How to Prepare and Conduct a Difficult Conversation as a Manager

By People Leaders | People Leaders Podcast

For most of us, the idea of having a difficult conversation makes our heart race a little (or a lot). People leaders have an extra layer of difficulty because, in most cases, these are conversations that can’t be avoided.

Let’s face it, it’s part of the job and something that has to be done. In fact, if you aren’t having difficult conversations on an almost daily basis, you probably aren’t doing your job to the best of your ability, and nor are you serving your stakeholders as well as you could be. It’s part of the duty of care of being in a leadership role.

Listen to the podcast here or continue reading below. 

What is a difficult conversation?

Difficult conversations can be required with stakeholders in all directions, not just to your team or employees. You might need to have a difficult conversation with your upline manager about how you are feeling undermined in a situation. It might be with a client about their expectations vs your ability to deliver. It could even be about overdue payments. Any upcoming conversation that you are feeling apprehensive about is probably a difficult conversation in the making.

Every difficult conversation that is avoided is actually a missed opportunity. Through our coaching work, we’ve often come across employees who are going through an exit process who say if they’d been more aware an issue that they were contributing to, they could have been more proactive in resolving it.

So today we want to run through a few tips and give you a framework so you can feel comfortable, confident and empowered. We want to help make difficult conversations easy!

Keep in mind that while a lot of the angst around the upcoming conversation might be about what to say, equal weight needs to be given to how you say it, how you prepare for the conversation, and how you follow-through from the conversation.

To that end, we’ve broken down the process into three phases, prepare, conduct and follow-through.

Prepare for a Difficult Conversation

There are at least two parties to the upcoming conversation so preparation must involve both parties.

This includes:

1 - Inform the other party

This simply means giving the other party fair notice that you’ll need them to take part in a conversation with you. Let them know when and where the conversation will be held and the subject matter.

Be conscious of how and when the notice is delivered. Calling out as they leave the office on a Friday afternoon that you want to see them in your office first thing Monday to discuss X probably isn’t the best setup.

Give them enough notice so that they can prepare for the conversation but without dragging it out so long that they end up turning up for the meeting full of apprehension. It’s fine for them know that the subject is a ‘serious’ matter but without feeling like it’s ‘life ‘threatening.’

2 - Set the stage

For some difficult conversations it is going to be appropriate to hold it at the office. For some people, like a client or an external stakeholder, it could be at a coffee shop or just somewhere neutral. So just be mindful that you have thought about the physical environment that you're going to have the conversation.

If possible choose a round table and avoid sitting directly opposite the other party.

3 - Assess the facts

What are the facts? What is the physical evidence that you can convey to other person that they can agree with?

Assess The Facts

The quicker you get them to ‘yes,’ the less inclined they are to be defensive and the more likely they are to be open to hearing and having the conversation.

For example, ‘The report that is due in on Monday comes in Tuesday.’ ‘There are several spelling mistakes that I've picked up on that you've had feedback on over the last three reports,’ etc.’ These are facts that the other party can only acknowledge as being true.

Having these facts at at hand in advance helps set you up to be more qualitative with your analysis. You could follow up for example with something like, 'I would like us to be able to work better together because with these errors we're not as effective as what we could be.' (Note the inclusion of ‘we’ in this. That’s deliberate.)

4 - Address the Emotions

Both parties are going to experience emotions during the conversation. As much as possible, try to preempt what your emotions might be and what the other party might be feeling as the discussion progresses.

If you know what ‘buttons are going to be pushed’ (yours and theirs) in advance, you can avoid emotional surprises, which often trigger the reptilian part of the brain, thus setting off a reactive ‘fight or flight’ reaction, instead of a more proactive and positive response.

Prepare yourself in advance to pause the conversation if necessary. Be ready to check in with the other party: ‘Is there anything that I can do right now to make this conversation easier or more effective for you;’ ‘What can I do right now? I'm starting to notice or I'm seeing that you're getting upset and that's not my intention;’ ‘What do you need right now?’

Be prepared in advance also to notice the body language of the other party. Be on the lookout for folded arms, leaning away from the table, etc. These will all give you clues as to what is going on in their head.

5 - Acknowledge Your Part

So where are you responsible for the problem that’s up for discussion?

Could you have been clearer with your instructions? Have you let standards slip or ‘little things’ go by without comment?

Acknowledging your role in the situation, both in advance and during the conversation, will show that you share the burden of responsibility for it, and share responsibility for making it right again.

6 - Identify Positive Outcomes

If you don’t go into the conversation with an expectation of one or more positive outcomes, chances are that you will settle for something less. That doesn’t serve either party.

Even if the positive outcome is simply an agreement from both sides that the problem is real and that a solution can be worked on together then that’s fine. Ideally though, you want both parties to walk away feeling upbeat about it.

Positive outcomes could be something like, an action plan, an agreed timetable to get things done, a specific goal to work towards, an undertaking to report back within x days...

7 - Develop a strategy not a script

You don't want to be a robot. However what we coach people on is the need to be really clear about what your opening sentence might be.

Authenticity is important so it might be something like, 'This is difficult for me, what I'm about to say, however this is very important for your growth and development and the team's level of cohesion.'

This not only sets the tone but it also shows a level of honesty about the situation. The other party will respect you more for your authenticity than any displays of power you might otherwise use in such a conversation.

If you follow the steps given already, you’ll already have a solid strategy in place. It’s no mistake that the Prepare step is the most detailed phase of all. Let’s move on to the next phase...

Conducting a Difficult Conversation

It’s a good idea to set the other party up for success with an affirming start.

1 - Acknowledge, articulate, then ask

Acknowledge what they are good at in their work, what they are delivering that is working, and thank them for being prepared to have this conversation with you.

Articulate and Ask

Then frame the problem, being articulate about what the problem is and the impact that it's having.

Ask them if they understand the problem fully and what their position is on it. When asking questions, remember to listen, give them space if necessary and remember, the quality of the answers given will relate directly to the quality of the question asked.

And don’t be afraid to ask, ‘If you were in my shoes what would you be doing?’ This can often led to a light bulb moment as they now need to look at the situation from your point of view.

2 - Look for common ground

Look for areas or issues where both of you are feeling the pinch, are being challenged, or have got similar strengths. Just find something that is common to you because this develops an aspect of relatedness and avoids any need for either party to feel defensive.

Find a place where you can each agree that you both want to solve this problem. ‘This isn't your problem and I'm not the problem you are trying to solve. It's both our problems in this situation that we're trying to work through.’

3 - Adapt and rebalance

Having prepared yourself in advance, you can be ‘in the moment’ and be vigilant for what’s working and what’s not. Keep an eye out for the body language triggers mentioned earlier, and, if necessary, suggest a break so you can each have time to reflect and refocus.

This is especially important if you learn new information during the conversation that you may not have been aware of earlier. Take the time to process this and change your expectations of the discussion if necessary.

4 - Establish commitments

Before finishing the conversation, ensure the each party is in agreement about what they are committing to doing as a result.

Have any goals or timeframes been set? Are any behaviours to be adjusted? Are there any agreed strategies to be implemented? Are expectations clear moving forward?

Make sure these are written down and that the respondent articulates them back to you. You want to be clear that they are agreeing to something that they understand rather than just agreeing to get the conversation over and done with.

5 - Finish on an affirming note

It goes without saying but choose closing words that leave the other party feeling like they can move forward easily.

‘So if we were to move through this situation as we’ve agreed, I can see the team being so much more effective and you enjoying the work that you're actually doing more. Would you agree?’

If they can finish with a strong yes then the conversation will have been successful.

Follow-through From a Difficult Conversation

The conversation doesn’t end there of course.

1 - Follow up

Now that commitments have been made you need to keep track to make sure they are kept. Diarise a check-in so you don’t forget the conversation.

Follow Up

Remember to follow up with the other party to acknowledge that they have lived up to their commitments (and you yours), to see if they need further help on the issue, or to remind them if they haven’t.

2 - Reflect

Equally important, take some time immediately afterwards to reflect on the process. How well did you do? What could you have done better? Do you need to have a conversation with your mentor, your coach or your upline manager to help with a debrief?

Make notes in your leadership journal while they are fresh in your head. When you look back on them later they will be a valuable asset.

Further Reading about Difficult Conversations

One book that we highly recommend is Fierce Conversations : Achieving Success at Work and in Life One Conversation at a Time by Susan Scott. In this book Susan covers seven principles of fierce conversations, including - Let silence, do the heavy lifting - especially important for extroverts, and - Obey your instincts - which is all about being present to what’s going on as the conversation is happening and responding accordingly.


Harvard Business Review also have an excellent book about Difficult Conversations in their 20 Minute Manager series.


So there you have it. Difficult conversations are a skill that you will continue to develop over your career. The more you practice the more masterful you will become and the less difficult they will be.

We’d love to hear your insights, questions or comments on the subject. Please let us know your feedback in the comments below.

Every difficult conversation that is avoided is actually a missed opportunity. #difficultconversations #leadershipskills #leadership

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