FOR NEW SALES MANAGERS
CHAPTER 2

The first talk with the owner

IN SHORT

Before you change anything, agree with the owner what you are there to fix. It takes one conversation and fifteen questions, and it ends with two written goals: one for day 30, one for day 90.

By the headofsales.me teamUpdated 20267 min read

Where it goes wrong

A FICTIONAL EXAMPLE

Marcus joined a small distribution company as head of sales. The owner, Irina, said on day one: “Just make the team sell more.” Marcus nodded, spent six weeks rebuilding the pipeline and presented it with pride. Irina looked at it for a minute and asked why he had not touched the pricing, which was the thing she had worried about for a year.

She had never said so, and Marcus had never asked. Both of them took that first sentence for the brief.

Ask before you propose

The owner knows things no report shows: why they hired you, what they tried before and what they will not change. None of it will come out if you arrive with a plan. Arrive with questions, and write the answers down.

Ask about the past as much as about the future. An attempt that failed two years ago tells you what the owner is afraid of, and that fear will shape every decision you bring them.

  • What should be different in three months?
  • Which earlier attempt failed, and why?
  • What is off limits?

Separate the symptom from the cause

“Sales are down” is a symptom. Ask for the last three lost deals and the last three won ones, and let the owner tell each in one minute. Patterns show up in the stories before they show up in the numbers: the same objection, the same kind of customer, sometimes even the same week of the month.

Do not argue and do not defend the team. You are collecting material. If a story sounds unfair to a seller, note it and check it later with the seller. Today you listen.

Write two goals

Agree one goal for day 30 and one for day 90, a sentence each. Day 30 is about facts and one small fix. Day 90 is about a rule the team keeps without you. If you need more than a sentence to check a goal, it is still a wish.

Read both back to the owner and ask: “If this is true on day 90, will you say it was a good quarter?” If the answer needs an explanation, rewrite the goal. The free guide has the fifteen questions for this conversation.

Get the 15 questions, free

Close with a date

End with the date of the next talk and what you will bring to it: three things you learned and one thing you ask for. A 20-minute slot every two weeks is enough, and it keeps the owner from learning about your plans from a seller.

After the conversation, send a short note with the two goals in the owner’s own words. It costs five minutes and saves you the most common argument of the first quarter: what you actually agreed.

Do this week

  • Book 45 minutes with the owner.
  • Write the last three lost and three won deals as one-minute stories.
  • Send the two goals back in the owner’s words and agree the date of the next talk.
First page of First Week: The Conversation with the Owner
FOR THIS CHAPTER · FREE
First-week talk with the owner

15 questions for your first conversation with the owner, plus goals for day 30 and day 90.

CITE AS: headofsales.me, “The first talk with the owner”, Handbook I, chapter 2, updated 2026. headofsales.me/handbooks/first-quarter-in-charge/the-first-talk-with-the-owner/