The Art of Difficult Conversations (Part 1)

Welcome to the latest edition of the “How to be a Co-Creative Leader” newsletter!

There is a definite theme showing up lately in my coaching sessions with various leaders, and it’s how to have difficult conversations. For some of them, the challenge is around how to be ready for it; for others, the challenge is how to manage the discussion effectively. No matter where you stand, the key to successfully navigating these conversations lies in your approach and mindset.

In this edition, we will break down some essential steps to help you get ready for difficult conversations with confidence and empathy. These steps will provide you with a structured approach to get ready, making it easier to handle challenging discussions without feeling overwhelmed. Whether you're dealing with unplanned encounters or providing feedback to your team, these strategies will help you turn potentially stressful interactions into productive dialogues.

What’s Difficult About Difficult Conversations?

I could start with a slightly different question to make my point: What comes up for you when you think about having a difficult conversation? For some people, it’s the idea of conflict or violent disagreement. For others, it’s the idea of arguing with someone and the conversation spinning out of control.

With these initial impressions as a starting point, would you want to dive into a difficult conversation? Probably not. The ideas above are the potential negative sides of having these discussions, and they can scare you into not having them at all.

I often tell people, the only thing that makes these conversations hard is the fact that we tack on the word “difficult” in front of them. The conversation will be as hard and difficult as we choose to make it. The question now becomes, what can you do to have your conversation in the healthiest and most productive way possible?

Start with some preparation

Preparation is an important step. You may have noticed that you jump into these conversations when an opportunity arises rather than when you would like to have it. It may feel right at that time, but let me give you a quick hint: if it feels as if you are doing it to get rid of it, this is not a good sign.

Before you have a difficult conversation with someone, it is important to prepare yourself. I don’t mean over-preparing and overthinking it until it is perfect. This is the wrong extreme. You need to do just enough preparation to get some clarity around what you want to discuss. It can even be helpful to do this sometimes before inviting the other person to have a conversation.

Here are a few key questions to get started:

• What is your real intention for this conversation? Do you want to explore a topic with the other person? Do you want to better understand a situation that happened? Do you want to give someone feedback? Do you want to help people on your team talk to each other better about an issue they are experiencing together?
• What is the situation or the problem that you want to discuss? Keep this short and factual. Running too long in explanations will lose the person you are talking to.
• What is the outcome you want to get out of the discussion? Are you looking for a change of behavior? Different actions next time? How will you measure success?
• What is your contribution to the situation? How did you make this situation possible? How did you attract it? What are some of the tangible parts from your 50% of the situation?
• What was the other person potentially trying to do? What good intentions can you see in their actions and efforts that you would like to acknowledge in the discussion?
• What is the impact this situation is having on you? How does this affect your comfort level or your performance? Why is this important to you? How do you feel about what happened?

You don’t need to write a Harlequin romance novel here. Write down enough notes for yourself to get some clarity around what you want to discuss.

Managing Unplanned Conversations

There are two types of difficult conversations you may encounter: the unplanned ones that may pop up in the moment and planned ones, which I’ll call the feedback conversations.

For unplanned conversations, you may not always be able to prepare (unless you have done it preemptively because you were planning to have this conversation soon with the person).

The easiest strategy for this kind of conversation is to take a moment to listen to the direction of the conversation and assess whether you feel ready to have it right then and there. If you're ready, go ahead and engage in the conversation.

If you are not ready, there are a few ways that you can proceed:

• Express Your Readiness: You can name that you are not ready to have this conversation but that you are interested in knowing more. Ask if the person is ready for you to mainly listen to them now and have a deeper discussion later. Chat a little to better understand and plan a meeting at a different time that suits everyone.
• Schedule Another Time: You can say that this is not a good time for you to have this conversation and that you would like to schedule another time to have it.
• Redirect the Conversation: You could name the fact that you don't think you are the right person to have this conversation and direct them to the right person.
• Decline the Conversation: You could name the fact that this is not a conversation you wish to have. For example, a more negative or toxic person might want to pull you into a conversation that you don't want to have.

The Feedback Conversations

Sometimes the conversation you want to have can be a feedback conversation with a peer or an employee. For a feedback conversation, it may be helpful to set the table with the other person about the conversation before you have it.

For a colleague, context and permission are important. Do you have an agreement with this person to give them feedback? Is this a conversation you are starting on your own initiative? Each situation has its own unique approach.

• If You Have an Agreement: If you have an arrangement with them to give them feedback, you can approach the person either in their office or elsewhere, and ask if it is a good time to give feedback.
• Timing and Location: If it is a good time, sometimes the ideal is to do it somewhere private, like a conference room or somewhere that is a little further from their desk. This will allow you to keep your attention on the conversation.
• Rescheduling: If it is not a good time, you can ask when would be a better moment and schedule the meeting in your calendars. Schedule enough time to have the conversation properly, and if it ends sooner than expected, then that's okay.

If you do not have an agreement to give feedback and the person is a colleague or peer, the approach has to be a little different. It is typically easier to ask for permission first, which can be done in different ways, for example:

• “I would like to talk about something that happened in the meeting this morning. Is that OK with you?”
• “I was thinking back to the meeting this morning and I had a couple of things that I would like to share with you. Is that OK with you?”
• “I was thinking about the meeting this morning and I have some ideas and feedback for you that would make the next meeting more effective. Are you open to this? Is now a good time?”

I shared some ideas with you here that you can rephrase, but the basic idea is to ask permission first. You may come across circumstances where the person will not be interested in receiving feedback from you. This can be okay too, and it is better to know that before you force a conversation that the other person is not interested in having.

Giving Feedback to Employees

There is an important nuance to consider when giving feedback to one of your employees. The notion of permission is a little less applicable here because it is part of your role as a manager to give it. In this case, the important concept to consider is finding the right time.

Does the topic you want to discuss fit into your regular one-on-one meeting with the person? If so, the decision will possibly revolve around how best to have the discussion. Is it at the next meeting or the one after that? Should you set the table and let the person know beforehand you want to talk about this topic? If so, is it too early to do so before the next meeting, or could you take advantage of this meeting to introduce the subject for the next one?

What you want to find out with these points is the best way to plan the conversation! If the topic is short and the next one-on-one meeting is very soon, then it may be a good topic for that meeting.

If it is coaching feedback or a regular follow-up, ideally this is discussed in the meeting where these points are covered. Sometimes this is a topic for the regular one-on-one and sometimes it can be in a regular meeting that is less frequent than the regular one-on-one.

For regular meetings, it is important that these be scheduled neither too often nor too occasionally. This might give the impression that the meeting only happens when you have negative comments to give.

If it is a bit of a longer conversation (too much for the regular one-on-one) or an important conversation that you need to have now, it may help to schedule a one-time meeting in the short term.

Conclusion

Difficult conversations are an essential part of leadership, and handling them effectively can lead to significant growth for both you and your team. By preparing thoroughly, initiating conversations thoughtfully, and understanding the dynamics at play, you can navigate these challenging discussions with confidence and empathy.

In this edition, I share with you some initial steps to prepare and initiate difficult conversations, in the next edition of the newsletter, we’ll go deeper into the actual dynamics of the conversation itself.

I hope you found these initial steps helpful and that they empower you to tackle difficult conversations more effectively. Share your experiences and thoughts in the comments below—how have you handled difficult conversations, and what strategies have worked for you?

Call to Action

Are you ready to dive deeper into mastering difficult conversations? If today’s insights sparked your curiosity and you are ready to explore further, I’m here to guide you. Click here to schedule a discovery call with me. Together, we can tailor a development plan that aligns with your unique leadership style and goals.

Thank you for taking the time to engage with this newsletter, and I look forward to supporting you in your journey to becoming a co-creative leader.

About Steffan Surdek

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With over a decade of experience in leadership coaching, I've dedicated my career to helping executives and management teams unlock their full potential. My approach is centered around the concept of Co-Creative Leadership, focusing on fostering a culture of collaboration and action-oriented learning.

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