10 ways to successfully navigate a difficult conversation with your boss

Nobody relishes the challenge of having a ‘difficult conversation’ in a professional or personal sense, however, these can unfortunately occur frequently in the workplace; the most challenging of these being the need to stand up to your boss.

The trouble with ‘difficult conversations’ is that it’s hard to have them when we’re feeling upset – if we do, the chances are we will blurt out our emotions and say things we might later regret.

And it’s not just our boss that we have these difficult conversations with in times of pressure. Entrepreneurs often have to stand up to their backers and work life can be extra stressful for start-ups due to tight budgets and strict targets. Young businesses often don’t have established HR practices in place, which can lead to awkward conversations. Plus, there’s our personal life, which can impact our mood too!

Now, this is all further compounded by the fact that many of these conversations need to be in an unfamiliar environment such as video call, Zoom and Skype sessions!

So how can you say, what you really want to convey, in a way that your boss will really listen to you, without flying off the handle? And, how can you turn these situations into a positive opportunity?

Here are my top ten suggestions about how to have a difficult conversation:

1.    First, be practical   

Keeping the emotion out of it for now and think about what practical steps would make the current situation better. Letting off steam can make you feel better but it rarely helps the situation. Practical solutions usually work better. Once you’ve come up with a plan, then you have to say it in a way that your boss will want to hear it.

2.    Make it sound like their idea

Don’t put forward your solution right away – make some suggestions that will lead your boss into thinking that he has come up with (your) solution, all on their own!

3. Flatter bullies

If your boss is a bully, try flattery. It always works. “Could I pick your brains?” or “Could I ask your advice, as this is your area of expertise?”

4.    Give both sides of the argument

To sound reasonable in a difficult conversation, try to see how things might look or feel from your boss’s side. Then remember to give both sides of the argument to show that you understand how they might be feeling.

5.    Chose the right time to speak out.

All your hard work will have been wasted if you chose the wrong moment. Chose a time when they are not hassled and have to time to listen to you.

6. Stay calm

When you’re ready to have the ‘difficult conversation’ try not to look or sound angry – keep your voice and face relaxed. To help, try this breathing exercise beforehand: breathe in for a count of three and then out for a count of three. Repeat this three times. It lowers your heart rate and really helps with centering yourself.

7. Don’t give mixed messages.

As you speak, try not to give mixed messages. Smiling when giving bad news, for example, will not make the news any easier to hear. Mixed messages usually make things worse!

8. Speak slowly

When we get upset we often speed up our speech, which can make us look out of control. We want to look and sound strong, so slow down.

9. Don’t justify

Once you’ve said your piece, stop. When we get upset, we often repeat our argument to make it more forceful. But has the opposite effect. Say to once and then stop talking.

10. Listen

Once you’ve finished, listen to the reply. Nerves and anger can make us stop listening. I’ve seen people repeat their argument even after the other person has agreed to their conditions. Listen and remember to thank them if they’ve taken what you’ve said on board.

By learning to have these difficult conversations in a calm, practical manner you will show your boss that you are someone with clear boundaries, who is strong and reasonable – which can only be a good thing.

I wish you the very best of luck!


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