February 9, 2026
Hi Everyone,
Before you go into any difficult conversation, start with one fundamental question:
What decision are you actually driving toward?
Forget the scripts and feedback frameworks for a moment. Are you trying to help this person improve in their current role, move them to a different role, or end the relationship?
Coach, reset, or replace. Everything else comes after you've answered this.
The three buckets
Before any hard conversation with a direct report or key team member, force yourself into one of three buckets:
Coach: You believe this person can succeed in their current role. The gap is fixable – unclear expectations, missing skills, a rough patch. Your job is to name the problem, set a clear bar, and give them a real shot (with the right support) to hit it.
Reset: The person has value, but not in this seat. Maybe they were right for the scrappy early days and can't scale with the role. Maybe they're strong in one area, but you need something different now. Your job is to propose a new arrangement – different scope, title, or responsibilities – that works for both sides.
Replace: You've lost confidence that this person can do what you need, in any configuration. The gap is too wide, the pattern too fixed, or the trust too damaged. Your job is to end the relationship cleanly and kindly.
You don't have to decide the final outcome before the conversation. But you should know which of these three directions you're leaning toward and what would change your mind.
How to know which bucket you're in
A few questions that help:
If this person came to you tomorrow and said, "I quit," would you feel relieved? If yes, you're probably in Replace territory.
Have you given clear, specific feedback and seen no improvement? One round of vague suggestions doesn't count. But if you've had two or three direct conversations with concrete expectations, and the pattern hasn't shifted, coaching has likely run its course.
Is the problem skill, will, or fit?
- Skill gaps can sometimes be closed with support and time.
- Will problems where someone isn't putting in the effort rarely resolve through conversation.
- Fit problems, where the role has outgrown the person, or values don't align, usually need a reset or exit, not more coaching.
What's the cost of another 90 days of the status quo? In a small business, carrying a single person who isn't working can limit the entire company. If the cost of patience is high, lean toward faster resolution.
Avoid this trap
Many leaders stay in "coaching" mode long past the point where it makes sense. They keep giving feedback, keep hoping, keep extending deadlines because coaching feels kinder than the alternatives.
It isn’t. Keeping someone in a role where they're failing is hard on them, the team, and the business.
If you've genuinely tried to help and the gap remains, moving to a reset or replace conversation is the more honest path.
Before your next hard conversation
Write down this sentence: "I'm walking into this conversation to [coach/reset/replace].
If you can't finish that sentence with a clear verb, you're not ready for the meeting.
Go deeper
👉 Lucy Georgiades: How to Have Difficult Conversations with Employees (With Scripts & Examples)
👉 First Round: The Best Approach to the Worst Conversation: "You're Fired"
👉 Forbes: Have You 'Outgrown' Your Original Employees? Here's How To Assess Their Evolution
Coming up tomorrow
Tomorrow, we’re sharing what connects a vision to daily work.
Have a great week!
P.S. We’re still learning what's actually useful for you. If you've got a second, reply "useful" or "meh". We read every response, and it’ll shape what we write about next.