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Firing my first person because of avoidable mistakes

The first time I fired someone was one of the hardest experiences of my life.

It didn’t make it easier that I had zero doubt that this was the best decision for the company and my team. It didn’t help that we had exhausted multiple measures to try and course correct.

Sometimes knowing something is right does nothing to make doing it easier.

So OK, it sucked. Obviously. You have to pretty messed up to not be affected by making this kind of decision.

But the emotional side isn’t really what I want to focus on here.

I think it’s probably more useful to walk you through the key mistakes I made during the entire three month process from making an offer to letting my team member go.

The Background


So let’s get one thing straight.

My team member was in over their head. Period.

The job was big. They were a bit underqualified. They demonstrated a lack of work ethic, and finally, within just a couple of weeks personal issues started cropping up around the simple act of being an accountable professional.

This wasn’t a good fit. And it was clear SO early on in their tenure.

Clearly I had missed something. Could this situation have been avoided?

The answer to that question is yes. I made a lot of rookie mistakes.

Mistakes During the Interview Process

Hiring the Wrong Candidate

Let’s start with my mistakes during the hiring process. I’m pretty sure based on the size of this list that I made all the classic mistakes:

  • Ignoring red-flags on reference checks – One person never called back. Two of the references only had phone numbers listed (no email, really?), and the longest call I had was with a very odd reference, who although he spoke highly of the person, was a red-flag unto himself. None of the senior references were from jobs relevant to what they were going to be doing for us. Yep. References matter.
  • Over-prioritizing a person in the seat vs. having the right person – I wanted this person to succeed and be the right fit too much. Part of this was a desire to not have to interview anymore. Interviewing takes a lot of time, and if you’re trying to fill a job for awhile all the ups and downs can really wear on you. Plus, in this instance the Candidate offered much needed diversity of life experience and perspective which I thought was a real strength and led me overlook a few critical things…
  • Failing to establish strong enough “must haves” – As an interviewer you try not to fall in love with how people interview because some people who don’t interview well might still be your best contributors. You need to get past personality and try to understand the skill set and long term dynamic a person will add to the team and culture. It’s really hard. One thing I found helpful was taking the time to have a clear mental picture of your ideal Candidate. What tasks do they own without oversight? How do they interact with you on a day-to-day? Where do you see them growing within the organization? Once you’ve built that model I think it’s easier to define what skills you think are non-negotiable vs. what trade-offs you’re OK with.
  • Under-appreciating past accomplishments – I have a natural aversion to credentialism, and I think I often sub-consciously root for the underdog Candidate. I’m not really sure where it comes from, but sometimes that conflicts with my belief that the best proxy for someone’s performance is how they’ve done previously. Inferring things from what they’ve done in the past (played a sport and crushed their GPA? Gotten into an amazing school? Built a high traffic website?) can help act as a good screen and give you a better understanding of how they’ll approach this job.
  • Under-appreciating experience – The difference between someone who’s done the job before and knows a lot of the potential pitfalls and key ingredients to success is big. I think sometimes, especially in earlier stage startups, it’s easy to go more junior to save cash or equity, but that isn’t always worth it (note…sometimes it is, but promoting that person once they’ve proven it a bit at your company won’t kill you). Reward contributions over outside potential.
  • Under-weighing the (culture) risk of the wrong person – If I had fully considered the Candidate in the context of working with them 9+ hours a day I think I would have been more conscious of the risk of saying “yes” to one person. First of all, it shuts the door on continuing to look for someone that might be a better fit. Second, you’re responsible for their results. Finally, from a culture perspective, it’s vital that people are a good fit for your team. Managing people is hard no matter what, but if someone isn’t naturally compatible with your management style, it’s going to take that much more time and energy to get meaningful, sustained contributions from them. For me, I’ve come to understand that what I most value in my teammates is that they are self-driven, curious problem-solvers, who don’t mind rolling up their sleeves and owning goals/projects start to finish. I find Zuckerberg’s guideline of only hiring people he’d be willing to work for if the roles were reversed a good guide post for all of this.

Welcome to the team

So we hired our Candidate. There was a lot of work to do and we wanted them to succeed. The ramp up was aggressive in terms of training, and we started shipping projects quickly.

Despite sinking days into onboarding things never took off quite the right way, and they got worse not better over time. Part of that was definitely my fault.

The single biggest mistake I made was not being direct enough with immediate, timely, and actionable feedback. It was a combination of being too high level on how to improve their performance and yet not high level enough with communicating where they were failing to meet company and cultural expectations.

The worst part is, I knew that I should be changing the approach I took in giving feedback.

I’m always honest about the standards I expect and I try to model those for my team.

Mostly, I think this has lead to a great ego-free, team environment where we like working together and getting stuff done.

But I know I can be overly circumspect with observations and that doesn’t always work 100% of the time or with 100% of people.

Sometimes subtle isn’t the right approach.

Clear, concise, timely, and occasionally very blunt feedback (as long as its constructive) can be useful. Doing this well is still a work in progress for me, but I think that had I done more of it I had very early opportunities to level-set expectations and highlight specific instances where we could improve things and (maybe) right the ship.

Bottom line: it’s easier to make minor adjustments than to stop a boulder that’s gotten some downhill momentum.

The Good

The good news, if there’s any from an outcome like this, is that we did enough right to make sure this didn’t end up worse than it could have.
Some of the right calls included:

  • • Cutting ties early – Less than two full months of employment passed before we made the decision. Once we knew we were decisive
  • • Being upfront and honest
  • • Treating the person fairly
  • • Not repeating the same mistakes in the second round of interviewing
  • • Explaining the decision to the team in the right way
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Last modified: May 27, 2018