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Owning your mistakes as an operator
How to address when you’ve messed up with grace - because sometimes, it’s necessary.
Regina Gerbeaux
April 20, 2025 • Reading Time: 12 minutes
Hi! Welcome to another issue of Force Multipliers, your weekly briefing from Regina Gerbeaux, where Silicon Valley's behind-the-scenes operators get battle-tested frameworks for their toughest challenges, from putting out chaotic fires to managing strong personalities.
Dear Regina,
We had to fire someone from our Executive Leadership Team - a C-Suite - after we discovered some seriously egregious illegal activities.
Unfortunately, this person has spun the story differently and has made me out to be the bad guy. They are now demanding a public apology in front of the team and our customers, and a private one in a board meeting in front of our investors, claiming I’ve utterly ruined their reputation. They also want me to publicly beg them to come back as a leader in the company. There is absolutely zero chance this will happen - I’d rather die than do this.
I’m so frustrated that I have to clean up their shit every single time. This isn’t the first time I’ve butted heads with them.
While I know I made the right call to let this person go, I admit I was pissed and didn’t conduct myself in the most “conscious leader” kind of way. My ELT has given me that feedback that I could have fired this person with more tact and empathy, and I know they’re right.
Now, I’m stuck trying to figure out how to acknowledge that I wasn’t at my best in that moment…but I also refuse to apologize for holding someone accountable for their actions. Should I suck it up and just apologize, or stand my ground and risk escalation? Where is the line between admitting imperfection, without seeming weak or like a pushover?
(Cofounding operator, Series A, ~30 people, ~$20M raised)
Dear Operator,
It’s easy to spout Coaching Wisdom™️ by saying, “Simply never make mistakes, and always lead from above the line!”
The reality is, we’re all human and we make mistakes. It happens.
So what do we do when we’ve made a mistake - especially when the potential consequences can be so dire?
Here’s the playbook on how to own up when you’ve made a mistake, without groveling, apologizing for things you don’t need to apologize for, and when emotions run high.
The Playbook on Handling Mistakes
as an Operator
Step 1: Identify all emotions.
When you make a mistake, first, identify how you’re feeling.
If you’re an operator that prides yourself on almost never making mistakes, it can be easy to beat yourself up for them. You might feel:
Embarrassment (”I never make mistakes - why the hell did I do that this time?”)
Self-deprecation (”How stupid do you have to be to make this mistake? I’m an idiot.”)
Shame (”This mistake reflects so poorly on me; now, everyone will think I suck as an operator and I’m a bad human being.”)
Indigence/desire to point fingers (”Well, I wouldn’t have… if so-and-so had…”)
Name the emotion, then observe it - all without judgment. All of the reactions above are totally normal to experience, and you do not need to feel shame for feeling any of the above. (Just don’t use them to act!)
What happens when your mistakes involve other people?
Like the original Operator of the scenario above, it’s even more painful when your mistake has caused someone else to feel hurt.
Force multiplying operators understand that dismissing someone's reaction - even if it seems unreasonable - is a critical mistake. The most effective leaders acknowledge and validate others' emotional responses, regardless of whether they agree with them.
Your job is to identify:
What is this person feeling right now?
How can I play devil’s advocate for their position to better understand where they’re coming from?
Applied to OP’s story:
After sharing the question with me, I asked the operator above how the fired leader probably felt. The reply:
“They probably feel hurt and embarrassed. Like I mentioned, I was not a class act or conduct myself professionally when I fired them. I did it in front of the whole team. I was angry and impulsive. I said some really messed up shit.”
Identifying not only their own emotions, but also the emotions of the person that felt wronged, was a mandatory step to move forward. This cultivated compassion, empathy, and understanding.
Step 2: Identify where you can take full responsibility, and where it’s inappropriate to do so.
Now that you’ve named all the emotions (yours and theirs), zoom out and get clear on what’s actually yours to own. Where can you take radical responsibility?
This is where a lot of operators mess up: they either take too much responsibility and start groveling, or they take too little and come off as defensive (defensiveness is not sexy, by the way. It makes you look weak.) Your job is to separate those out.
Three questions to identify Zones for Radical Responsibility:
“Where did I behave reactively, rather than intentionally?”
“Where was I committed to being right, instead of being curious?”
“Where did I make mistakes that could have been avoided if I were a little more thorough and moved a little more deliberately?”
And one question to identify where it’s inappropriate:
“Where does it make less sense to apologize?”
This part is tricky because your ego will want to scream, “I refuse to apologize for that!” Lots of people use this prompt to get defensive and dig their heels in. Notice if you feel indigence, defensiveness, or anger anywhere.
I recommend consulting a coach or trusted third party to check your blind spots.
Applied to OP’s story:
The operator above ended up saying they would take ownership in being a “total non-class act” in how the firing went down (their words, not mine.) They also agreed they wish they had protected the exec’s dignity better, by doing the firing more intentionally, and certainly not in front of the whole team.
And finally - at some encouragement from me - they were willing to take responsibility for hiring the wrong person in the first place.
One thing I coach all my coachees into realizing is any time there is someone at your company who doesn’t belong there, you are the responsible party. You can ALWAYS take responsibility for hiring a person who turned out not to be a good fit for the role. Doesn’t mean they’re bad! Just incompatible.
This operator decided, and I agreed, that they would not take responsibility for letting go of the exec altogether - it was the right decision, even if done the wrong way. Right call, handled poorly.
Step 3: Craft your message so it’s empathetic and encouraging. Leave out anything you don’t need to apologize for.
This is the repair step, where you take the opportunity to apologize and take radical responsibility for your actions.
Begin by addressing the hurt feelings directly and acknowledge upfront the consequences of your mistake. Taking ownership in a sincere and empathetic way can help rebuild trust and demonstrate your accountability as a leader.
Don’t be afraid of using stronger language when you make your apology if that sounds like you.
For example - if you usually use swear words, don’t be afraid of saying, “I fucked up, and regret it tremendously. If I could do it all over again, I would…”
This kind of honesty shows vulnerability and a willingness to learn, which lowers peoples’ defensiveness and helps you connect on a deeper level with them.
Postmortem it!
Whether your mistake involved hurt feelings / had any emotional impact or not, you always want to declare how you intend to fix the situation. To fix, you must have next action items.
Clearly explain the steps you’re taking to make amends, and outline the actions you’ll take to ensure this mistake doesn’t happen again. By focusing on solutions and next steps, you shift the conversation from blame to constructive progress, demonstrating your commitment to improvement and growth.
Applied to OP’s story:
The operator crafted a sincere message of apology for the hurt and embarrassment they caused the exec - and delivered it privately in a 1-1 heart to heart first. This is what they said:
“[name], I’m so sorry for how I’ve behaved over the last 24 hours. I allowed my anger to get the best of me, and said some truly fucked up things. And I want to acknowledge the embarrassment and hurt I’ve caused you, especially in front of the entire team - I know a person’s reputation is one of the greatest things any of us have, and I tarnished it in a moment of anger.
Moving forward, I’d like to rectify the situation as best as I can - I’d like to share with the team my regret for not being more empathetic in the moment. I’d also like to highlight the many things I do appreciate about you, such as your detail-orientedness, being great at strategy, and getting things done. I want to point out the many great contributions you made to [company], and I genuinely want everything in your future to be the best, and that you’re ultra successful.”
In the end, after saying all of this, the fired exec accepted this operator’s apology gracefully - because it came from the heart. The impending fear that the fired exec would pursue legal action and drag the operator and their company through lengthy litigation disappeared in just ten minutes.
Notice the operator never apologized to the fired exec for firing them in the first place. The fired exec did not mind, and knew in their heart they were in the wrong there. They never once brought up the idea of the operator begging them to come back ever again.
This is the power of a true apology, while not saying sorry for the things you don’t have to be sorry for.
Word of warning: Things to avoid
Now that you’re armed with the playbook of a powerful apology and how to gracefully own your mistakes as an operator, here are some things to look out for in your journey:
Don’t give a half-hearted apology. “Mistakes were made” shifts the apology from being sincere to distancing yourself from the real mistake you made. Own where you actually messed up.
Don’t grovel. You don’t need to over-apologize. Allow the apology to match the gravity of the situation.
Don’t blatantly point out what you won’t apologize for. It’s already inferred in what you do apologize for, and unnecessarily calls attention to something people were otherwise not paying attention to.
Owning your mistakes as an operator is wonderful practice for demonstrating emotional intelligence, empathy, and a commitment to growth. By following the steps outlined above, you can turn challenging situations into opportunities to build trust, strengthen relationships, and enhance your leadership skills.
Remember, mistakes are inevitable, but how you handle them defines your character and sets the tone for your organization. Approach each situation with humility, clarity, and a genuine desire to make amends, and you will foster a culture of accountability and resilience.
Until next time,
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About Regina Gerbeaux
 | Regina Gerbeaux was the first Chief of Staff to an executive coach who worked with Silicon Valley’s most successful entrepreneurs, including Brian Armstrong (Coinbase), Naval Ravikant (AngelList), Sam Altman (OpenAI / Y Combinator), and Alexandr Wang (Scale). |
Shortly after her role as Chief of Staff, then COO, she opened her own coaching practice, Coaching Founder, and has worked with outrageously talented operators on teams like Delphi AI, dYdX, Astronomer, Fanatics Live, and many more companies backed by funds like Sequoia and Andreessen Horowitz.
Her open-sourced write-ups on Operational Excellence and how to run a scaling company can be found here and her templates can be found here.
She lives in the Pacific Northwest with her partner Lucas and dog Leia, and can be found frequenting 6:00AM Orangetheory classes or hiking trails nearby.
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