Managing difficult conversations

Difficult conversations can be the elephant in the room. We know they need to happen, but we stall, we put them off, we hope things will change.

Truth is, if they’ve reached that point then they aren’t going to resolve themselves on their own.

Instead we need to tackle them head on, but with the right tact, preparation and support to ensure the result is one everyone feels comfortable with.

What is a difficult conversation?

ACAS describes a difficult conversation as one “where you have to manage emotions and information in a sensitive way”. The truth is that difficult conversations vary from person to person, what one person finds awkward won’t phase someone else. That’s what makes the conversations so tricky to manage.

Research has found that57% of people would do almost anything to avoid having a difficult conversation. That’s because typically difficult conversations are emotionally charged or require an element of vulnerability.

Most difficult conversations in the workplace centre on a few topics, poor performance, investigating complaints, managing team dynamics or dealing with delicate personal situations. The worry about how the person or people involved will react puts people off from managing situations when they arise. 53% of employees handle difficult or toxic situations simply by ignoring them.

The danger of ignoring or stalling addressing issues in the workplace comes from the matter at hand escalating and causing further, potentially irreparable damage.

Pre-empting and preventing difficult conversations

Before we even get to how to manage difficult conversations, let’s look at how we can pre-empt or prevent them altogether.

Conflict often arises from confusion, secrecy or ineffective communication. Managers that establish open, regular and honest two-way communication channels are the ones who have the fewest difficult conversations. That’s because issues are aired or noticed as soon as they arise, and a conversation is had, all before anyone has time to become emotionally impacted.

The same goes for teams or workplaces that have clear expectations, goal-setting and performance reviews. Often target setting is seen as box ticking, but they can be a really useful way to manage expectations around progression, development and opportunities. Tie those clear targets in with explicit and consistent expectations around behaviour, attitude, culture and conduct and suddenly you’ve got a workplace where everyone knows where they stand.

When you’ve got both clear communication and consistent expectations those difficult conversations don’t seem so difficult.

Tips to handle difficult conversations

There will always be times in your career when you have to instigate a difficult conversation. Instead of feeling overwhelmed, here are some steps that can help you go into that meeting feeling prepared.

Choose the right time and place

Every successful meeting starts with an appropriate time and place. If it’s a conversation where the other person is likely to get upset, holding it first thing in the morning isn’t a great idea.

Similarly if you’re delivering an update with a result pending, last thing on a Friday means they’ll spend the weekend worrying.

Think about the likely outcome and try to ensure the timing is helpful and supportive to the individual.

Open plan offices are perfect for collaboration but not so helpful when it comes to privacy. Take advantage of private meeting rooms, or if that’s not possible look at off-site options where you can have quiet and you can freely discuss the issue without the whole office overhearing.

Remote vs in-person

In modern workplaces there’s a new challenge to difficult conversations. Remote working.

For some, they might not have ever had a face-to-face conversation with their whole team which makes engineering an in-person meet up to have that difficult conversation impossible.

Even hybrid teams will face the challenge of conflicting office schedules, making it harder to have any conversation in a timely manner.

In some instances it might be necessary to have a video call to talk through the issue, while not ideal there are still ways to make it an effective and safe space for both parties.

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• Prepare in advance and brief the other person to make sure they know what’s going to be covered

• Look at the camera - tempting as it is to focus on your own image, looking directly into the camera helps provide eye contact and show active listening

• Give the call your full attention - close all other tabs that might distract you and focus 100% on the call

• Choose the right time - timing still comes into play and can make or break the success of the call

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Those points might seem basic, and they are, but they’re also essential to making those difficult conversations a little easier.

Focus on facts

Before the meeting, it helps to take a moment to jot down the key details - dates, times, who was involved, and what happened. Keeping things factual can reduce the chances of confusion or emotional escalation in the conversation.

Having these clear reference points means you can speak with confidence, without second-guessing or relying on memory alone.

Be ready to explain what happens next. If your team member needs support, what options are available? If the issue is more serious and heading toward a formal process, make sure you're familiar with the relevant policies and procedures.

Preparation is key. Knowing the facts and being clear on the process helps you handle the meeting with more confidence and fairness.

Consider the other person’s perspective

Even when you have the facts, it’s important to recognise they might not tell the full story. Everyone experiences situations differently, and assumptions can get in the way of a productive discussion.

Approach the meeting with curiosity, not conclusions. Listening actively and giving space for the other person’s side helps build trust and creates a more balanced conversation.

If it feels like a tough conversation for you, chances are it’s just as hard (if not harder) for the other person. A little empathy goes a long way.

Take a solution-based approach

It can be tempting to zero in on what's gone wrong, but the goal should be to move forward. You’ll likely continue working with this person, so how you approach the conversation matters.

Think about what resolution looks like. What needs to change? What support is needed? Who’s responsible for each action?

Framing the conversation around shared problem-solving can make a big difference. When both sides are involved in shaping the next steps, it creates a sense of ownership and accountability without damaging the working relationship.

Reflect and take action

What happens after the conversation is just as important as what happens during it.

Once you leave the meeting, it's helpful to follow up with an email and a summary of what was discussed, outlining any next steps and noting relevant deadlines. It's also worth sharing links to any policies they should be aware of or forms that need completing.

Make sure to note deadlines in your calendar and update anyone else who needs to be in the loop. These small steps help keep things on track and make future conversations far easier. They also show that you're taking the conversation seriously and following through on what was agreed.

Difficult conversations can be tough on both sides. It’s worth acknowledging that it might take something out of you too.

If you can, build in 15-minutes after the meeting to take some time to yourself and check in on how you’re feeling before you have to get on with your day.

There’s no magic fix for tricky conversations, but they do get easier when we approach them with empathy and a bit of preparation. It’s about recognising that we’re all human and that sometimes, a little thoughtfulness goes a long way.

If you can spot and address issues early, you might avoid the need for those tough talks altogether.
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