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