The hardest hiring conversation is not the offer. It is the one a few months later, when you realise it is not working.
In my experience, the signs show early. The manager sees them, hopes they will pass, and waits. By the end of probation the new rep is surprised, the team is tired, and the territory has lost months.
Waiting feels kind. It is not.
What I try to do instead:
- Check myself first. Did they get the induction, the field days and the support I promised? If not, the problem may be mine.
- Name the gap early. In the first month, not the fourth.
- Separate skill from fit. A skill can be taught. Sometimes the role itself is wrong for the person.
- Agree a few clear goals, the support I will give, and a review date.
- Give that support for real. Extra field days, a buddy rep, practice on the hard calls.
- Bring HR in early and follow the probation process properly.
- Review honestly, and say the result plainly, either way.
If it is not the right fit, end it privately, with respect, and thank them for the effort. People remember how you let them go.
“Deciding late is not kinder. It only costs the new rep more of their time.”

Lesson 9 of 12 in Step 7: Hiring and onboarding, with the full guide and a checklist for this week.