FOR NEW SALES MANAGERS
CHAPTER 5

One-to-ones that are not status updates

IN SHORT

A one-to-one is the seller’s time. Keep it to 30 minutes, let the seller bring the topics and end with one thing they will do before the next one.

By the headofsales.me teamUpdated 20267 min read

Where it goes wrong

A FICTIONAL EXAMPLE

Every other Thursday a manager sat down with each seller for half an hour. The sellers came with their open deals, read them out and left. After three months one of them said, politely, that he had started to prepare for the one-to-one the way you prepare for an exam, and that he was not learning anything he could not read in the CRM.

To the manager the meeting felt productive. To the seller it felt like a report, and neither of them had meant it to go that way.

Move the status into the CRM

If you can read it in the CRM, do not ask for it in the meeting. Use the time for what the CRM cannot hold: a deal that worries the seller, a conversation that went badly, a skill to practice.

This asks something of you: you have to read the CRM before the meeting, so that you walk in knowing the status. Ten minutes of preparation saves the seller from reciting it.

Ask, then stay quiet

Ask one question and wait. Count to five before you fill the silence, because the first answer is usually the polite one and the second is the true one. Three questions are enough to start.

Write down what you hear in the seller’s words, not in yours. If the seller says “the customer went cold”, do not translate it into “lost interest”. Ask what happened the day before.

  • Which deal worries you most this week?
  • What did you say that you would say differently now?
  • What do you need from me?

Pick one thing

End with one action for the seller, small enough to finish in a week, and write it in shared notes. At the next meeting start with it. One finished action a week adds up to fifty in a year, and both of you can point to each one.

The 120 questions in the one-to-one kit are there to pick from, not to read out. Choose one or two that match what the seller is working on and leave the rest.

See the one-to-one kit

Keep the rhythm

Same slot every week or every second week, same length. Cancel rarely and reschedule at once. A seller reads a cancelled one-to-one as a message about where they stand.

If you have more than eight sellers, you cannot do this with everyone every week. Rotate, and tell the team how the rotation works, so that nobody thinks they were skipped.

Do this week

  • Read the CRM before each meeting so you know the status.
  • Prepare three questions and one thing to practice with the seller.
  • End every meeting with one action and write it down.
Cover of The 30-Minute One-to-One
FOR THIS CHAPTER · $49
One-to-one meetings

A 30-minute one-to-one with each seller, with an agenda and 120 questions to pick from.

CITE AS: headofsales.me, “One-to-ones that are not status updates”, Handbook I, chapter 5, updated 2026. headofsales.me/handbooks/first-quarter-in-charge/one-to-ones-that-are-not-status-updates/