The best salespeople are rarely the best sales coaches. The skills that make someone a top seller, thinking fast and winning people over, often get in the way of coaching. Managers who hand out answers create dependence where they were hoping to create growth. Strong coaches ask “What do you think?” when coaching sales.
Is the best salesperson also a good sales manager?
There’s a stubborn myth in sales: that the best salespeople make the best coaches. That’s wrong. The skills that make you a top seller, switching gears quickly, persuading, driving towards a result, aren’t necessarily the ones that make you an effective coach. Sometimes they actively get in the way.
I remember a conversation with an experienced salesperson, let’s call him Peter. Peter was a natural. He knew every trick, every way to handle an objection, every closing technique. His team looked up to him and he was proud of his reputation as the man who could rescue any deal. Then he was promoted to sales manager and hit a wall. His team was underperforming, the atmosphere was passive, and he was frustrated. “I give them all the tools, all the tips, and they don’t pick it up,” he told me. “It’s as if they’re waiting for me to do it for them.”
That was exactly the problem. Peter was an excellent salesperson and a mediocre coach. He told his team what to do, where he could have helped them work out how to do it themselves. And that’s the essential difference between managing and coaching.
The trap of the answer manager
It’s tempting as a manager to supply the solutions. You have the experience, you have the knowledge, and you want to help your team. But every time you give an answer instead of asking a question, you’re missing a chance. A chance to let your team grow, to let them take ownership, and to teach them to think like entrepreneurs rather than executors.
Take Lisa, one of the salespeople in Peter’s team. She was struggling with a complex deal at a large customer. Rather than asking her how she read the situation, or what steps she would take, Peter stepped in: “Do this, say that, offer this discount.” Lisa did as she was told, the deal went through, and Peter was satisfied. But what did Lisa learn? That when she got stuck, she should walk over to Peter for the answer.
3 months later Lisa ran into a similar situation. Peter stepped in again. And again Lisa learned nothing. Until one day she left for a competitor, because she wasn’t developing any more. “I felt like a puppet,” she told a colleague afterwards. “As if my opinion didn’t matter.”
That’s the paradox of the answer manager: in the short term it looks efficient, and in the long term you create dependence, demotivation and a lack of initiative. In a world where the sales environment keeps getting more complex, with longer cycles, more stakeholders and higher expectations from customers, that’s a recipe for standing still.
The power of a coaching approach
trong managers do it differently. They start with questions. “What do you think?” instead of “Do this.” “How would you tackle this?” instead of “Here’s how it’s done.” That’s more than a matter of style. It’s a fundamentally different approach to leadership and to coaching sales.
I saw this at a client in the financial sector. Their sales manager, Mark, had a team struggling with low conversion rates. Rather than telling his team how to sell better, he started weekly coaching conversations in which he challenged his salespeople to think for themselves. “What was the biggest challenge in this deal?” “What would you do differently next time?” “How could you map the customer’s needs better?”
At first it felt awkward. Some salespeople were used to direct instructions and didn’t know what to do with all those questions. After a few weeks something started to shift. The team came up with their own ideas, shared what worked with each other, and took more responsibility for their own deals. And the results? Within 6 months the conversion rate rose by 25%, and staff turnover dropped to almost nothing.
That’s the power of coaching: it’s about drawing out potential as much as passing on knowledge. And that potential is usually already in your team. You only have to let it come out.
Why it works: the science behind coaching
There’s a reason this approach is so effective. Research in psychology and neuroscience shows that people remember and apply information better when they work it out themselves, rather than being told. The phenomenon, known as the self-generation effect, shows that actively thinking through a problem leads to deeper processing and better retention.
A coaching approach also feeds intrinsic motivation, the urge to do something because you find it worth doing yourself, rather than because you’re rewarded for it or because someone tells you to. And intrinsic motivation is the strongest predictor of long-term performance and satisfaction.
Coaching this way also builds a culture of psychological safety. When people know they’re allowed to make mistakes and that their ideas count, they dare to take more risk and think outside the well-worn path. In sales, where creativity and adaptability matter, that’s worth its weight in gold.
How do you start?
If you want to move from managing to coaching as a sales manager, start small. Pick one conversation a week in which you deliberately hold back the answers and ask questions instead. Ask one of your team members to prepare a short case about a project where they feel stuck. Then open it up to the whole team:
– “What do you think is the heart of this problem?”
– “How would you tackle it yourself?”
– “What have you already tried, and what did you learn from it?”
And be patient. It takes time to teach a team to think for itself, especially if they’re used to a directive style. It’s more than worth the effort. In the long term you build a team that performs better, stays motivated, keeps developing and is ready for what comes next.
At Uphill Sales we train sales managers in this coaching approach. We do it because the best answers are usually already in their team. And that’s exactly where real growth starts.
Want to try this with your own team?
Switching from giving answers to asking questions takes practice, and it feels awkward for the first few weeks. Your team will wait for you to break the silence, and you’ll want to. That’s the part I help sales managers through.
Have a look at what Training and coaching, or get in touch and tell me where your team is getting stuck.
