Eat the frog
Parting ways with someone: how to approach one of the worst parts of being a founder.
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This oneâs heavy, but every founder will likely have to go through it.
Letting someone go is my least favorite part of the job. It always sucks. Iâve done it at a few companies, and I still feel the weight of it each time. I hope I never get numb to it because itâs deeply impacting someoneâs life and needs to be taken seriously.
Hereâs how I handle it today, based only on my own experience.
Why itâs hard, but important
We keep a high bar at Clarify because our teammates expect to work with and learn from the best. So when weâre vetting a new hire, weâre looking for someone whoâs going to raise the bar of the team. They share their expertise, are open to learning from others, and always bring their best selves.
But sometimes that doesnât work out. When a hire isnât succeeding, the failure is often two-fold: we may have hired wrong, or we may not have set the person up for success. Either way, founders should own it.
But leaving someone in a role where they arenât succeeding helps no one. They donât grow, and the team starts to wonder if weâre okay with average work. If I do nothing, Iâm sending a message that this high bar weâve set doesnât actually matter.
My job is to inspire and set context, not micromanage. I give people rope to make decisions and miss sometimesâthe question is whether theyâre more often right than wrong, and whether their judgment improves over time. But when I see a pattern of weak calls, I have to act.
What I try before parting ways
When I see a hire struggling, two things are essential:
Set clear goals with specific timelines for what âgoodâ looks like.
Give direct feedback, plus support and scope adjustments if that could help.
Iâll give more leeway to someone earlier in their career. But if itâs a senior person with 10+ years of experience, and the basics still arenât landing after clear goals and support, thereâs only so much coaching that changes things in a startup environment.
The best fix is prevention. Before we hire for any role now, I align the team on responsibilities, what good looks like, and how weâll evaluate performance. Clear expectations up front make the hard conversations easier, or unnecessary.
When itâs time to part ways (and how I handle it)
I know itâs time when the pattern is undeniable: clear direction doesnât change outcomes, the person needs step-by-step guidance for core work, peers raise the same concerns Iâm seeing, and the gap between their output and our bar stays wide.
I also know myself. When I find myself wanting to spend less time with someone, my gut is telling me something.
When the moment itself comes, I keep the conversation direct and respectful. Iâm clear about what wasnât working and what we tried. I share the impact on the team and outcomes. No theatrics, no surprises.
That means by the time we have the final conversation, it shouldnât feel like a shock. Iâve tried to have many direct conversations leading up to itâfeedback in writing, clear documentation of what wasnât landing. That protects everyone.
One approach thatâs worked: when itâs clear things arenât working, give the person a choiceâa PIP with specific goals and a timeline, or a clean exit with a severance package. Most people know when itâs not working too. Giving them agency in that moment is more humane, and it usually leads to a cleaner outcome for both sides.
On packages: be consistent. Tie it to tenure or set a flat standardâwhatever it is, apply it the same way every time. Cover at least a month of COBRA so theyâre not left without health insurance. Itâs the right thing to do and it reduces risk.
The worst mistake is waiting too long. Iâve made it. People told me it wasnât working, and I still held off, hoping things would turn around. That delay cost us months and sent the wrong message to the team: that maybe our standards were negotiable after all. It also might set a dangerous precedentâother hiring managers on the team could see it and learn that delaying those conversations is acceptable.
What the team needs to hear
Silence breeds stories.
I donât share private details, but I am transparent about the basics: we set goals, tried specific changes, and it didnât land. This is about the role and outcomes, not personal character. I explain how weâll cover the work and what changes now. Done well, the team sees we take the bar seriously and handle hard things with empathy.
Hiring better next time (and what Iâm still learning)
Iâve tightened references. Skipping them is a mistake. Now I ask past peers and managers how someone works, what they value, how they handle conflict, and whether they put the organization first.
One thing I underestimated: we didnât have shared alignment on our values as a team. That made everything harder. Without a clear foundation, itâs easy for standards to feel arbitrary rather than principled. Weâve since revisited and rebuilt that, and itâs made these conversations easier to have and easier to defend.
I also watch the first two to three weeks closely. You can usually tell if someone is lifting the bar or lowering it. Work trials have helped in the past, but theyâre not a cure-all. The bigger lever is alignment up front on the role and standards.
After a departure, we now do a quick retrospective as a team: what did we miss in the interview process, what questions should we have asked, what signals did we overlook? Itâs not about blameâitâs about getting sharper. Some of our best hiring questions came out of these conversations.
Iâm still finding the right balance between pushing and supporting. I hold myself to a high standard and naturally hold the team to it too. Thatâs unfair if I donât give enough context first. So Iâm more deliberate now about setting people up before I evaluate them.
Letting someone go is hard. But doing it with empathy, after genuine attempts to make it work, and with clarity for the teamâthatâs the job. The alternative is worse: a team that stops believing the standards matter, and a person stuck in a role where they canât win.
As Mark Twain said: âEat a live frog first thing in the morning and nothing worse will happen to you the rest of the day.â
This is a tricky subject for all founders. Would love to read your thoughts in the comments.
Until next week,
Patrick
Additional reads
The best approach to the worst conversation: âyouâre firedâ - First Round