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My Greatest Firing Failure + 10 Lessons I learned


When I fired a manager at a startup I was scaling, he broke all of the furniture in the room. It was terrifying.


I’ve been hesitant to write about this experience because it’s one of my darkest professional moments. Now, after many years have passed, I've decided to be vulnerable and share it. My goal is to help you learn from my mistakes.


Firing people one of the most important - and hardest - things a CEO needs to do. "Offboarding"comes up often with my clients, who are primarily first-time founders. Getting the right people on your team is equally as important as getting the wrong people off it.


To this day, I genuinely believe that most people exist within the bell curve of reasonable behavior and that this particular incident was an outlier. You will likely never experience anything like this. I sincerely hope you don't have to.


Here’s the whole story from the beginning.

In my head, I call this employee “He Who Shall Not Be Named.” But, for the sake of sharing this with you, we’ll call him “Tom.”


To this day, I know I did the right thing by terminating Tom. I could have approached the process differently, though, so it felt more measured, clear, and fair. Over the years I’ve reflected a great deal about what I’d have done differently. Here are ten lessons I learned, working backwards from the start.


Lesson #1: Don’t rush the hiring process


Before Tom was hired, I was drowning in work. I was scaling an organization rapidly and was stretched paper thin. I wrote and posted a job description, interviewed a handful of candidates, and pushed Tom through as fast as I could. Tom was the strongest candidate in a fairly weak pool. In my mind he couldn’t start soon enough.


Instead of sprinting forward, though, I wish I’d spent more time recruiting talent into the pool so I had more than one viable option to consider.


No matter how much pressure you feel to hire quickly, it’s so much more work to hire the wrong person and have to fix it. Trust me: it’s worth waiting for the right person.

Lesson #2: Design a hiring process that surfaces key skills, values, and competencies


I was so focused on getting key technical abilities covered that I didn’t identify the other critical success factors for this role. A few weeks into working with Tom, I started to get worried about the quality of his work. I also grew concerned that Tom appeared more interested in self-promotion than prioritizing what was best for the team or the work identified in his job description.


I now know to label these concerns as performance issues and culture issues. Here’s how I could have screened more effectively in the hiring process, I could have:

  • Identified a rubric of skills, competencies, and values for this role and marked which were “nice to have” and which were essential

  • Designed a hiring process to help candidates demonstrate if they’re a match by sharing past experiences, having candidates walk me through how’d they’d approach a new problem they’d face (i.e. scenarios), and by assigning a standardized and relevant “assignment” to see an exemplary work product

  • Invited more people into the process to help articulate the criteria for success and to standardize our decision-making processes

Lesson #3: Invest in onboarding


Although I did invest sufficient time in onboarding Tom, I don’t think I necessarily spent our time on the right things. I provided Tom with organizational context, I made key introductions, and provided him with all of the tools he needed to operationally get moving. But I missed the most important thing: clarifying what success looks like.


Here’s what I’d wished I had done differently:

  • Established clear performance goals (OKRs) for the first 30-60-90 days as well as the first year. It would have made it so much easier to give feedback if we’d first identified the benchmarks, quantified them, and bound them with timeframes.

  • Explicitly articulated organizational culture and values. You have to name what is important and find ways to reiterate and reinforce them regularly. Company values are how you communicate how you want people in your organization to behave; they’re the roadmap for how you want the work to get done. You can’t punish someone for rules they didn’t know exist. To ensure that you not confusing values with bias, you have to be explicit. I wish I’d named what is important and given examples of what these norms look like in practice.

Lesson #4: Provide regular critical feedback


I was uncomfortable giving critical feedback. By nature, I’m a pretty cheery and positive person. In this case with Tom, I definitely erred way too far on the side of noticing the positive without also nipping critical issues in the bud. I hadn’t been clear enough about what wasn’t working, so Tom thought things were going better than they were. I wish I’d gotten into a practice of giving critical feedback effectively and regularly so it was a norm.


Lesson #5: Loop in HR and legal early on


As we neared our 90-day check-point, I decided it was time to escalate my concerns into a Performance Improvement Plan. I made sure to get guidance from HR and legal every step of the way to ensure I was doing this by-the-books.


At this point, I had already come to the conclusion that Tom was not the right person for the job. I still had to go through this process, however, to be fair and align us. On the first day of our Performance Improvement Plan, I gave him hard feedback, made it clear what success looked like over the next two weeks, and set up daily check-in meetings so I could give him timely feedback. I tried to make it clear that his employment was at stake and followed up every conversation in writing.


This is when I finally figured out the critical feedback formula to ensure I didn’t sugar-coat the message. I felt cruel and heartless and wished I’d given him more critical feedback earlier on so it could feel more balanced.


Lesson #6: Never fire someone alone


On the morning of the day in which I had to deliver the final feedback about being terminated, I was nervous. I didn’t want to have the conversation. I had a great deal of empathy. He had a family and this was going to have a big impact on his livelihood.


I’ve come to realize that firing someone should never feel easy. If it is, you’ve lost your humanity. It does get easier with experience, but it should never feel easy or rote. To this day, after firing someone, I still cry as soon as the employee leaves the room.

The day of the firing incident.

The meeting was at 8 AM and the office area was mostly vacant. I’d kept the door ajar and was alone with Tom delivering this final message. I was brief and to the point.

He took a minute to process that he was fired, then he stood up. First he raised his voice. Then he grabbed a chair and threw it. He smashed the desk and the walls and the filing cabinet. It was violent and scary. I was shocked and feared he’d turn his anger towards me.

I told Tom that I needed to leave and started walking down the hallway. Tom followed me, raising his voice louder and louder. I started to run. I found a private bathroom and called a mentor. He told me to go somewhere public immediately. I left the bathroom and headed into a foyer. I called the police and my boss to alert them of the situation. Later on I learned that construction workers nearby had called the police before I could.


To this day, I will never fire anyone alone again. I now proactively plan for the worst-case scenario and breathe a sigh of relief when it goes relatively smoothly.


Here are some tips you may want to consider before you have the firing conversation:

  • Ask a senior leader or HR to join you for the conversation so you are not alone

  • Pick a time when there are people around like mid-day

  • Have an exit plan if things go south - on Zoom you can sign off; in person you may want a route picked out

  • Plan your message carefully - consult your lawyer and/or HR for verbal language and an approved written communication. What are you going to say? What are you offering? Severance? The opportunity to resign first? How much time and money are part of this separation? What does the employee get to say about his/her departure? You’ll want legal advice on all of these in advance of this conversation.

  • If in person, consider asking plain-clothed police to monitor the scene. As soon as the date and time of the meeting are scheduled, I now call up the building security and/or police and ask for plain-clothed officers to be nearby in case the employee does not handle the news well. Police do this often and are very comfortable wandering the halls, looking busy, so that you don’t even know they are there. It’s a huge peace of mind to know you have backup ready and it costs you nothing to ask.


Lesson #7: Have a communication plan ready - with options


Depending on how the conversation goes, you’ll want to discuss how you - and the employee - are going to communicate this change and to whom. The more graceful the exit, the more control the employee can have over their narrative.


If something egregious happens, such as was the case in this situation, the employee does not get any choice on communicating the departure. In this situation, HR immediately shut down his email and his building access.


As the leader of this organization, as soon as the situation unfolded, I focused on damage control. I wrote a calm but urgent email to everyone who was closely affiliated with the organization and hosted an emergency hybrid town hall meeting to share essential information. I wanted to proactively answer questions in case the team arrived at an office full of broken furniture before we had the chance to clean it up. I stuck to the facts, guided by HR and legal.


Lesson #8: Self care


Firing Tom was one of my worst professional moments to date. I tried to just push through it but I was scared to physically head back to work for a little while. The experience shook me.


Tom knew where I lived because I'd hosted a team BBQ at my house. I called up my local police and asked them to do rounds by my house for a couple of weeks to help me sleep better at night.


I worked from home for a week or so afterwards and leaned heavily on trusted friends, mentors, family, and advisors to help me get back on steady footing.


Even if everything goes according to plan, firing someone is hard on everyone. I’d encourage you to not just barrel through to the next thing on your task list but, instead, to do whatever you need to do to manage yourself first. It’s important to have a moment of closure and processing.


Lesson #9: Learn what you can from the experience


Sometimes a little time needs to pass before you do a team post-mortem to figure out improvements you want to make to your hiring, onboarding, managing, or offboarding processes. It’s important to do this, though, even if you need a some space and time first.


Lesson #10: Sometimes, it’s not about you.


I’m the type of person who always tries to own my contributions to every problem and learn from everything. I've done this over and over again with this incident. How did I make this situation go sideways? I'm come to accept that, sometimes, you can't take responsibility for too much of a problem. Sometimes people are unpredictable and unbalanced. I know that this wasn't entirely my fault. Tom's temper was there - just below the surface. It probably would have shown up at work sooner or later. This is why it’s helpful to reflect with a trusted colleague, a coach, or a mentor so that you can separate out the valuable learnings from the things that are truly are out of your control.


Here are some resources to help you:

I put together an Offboarding Guide to help some of my clients understand the firing process. It's best to use a guide like this in conjunction with a coach and with the support of an HR consultant and a lawyer. I encourage you to check it out, as well as to explore other relevant resources here.


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