How to Approach Having a Difficult Conversation with Someone

Most of us don’t enjoy difficult conversations. But when you’re a manager, chances are that you’re going to have to have difficult conversations at some point or another. A few common examples are:

  • Telling someone that they’re underperforming and need to improve.
  • Telling someone that they’re not getting the promotion or pay rise that they were expecting.
  • Letting someone go from their job.
  • Highlighting a behaviour that you can’t accept within your team.

It’s not easy and in my view, that’s how it should be. The anxiety and nervousness that we all get prior to having a conversation like the above is a good thing because it shows that you care about the person you’re speaking to. When you care about a person, then of course you don’t want to have a conversation that may hurt or upset them.

Of course, there is a line here. 

I’ve seen managers who care about upsetting someone so much that they avoid having difficult conversations altogether, or watering them down so much that the core message isn’t received. 

Your desire to not upset someone can’t be allowed to get in the way of doing the right thing for your team, organisation or individuals.

Having said that, I know how hard it can be to have difficult conversations and this is why it’s useful to have a solid plan and approach to them. It doesn’t remove your worries completely, but it will make the process easier and repeatable. Having a solid plan and approach also ensures fairness for the person you’re speaking to because you’re making sure that you deliver the right message in the right way.

Worst than not having a conversation at all is having a conversation that leaves the individual more confused than before, whilst not solving the problem.

So, let’s look at one way that you can structure a different conversation.

Be very, very clear on what you’re going to talk about

One sure fire way to not only make a situation worse, but also to do nothing for your own feelings of nervousness or anxiety, is to walk into a difficult conversation without preparing for it. 

Whilst it’s always best to deal with problems as quickly as possible, it’s also important to take some time to outline the key points of a conversation and know how you’ll go into it. 

One of the most effective ways to do this in my experience is to write the conversation in email or letter form first. Obviously, you’re not going to hit send! But if you imagine that you are going to, then write out what you’re going to say, this can be a great way of getting everything out of your head and onto paper.

From here, read through what you’ve written and pull out the key themes of what you’re going to say. These form the key points that you should try to cover. Obviously, you’re unlikely to remember and recite the entire email, so the goal here is to extract the key points and use these to guide the conversation.

Learn their story, exploring their perspective

Let’s imagine that you need to address some underperformance issues from a team member. Perhaps the quality of their work has dropped recently and you’re having to correct their work a lot more than usual.

You shouldn’t walk into the conversation with an assumption that you know what is causing these issues or even that the person is aware of the issues. No matter how obvious it may be to you or others that they are underperforming, they may not realise that things are that bad. Sure, they may be aware that something is different about work at the moment, but they may have no idea of the extent to which it’s concerning you.

Start the conversation with a short, but clear summary of the problem that you want to fix and then give them time and space to respond. Remember that this may be hitting them out of the blue a little, so they will be thinking on their feet a bit. So listen carefully to their perspective and try to understand their point of view on the problems.

If they don’t understand the problem, go further and give them more detail and examples. Then listen again and get their perspective.

Express your views and feelings with clarity, honesty and respect

Once you’ve laid out the problem, go further into why the problem you’ve highlighted is a problem, along with the consequences of that problem. For example, if you’re dealing with an underperformance issue, the consequences of that may be that your team doesn’t hit their goals for the quarter. Or if you work at an agency, the consequence may be that you deliver subpar work to a client who then fires your agency. 

Don’t underestimate the power of describing the consequences of their behaviours. In isolation, their behaviours may not feel like a big deal. For example, if they send over some work to a client with a couple of typos, it may not feel like a big issue. However, if this causes the client to question your quality of work and standards, it can have much bigger consequences in the long run. 

When expressing your views, it’s important to do so with clarity, honesty and respect. This is where your caring side as a person and manager is important because it can be turned into a positive part of this conversation. 

Address the situation together, given what you’ve learned, what’s next?

Once you’re both clear on the problem, the consequences, and shared both perspectives, you should move forward and focus on how the situation can be improved. 

Try to focus on clear action points and changes that can move them towards fixing the problem and be realistic about timelines for doing this. It’s ideal to fix the problem as quickly as possible, but this needs to be balanced against a timeline that gives them the best chance possible of being successful.

One approach that I’ve found effective here is to focus on the outcome that you’re looking for and be super clear on what this looks like. For example, if you’re asking someone to improve the quality of their work, show them what quality looks like. This is particuiarly important when the problem is subjective. 

Agree on actions, next steps and a timeline for checking back in on progress. Ask if they have any questions or anything else that they’d like to discuss. 

Do your part, but hold them accountable for their part too

Finally, it’s important to instil accountability for what happens next. As their manager, you’re accountable for getting the best out of them, but you can obviously only do so much. The rest is down to them.

One way to drive this accountability is to give them clear actions, a timeline for those actions and to stick to those timelines. It sounds too simple, but so many managers don’t drive accountability in this way. Often, they’re scared that if they check back in, they may hear something that they don’t want to hear and the problem may still be there. 

Ultimately, these conversations are never easy, nor should they be. But the principles above will help make it easier and ensure that you’re approaching conversations in the best way possible.

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