PEOPLE · ONE-TO-ONES

How to run a 30-minute one-to-one with a salesperson

“One-to-Ones and Growth” is a kit for a sales manager who meets each salesperson one on one. The meeting follows a 30-minute agenda and ends with a written agreement. If a salesperson needs to build a skill, one of 12 scenarios gives you the questions and a practice task until the next meeting.

$49PDF, Word, Excel · English

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English
updated October 13, 2026

A desk with two notebooks facing each other, an hourglass and a stack of cards: a 30-minute one-to-one

Who it is for

For a sales manager whose meetings with salespeople come down to a recap of the numbers or a “how is it going.” Especially if not long ago you were a colleague of these people.

What this means for you

Pick the option that fits you, and the answer for your situation appears below.

Your experience in the role

First month in the role Up to a year More than a year

First month in the roleThe first meeting with former colleagues is usually the most awkward. The guide has phrases to open it with, and a short brief to help you come prepared.

Up to a yearIf the meetings are already happening, start with the log: it highlights the people you have not met for more than 10 days. You can bring in the agenda from next week.

More than a yearYou already know how to talk to people. What will help are the 120 questions and the development scenarios, so that your meetings do not repeat each other.

Team size

1–3 people 4–10 More than 10

1–3 peopleYou can meet every week: half an hour per person is under two hours for everyone.

4–10Every week that is up to five hours. You can meet every two weeks: the log highlights the people you have not met for more than 10 days.

More than 10Meeting everyone regularly will not work. Hold the meetings with senior salespeople or group leads, and give them the agenda and the cards.

The industry hardly matters here. The scenarios are tied to deal stages. The stage names in your CRM can be anything: the scenario shows what to do at a given stage of the deal, whatever you call it.

What it does not do

it is not a coaching course and not a psychological method;
it does not judge people for you: you pick a scenario based on what you saw in the salesperson’s work;
it does not store notes with us: the log and the notes stay in your files.

What is inside

What you get

Start-here.pdf and Kit-map.pdf
where to begin: one page, and a kit map of 3 pages with a path for four weeks
The-30-Minute-One-to-One.pdf
35 pages: the four-block agenda, how to open the conversation, 12 development scenarios (9 by deal stage and 3 by work habits)
Question-cards-A6.pdf
28 cards on 7 sheets to print
Worksheets.pdf and Fillable-worksheets.pdf
6 pages each: a pre-meeting brief, the meeting sheet, the Development Map and a monthly summary
Filled-example.pdf
4 pages, one fictional meeting from start to finish
Meeting-notes-and-recap-template.docx
Word: invitation, notes during the meeting, recap message to the salesperson
Meeting-log.xlsx
a log of meetings and agreements, with the people you have not met for more than 10 days highlighted
Question-library.xlsx
120 questions by skill and deal stage

ZIP 1.2 MB, English; the spreadsheets use Excel 2016 functions. Pages are A4; on US Letter, print with “fit to page”.

How it works

A 30-minute one-to-one agenda

How it works. Twenty-five minutes of conversation in four blocks, and five minutes for notes right after. The agreement is read aloud in the “Wrap-up” block.

Five fields of an agreement

What is left after the meeting. A record you can check at the next meeting.

Questions

Questions and answers

How do I run the first one-to-one with a salesperson?

Book 30 minutes, fill in a short brief in advance, go through the four blocks of the agenda. Finish with one written agreement: what, who, by when and how we will know it is done. The guide has phrases to open the conversation.

What do you talk about in a one-to-one besides numbers?

About a specific deal, the skill behind it, and a practice task until the next meeting. Twelve scenarios link what you noticed in the salesperson’s work to questions and a task.

How often should I meet each salesperson?

On a schedule you can keep: weekly or every two weeks. The log highlights the people you have not met for more than 10 days.

What do I write down after the meeting?

The agreement in five fields: what, who, by when, how we will know it is done and the check-in point. And a short recap message to the salesperson: the Word file has a template.

Do I need to print the cards?

No. The 28 cards are handy to keep on the desk during the meeting, but the same 120 questions are in the spreadsheet.

Where are the notes about people kept?

In your own Excel and Word files. We do not store them. Write only what you would be ready to show the person: whether they have a right to see the notes depends on the rules of your country and company.

How do I get the kit?

Click “Buy for $49” and pay on the Gumroad page. After payment is confirmed, we’ll email your download link. Your materials will also appear in your account. Questions: info@headofsales.me.

Author

Who made this

Author: Natalia Kotovich. About the author: nataliakotovich.com.
Updated October 13, 2026.

Route

Before and after this

Before thisFirst 30 Days Sales Manager Operating Kit Before thisSalesperson Diagnostic After thisSales Manager Decisions After thisSales Audit

Every term on this page is explained in the sales manager’s glossary, the same one for all our materials. Free: the Sales Manager’s Map, the conversation with the owner, the first 30 days checklist, the guides “How to run a sales meeting” and “Sales funnel stages”.

Thirty minutes, one topic and one written agreement with each salesperson.

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