There comes a point when your team takes over your day to day responsibilities. It begins with the decisions they make without asking. And it ends with a full scale management team that reports back in weekly meetings. But in between these two points is a mess of personal conflict for any founder.

Early in a company’s existence, the founder is responsible for nearly everything, or at least they think so. Constrained by a lack of cash, founders develop raw survival instincts. Their ability to conserve, out work their peers, make quick decisions, and inspire are all critical traits to turn an idea into success. Being praised as a tenacious hustler is a compliment that any founder would be proud of.

With success comes confidence. Emboldened by the results, the founder continues to do more of what has worked…obsessing about the company, pushing everyone to work harder, and tackling every important decision by themselves.

It is a process that works until it doesn’t. And when it no longer works, the result is hitting a concrete wall at a culture destroying pace.

The truth is, this pattern is nearly impossible to change once it has become the personal culture of the founder and the collective crutch of the company. Although a Board thinks they can fix the problem with a management consultant, you really can’t. Not without dismantling the founder centered culture that built the very company they invested in. It’s like trying to train a lion that lives in the heart of the jungle. You first have to catch it before you can tame it.

The only way to escape this pattern is for the founder to create a company that is so off the charts valuable that they can do whatever the hell they want. Insert Steve Jobs and Jeff Bezos.

The alternative is for the founder to avoid this path altogether by building team, empowerment and decision making into the early fabric of the company. To the point that these traits become so engrained into the culture that the team knows no other way.

But in order to do this the founder has to wrestle with two truths.

1. This journey is not about them.
2. The team is going to fuck it up.

Tactically these are easy to accept. It’s the mental and emotional struggle that is so challenging.

The realization that this journey is not about the founder won’t become clear until the end. Living without the very company they poured their existence into, is the only way to really appreciate what they had.

The team fucking it up is merely an illusion that the founder has to personally reconcile. Just because the team would do the work differently doesn’t actually mean they are going to fuck it up. It’s just going to end up different than the founder’s “inner control freak” wants.

But getting these two truths right isn’t about doing the work for the team or telling them how you want it done. It’s actually about creating a system of play that empowers the collective group to punch above its weight.

One of the best, modern examples is Pete Carroll. He has spent his lifetime creating a system of play that enables his players, coaches, and general mangers to deliver their best work.

• He made over 200 roster changes, until he found players that believed in his system. Sometimes removing star players to make room for the yet to be discovered.
• He trains his staff to become future head coaches. Graduating the next in line when top coordinators move on, he is expecting to spend as much time developing his coaches as his players.
• His general manager believes in the same system and together they continue to find talent that everyone else ignores.

What inspires me the most about Pete Carroll is he’s not afraid. Even on national TV, while still hurting from an emotional Super Bowl loss, he stood up for what he believes in. Not even presidents will do that.

What you have to realize about Pete is the work you see today has taken his entire professional lifetime to create. This is not an accident, but instead a culmination, anchored in his commitment as a leader to create a system that he believes in. One that even got him fired along the way.

When I built Contour I didn’t understand any of this. I bootstrapped the company out of a cold warehouse, running it the same way in the end as I had started in the beginning…like a bulldozer that would run over anyone that didn’t go the direction I was running. Our system of play never advanced beyond “survive.”

This time around it’s very different. Moment is now 8 people that represent a group tighter than anything I have experienced. We have a printed playbook that is our system of play. We spend days together every quarter outside of the office exploring, talking, and building deeper relationships. We have no vacation policy, no hr department and no bullshit. What bonds us together is a shared commitment in our purpose.

In learning how to build a team the wrong way and now in pushing myself everyday to do it the right way, here are a few practical lessons I have learned.

1. Define A System Of Play
A good friend of mine introduced me to a framework he calls promise (our purpose), offering (what we make), and delivery (how we win in the market). It’s a system of play I have adopted as my own, building upon the foundation he provided. This has to be visibly clear to your team within the first year of the company’s existence. Our version is a printed book that we update every six months.

2. Don’t Compromise On Passion
The first 10 people you hire will cement everything about the culture which means all of them have to be personally passionate about the problem, lifestyle, and opportunity you are solving. This can not be faked and it can not be added down the road. Everyone at Moment is passionate about mobile photography.

3. Inexperience Is OK
It takes a while for a team to learn how to play together. Like seasons in sports they have to go through cycles together (product launches, announcements, new features, etc) to learn how to win. It takes a soul testing amount of patience to let this happen over time. And despite what everyone says you can take a collection of young, less experienced people, and develop them into champions. There is a lot of talent already on your team if you enable, push, and challenge them to be great.

4. Teach A Team How To Make Decisions
Decision making is second nature to a founder. They make so many decisions early in a company’s history that they have a distinct experience advantage over the rest of the team. Therefore it’s the founders job to teach everyone how to make better decisions based on the information they have on hand. Enabling people to make decisions, learning from them, and making better ones next time is critical to building a culture that scales.

5. Don’t Pick Up The Pencil
Hardest of all is NOT doing the work for the team. Make it clear who owns what decisions and when goals are made make sure there is a different owner for each. It’s critical that everyone on the team learns how to deliver a goal to completion. This will be important down the road when the current team needs to lead the next team members.

6. Build Real Relationships
This doesn’t happen at the office or at happy hour or in half day fun-park outings. It takes days together, outside of work, overcoming challenges while sharing personal feelings. Every quarter we go exploring together, which forces us to overcome basic human challenges such as navigating our route, making meals together, and setting up camp. We combine these experiences with team sessions where we talk about what’s working, what isn’t working, and what we want to improve upon.

7. Find A Group of CEOs You Trust
Most important of all is that in order for the team to deliver the founder has to learn how to become a better leader. They can hire a personal coach, but one of the best ways is to meet with a collection of fellow CEO’s on a regular basis. If the group is small and confidential everyone will begin to share very personal and real struggles.

Personally, I struggle everyday with becoming a better leader. Unraveling all the instincts I developed as a first time founder it has taken a lot of anguish to arrive at the point where I finally understand the type of leader I want to become and the system of play I want to run.

At the end of the day your team will win and they will lose but all that really matters is how you prepare them for the battle.

*Image Credit: Rob Carr and Getty Image via Creative Commons.

Entrepreneur: “I need a VP of ______. Know anyone?”
Me: “Maybe. Can I ask you a few questions?”

At this point in the conversation I’m thinking, okay she wants to add someone senior to the team. The Entrepreneur, with her pen out, is clearly waiting for me to spout off a list of amazing people. And so for the next five minutes it’s a delicate balance as I try to understand the real role, while the Entrepreneur just wants a name.

Stepping back, it is clear the entrepreneur made a series of assumptions and decisions to arrive at this role. Probably drowning in too many roles herself, she is raising her hand to say I need some help. And although a title is the easiest way to say just how senior of the help you need, it is irrelevant to finding the right person for the role.

To make matters worse for the entrepreneur, the advice you receive is incredibly conflicting. Your investors often tell you to hire the most senior person possible. Your existing team is saying we just need another worker and not another boss. Other entrepreneurs you ask have organized their teams in completely different ways, making their input even more confusing. All the while, the work piles up by the minute, making it nearly impossible to keep your head above water.

So how do you define the role you really need?

Define The Functions
Before you even start defining this new role you need to understand why you are hiring someone. The easy answer is, I’m underwater, while the more difficult answer is to challenge if the existing team has too much on their plate. I could write pages just about this topic, but for now you should really ask “why” before you define “what.”

Assuming you move forward with hiring someone and putting the title aside for a minute, let’s understand what you are really looking for. Don’t start by copying random job descriptions that you think express what you want. Most of the time they are filled with meaningless words designed to inspire people to apply.

Instead I find the easiest place to start is to build a list of all the things you want them to do. I’m not talking about areas they will help, but the functions they will be 100% responsible for on a daily basis. If it helps, imagine this person walking into a bar with their friends and answering the question, ‘So what do you do?’

Ideally, your team built the list for you, but if not, they need to provide real input. Especially if you are outlining a manager’s role, you need everyone to understand why they are being added to the team, what this new person is going to do, and how they complement the existing team members. The worst is when the CEO is running around hiring roles that the rest of the team doesn’t understand or worse, disagrees with. Even if there is a discrepancy between you and the team in regards to seniority of the role, ambiguity only sets your new hire up for failure with the existing team.

Understand What Type of Leader
This is harder than it looks. Sure you’d hope that everyone can grow into leading and building teams. The reality is they can’t nor should they. Some people are great as individual contributors while others are better at people wrangling, a phrase Rand recently discussed in detail.

Having everyone reporting to you doesn’t scale, believe me I tried, so you need to be thoughtful about what kind of leader you are looking for. If you are looking for more than an individual contributor I have found two types of leaders.

The first is a team lead, aka a manager, in a big company. You are looking for someone great with people, someone with experience having direct reports, and someone who is a really good listener. If you have an existing team that just needs some daily guidance this can be a great fit. I have found the best team leads will give you references with raving reviews from people who worked for them in the past.

The second, and much harder to find, is a team builder. Not only are they great at leading people but they are amazing at finding talent. Hiring a recruiter doesn’t count. I’m talking about someone that others will follow to your company when you are ready to hire them. Much more experienced, team builders have seen it all, living the startup life. Just remember if someone hasn’t laid people off, it means they really haven’t built a team before. Unfortunately it’s a horrible part of building.

If you are hiring your senior leadership team they should be fantastic at leading people and building teams. Hiring for them will undermine their leadership with the rest of the organization, plus you don’t have enough hours in the day to do your job and theirs.

Leave Room In the Title To Grow
Before you slap a title on the job, understand you are building an organization over many years. The structure you use today will be very different once you hit market fit and even more complex once you are ready to really scale the company.

For example, just because this is your first sales hire, doesn’t mean they are the VP of Sales. Sure they are the most senior person on the marketing team, but it’s not a game of fill up the highest, open title slot. It creates a dangerous expectation and devalues real leadership. Even if you have to start with a vague “marketing leader” title, that’s okay.

But if I want someone really senior don’t I have to give them a VP title?

The easy answer is yes. In the short term it will satisfy a recruit, even if it undermines the organization down the road. It is also true that the more senior the title you place on the job description the more people who apply. I mean who doesn’t want to be a VP in a startup? It sounds so awesome!

But the hard answer is no. Down the road when you realize they aren’t the leader you thought they were and you need to hire someone more senior to lead the team, you will either have to demote their title or fire them. Although they provide tremendous value a demotion in title is something you rarely recover from.

I have found that until you have about 20 people, it’s okay to start with directors and team lead titles with a clear plan how you will build your leadership team. The people you have on board today, may not be your most senior leadership team as the company begins to scale. A difficult subject Ben Horowitz covers well in his post about staying great.

Conclusion
I wish I could say building a team is easy. It’s not.

Finding random people will satisfy the pressure you feel, but assembling a really awesome group is incredibly difficult. Trying to balance thoughtful with opportunistic hiring, will drive you crazy, especially when you recognize that not everyone you hire today will be what you need a year from now. A disparaging feeling you can do nothing about until you get to that point.

With a much better understanding of the role, the type of leader you are looking for, and a title that gives you room to grow, you are ready to start looking for people.

Image Credit: Brenda Gottsabend via Creative Commons