“What went wrong?”
That’s the question I debrief my team with after every customer engagement. It’s how we review what happened in the previous meeting, with the intention of improving the next.
This is what a small business owner shared with me a while back. It applies to sales managers, and salespeople, seeking to improve their lot, alike—the sales debrief.
He continued
“My team is still small. I have only three salespeople. But being a business owner, having been thrust into selling, I learnt the hard way. My experience, however, informs my training—and I find that the sales debrief after every meeting is proving to be a very effective way of orienting my sales team to how I would like them to sell while growing their sales muscle in the process.”
And he is right.
There is something powerful about reviewing a sales engagement while it is still fresh. What did the customer say? What did we say? What questions did we ask? What did we miss? Where did the conversation change? And, most importantly: “What went wrong?”
Not as an exercise in blame. As an exercise in learning.
It is also the answer to a question many business owners and leaders quietly ask: why salespeople don’t improve. The answer is rarely talent. It is the absence of structured reflection.
The CAD seller: when a sales manual isn’t enough
“We sell Computer Aided Design. I had recruited what I was told were pre-trained salespeople.
Unfortunately, three months in, my expectations that they would hit the ground running were dashed. They followed the Sales Manual I had developed, but as a rule book, not a guide. ‘Sent email, or called, and customer not responded’ became irritatingly common in their reports.’
“I had a good mind to fire them but opted to pay for their coaching instead. On advice from the Sales Coach himself, I opted to coach them myself. I started by letting them know that things cannot continue as they are—it’s not working.
Read: Get your salespeople off the path of least resistance
“Over the next 90 days, you will have the opportunity to learn how to sell more and improve your income significantly.
Month 1: You will shadow me as I sell.
Month 2: I will watch you sell and review what happened after every meeting, with pointers to improve on the next.
Month 3: I will expect you to be doing it yourself.”
Notice what he did. He didn’t simply tell his salespeople to “sell more.” He created a feedback loop.
Observe. Try. Review. Improve. Repeat.
That loop is the essence of how to coach salespeople effectively. Not with lectures, but with structured observation and sales debrief conversations.
Read: Fire that poor performing salesperson, but first…
When the ground shifts but the rep doesn’t : A sales debrief for Farouk, Maria and Kibet.
Now, here is a third example, and it may be the most instructive of all because it involves a seasoned rep who almost quit. The ground shifted but the rep didn’t.
Farouk: the leading rep whose star dimmed
Farouk was the leading sales rep at the Investment Bank he sold for. Over the last two years, his star steadily dimmed.
“I take the blame,” the CEO explained. “The problem was that I had assigned him my accounts—which, as founder, I had acquired. The last two years, he got new leads. Listening in on how he engaged with the new customers, I realized he knew how to maintain accounts, not grow them. I taught him how, and boosted his confidence—especially with the legacy accounts running out”
Maria: the HR consultant whom AI almost fired
“Maria expected to be fired and was already shopping for another job.
We run an HR Consultancy firm. For years, writing up basic contracts guaranteed steady cashflow. We would easily get three or four house-help contract requests per month, for example. That was until about 18 months ago, when they almost vanished overnight. Contracts was her docket.
With the rising awareness of AI, customers now write up their own contracts. I had assumed Maria would adapt to the new role—repositioning herself from writing contracts to advising on the complexities AI cannot handle. She hadn’t. She was still looking for dwindling prospects seeking contracts, while ostensibly advising. The market had moved. Maria hadn’t.
In her panic she started looking elsewhere. This revelation came out when, rather than asking her what she was doing wrong I listened in on her sales calls. We rebuilt her pitch around what AI cannot do: interpreting complex employment situations, advising on disputes, and designing bespoke contracts for unusual cases.
Within weeks, her pipeline was not just revived—it was aligned with where the market had gone.
Read: AI is not coming for your job—your poor performance is
Kibet: the leading rep who was still pitching like a monopoly
“When fuel with additives hit the market, we were the only manufacturers. Kibet was the leading salesperson for 12 months—until suddenly he wasn’t.
He knew the product inside out yet his close rate had been declining for three consecutive quarters. His manager tried everything—a negotiation workshop, tracking his activity more closely on the CRM and giving him easier leads. Nothing worked.
Finally, he stopped asking, “What are you doing wrong?” and started asking, “Walk me through your last five meetings. What happened?”
What emerged was revealing.
Kibet was pitching the same way yet customer was now spoilt for choice. We were no longer a ‘monopoly’ but Kibet was still pitching like one.”
Sales debrief: What went wrong?
“He was still using the same opener: “I wanted to follow up and see if you had any questions.” In a crowded market, that positioned him as a salesperson chasing a decision, not a partner helping a client.
Worse, he wasn’t asking discovery questions. He assumed he knew what customers needed. When they went quiet, he followed up with “Just checking in”—the weakest phrase in sales.
The manager didn’t fire him or send him to another workshop. He asked him to record his next three meetings and reviewed them with him.
What went wrong? He talked 80% of the time.
What went wrong? He never asked about the cost of inaction.
What went wrong? He ended calls without a clear next step.
Within 60 days, Kibet’s close rate doubled. Not because he learned a new trick, but because he and his manager made the sales debrief a habit.”
This is also where the sales review meeting earns its place. Not as a monthly interrogation of numbers, but as a weekly habit of reviewing real conversations. Numbers tell you what happened. The sales debrief tells you why.
Read: Manage people, not just numbers – targets are lazy management
Sales debrief: the lesson
The lesson across all these accounts is the same.
Sales manuals, training programs, and CRM tools are only as good as the reflection that follows real customer interactions. The question “What went wrong?” is not an accusation. It is a coaching tool. It forces specificity. It replaces vague feedback like “be more confident” with actionable insight like “you didn’t ask about budget until the third call.”
The goal isn’t to make every salesperson perfect. The goal is to make the next sales conversation better than the last one.
And that is ultimately how to improve sales—not by chasing new tactics, but by learning from the last conversation before it fades.
Whether you lead a team of three or thirty, build the sales debrief into your culture. After every meeting, ask the question.
Review what happened. Improve the next.
That is how sales muscle is built—one honest conversation at a time.
If you would like to have your sales team sell more, we can help. In order for us to do so we propose a free consultation meeting or a call. If in agreement please complete the form below and we will get in touch after receiving your details, none of which will be public. Thank you.
You may like to see our sales training programs
