Before You Call Someone “Difficult”: Ask Yourself These 5 Questions First

Before You Respond — Thinking on Purpose. A woman listening thoughtfully to a man across a table.

Thinking on Purpose — Practical self-coaching with Anna

If you’re wondering how to handle difficult people, these five questions can help you clarify the problem and consider how to respond.

When you hear “difficult person,” is there someone who immediately comes to mind?

Most of us have at least one. It may be a colleague who irritates you within five minutes, a manager who seems impossible to please, a friend you constantly misunderstand, or your partner, where the same argument keeps coming back.

And sometimes, yes, that person really is difficult for you.

But “this person is difficult” may describe your experience without telling you whether the problem is worth your energy, what exactly is going wrong, or what you could do next.

So before you spend another hour thinking about this person, here are five coaching questions to ask yourself.

1. “I find this person difficult. So what?”

Yes, really. Does this actually matter to you? What is their behavior affecting — your work, an important relationship, your ability to get something done? Or are you simply irritated by somebody you hardly need to interact with?

Sometimes the problem genuinely deserves your attention. But sometimes the most useful conclusion is: actually, this is not important enough for me to keep giving it so much energy. Not every irritating person needs to become a problem you have to solve.

2. “What exactly do they do that makes it difficult for me?”

Now translate “difficult” into specific behavior. “She is controlling.” “He is arrogant.” “My boss is impossible.” What exactly does the person say or do?

Do they interrupt you, change plans without telling you, question every decision, criticize you in front of others, or refuse to discuss something important?

The more precisely you can describe what is happening, the more useful your thinking becomes.

“My boss is difficult” is a very large problem. “Whenever I present an idea in our management meeting, he starts pointing out what could go wrong before I have finished explaining it” is specific. And specific behavior gives you something you can actually work with.

3. “When exactly do they behave this way?”

And no, “always” is not an acceptable answer.

When does it happen? In meetings? When you disagree? When they are under pressure? When money is involved? In front of other people?

Identifying the context puts boundaries around the problem. Perhaps your colleague is not difficult in every interaction; perhaps this behavior appears mainly when the two of you disagree publicly. Perhaps your partner is not “never supportive”; perhaps the same pattern shows up around one particular topic.

A problem that seems to happen everywhere and all the time can feel enormous. Once you identify the context, it becomes much easier to examine.

4. “What would I want them to do instead?”

We are usually very good at knowing what we do not want. “I wish she wasn’t so controlling.” “I wish he wasn’t so insensitive.” Fine. What would you like instead? What specifically would that person need to say or do?

This can be especially useful in close relationships. You may say that your partner is not supportive enough. But what would “supportive” actually look like? Listening without immediately giving advice? Helping more with household chores? Backing you up in a particular situation?

If you are not clear yourself about what you want the other person to do differently, it is difficult to communicate that clearly to them. Before asking someone else to change, become clear about what you are actually asking for.

5. “How could I respond differently?”

The important word here is differently. Not simply: What should I do? Ask yourself what you could change from your usual response.

Perhaps they criticize you, you defend yourself, they push harder, you explain more, and within minutes you are back in the same argument. What happens if you interrupt that pattern? Could you ask a question instead of defending yourself, say less, be more direct, choose a different time, or set a clearer boundary?

You cannot control another person’s behavior, but you can change what you bring into the interaction. When one part of a familiar pattern changes, the other person has something different to respond to. That does not guarantee a different outcome, but it creates the possibility of one.

Responding differently also does not mean tolerating disrespect, misconduct, or behavior that requires a firm boundary or appropriate action. Sometimes the different response is precisely to become clearer and firmer.

Better Questions Before Better Answers

Good coaching questions are not there to tell you what to think. They help you look at a situation from an angle you may not have considered before.

So the next time you catch yourself thinking, “This person is so difficult,” you do not need to stop yourself from thinking it. Just do not stop there. You may discover that the problem is not worth your energy, become clearer about what the actual problem is, or notice one thing you can do differently next time.

One of the things I value in both coaching and NLP is learning to become more precise about a problem before deciding how to respond. The more clearly you can see what is happening, the more choices you usually have about what to do next.

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