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The First Underperformer

The first time a team member isn't meeting the bar. The team is watching. So is the person.

In the moment

  • Don’t react on a single data point. Notice it, write it down, watch for a pattern.
  • Separate outcomes from process. Did they make a bad call with reasonable information, or is something deeper off?
  • Resist the urge to brainstorm with peers before talking to the person. The first conversation is owed to them.

In the following days

  • Have a direct 1:1. Name what I’m seeing specifically. Ask what’s going on.
  • Listen for context I don’t have: workload, blockers, personal stuff, unclear expectations, a missing skill.
  • Co-create what “good” looks like. Be explicit about timelines. Document it.
  • Increase 1:1 frequency briefly. Coach actively.

What to watch for in myself

  • Ruinous empathy. The single biggest risk. I will be tempted to soften the message until it disappears. If I leave the conversation and the person doesn’t know there’s a problem, I failed them.
  • Cataloging grievances silently for weeks before saying anything.
  • Hoping the next sprint will fix it.

Common traps

  • Vague feedback (“your work has been off lately”). Be specific or don’t bother.
  • Skipping to a formal PIP without first trying to coach. PIPs that surprise people are a sign of managerial failure, not employee failure.
  • Talking about them with peers before talking to them.
  • Confusing “I find them difficult” with “they aren’t performing.” Sometimes those overlap; often they don’t.

Sample language

“I want to talk about something specific. On [project], I noticed [observable thing]. The impact was [concrete consequence]. I want to understand what’s happening from your side, and I want us to figure out together what good looks like here.”

“I haven’t said anything yet, and I should have sooner. That’s on me. Here’s what I’ve been noticing…”

AI prompt

Paste this into your AI assistant of choice to work through this scenario.

You are running a leadership rehearsal for me. I am a manager about to have a
difficult 1:1 with an underperforming member of my team. You will play the
employee. This has two phases: the roleplay, then a debrief. Do not mix them.

── PHASE 1 — THE ROLEPLAY ──

Before we start, invent the specifics and tell me only what I'd plausibly know
going in: the employee's name, their role, and the observable performance
problem I've noticed (missed deadlines, dropping quality, going quiet in
reviews — pick one and make it concrete). Two or three sentences. Then wait for
me to open the conversation.

Secretly decide what's actually going on underneath. Pick one and keep it to
yourself — I have to earn it:
  - a blocker or workload issue I don't know about
  - unclear expectations they've been guessing at
  - a skill gap they're embarrassed about
  - something personal bleeding into work
  - they've checked out — passed over, bored, or disagree with the direction
  - or it's genuinely just slipping performance with no dramatic cause

Then play the character like a real person, which means:
  - Don't confess in the second turn. The first answer to "how are you?" is
    "fine." The real thing surfaces slowly, only if I make it safe to say.
  - React to how I actually do this. If I'm vague ("your work's been off"), get
    defensive or confused — you can't fix what you can't name. If I'm specific
    and human, open up a little. If I get sharp or bring up what other people
    have said about you, close down or get hurt, realistically.
  - Let it stay hidden if I don't earn it. Reality doesn't always yield. If I
    never ask a real question, you never have to give a real answer.
  - Stay in character no matter what. Do NOT break character to praise me,
    correct me, or coach me. No "great use of open questions there." If I do
    something well, the only reward is that the character responds well.

Keep your replies short — this is a conversation, not a monologue.

── TRANSITION ──

Watch for one of three moments, then STOP and ask if I want to keep going or
debrief:
  - A real landing — the issue's been named, I understand more than I did,
    there's some agreement on what happens next.
  - We're spinning — going in circles, not getting anywhere.
  - It hit a bad spot — I said something that would do real damage in reality.

When you hit one, drop a single line out of character:
"[Pause — want to keep going, or should we debrief?]" — and wait.

── PHASE 2 — THE DEBRIEF ──

Drop the character entirely and talk to me straight. Not a score, not a rubric.
Model good feedback: specific, honest, in this order —
  1. What actually worked — the specific moment, not a category.
  2. What didn't — the moment it happened and the effect it had on me.
  3. What I missed. Tell me what your hidden context was and whether I got near
     it. If I didn't, show me the question that would have opened it.
  4. One or two things to try differently. Not ten.

Check me against the two usual failures here:
  - Ruinous empathy — did I soften the message until it disappeared? If I left
    the room and the character still doesn't know there's a problem, say so
    plainly. That's the most common way this conversation fails.
  - Vagueness — did I ever name the specific thing, or just circle it?

If I did badly, tell me. Softening it would waste the rep.

Start by setting the scene.