps quality and it takes away valuable thinking time as I get hooked on the feedback loop of reply, wait, and reply again. I send way too many messages and it’s not good for anyone, me included.

Finish And Take Short Breaks

When working on multiple subjects I focus on two micro habits.

1. Finish the subject.
2. Take mental breaks.

When focusing on a topic I have to finish it. this means taking the work to either a spot where I can re-start quickly OR to the point that I can publish my feedback.

When focused on a single topic you can get in the flow so starting or stopping isn’t as big of a deal. But when working on multiple topics you have to artificially create your flow by learning how to stop and re-start at the right point. It takes at least 15 minutes just to mentally catch up to where you left off on a subject so these start and stop points are critical.

The second habit is taking a mental break in between topics. If the work is along the same thread, lets say a product, then I can turn that on and off in the same day. But if I am switching topics, lets say looking at finances, I have to start fresh as if I was starting my day over.

Generally this means…

• Closing my browser and all the tabs.
• Getting up and walking around.
• Getting something to eat or drink.

These are sub 5 minute breaks but what when I sit back down and open my computer to a blank screen it gives me a fresh approach on the next topic. If I sit back down and the last project is open and half done I can’t clearly think about what’s next.

Proactively Communicating

A word of caution is learning to switch between topics can be overwhelming, especially as the work stacks up. I don’t have any feedback for how to tackle this feeling other than working through the list.

But I can say the best way to manage this is to pro-actively communicate. A simple, I got your message and will get back to you by blah, really helps. This gives people confidence that you heard them and are working on it.

If you have questions email me or dm me @marcbarros.

I was 16 at the time. It was early summer and we were training twice a day for a regional soccer tournament. Our coach was a former national team player. Old and out of shape I didn’t realize he was more than just a player during his day. He was the top US player by 19 years old, playing for the Cosmos with the likes of Chinaglia, Beckenbauer, Oscar, and Alberto. These are soccer legends.

Our drill wasn’t going well so he stopped it. He brought everyone over and explained something that would stick with me for a long time.

He said close your eyes and just listen. Bop…..bop..bop….bop….bop.bop.bop. It was the sound of a touch, a pass, and a few more touches. His advice wasn’t tactical to fix this or fix that. It was much more fundamental…the game has a rhythm. It has a style and when a team is connected, you can close your eyes and listen to how they play.

I remember just standing there. Dumbfounded by the simplicity I began to think about all the teams that I love to watch. He was right. My favorite teams had this smooth style to them. From the way they defended to the way they attacked they had an approach that looked effortless.

Fast forward 15 years and I believe this lessons translates to any team, especially startups. Because in a startup you’re bringing a new group of people together in an accelerated manner. Each person has their own approach and it’s your job to assimilate them into a single style of play.

This is harder than it looks. Most people just skip by it and get to work. That’s fine…when there are just a few of you. But as you start to add more people, a lack of cohesive style creates dysfunction which leads to miscommunication which leads to mistakes which leads to running out of money and the game being over.

My Own Style

It has taken me two startups and 15 years to be honest about my own style. It’s based on the following tenants.

1. Be consistent. GoPro kicked the s%*# out of us in my first company by being ruthlessly consistent. They stacked their entire culture and company around being the best in the world at one thing…marketing. Even with an average brand the found a recipe that worked and stuck with it from small to becoming a public company. It’s easy to change stuff, it’s harder to be consistent about it.

2. Play With Urgency. I believe that Paul Graham is right, speed wins. This doesn’t mean play dumb. It just means to be aggressive and play with urgency. I like to prototype and test the market before manufacturing. Ship and then improve. Publish and listen to feedback. I prefer my teams play quickly so we can learn faster. It’s a style that is hard to maintain with scale.

3. Make It Repeatable. If you are going to do something, then document it so others can repeat it. It’s more work upfront but documentation and basic templates enables everyone else to go faster in the future. I try to do this everything…briefs, hiring, company meetings, off-sites, etc.

4. Don’t Hide. This applies to everything. Take setbacks head on. Be transparent. Tackle everything that’s not working. And create a culture where people can’t hide. The more honest and direct you can be, the better a team plays.

Creating Your Style

You already have one. It started with your childhood and was shaped over time with your experiences. All you have have to do now is to be honest with yourself about what it is so you can figure out how to apply it to a group of people.

To figure out your style ask yourself…if I could start my company over tomorrow, how would it be different?

It’s so obvious that most people answer this question with an immediate list. Take that list and look at the core tenants. Your answer is in there.

Take my first company, Contour. I started it as a 21 year old just out of college and without any real work experience. Ten years later I built a culture that looked nothing like my soccer style. It was a disconnected team with people there for different reasons, each applying their own style. It lead to losing the market, me getting fired, and watching the culture that I had built go on to bankrupt the company nine months later.

Ultimately that was my fault.

So before starting Moment I made lists…

• What success looks like.
• What I want in co-founders.
• What I’m passionate about in a company.
• What’s important to my wife.

From those lists I was able to create my why, what, and how for Moment. I did that before making a product.

Applying Your Style

I’m a big believer in showing, not telling. People will watch what you do and it trumps anything that you say.

If you already built a culture and it’s not true to your style then this process is much harder. It might be easier to just start over then to try and fix it.

First you need a reason to change it, like a company set back. Second you’ll need to stop and address this with the whole company so they understand what you want to change and why. Third you’ll have to change people who don’t want to play with this new style. Fourth you will have to reinforce it on a daily basis over several months until you can change the bad habits you previously let form.

Otherwise here are some ways to instill a consistent style of play.

• Lead by example. Keith talks about this in his YC class on How To Operate A Company.

• Teach It. New initiatives are the best opportunity. They are a micro version of fresh start. From how you outline the project to run it to reflect on it, it’s a great way to demonstrate how you want your team to play.

• Discuss It. You can do this at off-sites or company meetings but run sessions about your personal style. It will help your team to understand the why behind what you are doing.

• Hire It. Layer these traits into how the team filters candidates. If you find people who already share your same style it gets much easier to scale. Changing people isn’t realistic.

• Provide Feedback. Immediate feedback works best. This can be in chat, on the phone, or in person but look for every chance to provide bite sized pieces of feedback that reinforce your style.

Please realize that applying a style does not happen in days or weeks. It will takes you years to do well.

A Word Of Caution

Your style of play won’t be for everyone. And that’s ok.

In fact, it’s what you want. But if you do this right, you will create a core team that stays together for a long time. And the more time you get on the field together, the easier everything gets.

It’s important to note, this doesn’t mean everyone has to be the same. You want diversity of thought and opinions. You just want everyone to apply those differences with the same style of play.

If you have questions dm me @marcbarros.

When starting Moment we didn’t have a hiring process. We also didn’t have money to hire anyone, making it a moot point.

But we did need help with specialty skillsets that we didn’t have on the team. So we ended up carving up the work into micro projects and paying what we could. Thankfully friends and friends of friends were willing to help in those early days. I like to call this stage…a collection of bandits.

What we didn’t realize is at the time, was that our use of micro projects would be the basis for how we’d build the company. The process of scoping the project, costing it, and running it showed us everything about how someone works. It also quickly showed us who we should work with again and who we shouldn’t.

Fast forward five years and we’ve built a team of 40 using what we now call Project To Hire. It’s a hiring process that inverts the triangle from lots of interviewing and little work to little interviewing and lots of work. We found that you can interview people all day long, but until they bring their laptop and get to work, you have no idea if they are a fit.

At Moment we’ve had nearly 1K applicants. We’ve run about 100 projects, hired 55, and 40 still remain.

Before outlining how this work, it’s important to note this isn’t just a really long interview process where you use up people for free. This is a paid project to hire process that forces you to refine who you hire and why. When money is on the line you’ll be amazed at fast how teams narrow their focus.

Why Project To Hire

Project To Hire has been transformational in building Moment. Not only has it helped us to hire the right people but it’s enabled the team to see a lot more talent. This means everyone is better calibrated to thee differences between amazing and ok.

Most importantly, project to hire has pushed the team to think about scale from an early company age. In order to project people you have to have a tight brief, clear documentation, and a process to on-board and off-board people.

Getting this right has enabled us to focus all of our energy on the work and the people.

The benefit to your team…

• See More Talent. They get to work with a lot more talent. It helps everyone calibrate fit, while benchmarking themselves against the people they are projecting.
• Learn To Scope. A great project always has a tight brief. It takes a lot of practice to do this well so every project is another chance to learn.
• Process Documentation. The team gets very good at documenting their internal process because they can’t quickly on-board new people without it.
• Faster Starts. Once a new hire joins the company, the process to get them ramped is faster. Day 1 is really like their second week so people get shipping real work faster than a traditional, cold start interview process.

The benefit to employees…

• Self Select. Biggest value is that potential hires decide right away if a project to hire process is right for them. The people who don’t want to help on the side or weekends are the wrong fit anyways so it’s great if they opt out.
• Date The Company. The fear of changing jobs is lowered by doing real work with potential co-workers.
• Stress Free. They are paid for their time so they aren’t stressed about paying their bills. That’s in direct comparison to competing jobs where they don’t get paid to interview and are required to participate in multiple interviews.

Even if a project doesn’t work out I’ve found that our team gets better. It crystalizes the role, who we need, and why we need them.

How It Works (potential employees)

There are two flows you have to worry about.

1. Your Team – from posting the job to projecting to hiring.
2. The Employee – from applying, to projecting, to joining.

We’ll start with #2 as it’s simpler.

To create your process use a customer journey. Map out the potential employee’s experience before, during and after a project. The before starts at reading the job description and after ends with joining (or not joining) the company.

Their process generally looks like this…

• Apply. We post all of our jobs on Angel List and link from our careers page.
• Phone call. They receive back a yes lets chat or no thank you. The team generally uses Calendly.
• Email. Post call they get an email with the project brief and a doc called "Moment Projects (the why, what, and how)." It explains everything they need to make a decision about doing a project and joining the company. It’s important that BEFORE they do a project they have already internalized this doc and made a decision that Moment is the right place for them if the project works out. We include our compensation model so they already know what they will be paid based on what level we assess them at.
• Scope the project. If they are still interested they do the first part of the project by sending back a scope in the project brief that outlines their plan by phase and includes their time and hourly rate.
• Run the project. If the scope is approved they are added to a temp channel in Slack and are asked to lead the project. It’s their project to drive.
• Feedback. Once the project is done they are given feedback and told if we think it’s a fit or not. If it is, they send over three references. While waiting to connect with those references they also receive a personal review which outlines their compensation level and why.
• Paid. Regardless of outcome they are paid for their project as soon as it is over.

What you’ll find is that people either love or hate this process. We look for people who love it and jump in with two feet. We find that the best candidates…

• Reply quickly. They schedule calls as soon as available, complete the scope the first night, and wrap up their project within a week.
• Succinct writer. The scope is tightly outlined and they are direct in their communication.
• Drive. Once the the project they really drive in getting the team to help them, schedule their recaps, and post their work.
• Use Google Docs. You’d be shocked but being given a google doc and then not using it is the fastest sign that someone isn’t a fit. Especially if they send you back a pdf or presentation.
• High energy. Their calls have high energy and are engaging.

What’s amazing is that before they even ship their work you can already tell if they are on the right track or not. And if they aren’t we stop the project before it’s completed. There is no sense wasting their time or ours.

How It Works (your team)

The process you use with your team should start simple and evolve over time. We are on version 3.0 of our process. It’s written so that anyone can successfully run a project.

Our process has four stages.

1. Posting – write the job, write the project brief, and post the job online.
2. Filtering – reviewing, interviewing, and starting projects.
3. Projecting – the actual running of the project from kick off to final review.
4. Closing – process to conclude the project and close the candidate.

I will provide some additional context to each stage.

1. Posting The Job
In this stage the team completes the following.

• Writes the job description.
• Writes the project brief.
• Posts the job and starts the inbound funnel.

What’s important in this stage is that we expect the hiring lead to write the project brief BEFORE they post the job. It’s very important to know the core skill set you are looking for. Therefore by writing the project brief it forces you to dig in and clarify where this candidate has to be amazing.

The way to create the project brief is to ask yourself…what thing/skill do they have to unbelievably amazing at? Is it curating? Is it refining existing products? Is it prototyping? Is it creating from a blank piece of paper?

Once you know the area you then build the project around it.

Basic project rules…

• They need to ship something.
• Scope should be clear and tight.
• Total cost should be under $2K per project (usually under $1K)
• Total time is sub 15 hours of work.
• Ideally they complete the work within a week, maybe two.
• It should include at least one review meeting so you can see them in a group dynamic.

I made a Project Brief template for you.

2. Filter Candidates
In this stage the team completes the following.

• Reviews and filters resumes.
• Phone screen with candidates.
• Send project brief and process doc about doing a project.
• Review their scope and decide if the project should start.

This section looks a lot like a traditional hiring process, except instead of offering them a job you are offering them a project to try.

You can let different functions modify this stage to whatever they need in order to make a project decision. For example our technical teams want to review engineering samples to make that decision, which is fine. All you care about is that they are consistent in deciding who is and isn’t worth running a project.

The biggest benefit to this process is that you can test people you were on the fence about. Traditionally you have to say no as the risk of hiring someone on the fence is too high of a cost. It’s more more expensive to get a hire wrong vs a project wrong.

The most important step in this stage is reviewing their scope. Post phone call you send them the project brief. It’s on the candidate to send back a scope and the best ones do it quickly. This is the first time you’ve seen them work and it will tell you a lot.

• Speed. How fast did they reply to your post call email? How fast did they send back a project scope?
• Communication. Beyond speed do they tell you when they will have the scope back? Are their emails succinct?
• Outline. How detailed is their outline? Is it even in the google doc you sent them or did they try to make a pdf, presentation, or a new doc?
• Time. Are their hours reasonable for the project scope? Were they clear with their time estimates for each section of the project?
• Costs. Was their hourly rate in line with the expected compensation?

Out of everything they send back you really want to look at the hourly rate. If they send back something too high this is your chance to re-address compensation before they start. I’ve often found people taking a pay cut isn’t a good fit and therefore you have to address this upfront and potentially stop the process.

Additional recommendations for this stage…

• Have a clear filtering criteria. Be very clear about either core experiences or passions that every hire has to have. In our case it’s publishing publicly and having a passion for photography. If they don’t have either then we move on. Photography are the problems we’re solving and publishing is the shipping culture we foster.
• Pre-write the followup email. Candidates will show as much interest as you do, which means as soon as your screening call is over send them the post call email.
• Group candidates in the same stage. I recommend you interview everyone the same week and try to run projects at the same time. This ensures candidates are at the same decision process and gives the team the optimal chance to compare multiple candidates.

3. Running The Project
In this stage the team completes the following.

• On-board the candidate.
• Kick off the project internally.
• Run the project.
• Provide feedback post project.
• Decide which candidate you want to hire.

You can run the project any way you want. Ideally it’s run like you would any new project at your company. We run the company in Slack, which makes it easier for spinning up and closing out temporary projects.

What we generally do is…

• On-boarding checklist. Have one and list either what function or who does what column. I made you an on-boarding template.
• Create a channel. The hiring lead makes a temp slack channel, adds the teammates needed, and writes a first post in the channel with everything the employee needs. It includes introductions and links to both the project folder and working brief.
• Candidate leads. We let the candidate lead the project, interacting with the team as they need. The best candidates are actively engaging the group as they see this as their own chance to validate the company is fit for them.
• Reviews. Projects can have multiple review sessions. Each is lead by the candidate so we can see how they do in getting a group to provide the feedback they need to keep going. A project always ends with a final review where work is presented to the team.
• Feedback. Once a project is over we give every candidate direct feedback on the project and why it was or wasn’t a fit.

Overall what matters is in this stage is consistency. That means everyone does the same project so you can compare apples to apples. It’s also important the project is run in a public channel so everyone can see how they work.

This consistency will help you better select who stands out from the group.

4. Closing The Candidate
In this stage the team completes the following.

• If not a fit, close the project and pay them.
• Review references.
• Write a candidate review.
• Verbal agreement.
• Sign the offer.

It’s important to show urgency at this point. The candidate is a few weeks into the process and there is always a risk that they go somewhere else.

The area we see the biggest break down in this stage finalizing their compensation.

At Moment we use a compensation formula. We provide our compensation philosophy before the project starts but it’s important to bring this back up and let the candidate know which level they are starting at and why. We do this through our 1:1 review template. Yes you are limited on data to provide a detailed review, but it’s a start and clarifies for candidates where they stand and why.

What Are The Issues

This process isn’t for everyone. We’ve used it from our inception which makes it easier to improve upon. But a big word of caution is to make sure you don’t half ass it or you won’t get team buy in.

Some things you have to watch out for….

• Talent not projecting. It will bother you that some people who look great on paper choose not to do a project. As painful as this appears, this is a good thing. You want people to love or hate the process so having them not even try a project is okay. You may think you are missing a chance at top talent but in reality you need people who are so stoked on the company they want to work on it in their free time.

• Rushing the process. You can go as fast as the candidate does the project. It’s hard but you have to avoid the…oh this person is amazing so lets skip the project to hire process because they are going to take another job. Don’t do this. If someone is in such a rush that they don’t have time to try out then you don’t want them. It means they will leave your company in the same hurry.

• Not being consistent. Most of our misses have come from not using our own process. We get excited about someone and skip steps or don’t analyze their project thoroughly enough.

• Single candidate projects. You want to avoid single candidate projects. It’s really important to run multiple candidates at the same time to create momentum and urgency. It takes time to get people into a project, therefore you don’t want to be starting over if your one candidate doesn’t work out.

• Candidate details. This project gives you a lot of candidate interactions so look at all of them. It’s easy to just jump to the work and assume you can teach the rest.

The Tools We Use

Here is a short list of the tools we use. I created some templates for you as examples.

• Angel List – where we post our jobs, filter candidates, and manage our pipeline.
• Calendly – candidates schedule a 30min call with the hiring lead.
• Slack – where we run the project.
• Google Docs – we make a project folder and brief for each candidate.
• Project Brief Template – an example outline for each project brief.
• Onboarding Checklist Template – what we use for on-boarding and off-boarding candidates.

There is a lot of startup advice that says you don’t have time to coach your team.

Ben is a legend and I don’t doubt his advice. A lot of what he says is right. You are hiring them for their ability and you do need them to scale their function without you. You also don’t have the experience to train them at their job.

All of that is true.

The part that isn’t true is that you’re building a team. Which means you care more about how the collective success over the individual pieces.

The best examples are in sports. As Malcolm Gladwell recently points out in this podcast…"But certainly, in this moment in basketball, it seems like it’s very coach-dependent. And when you see those..you then begin to wonder, how many players on basketball teams, who we consider mediocre, are actually really good but just in the wrong environment? Is Victor Oladipo an exception or is he part of a larger trend? I’m increasingly of the opinion that there must be lots of Victor Oladipos out there."

In the context of building a team, I agree with Malcolm more than Ben.

Granted, I don’t blitzscale. And in blitzscaling, Ben’s advice might be right on. You might not care about team performance. Instead you probably care about acquiring all-stars and assuming that they can play cohesively long enough to win.

Even if you aren’t blitzscaling you do need some all-stars on your team. It’s hard to build something great with zero talent. You just need to find the right all-stars that fit to your style of play.

Hiring A Leadership Team

I’ve built two leadership teams over 15 years.

The first time I followed the traditional, exec hiring process. I searched, met, sold, and hoped that they work out. I tried to set expectations and pretend that I knew what you’re doing in leading people more experience than myself. I even brought in an exec coach because that’s what happens when your own team complains about your immaturity.

The second time I built a team. I took a less experienced group of people and spent two years teaching them on how to become executives. They start as product owners, learning how to get a group to deliver. And over time you have to turn them into business owners that know how to make executive decisions about where to invest and why. The question now, is if they can continue to lead as the numbers become significantly larger than where they started.

Through it all I’ve learned a few things about hiring a leadership team.

1. You have to develop your team philosophy before you hire leaders. It’s on you to develop your own framework for how and when a team works together. You can’t ask a leadership team to build this for you. It has to be more defined than just…we’re succeeding.

2. You can hire well beyond your experience level, but it doesn’t mean you can coach it. People get confused in thinking that landing an all-star on the team means they have succeeded. It’s like saying that raising money means you’ve made it. Neither are true.

3. Melding experienced leaders to adopt your philosophy is much harder. When you hire a team leader they will say…oh yeah I believe in that same philosophy too. What you find, is that over time they really don’t change. They have their way of doing things and you need to know that is and understand how to manage it.

4. Don’t underestimate inexperience. Once people have success they forget that their inexperience was part of the formula to achieving success. Therefore don’t overlook inexperience as solutions to team leadership. Often times people just need a chance and direction to learn. And the hungriest can often outperform the experienced if given the right environment.

To Understand Before Coaching

There is something you have to understand about coaching. It only works if your resume is more successful than theirs. And it only lasts if you continue to develop as a coach.

For example, I would love to coach Barcelona. Except I can’t because Messi would never meld to anything I’d put on the table. Forget my experience in playing college soccer, Messi has developed his way and unless my resume is better than his, he isn’t going to meld to my culture.

But Guardiola? They listened to him, at least for awhile. His championship resume was longer. Once it was shorter, his time was up. So what did he do? He moved to a club that needed his winning coaching. Until they too were too successful. He’s now on to his third club, teaching the next group how to win.

What you notice about the best sports coaches is they aren’t teaching each player how to be great at their function. They rely on the player to develop that on their own. Instead they focus their energy on the system, repeatable processes, and how the group works together. The more experienced your team is, the better you have to be at this.

Take Phil Jackson. He created a system and used psychology to keep his players motivated. The talent on his team was so great there wasn’t anything else he could do other than focus on their mental state.

How To Coach Your Team

There are lots of ways to do this.

I don’t believe you should outsource it. I’m doubtful that an exec coach shares your same team philosophy, which means what they teach could be in conflict to what you believe.

Instead I suggest learning how to coach it. The easiest place to start is in teaching your team how to run a business. Normally they get a lot of practice at their specific function but little experience translating their function into business speak, which is what is expected at a board level.

Here are a few ways I’ve coached my own team…

• Read Bezos annual share holder letters. Or have them read the annual letter from any public CEO they admire. Reading these teaches them business speak, which is a foreign language from their function speak. We talk about these in 1:1 sessions.

• Write business summaries. We hold six board meetings a year. At this point we don’t have that many strategic topics to fill six meetings, which means the reason for the meetings is to give the team more practice at a board level. Before every meeting they have to write a short summary. This isn’t a ppt deck, it’s a business summary in a google doc. They write it and I edit it. In the beginning you basically re-write it. But over time they get better and better where they don’t need your editing.

• Phone call before the board meeting. As part of their weekly 1:1 they will practice the meeting out loud. I’ll ask questions like a board member and then give them feedback on the structure of what they said. Generally what you are coaching is their language and how to succinctly summarizes their learnings. What you discuss at a board level is different from a daily team level so you need time to teach this.

• Learning how to win a market. Figuring out the quadrant you can win is hard and you need team leads that know how to do this. It’s not a skill that is taught and so I’ve run some sessions that teach them how to look at the existing market to then figure out how they could win it on a new paradigm.

• Tools they can use. Few executives have tools they use to break down problems, organize people, and communicate. I share my own tools and work with them to learn how to use them. Tools like a customer journey, a brief, and documentation. It gives them structure they can use with their own teams. It also make sure all of us are speaking the same language.

• Consistent 1:1 sessions. I call them workouts. They are an hour long, every week. And I do everything I can not to miss them. They set the agenda and although most of the time spent is on their projects they are a chance for me to provide coaching feedback.

In Summary

I believe you can coach your team.

If you are playing the long game, both at your company and as a member of the startup community then this work will pay back. Happiness is higher. Churn is lower. And team speed starts accelerating over time.

If you are looking to torch the earth and go fast, then coaching is a waste of time. You’d be better off learning how to manage and turn through all-stars. And as long as you are succeeding and stock value is rising, you can deal with the negative impact it can have on your culture.

If you have questions, email or dm me on twitter.

The first company I built didn’t have a cohesive culture.

We had amazing people and those people worked hard, wanted to win, and were passionate about beating our competitor…but we didn’t have a culture. That was my fault.

Everyone was there for a different reason and I didn’t know how to bring them together under one purpose. We had two co-founders with differing philosophies on just about everything. We had a Board and investors who didn’t like each other. We had Sr. execs from different planets who had different beliefs on how to shape a company.

In the end we had a group of people spread across two offices with varying levels of interest in the core customer problem we were solving. It was a mess.

There I was, a sub 30 year-old trying to pretend that I had any idea about what I was doing. I had never had another job before, let alone experience in creating a culture.

Fast forward and my second company has been different from the beginning. My own maturity has a lot to do with that, but like any new relationship you learn from the last one. I’m clearer about what I believe in and what I’m looking for, which makes culture building easier.

In company #2 you fix a lot of the cultural basics that were broken in your first company…communication, cadence, hiring, team process, etc. You do a better job of selecting people who share your passion for the same problem. And you are more consistent in your approach, which everyone appreciates.

Even with those improvements I never would have guessed that the single most important cultural ritual that we would develop would be our Off-sites. We’ve taken 17 of them over the first five years at Moment and they have changed everything.

What I’ve come to realize is that off-sites are serious. They aren’t bro time or hang out time. They aren’t random and they aren’t treated with…oh I should do one of those.

Ours are a week long and we hold them three times a year. That means we ask people to be away from their families for three weeks a year. Anyone with young kids they understand just how serious this is.

Therefore if you are going to include off-sites in your culture make them matter. Realize this is your chance to develop the team, fix issues, and get everyone on the same page. They are a big deal and if done right they will unlock a group of people to deliver the best work of their lives.

Everyone has their own structure, this is mine and it has scaled up to 40 people. I’m not sure how it’s going to scale to 100 people where frequency becomes a lot more expensive.

Set Your Offsite Cadence

Before you create off-sites it’s important to first set your company cadence. Off-sites are not random gatherings. Instead they should be timed based on the cadence by which you set goals.

We run Moment on trimesters. Therefore we have an offsite every four months to end the previous trimester and to start the next one. This allows us to dive deep into our recent performance, work on our team dynamics, and set new goals to sprint again.

A side note, but I found that business quarters are too fast. By the time you set goals you only have 10 weeks left to finish them. Having four month chunks gives the team more time to deliver meaningful work. It also better accounts for vacations and personal issues that arise during a trimester.

What Off-sites Are About

You should set a clear purpose for what your off-sites are about.

Our off-sites are about surviving together. They take us back to the basics in life with traveling, cooking, eating, exploring, talking, and connecting. Accomplishing these feats brings us closer together. It forces us to work as one in ways you just can’t accomplish during work hours.

All of our off-sites have these same elements…

• Travel – we started by caravanning to spots within two hours of Seattle and over time we’ve expanded that circle to the broader NW.

• One House – staying under one, shared roof is important. We started with camping and over time rented larger and larger homes. We’ve always tried to balance comfort with uncomfortable. Again it comes back to surviving together.

• Team Made Meals – we make our own food and clean our own dishes. It’s basic, but conversation happens in the kitchen that you’ll never get out of people any other way. What’s beautiful about shared meals is they require empathy. Not only do you have to consider everyone’s allergies, but you have to clean the mess someone else made.

• Adventure – accomplishing feats matters. It puts people outside of their comfort zone, but over the years we have seen people accomplish hiking feats they never thought they could do. These adventures don’t have to be expensive. Walking on your own two feet enables conversation. These adventures often become the stories people remember.

• Team Sessions – we deliberately work on the team. There is an agenda with pre-planned team sessions. I keep some of the session cryptic as surprise gets people to focus on the problem at hand. Most importantly this your chance to enable important conversation about the team and how it can run better. It will take practice but over time the team will begin to open up to one another.

Off-site Agendas

To get more granular about the week here is the agenda structure we use. It has stayed consistent over the years.

Pre-Read

Before you go, I give the team pre-read. It’s my job to give them context to where the company is today and where it needs to be in the future. The team needs this in order to set relevant goals. In the pre-read I try to include…

• Table of contents with how long to spend on each section.
• Review last trimester’s goals, to get them thinking about their own performance.
• Business recap for the last trimester, teaches them how to think about our business.
• Remind them about the bigger vision of where we are going.
• Remind them to re-read our annual plan.
• Provide context to what matters in the up coming trimester

In general I want most of their time spent thinking about the future and what goals we need to set to get there.

Day 1

In the first day I want to get the group connected talking. In order to go deeper the rest of the week I need to get the broken shit on the table. This is the chance for people to both celebrate and vent.

• Arrive by 4pm.
• Session 1: team(s) review their last trimester goals. They go goal by goal, scoring each cool between 0-1 based on how much they accomplished. They then list out why they did or didn’t hit the goal.
• Session 2: company recap. Each team shares their score and the trends behind why they did or didn’t hit them. We also go around the room and give individual props. This is really important.
• Session 3: if there is time I have teams break down what is broken. It’s their chance to vent and get stuff on the table they are frustrated about that we need to fix. I write these down and I figure out how / when to work on them during the week.
• Dinner: this is the first chance we get to connect as people instead of co-workers.

Day 2

The second day is about exploring and thinking big. Depending on the time of year we either get out first thing for a half day adventure or we run some team sessions and explore in the afternoon. Looking at our winter off-sites the day looks like…

• Breakfast: We have found cold, self serve breakfasts work the best.
• Adventure: During the winter we try to be out early to maximize the light. We’ve done everything from snowshoeing to snow bike riding to skiing / snowboarding. We make sure each adventure accomplishes something together.
• Session 3: The first session is always about thinking big. Generally I’ll run a session about how we grow 3-4x in revenue or team size. Below are notes on how to run a growth session but this lets the team think about scale without constraint.
• Break
• Session 4: This is a follow on to session 3 where we go more tactical to idea generation. These can be ideas to hit the growth we talk about in the previous session or can be tactical to our next 12 months. These are always in cross functional teams to get new relationships started. It also forces people to learn how to present their results in front of the whole company.
• Dinner: Deliciousness.

Day 3

The third day we get tactical to what we need to culturally fix. This is where I bring in issues from Day 1 or issues I know we need to work on. The structure of the day is similar to Day 2, but instead we hit a series of short culture related topics. The key is keeping the energy high during the sessions.

• Breakfast
• Adventure: We do a second adventure, again with some form of accomplishment.
• Session 5: In 60 minutes we’ll cover the most important cultural topic. That can be anything from compensation to communication to process, etc. It’s always about…how could we do "blah"? Or how could we fix "blah"? Again done in cross functional teams.
• Session 6: This is the second most important topic.
• Session 7: This is the third most important topic.
• Dinner: Followed by drinks and hanging out.

This topical patter continues until we’ve spent about four hours together. After that the quality of the sessions begin to drop off.

Day 4

This is the hardest day. It takes a lot of mental concentration to crank out four months of goals and tactical objectives to hit these goals. Over time this day has gotten easier as team leads have done pre-offsite planning.

• Breakfast
• Session 8: I bring the whole company together and we go over the pre-read. This is my chance to make sure everyone understands where we’re going and why. We move from the big picture to the annual plan to the trimester plan.
• Session 9: Teams split apart and start setting goals. Generally teams end up with 3-7 goals depending on their scale and maturity. Each goal is measurable as an end result or measurable in progress (i.e. development stage of a new product).
• Lunch: Often self-serve the teams eat and keep cranking.
• Session 10: Once goals are set they work through the tactics to hit their goals. Then they map out what they are going to work on and in what order. This is tedious work.
• Snacks: everyone needs a break by the afternoon.
• Session 11: We bring the whole company together to go over goals by team and review these against a company calendar. Our calendar is very basic, but includes any cross team initiatives we all need to know about. This session has gotten better over time as the teams have improved at saying what they need from other teams.
• Closing: This completes our off-site. All sitting together this is a chance to congratulate the group on an amazing week. It’s also a chance to get feedback on the week while it’s fresh.
• Dinner + Relax: The rest of the night is just about hanging out together. We share a last meal, connect, and sometimes a dance party breaks out.

Day 5

We pack up and go home. Everyone cleans the house together and we caravan it back to the airport or the Seattle studio.

Recap

After every off-site I document it on a private web page. It becomes our company history and provides reading context for new teammates. Understanding where a team came from is really important to understanding where they want to go.

• Collect photos from everyone on the team.
• Write a day by day recap with notes form every session.
• Drop in photos as they happened so the reader gets a sense of what it was like.
• Post it to a private page for your team that links to a master Off-sites website.
• Make this page part of pre-read before next off-sites so people can remember what we did last time.

Immediately Fix What’s Broken

After an off-site it’s important to immediately fix the broken items you. Any simple ideas or changes to process I try to fix before people start work on Monday. That way people can see a direct impact to the feedback they provided.

This builds trust and carries your momentum from the off-site into the trimester.

If you go into the next offsite with the same foundational issues then you’re doing something wrong.

Off-site Exercises

I wanted to break out a few exercises you can use with your teams.

Session – Review The Past

We have done this a few ways over the years. As the group has gotten larger we’ve moved from doing this company wide to doing this by teams and then recapping with the whole company.

Our general process is…

• Review the goals. Here we go goal by goal. We score each goal from 0-1 depending on how much of it accomplished. With each goal we list a few why’s. This helps us learn how to set better goals.

• Highs and Lows: Each person goes around and shares their personal highs and lose from the last four months. We now do this within teams but we used to do this company wide. It was very powerful as it pushed people to be open with others.

• Props: Public acknowledgement matters. We have each person go around the room and give props to their teammates. You can see how body language changes immediately when this happens.

What’s important during this session is you take notes. You are looking for threads for things you need to fix. Working through these issues is very, very important.

Session – Think Big

I’ll write a post about this but on Day 2 I run a series of sessions that teach the team how to think big. People aren’t taught how to scale teams or revenue and so these exercises give the team a chance to learn how. I’ve run this exercise in terms of revenue and/or team growth.

You post a questions…How would we get to $X in revenue?

You have them for cross functional teams (4-7 people) and they get 20 minutes to do this exercise. After 20 minutes they will come back and present their brainstorm. Generally what you get are a list of tactics.

This is your chance to teach. First you let them know you only gave them 20 minutes on purpose which means there was no way to get into tactics. You were looking for the "how" which means they have to start at the highest level and then break down your path into smaller details…

• Start with the most basic unit in your business. In ours, it’s customers.
• Map out how many you need to get to answer the $X question.
• Once you know how many customers break down what percent comes from new versus repeat.
• Once you know the mix you need a framework for how you get there.

….a very efficient group can maybe get this far in 20 minutes.

You then send them back to do the exercise again this time having them come back with a framework for how. They return with something that’s closer on number of customers but the how goes back into tactics versus outlining a strategic framework for how.

You then would show them that in order to get growth you either need to go wide (more offerings to the same customer), go deeper (more customers with the same offering), or expand distribution. You send them back to better outline a framework for "how" they are going to get $X from new and $Y from existing customers.

After 20 minutes they are closer. They have made some assumptions about what would work in order to reach those customers.

Depending on how much time you have, you continue to repeat this process until they have a rough plan of how to get to $X in revenue.

In doing this kind of exercise you quickly realize that you need to understand the process in order to teach it. Secondarily you realize this kind of strategic thinking is not taught.

You can run this type of exercise at every off-site, you just increase the revenue scale of the initial question to make it harder.

Session – Role Playing

These sessions are my favorite. I’ve run different role playing scenarios to get the teams thinking about topics they would never expect. Generally I’m creating scenarios so they can see elements of a shitty culture. This helps them clarify what they want in our culture.

An example would be…I wanted to teach people how to quit. No one teaches this and whenever someone quits it’s terribly done, which leaves the existing team in a bad spot. Therefore while doing a team hike we had a 30 minute break to run this session.

I paired everyone up and gave them one of two cards.

Card one said you had to quit. Each card was a slightly different version of quitting. I had the passive aggressive quitter, the angry quitter, the I don’t give a shit quitter, the over apologetic quitter, etc.

Card two said you had to fire the person. I again came up with different versions of firing someone from passive aggressive to direct to excuse filled.

It doesn’t take too long for people to catch on to what is going on. They can somewhat overhear other teams, which makes it funnier. This ran for about 20 minutes and then I brought the whole group together and let them share what they liked and didn’t like about the person they interacted with.

In the end I was able to teach that what matters in the business world is your legacy. Therefore if you are quitting, here is how you do it.

If you get creative you can come up with all kinds of role playing scenarios like this. They are fun and give you a chance to teach something often missed in startups.

There is one tool I use for everything. It’s called a Customer Journey.

It’s name implies that it’s just for customer experiences, but that isn’t true. I use it to walk through the before, during, and after…of any problem.

Working on your hiring process? What happens before, during, and after someone is hired?

Acquiring customers? What happens before, during, and after closing a customer?

Reviewing a campaign? What happens before, during, and after the campaign?

Working on a marketplace? What happens before, during, and after a customer buys OR a vendor starts selling?

This tool takes practice. Most people give up on it too early because on the surface it looks like a waste of time. But over the years you find that a customer journey enables you to break down problems faster, while enabling groups of people to deliver work that contributes to the same overall problem.

What makes this easy to learn is that everyone goes through this process in their head. People mentally build their own map and work through how they are going to solve it. All a customer journey does is take everything out of your head and map it into a structure that everyone can use.

How To Make A Journey

You start by taking a problem you’re working on and then go through the before, during, and after for that problem. Lets use a generic problem…completing the morning with my three little kids. Ultimately we need three kids who are fed, dressed, happy, and mentally ready to start their day.

I would start a journey by listing…what happens before they wake up, during wakeup, and after they wakeup?

Before

• i wake up (without waking up my wife).
• do my stuff (breakfast, coffee, work, etc.)
• grab the kids (hearing, picking up, and taking to our room).

During

• kids wake up (cuddle, make a plan, etc)
• do their morning list (teeth, bathroom, clothes, etc)

After

• eat breakfast (make, serve, and sit with them)
• clean breakfast (clear table, clean, etc)
• first play (suggest, decide, and play)

Once you have everything down you can start grouping steps.

Continuing the example above, I started by listing each morning thing I did…bathroom, drink water, make coffee, eat breakfast, etc. After seeing all the steps on paper I then realized that really this was all one step for "do my stuff." Everything I listed was all the same effort with the same goal of completion without making up my kids. So I grouped it as one step.

My morning journey would look something like this.

Once I have a customer journey I can then look at each step and come up with solutions to better solve it. Continuing with "do my stuff," I would generate ideas that improved the process.

• closing their bedroom doors first to cut down noise and light
• pre-make my bowl of cereal the night before.
• plastic bowl and spoon so it makes less noise when eating.
• cold coffee in the am instead of hot coffee.
• laptop pre-charged so don’t have to make noise with cables, plugging in, etc. …etc.

Once I had potential solutions I would refine my customer journey. I might even add a new column, such as "the night before." Here I could list out steps I could take the previous day to make my morning better.

Why It Matters

A customer journey helps you scale.

Lets say I added my wife to this problem and together we were working to improve our mornings. If she had her own mental map and I had mine then we won’t get very far. Secondarily if she didn’t have a mental map and just jumped into "make breakfast" the solutions could be in conflict to the broader problem we’re trying to solve over the long term.

Scale this out and say you had a team of five people working to make our family mornings better. Without the entire problem mapped out you get into solution mode without context to how the solutions impact the overall objective. Therefore when each person finishes their work you then have to make changes if the solutions don’t fit together. If everyone first started by looking at the same customer journey you’d get 5x the amount of mental horsepower on how to reduce steps and build solutions that scale across the steps.

Now substitute my family morning problem for any problem in your company.

How To Start

If you have time, I’d recommend learning customer journeys on your own before bringing them to your team. Start with a piece of paper and learn how to map out steps, edit them, and brainstorm ideas.

Your structure is…

• Before, During, and After stages placed left to right on top of the page.
• Start listing out all the steps that coincide with each stage.
• Group similar steps until you have a handful per stage.
• Refine the detailed steps within each vertical grouping.
• Brainstorm how you’d start solving problems to reduce / simplify steps.

A template for this could look something like this.

Then practice this for any problem your company is facing. It will help you think about the whole problem and point out holes in the team’s work. It will also help you look at how to group the work while ensuring their solutions aren’t in conflict to the larger problem they are solving.

Once ready I’d start creating digital versions of the customer journey you then use with the team. Trello or Google Spreadsheets works well for this. Their first step is to learn how to read them and yours is to learn how to explain them.

This will go on for a few projects until the team is ready to start writing their own. Keep in mind they will need to go through your same learning curve so don’t get frustrated when their initial customer journeys are terrible.

A secondary caution is that customer journeys are best if created by one and edited by many. Multiple authors is hard as you need one person who ultimately refines this to one experience.

If you don’t have time to develop this skillset on your own before teaching it, then you’ll have to accelerate it with just your leadership team. You’d ask to see a customer journey for major projects they are working on which will force them to learn the skill faster. You won’t care how they do it other than you can follow their logic while showing you how big the problem is.

When To Use It

Personally I use them all the time. Even if just on a scratch piece of paper, it helps me understand the whole problem and how the team is solving it. I can edit work better if I have a clear journey.

Within a team environment we only create them for major projects or brand new experiences. They are included in our Creative Briefs, but not used for every project. Coincidentally, the project leads who use customer journeys often deliver tighter projects. Their teams appreciate that the details were thought through and people are scrambling to patch holes that were missed.

Please keep in mind any changes to team process can take time so if you implement a Customer Journey be patient as your culture learns to use them.

Conclusion

This is the tool I use more than anything else in creating and running a company. I use it in a variety of ways and whenever I help a new startup the discussion always ends up in a customer journey discussion.

To help, I created a basic template in google docs. You are welcome to copy it and improve it for your own needs. You are welcome to email or DM if you need help with your own customer journeys.

Customer Journey Template

(below are a few examples i outlined.)

Example – Product Roadmap

This is an example for how you’d build a product roadmap.

For this example I’ll assume I’m a startup who is looking to make tools to improve the manufacturing of products. These would be software based tools to make it easier for smaller companies to manufacture better products.

I would start with a single manufacturing type, lets say soft goods. Once I had a journey for this segment I’d repeat this exercise for each new market we’re entering…lets say consumer electronics was next.

To map out soft-goods I would interview potential customers to understand what they do today before, during, and after they manufacture a new product. Without coming up with solutions I would just start listing, interviewing, and looking at their existing tools. I’d do this with a handful of different companies with different types of soft goods. Ultimately I’m trying to create a mental map of me being on their team, manufacturing new products.

I would then group my steps such as…

• Research the market
• Concepts
• Prototypes
• Factory selection
• Manufacturing setup
• First samples
• Second samples
• Production
• Shipping

I would then flow steps within each grouped column to deeply understand how they solve these steps today. It would help me better understand all the problems from their POV.

Once I had this mapped out I would then look at which problem I can solve first with the resources I have. This would be product one, version one. Over time I would add new versions to my first product followed by new products that tackle different problems within the journey.

I could add new products within my first market (soft-goods) or take this same playbook to similar markets (consumer electronics).

If done right, this journey could take me 10 yeas to execute with products and services.

Example – A Marketplace

This is an example for how you’d build a marketplace journey.

In this example you have to map out two customer journeys. The first for the supply side of the marketplace. The second for the demand side.

To map out the supply side I’d work through before, during, and after the joining of the marketplace. I’d look at how people do this today with other marketplaces to get the core steps down of what people have to accomplish. I would then look at which of these problems we would have to solve first and in which order.

To map out the demand side I’d go through a similar process to look at before, during, and after making a first purchase. Assuming that after a first purchase I can start a relationship I’d be focused on what the major steps are, followed by how we’d solve those steps.

It’s important to note you can solve these customer journeys in a variety of ways. The solution isn’t always a new feature, product, or service. Sometimes you solve it with content or marketing or sales. You can also ignore whole problems until you have time to really solve them.

We created a similar journey for Moment Travel. It’s a marketplace for photography trips. We’re 18 months in and on version 3 of the journey as we learn what works to improve the Guide and Customer steps.

Example – Internal Process

This is an example if you are creating any internal team processes.

We recently improved the first two weeks at Moment. This work was part of a customer journey I had built and refined a few years ago…working at moment.

To start I built a journey for before, during, and after joining the company. I looked at how other companies do this and interviewed people on the team who recently joined.

I started with lots of lists for steps people go through. I then grouped those steps…

• Discover the job.
• Apply
• Filter and interview
• Project to hire
• Close
• Day 0
• Week 1
• Week 2

Ultimately this work has resulted in two separate journeys. The first is process within Moment before, during, and after hiring someone. The second is the new employee process before, during, and after they join. They are connected but separate journeys.

Over time we have picked off chunks of this journey work on.

1. Project to hire: We spent a few years improving our process between interviewing and selecting the potential employee.

2. Application: Later we went back and simplified our application process through one tool and one internal process.

3. First Two Weeks: Now five years in, we are shipping a 1.0 version that improves your firs two weeks at Moment.

By having a broader customer journey we were then able to decide what to work on and in what order.

Startup founders are told to write investor updates. You can search google for lots of articles about why. You can even find "fill in the blank" templates.

I’ll skim the advice for you…engaged, positioning, intros, want to help, in the loop, etc. You’ll notice a trend. All of the reasons given are to benefit other people.

I think that is bad advice.

Yes people in and around your business need to know what’s going on but investor updates aren’t the way to do it. If people want an update you can just email them this every day…"This is hard. I got kicked in the teeth again today and the hill we’re trying to climb looks more like a mountain. Please make more hours in the day and send help that doesn’t drain my bank account."

Instead try Business Updates.

What’s A Business Update?

They are similar to an investor update, but different. First, Business Updates are for you. Others read them, but the purpose is to help you run a more successful business. Second, they are about the past and not the future. We aren’t hyping. We’re learning.

Business Updates analyze the past few weeks. They force you to look at the data, ask what happened, and come up with new hypothesis’ to test next. They are uncomfortable, especially when something isn’t working. But over time you’ll come to realize they are the most important tool to teaching you how to think, distill, and run your business. Public companies write quarterly updates (i.e. earnings calls) and the best CEOs write annual shareholder letters (See Bezos).

It doesn’t matter if you are bootstrapped or venture funded. Business Updates teach you how to analyze and communicate results. I call this business speak and you need it to raise, hire, and scale. Because if you can’t distill your business then there is no way you can execute it.

That’s cool, but I just started my company so what am I going to write about?

Everything you’re learning. Even if your updates start as product specific learnings, that’s ok. It’s a start.

When do I start sending updates?

As soon as you can and BEFORE you raise money. These updates will demonstrate that you are serious about building a successful company.

How frequently do I write them?

More than once a month. Once the business is mature you can push out the timeline. I started with an update every other Sunday. Three years in, I moved it to every three weeks. And now five years in, I publish about once a month.

Who do I send them to?

The people closely involved in the long term success of your company. This includes current employees, investors, advisors, and board members. Yes, even board members get the same updates as everyone else. You don’t have time to send different updates to different people. Over time you will forget who you said what to, so it’s easier to just be transparent from the beginning. It will make sense later.

Are they a lot of work?

Yes, especially when you start. You’ll quickly realize that to write about your business you have to be able to measure it. To be able to measure it you need tools to track it. To have tools to track it you have to have thought about what to measure and why.

Eventually you come full circle to realizing…shit I have to prioritize learning into the foundation of the company.

Bingo.

Wait, so how do I keep my investors hyped?

You don’t. You let the numbers do the hyping.

Ok, so how do I get my investor to help?

Ask them. Learn how each can help and message them when you need it. Unless they wrote the largest check, they have limited hours to help. Therefore be selective and specific in your asks.

Huh, sounds like a giant waste of time.

It is…if you don’t plan to build lots of startups. It’s actually easier to just write investor updates than to write Business Updates. With investor updates you just keep writing about the amazing stuff you are going to do and you can skip over the actual results.

Business updates on the other hand require you to be vulnerable. You have to look at results, especially the shitty ones, and decide what you’re going to do about it. Not everything you will try is going to work. But the process of trying, measuring, learning, and improving will deliver.

Update Structure

You are welcome to make your own structure, this is mine.

Intro Paragraph

I take the biggest learning since the last update and elevate it to the top of the email. This provide me with space to dive deeper into a single topic to analyze what happened, what we learned, and what we do about it. This section can include a few charts / images and about 2-4 paragraphs of analysis.

Need Help

In the early years I would list a single ask. The more specific you are the better. Overtime I took this section out and just messaged people with specific asks as needed.

Business Update

The rest of the email is a repeating pattern of single metric/chart with a short paragraph of analysis. I’m not writing accomplishment check lists, providing functional updates, or talking about the future. Instead I go over the last two weeks, looking at our dashboards and asking myself…what happened…why…what happens next?

In answering my own questions I start to find interesting pieces of data. These are small learnings we can use to improve future decisions. As I find these threads I pull out a single piece of data, screen shot it, and write a short paragraph of analysis about it. This pattern repeats itself for a few hours until I’ve gone through what we’ve learned since the last update.

It’s ok if your updates are short to start. As the business matures you will have more to analyze and learn from.

Writing Style

The language in Business Updates is business speak. The best way to learn it is to read quarterly updates and annual shareholder letters from your favorite public companies. Bezos consistently writes the best ones and if you read them over the years you can see how he think and talks about his business.

My rules….

• No hyping.
• No promising the future or talking about what your’e going to do next.
• Only cover the past.
• One visual data point per paragraph of analysis.
• Be vulnerable. You don’t care if it’s good or bad news. Your job is to report on it, what you learned, and what you plan to do about it.
• Don’t try to have all the answers. You just have to talk out loud to what you’ve learned and put down your next hypothesis to test.
• Don’t hide shitty data. The results are what they are so dig into them.
• Don’t organize it functionally. Review and publish what you’ve learned about your whole business, not just the functional accomplishments. Because no one cares how you structure your business or what the functions are shipping. They do care about your results and the decisions you will make going forward.

Sending Details

Pick a cadence to send your updates and don’t waiver from it. Whether good news or bad news, you ship your updates. Consistency wins.

Your entire startup journey is an unproven hypothesis. The faster you realize that you have no idea about what’s going to work, the faster you start learning. The numbers won’t lie so don’t worry about hyping something that isn’t real.

No matter how you publish your updates what matters is that you ship and don’t waiver from what you started. The quickest way to lose investor trust is to stop publishing.

Here is how I send my updates…

• It’s an email. I used Mailchimp in the past and now I use Klaviyo.
• It’s a text based email, not a marketing email.
• I try to send it on Sundays around 4pm pst. I found open rates were better on Sundays.
• I put current employees, investors, advisors, and board members on the update.
• When new employees join they get added to the updates list as part of the company on-boarding process. The opposite happens when they leave.
• I also archive all of the updates on a private webpage so future members can go back and read what we’ve learned.

Intro Examples

I can’t post current examples because we share financial data so I went into our archives and pulled out a few example intros. These are examples for how I would start a Business Update.

Intro Example – 1

[screenshot]

iPhone X has arrived. Even though it’s just a phone, it is arguably the most advanced camera ever made. Good news for us, is that our gear already works with iPhone X so we can capture immediate sales. Our lenses work. Our Photo Case is available for pre-order. And a new Battery Photo Case is going to be announced 11/14 for pre-order.

[screenshot]

It seems obvious in retrospect but it has taken us years to learn how to launch our capture products on time with each new phone. From the products to the content to the commerce we’re getting faster at capitalizing on launch day. Comparing our results to last year, both in dollars and percentage growth, we see just how important it is to have compatible products to sell. Last year our products weren’t yet available for purchase, which had a dramatic impact on weekly sales. This year we’re in stock or just a few weeks away from shipping.

Intro Example – 2

Our 72 Hour Sale just about crushed us.

This year we decided to close for Black Friday weekend and instead offer a 72 hour sale from Monday – Wednesday of the following week. The response blew past our most aggressive forecast, bringing in $270K on the first day alone. Comparing orders placed this holiday season to last season we saw 743% year over year growth. (Keep in mind we recognize revenue when we ship).

[screenshot]

This result was both amazing and terrible. On one hand it was amazing to have thousands of customers interested in buying Moment. We reached a level of momentum and excitement that surpassed even our biggest days on Kickstarter. On the other hand we instantly sold out of key products, which left little for customers to buy on the last day. To make matters worse we accepted some orders that were beyond our stock on hand.

Since the sale ended we have been in overdrive restocking products, releasing shippable orders on a daily basis, and managing a massive load of customer service emails. Backorders have been the largest contributor to the massive volume of emails we have received this season compared over last year.

[screenshot]

Despite dealing with backorders the team has managed to keep our customers happy. Which is never easy when thousands of people are anxious to have their order shipped.

[screenshot]

We are almost out of the woods as we expect to ship all open orders early this week, just in time for the holidays. Even though we haven’t had time to recap the holiday season one thing is clear, we left a lot of sales on the table by running out of stock.

Forecasting and inventory management is clearly an area we need to improve upon in 2016.

Intro Example – 3

It’s good to be shipping.

Launching and running a Kickstarter is exhausting but shipping might be even worse. Over the last three weeks we have shipped 12 new cases, four new lenses, and a new lens adaptor with two different suppliers across two warehouses, while using airplanes and boats to move the product. To add to the shipping complexities we received 7,150 emails alone in June, up 62% from the previous month.

Despite the stress of delivering we’ve managed to maintain a customer service happiness score of 85/100, reduce our first response time 3.5 hours, and reduce our overall response rate down by 27%. The whole team starting their day by answering 5-15 emails has made Kickstarter a massive team effort.

Best of all, the initial response to Moment 2.0 is higher than any previous launch. You can see the #momentgear feed or find YouTube reviews like the one below.

Business Update Examples

These are snippets from the middle of the update. It shows examples of analysis with a screen shot of data. I didn’t include actual screen shots so you’ll have to imagine. But generally I post a single chart.

Now that we are installing RJ Metrics we can begin to understand the business even better. The basis of our thesis is that Moment can grow to be a company with one million customers who on average spend $100 a year. Not counting our latest Kickstarter campaign we have passed an important milestone of our first 10K customers who on average have spent over $125 with us.

[screenshot]

In selling out of our Wide Lens we’ve quickly realized the impact of our best selling product. Looking at the items per order over the last few weeks with and without the Wide Lens, it becomes clear to us that a lot of people come to Moment to buy the Wide and in the process by other items. This makes its absence greater than just the direct loss in sales.

[screenshot]

Adding our first US warehouse continues to prove that people want cheaper, faster shipping. The conversion rate ratio between US and International reached as high as 5x during the peak holiday season. Adding Amazon FBA in the coming days will offer Prime shipping for Moment products for US customers. Next we’re working to move our international warehouse in-region, to reduce the tax and shipping shock our customers experience at check out.

[screenshot]

We have maxed out performance on the current platform and the only way to make speed and shopping improvements is to move platforms. While making that move, one of the key learnings over the lats month is that what we place “above the page fold” matters. A few months ago we tested putting add-on accessory products below the add to cart button, i.e. below the fold. Our items per order dropped significantly. Moving those accessory items back above the fold has resulted in much higher attachment rates.

[screenshot]

What has surprised us the most about being on Kickstarter is that our existing sales have not tanked. We figured the introduction of new products would bring existing sales to a halt. Instead the announcement of new products has only increased overall sales, now averaging about $15K per day. This tell us that next time we should go faster in designing and announcing new products. [screen shot would go here]

Extra Tip

Writing a business update isn’t just for the CEO to do. You can ask the same of your leadership team before every board meeting. Instead of making slides in deck have them each write a short business update about what they’ve learned since the last board meeting. This teaches your own leadership team business speak and how to analyze / distill their work. You’d be surprised, but this skill is not done. Even experienced operators don’t know how to write tight business updates.

Before each board meeting, the leadership team writes a collective business update. It goes something like this.

Intro

The first page is mine to summarize the business and the traditional areas around cash, revenue, margins, spend, and team.

By Team

Each exec writes their own section. The template varies a little bit but generally the premise is to analyze what they have learned.

• List annual goals at the top of the brief and mention if ahead, on track, or behind. This reminds the board what the team is focused on.
• Go through their business and talk about 5-7 learnings since the last update. Each short paragraph is focused on a single core metric / learning that they analyze.
• These sections are written in business speak and not product speak. That means they are using business words and writing about the impact of their results.

Discussion Topics

At the end of the update I list 2-3 discussion topics for the meeting. We spend at least two thirds of the meeting on the discussion topics.

….hope this post helps. Please feel free to copy or use any of it to run your company.

Everything gets a brief. It does’t matter if we’re launch a product, a service, or a campaign…it has a brief.

Why a brief?

A brief forces you to write. And writing forces you to distill.

Why the f*%@ should I care?

You shouldn’t if you don’t want to win. This is a tool that makes everything you launch better and more consistent. Ultimately it will deliver measurable results.

A lot of people, especially in chaotic startups, underestimate how hard it is to distill a plan into words. They think it takes too much time to write and so they don’t. Or they assume that words take away from the organic nature of creating. It doesn’t, it improves it.

Putting words down makes you hone in the why, the what, and the how it’s different. It forces you to research and to think…how is the world doing this today and how can we do it different?

I didn’t start Moment with a brief. I wish I had, it would have been tighter. Instead, The Brief has been something we’ve developed the last three years into a staple for everything we do.

If you start using briefs, expect it to take time for your team to embrace it. You will get push back like this…why do we have to write all this down? Because it makes the work better. It makes it clear from 50′ down to the details why, what and how.

You’ll get this too…But everyone digests information differently, not everyone likes long docs. True, but we use words. You are welcome to add images, but words are a basic form of communication and we practice getting better at them.

And this…but I communicate better by talking. We can do that too, after you read and edit the brief. Because writing makes what you talk about more specific.

I didn’t work at Amazon, but everything they launch has a brief. Albeit a long one, but they use words to distill why, what, and how. It forces people to write down their assumptions and to validate if they were right or wrong. That learning is invaluable as you build competencies into the company.

How you execute off of a brief is up to you. We’ve evolved and struggled our way through this because it takes just as much discipline and process for people to pick up their sections of the brief and deliver them. We’ve tried check lists, Trello cards, and most recently Monday.

There are three levels you want your team to graduate to…

1) Read One – Reading, digesting, and executing their parts of the brief. Believe it or not, it takes practice to teach people how to read and understand it. They won’t ask questions and you will assume from that they understood it. This isn’t necessarily true. Reading and executing is something you have to work on internally until it becomes second nature.

2) Run One – The top of every brief has a project owner. It doesn’t mean they have to be author, but they do need to be the one who gets everyone to deliver. The best project leads are both charismatic and organized, two skill sets you need to get a group to execute.

3) Write One – Writing great briefs is hard. It takes a lot of re-writing and most people don’t want to do that. They think the time is better spent do anything other than writing. To do this well, one person in the company has to be excellent at this. Over time this has to grow into multiple, excellent brief writers. It doesn’t mean that writers have to run briefs. But it does mean they have to be excellent at creating break through ideas and distilling those into a plan.

I made a Brief Template for you and put in google docs. You are welcome to take it and make it better for your company.

Overview

This is your one pager. Anyone should be able to pick this up and understand the brief. If the project is really complicated, this section can be longer than one page, but that is the exception and not the rule.

Project Owner: This is the person who is going to run the project.

Problem: Distill this into a single sentence. You have to keep asking your self "why" until you are at the root problem you are trying to solve. This is harder than it looks.

What: This is an overview of what the project is about. If it has multiple parts then add "+" bullet points to list those. Here is where you want to really think about how this is different than anything else on the market. To do this section well is hard, you have to come up with a unique approach.

Measure Success: This how you keep score and should be 1-5 core metrics you care about. These metrics help you improve and measure future projects.

Dates: These are just high level dates. You can move to a more detailed project document to keep track of the more granular delivery dates.

Documents: How you organize your project folder is as important as the brief. From the folder to the sub folders to the key documents, finding things during the project should be simple.

Creative Direction

This section is not for everyone. One person on the team should write this section and do it for every project when you are small. That can be the CEO, a designer or a creative on the team. What’s critical is this person use the same template and process every time. If you don’t know how to do this then make friends with an awesome Art Director and have them teach you. Very few people know how to do this well.

Visual Theme: This is hard for people to wrap their head around but the template above has an examples. It’s about taking two contrasting inspirations, identifying 2-3 traits per, and then putting them together to create something new. The sentence is Blah (trait 1, trait 2, trait 3) meets Blah (trait 1, trait 2, trait 3).

Imagine…Apple (minimalism, detailed, precise) meets Patagonia (big beautiful images, adventure, and connection).

That mashup contains two polar opposites. Together they provide inspiration so your team can make something totally new.

Mood Board: This is also hard. You have to pick just 6-8 images that represent the visual theme you outlined. Each image should come from a side of the mashup. In the case of Apple and Patagonia you have to go deep in researching each brand and selecting specific image that represents the mash-up of (minimalism, detailed, precise) and (big beautiful images, adventure, and connection).

People get too literal in thinking this mood board has to include the exact fonts and colors they want to use. You can include these items, as long as the images selected come directly form the mashup and not other sources of inspiration.

Campaign Name: The external name for the campaign. It should be short and easy to understand.

Inspire: More to come about how to write messaging, but this is a 3-5 word phrase or short sentence that sets the inspire level of the campaign. Such as…Small Camera. Big Films.

Explain: If you ignore everything else and just practice explain level messaging you’re ahead of the game. Here is where we write a 1,2,3 that the public will read to understand what your campaign is about. It should be actionable and easy to understand.

Example…. Introducing the Moment 58mm Lens. Closer, tighter, crispier shots. Buy it today, save 20%.

How – By Phase

You can do this part of the brief any way that you want. The purpose is for one person to think through the whole experience of the campaign and then break out all the parts you have to launch. This isn’t a long checklist. Instead it’s organized into clear phases and within each phases chunks of experiences that have to ship together.

How: Each phase of the project starts with a new How section. This makes it clear to the team for how this project rolls out. Often we’ll have Teaser, Launch, and Post Launch phases to every project.

Touch Point Template: As we get into each piece we have to launch we use the same template with a title, problem, statement, and bullet points of what has to happen. This again reinforces people learning how to distill problems and then come up with ways they want to solve those problems.

Downloadable Template

If you missed it above I created a google doc with this template that you can use and make better for your company.

The Brief – Template

If you have any questions, email me or dm me.

Starting your next company is easier. It’s still just as hard to win a market, but the way you’d start is completely different from how you started your first company.

The path to starting something, especially your first, is often random. My own path began through a college roommate who entered a business plan competition and needed help. I said sure and somehow that yes became a 12 year journey from the competition, to starting a different company, to building it, to being fired, to watching someone else crash it.

I never could have planned that path. It was organic, amazing and painful.

It was also chaotic. A lot of energy was wasted on the wrong things. because I had no methodology for how to build a company. I was reading everyone’s philosophy and trying to patch my own together.

The end result was a culture with massive disconnect in why they were there, what they were interested in, and how they worked. From the startup vets on the team to the kids just out of school. From the sales team who thought the retailer was our customer to the rest of us who wanted to serve the end consumer. From the lack of operational process to the dysfunction on our board. What I had built was a reflection of myself.

It turns our I was learning. You can take it one step further, I turns out I was discovering who I was. I was just doing it while trying running a multi million dollar company…not realizing that the end result would be a dysfunctional company.

I left that journey with less money than my friends who just got jobs out of school. I had no debt. But at the same time I had nothing, just a decade of learnings and a bankrupted startup on my resume.

If I had to do it again there is no change I could have or would have made. I had to struggle. I had to get my heart broken. And I had to pick myself back up.

In everything I learned from Contour there is one lesson that I’m building the rest of my startup life around…to succeed in building a startup you need a philosophy.

You need your way of working, making, and building teams. There is no other way that is going to work for you. There is just your way. Which means you have to discover it.

I’m now 17 years into creating my own startup philosophy. I spent 12 years absorbing and the last five years writing it. It’s not perfect, but it’s mine. It’s not even clear it will scale past $50M in revenue, but that’s ok. I trust that over time it will continue to evolve.

My inspiration are successful coaches. Yes sports is an easier analogy because the season starts over every year, but it’s also clear the best have a methodology that brings success no matter where they go. They create a system of play and then develop, teach, and empower their players to succeed with it. John Wooden, Pete Carrol, and Johan Cruyff have published theirs. I’m looking forward to Pep Guardiola publishing his.

I’m now documenting mine. It’s still functional as I practice the pieces, but over time I hope to make it as simple as those further along.

I hope by publishing my own philosophy helps others to discover, make, and document theirs. I believe the world is a better place with new, well run startups.

My Startup Philosophy ->

Thanks to everyone who has been a part of a company i have started. you have shaped me and my beliefs along the way.

If you raise venture or angel money there is one expectation…grow. It is the one metric every investor values, whether private or public. Everything else is just noise.

How fast do you have to grow?

It depends. It’s not actually easy to control your growth rate as it’s highly dependent on your timing, team, and luck. In consumer 6x annual growth is really strong, 2x is good, and below that you get a "meh."

Personally I’ve found that a 2x annual revenue growth rate is fast enough but not too fast that you can’t develop the team. This is a far cry from blitz scaling, but over time 2x compounds into real revenue numbers.

If you have to grow, it’s a stressful reality. Grow and everything is easier. Raising money, hiring people, working harder, and everything in between.

Don’t grow and you’re on the path to running out of money. Or worse and you’re stuck running a company that is slowly dying.

Slower growth isn’t just that life got harder. It’s much more binary than that. It changes your entire trajectory to survive.

Going back to the public markets, growth drives the stock up. Missed numbers or slower future growth brings it crashing down. Recent startup examples like Blue Apron, Snap, GoPro, Fitbit, and Stitchfix stand out. These companies won the startup game, but are getting trashed because they aren’t growing fast enough.

The same phenomena happens in the private markets, you just don’t directly see it until you can’t raise money. It’s unclear until you’re writing your startup’s post mortem about how you were so close…just missing this one thing. That one thing was growth. You didn’t have enough of it.

A cold reality is that people won’t directly tell you how f’d you are. Investors will still take your meetings. Press will still write about you. New employees will still apply. The perception is that if you just try a little bit harder it will click. That’s not true.

If your growth slows you have to dramatically change your trajectory to get back on track. These are not small decisions. These are massive decisions that may require restarting your own company to create the growth required.

In making that pivot, what is underestimated is the personal toll this expectation takes on a CEO. Yes it’s their job, but it’s incredibly stressful.

And to a founder it’s even more peril. To everyone else your startup is just one of many opportunities. To your investors you are one bet within a portfolio. To your employees you are one job in their career. To your customers you are a solution they will find a way to move on from. But to a founder, this is one of the few companies you get to start in your career.

The energy it takes to start a new company is too great to start over multiple times. It’s one thing to run a company you scaled, i.e. Bezos, Musk, and Hastings. It’s another thing entirely to start over from scratch and build a new one.

Therefore if you raise money and can’t grow fast enough, good luck.

This is a cynical way to look at building of venture funded startups but it’s true. The outcomes are binary. Just ask every founder that didn’t make it. Or every founder that got stuck running a "not growing fast enough" venture backed startup. It’s just something you can’t fathom until it doesn’t work out.

How To Handle Growth

Everyone handles this expectation differently. Here is how I think about it…

• Set expectations up front about what rate you want to grow at. It’s ok to start slow and build into the growth as you understand your business. It’s not ok to start fast and then slow down. If anything you want to hedge towards growth accelerating over time.

• Determine how much growth you can personally handle as the CEO. If your team is new, it takes time to go faster. If this is one of your first companies it also takes time to learn how to grow. Growth is a learned skill and you need time to develop how to do it.

• Build this growth curve into the culture of the company. Your whole startup philosophy should be built around how fast you need to grow in order to win the market. The answer to that question is different for every founder.

• Teach your team how to grow. Constantly run brainstorm sessions about how you can 2-4x the business and the team. This gets people thinking about this earlier so as you make decisions they aren’t surprised. People don’t teach growth in a business environment. Therefore you have to work on teaching it.

• Find your outlets for the stress. If you show it, your team will sense it. The more they sense it the worse they perform. Learning how to handle your emotions is critical to achieving the growth you’re searching for.

What Happens If Growth Slows

If growth is slowing here is how to think about it…

• Pivot to a market segment where you can be number one. Investors fund and companies buy market leaders.

• Dig deeper to figure out what is and is not working. Here is where a Customer Journey can help you. Be ruthless to cut what isn’t working and shift to things that are working.

• Watch your burn. Cash is survival so if you want any chance to change your growth rate make the business profitable so you have more time. Generally those cuts come in the form of people, which is really painful.

• Sell the business before it’s a fire sale. Selling the business doesn’t mean you’ve given up it just means someone else is the owner of the upside and downside. This path can allow you to still serve your customers without the same stress of survival.

Conclusion.

If you crack growth everything else gets easier. If you don’t crack it, you’re in a tough spot.

Alternatively don’t raise capital and just worry about one half of the equation…enough cash in the bank. This stress comes with investor backed startups, but isn’t compounded by the requirement to grow.