How to Have Difficult Conversations at Work and Win

Hi, I’m Nicola from The People Mentor, and in today’s podcast, I want to talk about how to have difficult conversations and win. 

Now, by winning, I mean how to have the conversation successfully. It’s not about winning. 

I’ve seen it so many times. Managers go into difficult conversations and their goal is to try and make someone see their point of view. 

But trying to ‘win’ someone around to your way of thinking will only make the conversation more difficult and damage trust between you. 

So, how can you avoid giving the impression that your only goal is to make the other person change their mind?

You can approach the conversation with an ‘and’ stance. 

That means you accept that both you and the other person can be right simultaneously, rather than thinking that you are right and they are wrong. 

This approach is far more likely to get you to a place where you and the other person can agree on a way forward that you’re both happy with. 

So apart from not approaching at difficult conversation with the intention of ‘winning’ how else can you make these types of conversations a success?

Before we delve into my tips, let’s think about what a difficult conversation is at its core. 

At its simplest, it’s something awkward and uncomfortable that we find difficult to discuss for various reasons. 

We don’t like confrontation. We want people to like us. We worry about how the person will react. 

Then there’s the fact that a difficult conversation almost always has the potential to have a personal impact on the person receiving the news or feedback. This means there’s a high chance that the conversation will provoke strong emotions. 

Difficult conversations you may have encountered include:

Rejecting a team member’s idea

Having to address poor performance

Resolving a conflict between team members

Terminating someone’s employment

Giving negative feedback

Speaking to someone about a highly personal issue like body odour 

None of these are conversations that managers relish, and I remember the dread I had when I had similar conversations. 

Of course, that’s just one example of a difficult conversation. While every situation is different, I’ve picked up some tips on how to have a difficult conversation and win throughout my time as a leader. 

The first tip is to be prepared. Don’t underestimate the importance of this. 

Once you know you need to have a difficult conversation, reflect on the purpose of it. 

What do you want to achieve, and what will success look like?

How can you approach it to improve your chances of a positive outcome?

Write down important points you need to mention, and make sure that you are going to be stating facts, not your opinion. 

Once you are clear on your objectives and what you want to say, invite the other person to have a conversation with you at a time that suits you both and in a place where you won’t be disturbed. 

When you have the actual conversation, make sure that you give some context. 

Don’t be vague. Tell them exactly why the conversation is needed and what you’ve observed. 

Hopefully, that will put you both on the same page from the beginning. 

The last thing you want is for someone to sit in front of you with no clue about what’s happening.

Say that they have something going on at home, for example, and it’s affected their performance at work. They may have been too distracted to notice how bad the situation has got, so it’s your job to point out the facts but to do it tactfully and sensitively. 

Throughout the conversation, make sure you listen. Listening to the other person is probably more valuable than what you say.

I mention listening a lot when discussing how to have difficult conversations and win because it’s so important. 

If you are only concerned with getting through your list of what you need to talk about and you’re waiting for the other person to stop speaking so you can jump in again, take a pause. 

Are you hearing what the other person is saying enough so you can understand their take on things?

It’s important to take a curious approach and speak honestly and respectfully. This is far more likely to get a positive response from the other person. 

It all comes down to understanding how the other person sees things; it’s not about who is right or wrong. 

A successful outcome to a difficult conversation is not about you ‘winning.’ Even if you reach a point where you can understand where each other is coming from, but you still don’t agree, it’s still a positive result. 

This is a good starting point for finding some common ground instead of getting stuck in a stalemate or having someone storm off. 

To find that common ground, consider what you share with the other person. Do you have the same values and goals? Do you both want the same thing but have different approaches?

That’s fine; it’s a good basis for finding a compromise and a solution that works for both of you. 

One mistake many managers make is going into a difficult conversation with the mindset that ‘I’m the expert here. I have the experience. So I’m going to come out on top, like it or not.’

This is very counterproductive. 

Once you think you know it all, it closes your mind to possible solutions to the issue you’re dealing with. 

That’s why I think a far better way to approach difficult conversations is by adopting a ‘beginner’s mind.’ 

That means letting go of the idea that you know it all because none of us do. 

It means taking a step back, looking at the facts without judgment, and being present enough to see what is going on. 

So, how can you adopt a beginner’s mind in a difficult conversation?

First, let go of the idea that you’re an expert. 

Next, forget about having to ‘win’ the conversation. Remember, it’s not about winning; it’s about finding common ground so you and the other person can find a way to move forward. 

Another important thing is not being afraid to admit that you don’t know if the other person asks you a tough question that you can’t answer. 

There are no ‘shoulds’- your mind will be screaming at you, saying, ‘I should know the answer to that’ or ‘I should be dealing with this better,’ but try to let it go. Be present, and let the conversation unfold. 

Lastly, focus on questions, not answers. Be curious, and listen to understand. 

Once you let go of the idea that you are the expert in the conversation, you can also let go of the need to drive the conversation to exactly where you want it. 

That can be hard to do, as we all want to ‘fix’ things and find a solution, but it’s important to keep an open mind when you go into a difficult conversation. 

Sometimes, if you’re only focused on reaching the end goal you’ve already decided on, you can miss out on the chance to look at things differently and come up with a solution you might never have thought of. 

Another important thing to do if you want to have difficult conversations and win is to think about what you’ll do if it becomes obvious that the conversation isn’t going well. 

If that’s the case, sometimes it can be better to press pause and revisit the conversation later. When both parties have had the chance to regroup, it can mean there’s a better chance of a calmer, more level-headed conversation. 

If the conversation has gone well, you and the other person need to think about how you work together to improve things going forward. 

It’s important, too, for both of you to be able to let things go. 

Treat your action plan to resolve things as part of you both ‘clearing the air’ and resuming your working relationship on a better footing. 

Do you need help mastering those difficult conversations?

Difficult conversations can bring up a lot of emotions in everyone. They can trigger bad memories of past issues, making you feel vulnerable and out of your depth. 

Of the questions I get asked about management, how to have a difficult conversation is probably the most common. 

So that spurred me on to develop and introduce my ‘How to make difficult conversations easier in the workplace’ journal for managers. 

Much more than a journal, it’s a guide to understanding yourself and your team members better, so you can plan those difficult conversations and feel more confident when you have them. 

There’s an absolute wealth of information in there that will get you thinking, and by the time you finish this journal, you will understand yourself a lot more. 

Pop along to Amazon and get your copy, and watch your confidence with difficult conversations soar! 

I hope you enjoyed today’s podcast; make sure you tune in for the next episode of the series to get your dose of management and leadership wisdom.

This is The People Mentor signing off.  

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