Let the Number Set the Date
Work out what each person you pay returned in the last four weeks. Let that number decide whether they stay, change role or go.
By James Schramko · Updated October 2026
Every founder has one. A salesperson, an agency, a contractor, an editor, a long-serving team member. You know what they cost to the dollar. You have never written down what they return. The feeling about them is strong and the number is missing. So the feeling runs the decision, and it usually runs it late.
The fix is one question, asked on a date you set in advance. What did this person return in the last four weeks, against what I paid them? The answer sets the date. The feeling gets to decide how you deliver it.
The Certain Cost and the Uncertain Return
What a person costs you is the one sure number in your business. The salary lands every fortnight. The agency invoice lands on the first. The contractor's invoice lands whether or not anything happened. The other side is a hope until you measure it.
I've met owners who paid thousands a month, for years, to have a podcast produced. When I asked how many sales it had made, nobody could point to a single client it brought in. When I asked why they kept doing it, they agreed it was a good question. The podcast felt like something a business should have, so nobody checked.
Every one of these decisions works the same way. The cost is certain and already paid. The return is a guess. The guess lives on because nobody puts a date on checking it.
The Four-Week Question
Pick a window and ask it plainly. What did this person do for me in the last four weeks that I would pay for if I were buying it fresh today?
It happens quietly. The work moves away from the person and nobody notices. The invoice keeps arriving at the same size, and the invoice is the only part of the deal that reports itself.
When the answer is clear, have the conversation that week. A fair timeline works well. The person can help build what replaces them and leave with the relationship intact.
When the Number Says Keep
The question cuts both ways, which is what makes it a measurement. When the number says keep, give them more room and get out of their way.
If you only ask the question when you already want someone gone, you are using it to justify a feeling. Ask it on the same date for everyone you pay. Then it becomes a measurement.
Tracking Is the Job
A salesperson who doesn't track their deals stops you asking the question at all.
So make tracking an order. Every deal for this month and last, written down, by a set time. Tracking is the core function of a salesperson. It's non-negotiable. If you have to ask for it, you have already learned something about the return.
Two cautions from my time running dealerships. First, people optimise for what you measure. In Italy I watched drivers brake hard for every fixed camera, then speed up the moment they passed it. The camera created camera-friendly driving. If you measure calls, you get calls. Measure the money.
Second, don't believe a statistic you haven't checked yourself. Salesmen used to hide month-end deals in the top drawer, dated for next month, to game the volume bonus. The number the team reports is a starting point. The bank statement is the number.
What Comes After
What stops most owners asking is fear of what comes after.
My own team went from five to four to three this year. The work moved away from them as the systems took it over. There was nothing left to hand them that didn't come back to me for review. I paid the last one a few months, he left, and my wages bill dropped. I feel fantastic about it. I say that as someone who had never let anyone go in my whole time as an employer.
Self-Diagnostic
List everyone you pay monthly. Beside each name, write the cost. Beside the cost, write what they returned in the last four weeks, in money or in a result you can point to.
Where the return column is blank, that is your first conversation. Where it is a guess, set up tracking this week and ask again in four weeks. Where the return is clearly above the cost, write down what would let that person do more of it.
Then set the date. Put the next time you ask the question for everyone in the diary before you close this page.
Quick Reference
- The cost is certain and reports itself. The return is a hope until you write it down.
- Ask the four-week question about everyone you pay, on the same date, so it is a measurement and never a grudge.
- A hire whose number says keep gets more room. A hire whose number is blank gets tracking this week.
- Tracking is the core function of a salesperson. If you have to ask for it, the answer has started arriving.
- Measure the money, never the activity. People optimise for whatever you count.
- Check the reported number against the bank. The top drawer is real.
- Deliver the decision with care and a fair payout. Let the number pick the date. Let your values pick the words.
This playbook pairs with The Founder Bottleneck You Can't See From Inside, which finds the work that should leave you. Fast Filter Hiring fills the seat once the number says you need one.
Want the four-week question asked about everyone you pay, by someone with no stake in the answer? I do that with founders in Mentor.