How to have a tricky conversation with your manager

How to have a tricky conversation with your manager

Posted byAlex Hepworth on

career growth

Everyone has a different relationship with their boss. Some are casual, while others are more formal. Maybe you go for drinks with your manager, see them on the weekend even, or perhaps your interactions are limited to stand ups and 1:1s.

But regardless of how you get on, it’s likely that some conversations will be more difficult to have.

In this blog, we’ll share the dos and don’ts for having a tricky conversation with your manager, and explain how you can get what you want.

Reasons why you might need to have a difficult conversation

There’s lots of different reasons you might need to have a tricky conversation with your manager. Here are just a few examples:

  • You want to ask for a pay rise
  • You’ve received disappointing or unfair feedback
  • You’re lacking career growth
  • You’re unhappy with the way you’re being managed
  • You’re unhappy with a teammate
  • You’ve decided to leave
  • You’ve made a mistake
  • You need more support
  • You’re burned out
  • Your boss is wrong.

Why you might be worried to have an honest conversation with your manager

70% of employees find it difficult to be honest with their boss

If you’re nervous to have a tricky conversation with your boss, you’re not alone. According to the Boss Barometer Survey, 70% of employees in the US find it difficult to be honest with their boss.

Here’s some of the reasons you might be worried about having that conversation:

  • You’re worried you might lose their respect
  • You might get emotional
  • Your boss might take it personally, and you don’t want to upset them
  • It might damage your relationship with your boss
  • You don't like conflict — let's face it, most people don’t!
  • You don’t want to rock the boat, or complain about someone else.

Benefits of having a difficult conversation

Yes, there are lots of reasons you might not want to have the conversation, but honesty matters. Often, difficult conversations are unavoidable, and the negatives of having them are far outweighed by the positives.

Here are some of the ways having a tough conversation can benefit you, your teammates and your company:

  • You’ll hopefully resolve the issue
  • You can develop a closer relationship with your manager, and be more open
  • You’ll gain respect
  • You might score a promotion or pay rise
  • You’ll feel happier
  • You’ll be more confident
  • You can help the company improve
  • You can help your teammates
  • You won’t build up resentment
  • You might avoid a bigger rift — it’s always best to nip things in the bud.

How to have a difficult conversation with your boss

Don’t avoid a difficult conversation when it’s necessary — avoiding a real issue will only make it a bigger problem. But take a step back and consider what you need from your boss, and how you can phrase your difficult conversation as a proposed solution. It’s far more likely to result in action.

So instead of;

‘I’m really struggling with my workload and want to talk to you about it.’


‘I’m really struggling with my workload and I’d like to discuss some of the ways I think we can work together to bring things under control.’

If you need to have a conversation with your boss, follow these steps.

Set a time to talk

Conversations like this are best planned in advance, and done in private. Carve out some dedicated time to talk, and don’t spring the problem on your boss. You want to feel confident you have their full attention.

Keep the invitation short and simple, elaborating briefly on the nature of the issue. If your manager wants to meet right away but you’re not ready, let them know that you’d like a little time to prepare your thoughts first.

Keep an open mind

It can feel excruciating waiting for the conversation to come around. Try your best not to build it up in your head, or project the possible outcomes — it’ll only make you feel upset or nervous. Remember, you’re having a conversation with another human being (yes, managers are people too). Everyone should want a happy outcome!

While I might have referred to this conversation as tricky and difficult (mostly to help you find my article in Google), it’s really important to shift your mindset. Try to reframe difficult as constructive; instead of having a problem, you’re finding a solution. Ultimately, this conversation is an opportunity to share your feelings and reach common ground with your boss.

Plan ahead

It’s OK to note down what you’d like to cover prior to the meeting, but don’t write out a full script. You might have an idea of how you’d like the conversation to go, but be flexible. Always have your facts ready.

It might be helpful to role-play how the conversation might go with a partner or friend, or even with yourself in the mirror.

And consider how your boss might react — try to see things from their perspective too.

Be clear

In the meeting itself, you want to speak as clearly and calmly as possible. Here’s how to do that:

  • Address the issue directly

Stay focused on the issue at hand, referring to your notes if you need to. Centre the conversation on you, use ‘I’ and ‘my’, and avoid drawing other people in unless you need to. Always be honest.

  • Use simple and direct language

Don’t tiptoe around the problem — this is your opportunity to share your views and, hopefully, find a resolution.

  • Keep your tone neutral

Don’t use accusatory language or raise your voice.

  • Stay calm

Even if your manager isn’t. Try to speak slowly, and remember to breathe!

  • Make eye contact

If you’re using notes, try not to bury yourself in them. Of course, it’s easier to keep eye contact when you’re meeting face to face, but try to do the same when you’re remote too (and always put the camera on).

  • It’s OK to cry

It’s totally normal to get emotional in situations like these. Prepare yourself with tissues, and if you do feel yourself wobbling, take a deep breath and slow down. You can always pause the meeting and come back later if you need to take a break.


Remember, it’s a dialogue, not a monologue — and it works both ways! So stay open and receptive, maintaining eye contact and removing distractions. That means phones on silent and off the table, and a private room.

If you don’t understand something, ask for clarification.

Avoid being defensive, and have some sympathy for your manager — it’s unlikely that they’ve had any specialist training, and it’s probably a difficult conversation for them too.

Reach a resolution

If you can, of course. A resolution might not come right away, and that’s OK. If you’ve managed to have an open and honest conversation with your manager, then that’s a great first step.

Of course, you need to come away with something. At the very least, you should have a clear idea of next steps, and any actions, goals and associated deadlines. Make sure these are noted down somewhere so you both have a record of them.

After the meeting, it’s important to take care of yourself. Tough conversations can be emotionally draining. Take some time out to calm down, take a walk, hug your dog.

And remember, it takes courage to speak out — you should feel really proud of yourself, whatever the outcome.

How to have a difficult conversation with your manager dos and don’ts

What to do if the conversation doesn’t go to plan

Sometimes, a conversation won’t go the way that you were hoping. But don’t be disheartened. You’ve taken the first step, and can hopefully build from there.

If you feel like the lines of communication with your boss have entirely closed though, or you’re uncomfortable talking to them for any reason, you can speak to someone else, like another manager or HR representative.

If you’re not sure what to do about a problem at work, Citizens Advice can help.

Picture of Alex Hepworth

Posted by Alex Hepworth

Content Writer at Progression

Alex on LinkedIn

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