Some rules for hiring in a startup

by Cameron Brain


Since 2004 I've hired around 60 people for a variety of roles in two software startups (I included a complete list at the bottom of this post). Some hires turned out amazing while others did not. Considering how critical people are to building a company, I wanted to put down my current framework for hiring.

Finding the best people

When I'm looking to hire someone, I have one primary goal: I want to hire the best person possible. By best I mostly mean someone who is going to progress our organization forward the most. The more they do that, the more critical a member of our team they'll be. How do we find these people and avoid the others? Below are my thoughts.

  1. Are they a missionary or mercenary? At the highest level, we always want to hire missionaries. John Doerr gave a talk at Stanford in 2005 about the difference between missionaries and mercenaries (I've included the video at the end of this post). Even when you're in a startup and have scant resources, there are people out there who want to suck you dry. Paying someone a high salary, granting lots of equity, or including a rich benefits package will not make someone more effective at their job. To the contrary, the folks who push for that up front probably aren't going to work out. Why? Because they're about themselves and a startup is about a shared cause d'etre. Stay away from the mercenaries. They promise, and take, and rarely deliver.
  2. Do they have previous startup experience? Another simple, gating factor for me is if the person has previous startup experience. In my opinion there are three types of people in the startup world: those who have founded a startup, those who have worked for a startup, and those who have done neither. I really want people in those first two categories and generally steer clear of those in the latter. Startups are crazy places. Things don't always make sense; you need to simultaneously make forward progress and remain open to making course corrections, sometimes big ones. People who haven't worked in a startup are not usually comfortable in this environment. 
  3. Are they familiar with your space? There's a value to involving someone who is familiar with your market. Maybe they worked on a similar product, sold to the same people you're trying to sell to, marketed to a similar audience, or developed partnerships with like players. Having a new hire producing results as quickly as possible is always one of my biggest goals. Hiring someone who's already familiar with the territory gets them to that point more quickly.
  4. Has someone on your team previously worked with them? I pay more attention to people who have worked with someone on our team. I think the challenge is to separate those who are looking for an "in" through a personal connection (i.e., they need a job) from those who can stand on their own. Further, I've learned to place a higher value on a personal connection if it's coming from someone on our team who I already think is stellar. Chances are, they're not going to want to work with someone who isn't.
  5. Are they smart and thorough? Both these items are critical in my opinion. To the first quality, I want to hire the absolute smartest people I can find, no matter the role. That could be a head of engineering, a sales lead, a freelance designer, or a kid just out of college with no prior experience. Smart people can figure things out, and at the end of the day that's a huge reason why you're hiring someone - you're certainly not hiring them to create more work for you! But, of course intelligence doesn't count for everything. That's where thoroughness comes in. Thoroughness in my opinion means owning something. When people own stuff, they complete it to a better degree. I want to look at someone's work and be surprised. I don't want to think "well, I could have probably done a better job".
  6. What do your team members think? Bad things have happened when I or my co-founder and I have unilaterally made a hiring decision. It just doesn't make sense to do so. You're hiring someone who's going to be a member of your team. Don't you think at least some of your team members should have a say? Culture and trust are two big factors in determining the effectiveness of a team. Hiring someone without involving others does a couple things. First, it erodes trust. You're saying "I'm going to make decisions that affect all of us without involving you". Second, it puts your culture at risk. What if that person doesn't mesh, you judged them wrong? In my experience only good has come from involving our team in the vetting process.
  7. What other projects/commitments are they involved with? Especially if you're hiring someone part time or for a trial period as discussed below, find out what else they're working on. Do they have other commitments? If so, how ridged are they and what are the particulars: how many hours per week, when does it end, who's involved, what's their role, etc. As we all know, context switching is hard; it means the quality of that person's work is going to be less, that its going to take them longer to get up and running, and that they may not be able to develop momentum of their own. No matter how good they appear, I don't want to hire someone who isn't going to be able to give my team and project the hours we need.
  8. Find out what they really want to do. So important and often overlooked. Before you can ask this question of the potential hire, you need to clearly understand what you want of them. Why are you hiring this person? Do you have a specific role that you want to fill? If what you have in mind doesn't match up with what they have in mind, it'll be like trying to fit a round peg in a square hole. Sometimes coming at this sideways is the best approach: ask the person how they see themselves at your organization, what do they really want to do, especially looking forward. Usually people will be pretty straight forward with what they're looking to do.

Some additional thoughts

The above points have helped me find great people who have developed into valuable members of our team. However, sometimes that hasn't happened and it wouldn't be a startup if we didn't have to change course once in a while. The three points below are some additional control factors I like to have in place for after I've made the decision to hire. Working off the premise that you're only really going to be able to understand if someone is a good fit after you've started working with them, I always want to leave some exits open. 

  • Don't belabor the process - There's a limit to the amount of time I spend doing background on people. There's only so much you can understand about someone without having worked with them. If you abide by the two points below - building in a trial period and not being afraid to let someone go if they're not working out - there's no reason not to take a chance. As with any opportunity, time is always a factor; you may miss your chance if you don't act.
  • Build in a trial period - As a continuation on the above point, I rarely if ever hire someone full time, right at the start. You want to make sure this person is going be a good fit and vice versa. Even after going through all the filters listed above, I still assume that I don't actually know if someone is going to work out until their boots are on the ground. Some folks can be hard to trial with - e.g., sales people, executives - however I still do my best to involve them as much as possible before brining them on full time. 
  • Don't be afraid to let someone go - When someone isn't working out, for whatever the reason, my experience is that they don't get better. Further, giving them time (which is usually just an excuse for you not wanting to take action) can have a deleterious effect on the rest of your team. Take action quickly, for your sake and theirs. There is always someone better to be found!

Conclusions

Hopefully you've found at least a few points in here to be of use. They're what I've learned over 10 years, two software companies, and a good number of blunders. If I had to put a number on it, I'd say that to date, maybe 25% of the people I've hired I'd be interested in working with again. Maybe 15% have been truly great. How to increase those percentages is something I'm constantly thinking about.

Another, purely selfish reason I'm interested in improving my ability to hire great people: I love working with them. Great people make everything worthwhile. In a startup you will spend more waking hours with your team than you will with your significant other/family. I want to really enjoy working with my team, to be confident in their abilities, to have strong rapport and trust, and all the rest. If that's not there we're not going to do our best work. 

From memory, the folks I've hired include co-founders, designers, business development managers, board members, advisors, investors, lead sales reps, front-end developers, back-end developers, assistants, patent attorneys, business attorneys, interns, pr reps, mobile developers, mobile designers, communications designers, heads of marketing, inside sales reps, copywriters, heads of finance, and seos.

John Doerr on missionaries vs mercenaries