#23 Dealing with Difficult People

Two knights facing each other on a chessboard

There’s no such thing as a difficult person.

I know you probably don’t believe that statement. But by the time you finish this lesson, I suggest you start believing it.

Now, I’m sure you can give me plenty of examples of ‘difficult’ people you’ve encountered in your career, complete with descriptions of their outrageous behaviour.

And I’m sure you can reel off a list of all the different ways you (and others) have tried to persuade them to change — arguments and appeals that no reasonable person could fail to respond to.

But the trouble is, there’s no such thing as a reasonable person, any more than a difficult person. People are much more complex than the labels we stick on them. Someone who is ‘difficult’ to you may be a beloved husband or wife, brother or sister, friend or teacher to someone else.

But that’s not the main reason I advise you to stop applying the ‘difficult person’ label to other people. The real reason is because it limits your choices and makes you less influential.

Think about it: if someone is just ‘difficult’, there’s nothing you can do about it, is there? You can’t change their personality. Whatever you do, they’re going to be difficult. Whatever you say, they’re going to be difficult. So you might as well give up, right?

But supposing you looked at them a different way. Supposing you stopped putting labels on them and simply accepted that they just don’t want to do things your way. And the reason they don’t want to do things your way is that — as far as they can see — there’s nothing in it for them them to change.

The nice thing about taking this approach is that you don’t have to rebuild their personality, just influence their behaviour. And to influence their behaviour, you need to show them what’s in it for them to do something differently.

Here’s a four-step process to help you do just that:

  1. Stop thinking of them as ‘difficult’.
  2. Ask yourself ‘What do I want them to do differently?’
  3. Ask yourself ‘What’s in it for them to do what I want?’
  4. Tell them exactly what you want them to do differently, including what’s in it for them.

The rest of this lesson will walk you through this process. But before we get into that, I want to distinguish this kind of influence from authority.

You may have the authority to compel them to do things differently against their will. Or you may be able to borrow someone else’s authority — by appealing to your boss, the police, the courts etc. This is generally a last resort, since they will resent you for it, but sometimes you have to resort to the last resort.

For the purpose of this lesson however, I’m assuming you don’t have that kind of authority. The odds may even be stacked heavily against you, because they have more authority than you do. So you have to rely on influence — and get creative about it.

1. Stop thinking of them as ‘difficult’

If you really want to use the word ‘difficult’, tell yourself you’re dealing with a difficult situation, not a difficult person.

And it doesn’t make any difference what other people think of this person. Even if everyone you know agrees that this person is difficult (or lazy, or selfish, or rude, or whatever), it’s still no reason to you to use the label. Your goal is to become an exceptional influencer, not to follow the crowd.

2. Ask yourself ‘What do I want them to do differently?’

Another problem with the ‘difficult person’ label is that it’s easy to lose focus of what you want the other person to do.

As a coach, I’ve come across plenty of situations where people were fighting over labels and calling each other names, instead of requesting specific actions. Chances are you’ll never get Steve to admit he’s being difficult, but he may consider sticking to his own parking space, or giving you more than a day’s notice of the next deadline.

When making requests, be as specific as possible about the desired action. Vague requests are open to misinterpretation, and can even sound threatening.

For example:

You should show me more respect.

This is almost guaranteed not to get you what you want. For starters, the word ‘should’ comes across as aggressive. And there are a million ways to ‘show respect’, so even if the other person tries to do what you want, their idea of showing respect may be very different to yours.

Instead, try something like this:

When we’re presenting to the client, please don’t interrupt or contradict me. If you disagree, talk to me about it afterwards.

This gives you a higher chance of success, because you’re being very specific about the context, the precise behaviour you don’t want, and the behaviour you want instead.

Here’s another example of What Not to Say:

We need to talk.

This statement can be frankly terrifying! On hearing these words, the other person’s mind is likely to be filled with all kinds of possible problems and grievances. They are instantly on the defensive. If they agree to talk to you, they may well feel they are letting themselves in for a long, drawn out argument.

Here’s an alternative:

There are a couple of issues that like to talk to you about from today’s presentation. Nothing major, but it would be good to agree some new options before next week’s meeting. Are you free to chat over coffee in the next couple of days?

This is a lot less scary, because you’ve made it clear there are just two items for discussion, and you don’t see either of them as being a huge problem. You’re also using positive language about agreement and options. And the invitation to chat over coffee is friendly and suggests it won’t be a long meeting.

Remember, you don’t need to rebuild their personality, just influence their behaviour. The more specific you are about the behaviour you want, the easier it is to reach agreement.

3. Ask yourself ‘What’s in it for them to do what I want?’

This is the million dollar question, and the hardest to answer. But if you can find a good answer, it’s amazing how amenable people can be to your requests.

The big challenge here is to stop looking at their behaviour from the outside, and to put yourself in their shoes for a moment. It’s helpful to assume that everything they do and say makes complete sense — including the fact that they have different priorities to you. Your job is to work out what their real priorities are. A bit like being a psychological detective.

Suppose you have a client who keeps interrupting you with phone calls and e-mails while you’re trying to work on their project. You’ve explained how inconvenient it is, and even tried ignoring them for periods, but it hasn’t made any difference. Reflecting on the situation after work one day, it occurs to you that the client is anxious about how he will look when he presents your work to his boss, and he’s really looking for reassurance.

So you initiate a meeting where you provide a detailed report on progress so far, and ask if they have any concerns about the upcoming presentation. You also explain that you are keen to deliver outstanding work in good time for the presentation, so you need as much uninterrupted time as possible. You propose a phone call at 5pm every day in the run-up to the presentation, where the two of you can deal with all the pressing issues that have arisen during the day.

The key point to bear in mind here is that appeals based on what you want (fewer interruptions) are unlikely to work. By focusing on what the other person wants (reassurance), you have a much better chance of success. You can ask for exactly the same behaviour, but frame it differently. (Remember reframing, from Lesson 5?)

4. Ask them to change by appealing to their self-interest

This is where you put it all together, telling them exactly what you want them to do, and what’s in it for them (WIIFT).

For example:

Hi John, I’m getting the message from your phone calls and emails that I’m not keeping you sufficiently in the loop about the project’s progress [concern]. I realise how important it is for you to be up to speed on the latest developments [WIIFT], so I’d like to suggest we do a phone call at 5pm each day, where I can update you and respond to any issues that have come up during the day [specific request].

I know you want the project to move forward as quickly as possible [WIIFT], so if it’s OK with you I’ll respond to any queries during the phone call at the end of the day [specific promise]. That way I get the work done for you faster, and we’ll also be more efficient dealing with all the queries in one go [WIIFT].

If you’re dealing with a particularly difficult person (ahem) situation, you may also want to mention the negative consequences if they don’t do as you ask:

I understand how concerned you are to get a quick response and to get problems fixed ASAP [concern]. But the trouble with trying to respond to every query instantly is that it breaks my concentration – which as you know, is essential for providing you with my best work [negative consequence]. It also means we’re less efficient at dealing with queries if we keep stopping and starting to do them one-by-one [negative consequence].

Net net: If we carry on as we are, the job will to take longer, cost you more, and could have a negative impact on quality [negative consequences].

Once you’ve highlighted the pitfalls in this way, end on a positive note by going back to your desired alternative and restating the benefits of doing it your way:

So as I say, if we can get into the habit of doing a regular meeting at 5pm each day [specific request], I’ll commit to dealing with all your queries during that conversation [specific promise], so that you leave the office at the end of the day knowing you’re fully up-to-date and I’m dealing with any concerns you have [WIIFT].

Plus I’ll be more focused and efficient during the day, meaning you’ll get better work, more quickly – and that will keep costs down as well [WIIFT].


Nothing works with everyone. But labeling people as ‘difficult’ is pretty well guaranteed not to work. So next time you’re tempted to… take a deep breath, count to 10, and try out this four-step process as a way of applying your creativity to the problem of getting the outcome you want.

Tune in Next Time …

… When we’ll look at how to become a captivating public speaker.


This is part 23 of The Creative Pathfinder, an in-depth free course about how to succeed as a creative professional. If you landed on this page from elsewhere, you can learn more about the course and sign up here.