July 13, 2026
Hi Everyone,
Someone on your team isn't performing. You've had a few conversations, but nothing has changed. The next step, in most companies, is a formal performance improvement plan (PIP).
Before you draft anything, ask the questions we cover in today’s issue. Depending on the answers, a PIP may not be what the situation needs.
The decision was probably made earlier
Michael Lopp, who has run engineering teams at Slack, Pinterest, and Apple, once said: "If you're lying awake at night thinking, 'God, Jeff is pissing me off,' your chance at a low-cost solution probably came about three months to a year ago."
By the time a performance plan is on the table, the real decision was often made much earlier.
A PIP is a slow, expensive process. It's worth being honest, before you start it, about what you're hoping it will do.
1. Would I feel relieved if they quit tomorrow?
This tests whether you still believe they can succeed in the role.
If the honest answer is yes, you've already decided they aren't going to make it. What you're planning is a formal process to protect the company on the way to letting them go. That happens, and it's sometimes necessary, but it isn't performance coaching and you shouldn't treat it like it is.
If the honest answer is no, the performance plan should reflect it, with a real bar, real support, and check-ins that treat them as someone you're trying to keep.
2. Have I told them, in writing, what needs to change?
Written feedback is clearer than a conversation. Both of you can go back to it later, and you'll both remember the same thing.
Send them a short note that covers what good performance looks like in this role, where their work is currently falling short with two or three specific examples, and what needs to change.
If you haven't done this, do it before you draft a formal plan.
3. Is this a skill, a will, or a fit problem?
Underperformance usually comes down to one of three things, and they each need a different response.
A skill problem means they don't yet know how to do the work. This is the one a PIP is genuinely useful for.
A will problem means they could do the work, but aren't putting in the effort. A PIP can help here too, but mostly because it forces them to decide whether they want the job.
A fit problem means the role has moved beyond what they can or want to do. This calls for a different role or a clean exit. A PIP won't fix it.
If you're not sure which one you're looking at, work that out before you draft anything.
4. What am I hoping the PIP will do that a real conversation hasn't?
Sometimes you've already had a clear conversation and the person hasn't changed anything, so a formal process is what raises the stakes. Sometimes legal or HR needs a written record before you can let someone go.
The answer worth watching for is that a PIP feels easier than sitting down with the person and telling them, in plain terms, that their work isn't good enough and here is what needs to change. It isn't easier. A PIP takes longer and still ends with you having that conversation. If avoiding it is why you're reaching for a formal plan, have the conversation first.
How to use these
Write your answers down before you start drafting anything formal. If the four questions point toward a PIP, you'll have a clearer plan when you write it. If they point somewhere else, you've saved yourself the wrong process.
Go deeper
👉 Radical Candor: Criticism and Ruinous Empathy – Useful if you tend to delay hard feedback because you don’t want to hurt the person. Kim Scott explains how that usually protects the manager’s comfort more than the employee.
👉 First Round Review: The Best Approach to the Worst Conversation – Read this before you put someone on a PIP. Michael Lopp explains why the real decision often happens months before the paperwork starts.
👉 First Round Review: A People Ops Veteran on Navigating the Gnarliest Conversations – Good if the underperformer is a manager. Meg Makalou explains why leaving the wrong manager in place can damage the whole team around them.
Coming up next
Tomorrow we'll break down when to hold your pricing, when to restructure it, and when to cut.
P.S. Which of the four is hardest to answer honestly? Our guess is the fourth.