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Managing difficult salespeople: From a troublemaker to a sales superstar

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We’ve all met them at some point in our careers: people with complicated or difficult personalities who, at the same time, are extremely promising salespeople, despite all their issues. It doesn’t take a manager to spot them, but it does take a damn good manager to get them under control while also seizing their potential.

It’s puzzling how often it occurs that the most annoying person in the room turns out to also be the best salesperson. The talent often comes hand-in-hand with an oversized ego, a not very team-friendly tunnel vision, self-centeredness or the inclination to being a lone wolf. And while it works for them, it creates tension in the team.

What can you do to keep your team working in alignment, without letting the difficult ones disrupt the atmosphere too much? Here are a few tips.


Before proceeding to any of the following steps, start with yourself and your own management techniques. Often employees end up out of bounds because of poor management, and you need to be honest with yourself in this initial phase.

Have there been any signs of bad or insufficient management with other people as well?

Have you ever purposefully avoided dealing with issues of this particular person due to their good performance?

Are you always being 100% clear about communicating your standards and expectations?

It’s easy to spot the mistakes of others, but it’s harder to track them back to our own errors. But be fair, and be a good leader, and make the assessment of your own management mishaps before you start pointing fingers.


Alright. So you’ve analyzed your management approach to this person to the moon and back and you came to the “it’s not me, it’s you” conclusion. It’s time to schedule a face-to-face meeting and talk it out. It depends on the severity of the case and also on your management style whether you decide to confront the issue head-on or to work through to it by asking some carefully aimed questions regarding the issues you’re having with them.

Either way, always make sure to know exactly what it is that makes your salesperson so difficult to work it, for you or for the team. You’ll save you both a lot of time and embarrassment. Most likely they know they are difficult and I believe that comes from poor managers or partners before. You have a tough challenge but time, patience and accountability are on your side.


If the personal talk didn’t work out — and I’ve seen cases where it didn’t in the slightest — you’ve always got the option of getting HR involved (bad idea). It’s not the most pleasant thing to do to someone, but people can be difficult, and if it gets too much and starts having negative side-effects on teamwork or the atmosphere in the workplace, it needs to be addressed and dealt with at all costs. Besides, that’s what HR is there for, anyway.

The last resort

Even mind-blowing results stop paying off if they cost you too much time and energy. It’s up to you to distinguish the ones who are worth “saving” from the ones you’ll be better off without. You tried all you could and the person is still not responding to your impulses? It may be time to part ways.