HARD SITUATIONS

What a sales manager should do in a hard situation

“Sales Manager Decisions” is a 47-page book about 12 situations where a sales manager struggles to decide what to do. For example: the plan is behind, a customer wants a discount, a strong salesperson starts to slip. Each case has a tree of 3 to 6 questions that leads to one action. You write the decision in a journal and 30 days later you check what happened.

$79PDF, Word · English
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Free: Chapter 0 and Case 9 “You keep selling yourself”, plus a one-entry decision journal in Word. Get the free part. It arrives after you confirm your email.

  • English
  • updated October 13, 2026
A sheet with an ink decision tree, one path from the root highlighted in saffron

Who it is for

Who it is for

For the manager of a sales team of up to 10 people, especially in the first months, when you still tend to decide the way a salesperson would.

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 roleUp to a yearMore than a year

First month in the roleStart with Chapter 0, on how a manager’s decision differs from a salesperson’s, and with Case 9 “You keep selling yourself”.

Up to a yearYou have already met some of these situations. Write your decisions in the journal: after 30 days the entries show which ones worked and which to revisit.

More than a yearThe trees give you and your senior salespeople one shared way of thinking a problem through when you hand some decisions over. You can give them the tree cards.

The situations in the book are common to small sales teams in any industry and of any size.

What it does not do

  • it is not legal or HR advice: where a decision touches employment or competition rules, a box tells you what to check and with whom;
  • it does not replace one-to-ones or deal reviews: the book points to them where they are needed;
  • it does not decide for you: it gives an order of questions and an action you can check.

What is inside

What you get

  • Start-here.pdf and Case-map.pdf

    where to begin, and a one-page map from what is happening to the right case

  • Sales-Manager-Decisions.pdf

    47 pages: Chapter 0 “How a manager decides, not a salesperson” and 12 cases. The free part (Chapter 0 and Case 9) is a separate download (ZIP 425 KB).

  • Tree-cards.pdf

    12 tree cards on 4 sheets

  • Situation-review.pdf, a fillable version and an example

    3 pages each; the fillable version has 99 fields; the filled example is 2 pages

  • My-decision-journal.docx

    Word: the decision, the criterion, a check date 30 days out, and what happened

ZIP 1.2 MB, English.

12 situations

  • mid-month, and the plan is far behind
  • the owner keeps changing priorities
  • a large deal is at risk
  • a customer asks for a discount
  • a strong salesperson starts to slip
  • a new hire is not getting results
  • the team cannot keep up and you need to hire
  • conflict in the team
  • you keep selling yourself
  • the forecast keeps missing
  • a customer complains about a salesperson
  • someone asks for a raise or plans to leave

How it works

How it works

How a decision tree works

How a decision tree worksHard situationone of 12Question 1yesAction AQuestions 2–6narrow it downOne actionyou can checkCheck in 30daysdecision journalHow a decision tree worksHard situationone of 12Question 1yesAction AQuestions 2–6narrow it downOne actionyou can checkCheck in 30 daysdecision journal
How it works. Each of the 12 situations has three to six questions. The answers lead to one action, and 30 days later you check what happened.

12 situations in the book

12 situations in the book1Plan behindat mid-month2Owner changes priorities3Large deal at risk4Customer asks for a discount5Strong salesperson slips6New hirewithout results7Time to hire8Conflict in the team9You keep sellingyourself10Forecast keeps missing11Complaint abouta salesperson12Asks for a raise or leaves12 situations in the book1Plan behind at mid-month2Owner changes priorities3Large deal at risk4Customer asks for a discount5Strong salesperson slips6New hire without results7Time to hire8Conflict in the team9You keep selling yourself10Forecast keeps missing11Complaint about a salesperson12Asks for a raise or leaves
What people come with. Twelve situations that come up most often in the first months in the role.

Questions

Questions and answers

What should I do if the plan is behind by mid-month?

That is Case 1. The question tree separates the possible causes: too few deals, deals standing still, or deals that are too small. You end with one action, a criterion for “done” and a check date.

Should I give the customer the discount they ask for?

Case 4 covers when a discount makes sense, what to ask for in return and when to say no. The decision goes into the journal.

How do I stop selling myself now that I manage the team?

Case 9 “You keep selling yourself” covers which deals to hand over, to whom and by when, and how to check after 30 days what happened. It is part of the free sample.

Why keep a decision journal?

Every decision has a check date 30 days later. After three months, 10 to 20 entries show which situations repeat and which decisions worked.

What if my situation is not one of the twelve?

The Situation review sheet is a blank worksheet. You can use it for a case that is not in the book.

How do I get the book?

Click “Buy for $79” 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 about the files: info@headofsales.me.

Author

Who made this

Natalia Kotovich

Author: Natalia Kotovich. About the author: .
Updated .

Route

Before and after this

Before thisFirst 30 Days Sales Manager Operating KitAfter thisPipeline Review in 45 MinutesAfter thisSeven Weekly Numbers

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”.

Twelve hard situations, one action you can check for each.

Buy for $79