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Dealing with Difficult People

I once ran a business training with a team of on-the-road sales people. They were great – bright, enthusiastic, professional and likeable. We had a lot of fun and got a lot of work done. Almost inevitably, one of their requests was for help in ‘dealing with difficult people’. This one crops up in just about every training I run, it’s up there with ‘How do I find more time?’ and ‘How do I deliver negative feedback?’.

When I asked them what they meant, they described ‘the people at head office’, who sounded like they were on a mission to obstruct the sales team at every step – ‘bureaucratic’, ‘nit-picky’, and ‘difficult’ were some of the nicer words used. So we spent some time looking at ways to influence these people and minimise the interference.

Spot the grey area?

From the feedback I got in the post-seminar coaching sessions, the new options were helpful and they were able to spend less time arguing with administrators and more time improving their sales targets.

A few months later I was working with another group at the same place. They were great too. Not such high energy as the sales team, but genuinely good company and just as professional. Inevitably, they wanted ideas for ‘dealing with difficult people’. So I asked for details and they told me about a bunch of fly-by-night salespeople who didn’t understand the importance of ‘doing things properly’ and had to be reminded of basic administrative procedures. Apparently things had improved a bit recently, but there was a lot of history to be forgotten. And guess who they were talking about?

My first reaction was that this was a bizarre situation – two groups of perfectly nice people, all working hard to do the best job they could, yet with a completely distorted image of the other side. Yet on reflection, I could see how the misunderstandings had arisen. For a start, we look for different talents when recruiting sales and admin staff. And it looked as though there there was a basic incompatibility between some of the targets set for the sales force and the processes that the admin staff had to implement.

The more I thought about it, the more I realised I was in a privileged position. As an outside consultant I was meeting both groups for the first time and there was no conflict of interest between their needs and mine. So it was easy for me to appreciate the positive side of each of them. Which of course made it easier to help them find new options for working together.

So next time I found myself fuming at a ‘difficult’ person and getting caught up in an argument, it was a pretty humbling experience. Afterwards, I realised that it wasn’t the other person (or even me as a person) that was the problem – just a conflict of interest and a clash of communication styles. But at the time it just seemed as though the other party was being obstructive.

Now that I’m specialising in the creative industries, I see examples of this all the time. The obvious one is the distinction between ‘creatives’ and ‘suits’, but there can be a similar ‘us and them’ mentality between all kinds of different people – agency and client, management and junior staff, programmers and designers, directors and shareholders. Apart from the fact that dealing in stereotypes isn’t very creative, the inefficiencies are glaring. And when communication breaks down and things go wrong, no-one comes out of it looking good.

So what can we do? Here’s an approach I use with clients – and when I catch myself getting frustrated with someone ‘difficult’.

  1. Take the ‘difficult’ label off the person. Tell yourself you’re dealing with a difficult situation, not a difficult person.
  2. Ask yourself ‘What do I want them to do?’ – and be specific. Remember, you don’t need to rebuild their personality, just influence their behaviour.
  3. Now the tricky part – ask yourself ‘What’s in it for them to do what I want?’. If you can give them a good reason from their point of view, they will do it.
  4. Be firm but friendly. Draw a line under the past and focus on the future. Ask for a specific change in behaviour. Point out what they have to gain from changing, and what they have to lose by carrying on as they are.

Yes, I know it’s easier said than done. I’m still practising myself. These basic steps can take a lot of refining and adapting to fit the people involved. But time and again I’ve found this approach helpful in making ‘difficult’ people easier to deal with.

Let me know if this works for you. And I’d love to hear your own experiences and creative solutions.

Some details have been changed to maintain confidentiality.


  1. A good post. I like your 4 step approach, especially #3
    Now the tricky part – ask yourself ‘What’s in it for them to do what I want?’. If you can give them a good reason from their point of view, they will do it.

    Thats the cruncher!

  2. Yep, that’s the crunch – from their point of view, not from what I think is a good reason!