How to manage people who are hard to manage

Have you ever lost sleep at night because you’re having a difficult time at work with a member of staff?

It’s not uncommon.

I work with a lot of managers. And whether they are a first-time manager, or have years of experience, they all have one thing in common. They all tell me they have “a member of staff who is hard to manage”.

So, let me help you get things back on track with these five tips:

#1 Look at yourself first

Before I go any further, it’s important to flag up that no-one (well, certainly that I’ve ever worked with) deliberately goes to work to be difficult.

So, whilst it’s a bit of an antithesis to the blog title, you need to get away from binary good/bad thinking. The notion that someone “is difficult to manage” suggests that it’s nothing to do with you. It suggests that all the fault lays at the other person’s feet. That’s a lot of responsibility for them!

The responsibility for every relationship is 50/50. Therefore, it seems sensible to start with the one thing you have control of. You.

How do you handle one-to-one meetings with the person concerned? What do you do in team meetings? What’s the tone of your emails to them?

Be really honest with yourself.

One of the things I find when working with people in conflict is that a vicious circle has developed. The manager dreads any meeting with the person and this then colours their tone in any interaction. Shouty emails (who doesn’t love CAP LETTERS?), accusatory tone in meetings, not listening etc. The other person picking up on this responds in kind. And so, the vicious circle continues.

#2 Assess the root cause

This links to the first tip. Here, you need to be that curious four year-old. You know the one I mean. The one who constantly tugs on your arm, asking “Why?”

Pick two to three of the last negative interactions you had with the member of staff concerned. Ask yourself where in the interaction things went wrong. Try to pinpoint where things turned for the worse. And then ask yourself ‘why’?

It may be that you pick up the same theme across the interactions.

For example, the exchange might have been about budgets and when you’ve questioned (interrogated?) them, they’ve got defensive. The more you have a think about it, the more you think that the root cause is a lack of confidence around budget management.

The root cause could also be something completely unrelated to work. The person could have something terrible happening in their personal life that you’re not aware of and this is impacting their work and subsequently, their relationship with you.

In short, dig down to find out what’s going on. Don’t assume.

#3 Confront not confrontation

The word ‘confront’ seems to be a bit of a red flag to most managers HALO works with. So, let’s be clear. ‘Confronting’ is different from being ‘confrontational’.

When you confront, you are clear, non-judgemental and have 2-3 examples to back up what you are saying. You give space to the other person to process what you’ve said. You listen to what they have to say. You have a two-way conversation.

When it degenerates in to a confrontation, you reel off a whole load of indiscretions. You don’t pause for breath (mainly because you’re on a roll now). You don’t give the other person time to think, let alone respond until… the very end. In this instance, you’re likely to experience ‘fight or flight’ from the other person – they’ll either shut down in fear and go silent, or they’ll lash back.

Check out a previous post which will help you get it right.

#4 Put yourself in their shoes

There may have been a time in your career when you went through your own difficult patch with a manager. Try and remember how you felt.

How did things get resolved (assuming they did)? What did you do to help get things back on track? What did your manager do to sort things out?

Empathy and kindness are key to resolving conflict. As the person in the hierarchical position of power, it starts with you (see the first tip).

Don’t mistake this for being a pushover, though. This is the assumption that some of the managers we work with make. Namely that being kind and understanding = being a soft touch.

If you’re confronting the situation (tip number three) then you are most definitely not a pushover. However, by going in with some empathy you’ll ensure that you manage yourself and the situation a lot more effectively.

#5 Ask the other person what they think 

Yes. You can actually ask the other person outright what they think of the relationship.


In my experience, not enough managers do this. Yet, by asking the other person what they think can lead to important insights to help get things back on track.

It also relates back to the point we made in the first tip

The level of honesty with which they answer you, however, is dependent on the climate you’ve created for that conversation. People need to feel safe and that they can trust you not to react badly to what they say.

You can set the scene by saying, “I feel like our relationship is going through a tough time and I’d really like to know what you think so we can get things back on track. I promise to listen to what you have to say and not react badly. You just need to be constructive in your feedback.”

Conversely, if you’re not confident in having this conversation or things have got so bad then you can get a third party in to help. This might be a member of your HR team, or an external mediator.

I’ll end with this quote I came across. Whilst the author is unknown, I think it neatly sums up how to get a relationship with a member of staff back on track.


Did you find this post helpful? I’d love to know, so Tweet me, or drop me a note on LinkedIn. If you have any colleagues that you feel should read this, too, please share it with them. I’d really appreciate it.

I also have a monthly newsletter which is a compilation of blog posts, helpful research, and reviews of books and podcasts – all aimed at helping managers and leaders become more confident in handling a range of workplace issues. You can subscribe here -> SUBSCRIBE

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