Managing Difficult Conversations: A Step-by-Step Guide

Imagine this for a moment. One of your team members keeps turning up late for meetings. It’s getting on everyone’s nerves and causing resentment. You know you must speak to them, but keep putting it off.

It’s natural that employees avoid difficult conversations. No one wants to have them. But the longer you delay, the worse things can get, causing a toxic issue that eventually causes disengagement. Our advice is to reframe the way you think about handling difficult conversations. Instead of your employees avoiding difficult conversations as ‘difficult’, think of them as ‘impactful’. Understand the upside to confronting things quickly and nipping issues in the bud.

When she was COO of Facebook, Sheryl Sandberg encouraged her employees to have difficult conversations at least once a week. ‘If you’re not having those difficult conversations at work sometimes, you’re not growing,’ she used to say. Holding conflict-resolution discussions is fundamental to being a successful leader and is something we all must work at. You’re fortunate if it comes naturally to you.

Remember, we judge our actions by our intent, whilst others judge them by their impact. With a difficult conversation, you’re informing someone about an action they took that had unintended consequences. Maybe their intent was misconstrued by other people. And by doing this with radical candour, you’re giving them this feedback because you want them to be the best version of themselves. It may be difficult for them to hear, but that’s not a reason not to do it.   

Some organisations are much better at difficult conversations than others. But it goes hand-in-hand with building high-performing teams. Every member of a team should be capable of giving and receiving feedback. And the whole team commits to a standard of behaviour that means they won’t react in rage or burst into tears. As a result, difficult conversations are easier for the recipient of the feedback and less energy demanding for the giver. 

We all have inbuilt fight or flight mechanisms that kick in during hard conversations. This blog will give you ways to navigate this successfully. So, if you want to improve at handling difficult conversations well, read on.

Step 1: Prepare by reflecting on the key message you want to convey

Before you do anything, think about your message. What are you saying, and why are you saying it? Writing it down can be super helpful. It will help you clarify the key points you need to get over. Think about it from the other person’s viewpoint and perspective. There has to be some upside to them – otherwise, why will they want to listen? Writing your message down will also help keep you on track and stick to the facts.

Consider how your conversation’s objectives or key points align with team and individual goals. What’s your purpose, and what key results are you working towards as a team? How will this difficult conversation help this move forward? 

And go into this difficult conversation with your eyes open. Human beings are naturally defensive. We have an incredible ability to misinterpret events or even lie to ourselves. Our subconscious will try to protect us from any feeling of self-hatred. Be prepared for this. Sometimes, you might have to point it out to people. They may have to confront a version of the truth they do not want to hear or see. 

Step 2: Focus on facts and your key objective

This leads us nicely to explain our next step – focus on facts. If your hard conversation will likely lead to an emotional response, make sure you keep the discussion factual. Also, keep in mind your desired outcome or objective.

Some people love to deliver a ‘shit sandwich’. The thinking is, ‘Let me praise you, then give some honest feedback, then praise again.’ My view is the psychology around this is broken. Humans are hard-wired to respond more to negativity. And people will no longer remember the good stuff you told them.

A shit sandwich may make you feel better but won’t help the feedback recipient. Don’t muddy the waters. Don’t sugarcoat it. This isn’t about making you feel better about delivering the feedback. It’s about having an impactful and constructive conversation that will make a difference. Give praise on a different occasion.

Step 3: Choose an appropriate setting

Be direct and honest. Tell the person you have some feedback for them and ask them when would be a good time to do that. You want an appropriate time and setting for this difficult conversation. 

You never know what’s going on behind the scenes. I recently talked to a client dealing with a grievance process over a dismissal. It turned out that the person who’d been dismissed had experienced a life-changing event in January. But they hadn’t told anyone at work. The reason for the employee’ dismissal was poor performance, but this issue in their private life made it impossible to perform their job at the required level. However, it was too late. Staff members must have an opportunity to express concerns or mitigating circumstances that might impact your conversation.

Sometimes, the person may be trying to avoid talking to you. In this situation, you have to push through and make it happen. Don’t use it as an excuse to put things off.   

Step 4: Stay calm and composed

This is why you prepared beforehand and wrote down your message. And this is why you avoid the shit sandwich. You need to stay calm and composed throughout. 

Consider being vulnerable and saying that you will find listening and giving this feedback challenging. This will make the person receiving the feedback more empathetic towards you. Try to avoid emotion and accusations. Always stick to the facts. And check these facts with them. Have you got them right? Before you give an opinion, make sure you’re 100% clear on what you’re discussing.

Step 5: Listen to understand other perspectives

Once you’ve established the facts, let the person you’re having your difficult conversation with speak without interruption. Don’t be drawn into an argument. Recognise there’s likely to be emotion in their response and let them get this out. 

If you’ve ever done any training around angry customers, you’ll know allowing them to vent is essential. After they’ve done this, return to the facts. Ask them from their perspective what the facts are. Staying angry for a sustained period is hard, so allow this to burn out.

Ask clarifying questions if you don’t understand what they’re saying or where they’re coming from. Attempt to find some common ground. If they have valid concerns, make sure you listen to them.

Step 6: Focus on interests, not positions

Ultimately, this awkward conversation has come about because you want them to be a better version of themselves and succeed. Always remember this. They likely want the same thing. 

Expect a range of reactions. Like the different stages of grief, you’ll likely get shock, denial, guilt, anger, acceptance and hope in quick succession. It’s an emotional roller-coaster that’s playing out in front of you. Sometimes, the person will need to go away to process your conversation. Only then will they be ready to discuss the next steps. Judge this as the conversation develops, and if you need to meet again, agree on when and where. 

Focus on shared skills and interests as much as you can. How can the two of you collaborate on something? You both have an interest in the team being successful. This isn’t a case of I’m right, and you’re wrong. That attitude never helps.

Step 7: Explore options together

Perhaps there are some creative solutions here that will address everyone’s interests. Be open-minded and flexible. Offer concessions where appropriate to show good faith. And discuss the pros and cons of different approaches.

At this point, you need to go into ‘coach mode’. Brainstorm and help them understand what their next actions might be. Get specific on a narrow, agreeable path forward. If you’re talking about performance, get granular on what performance will be acceptable.

Step 8: Close on a constructive note

Make sure you finish on a positive, constructive note. Summarise any agreements and next steps. Thank them for taking the time to listen and take on board the feedback.

When I think back to conflict resolution and difficult conversations at work, they’ve never been as bad as I anticipated. 99 times out of 100, they result in a corrective input rather than a catastrophe. Schedule any follow-ups that are needed and part warmly and politely.

Getting good at tough conversations builds trust in the team and your leadership. It helps people to deliver and irons out uncertainties and self-doubt. All of us want to succeed. And by identifying blind spots and taking corrective action through conflict resolution and challenging conversations, this is more likely to happen. Ultimately, high-performing teams will have a shared mission. Mastering difficult conversations makes this more likely to become a reality.

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Written by business coach and CEO mentor Dominic Monkhouse. Find out more about his work here. Read his new book, Mind Your F**king Business here.