Why your best salespeople underperform and what to do about it
May 06, 2026
Here's something I've seen happen in organisation after organisation: the same salesperson absolutely nails it with one sales manager, and completely falls apart with another. Same person. Different results.
That's not a talent problem. That's a management problem.
Too many organisations hire great people, hand them a laptop and a fuel card, point them at the door and say, "go sell." They set and forget. And then they're surprised when performance is inconsistent, culture is flat and turnover is high.
The good news? There's a better way.
And it's not complicated — it just requires intentionality.
After working with organisations across 25 countries, I've identified six building blocks that elite sales organisations consistently have in place. Not some of them. All of them.
1. The weekly team huddle
Thirty minutes, non-negotiable. The team gathers, shares what's working, fine-tunes messaging and works through live objections. It's the heartbeat of a high-performance sales culture — short, focused and impossible to skip.
2. The monthly deep-dive workshop
Two to three hours on one specific skill — better discovery questions, stronger proposal delivery, sharper objection handling. You don't build capability by scratching the surface once. You build it by going deeper, month after month, stacking skill on skill.
3. The quarterly bootcamp Half a day to a full day of intensive practice. Role plays, live drilling, new material. Think of it as preseason training — the team arrives to compete, not just to attend. It re-energises the group and prevents skill drift.
4. The annual conference and awards Your flagship event. You celebrate wins, recognise top performers publicly and set the vision for the year ahead. This isn't a vanity exercise — it builds identity, creates healthy competition and gives people something worth working towards. Think of it as your internal Olympics.
5. Incentive trips Done well, these are unforgettable. I remember receiving an envelope with cash on my first incentive trip as a sales rep — years later, I still remember it. The item is secondary. The recognition is everything. Tie these to the right behaviours and outcomes, not just revenue.
6. Regular one-on-one coaching Not a biannual performance review — an ongoing rhythm. The manager reviews calls, practises scenarios and invests genuine time in the individual. Great salespeople are often people-people. They want to feel valued, heard and supported. One conversation at a time is where individual excellence is built.
Here's the thing though. Having these six building blocks in place is a start — but it's not the whole picture. You also need strong onboarding (a structured 90-day plan, not a dump-and-run), a rolling feedback culture, a clear sales playbook that everyone speaks, visible recognition beyond commission checks, and performance data that tracks lead and lag indicators — not just activity metrics.
Success in sales isn't luck. It's architecture.
The organisations that thrive long-term are the ones that treat selling as a professional discipline — like law, medicine or engineering. They invest continuously, they measure what matters and they build a culture that attracts great people and keeps them.
If you're looking at your team right now and seeing inconsistency, high turnover or flat results — I'd love to have a conversation.
