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Navigating Challenging Conversations

Regardless if you manage a team, project, or family, challenging conversations will inevitably arise for you. How you choose to navigate those difficult discussions -- whether by turning away or leaning in – will impact the quality of your relationships.

I can recall facing that choice when a longstanding work colleague disclosed information I had shared with her in confidence in a larger work meeting. At the time, I felt betrayed. However, I had a choice to make: I could distance myself from this person or I could have a challenging conversation with her and potentially improve our relationship by establishing better boundaries. Did I feel hurt and blindsided? Yes. Would I have rather skipped an awkward and uncomfortable conversation? Absolutely. However, my desire to heal the relationship outweighed my initial discomfort, and years later we remain good friends.

Here are some ideas to try the next time you choose to navigate a challenging conversation.

Set an Intention

Beginning a challenging conversation from a calm, non-reactive state is one of the most simple, but powerful, ways to support a positive outcome. This can be done by setting an intention. Ask yourself: what do you want to come out of this conversation? For a leader, the intention is most likely to maintain some positive relationship with the other person – as a colleague, a direct report, or a member of your larger team. If you enter a challenging conversation wanting to prove your point or advance a specific agenda, you both may leave the discussion feeling unheard and unsatisfied.

Create Clear Boundaries

Having challenging conversations does not mean having a conversation without boundaries. In fact, as in my own personal experience, they can create new boundaries that result in healthier relationships. During a challenging conversation, be aware of the boundary you wish to set (or reset) with this person. If the other person chooses to continually cross it, you can always change your mind about the value of this connection and choose other ways to interact.

Don’t Delay the Conversation

Challenging conversations do not age well with time. In fact, the longer we wait to have them, the harder it becomes. And the longer time goes by with things left unsaid, the relationship may sour -- adding even more tension to an already hard conversation. So somewhere between the heat of the moment and the cold reality of a broken bond, it’s time to have the talk.


And as with all things, practice makes better. I’ve participated in and facilitated countless difficult conversations over the course of my career. Did it ever feel comfortable? No. Did it feel less intimidating with time? Yes. Thankfully we have the tools – and the vocabulary – to build more bridges than to burn them. What’s more, having difficult conversations also helps us to tap into our empathy. We all have bad days, and as a result, we can react poorly, misspeak, and make the wrong decision. It is during those moments when another human being extends to us the gift of grace that we can truly appreciate why having challenging conversations is worth the discomfort.

As I often share with my executive clients, one of the most powerful traits of an effective leader is self-awareness of their strengths and weaknesses. This is also important in leading challenging conversations. Here are some ways to leverage your self-awareness for better outcomes:

1. Be aware of your conditioning:

Were you raised in a home that was high conflict or avoided conflict all together? This can, subconsciously, inform how you approach conflict as an adult. The more conscious you are of your preferences and tendencies, the more options are available to you in navigating your emotions and others.

2. Be kind with others and yourself:

Leading challenging conversations rarely comes naturally to any of us, and it’s normal to feel resistant to having them. Remember to be kind and patient, both with the person in front of you and with yourself. The fact that you are having the conversation is already an achievement.

3. Block time:

When planning for a challenging conversation, consider blocking time on your calendar before and after your meeting. By giving yourself the gift of time, you can help ensure you’re in a calm mindset when entering the conversation and that you have some space to decompress afterward.

Challenging conversations are for learning, not winning, so it’s important your team have a healthy framework to practice discussing tough topics in the workplace.

Step 1: Be explicit with each other

Before there is a conflict in the workplace, help your team practice how to navigate a challenging conversation. The first step is for each person to be explicit in what they hope to achieve in the conversation. Start with the why before getting to the what. Saying things such as: "I value our relationship. You matter to me.” helps settle everyone’s nerves and illustrates goodwill.

Step 2: Listen to understand

While this is true for all conversations, it is even more essential for a challenging one: encourage each person to actively listen. This means listening to understand the other person’s perspective and experience, not listening to form a response or to advocate a point of view.

Step 3: Build resilience

Many of us may be conflict-avoidant, so helping team members build up resilience for uncomfortable conversations is key. One way is to practice, another is to engage in actual challenging conversations in shorter spurts. Start with a 15-minute discussion, so each participant can take a break and decompress. The key is that a conversation is taking place.

Remember to make time for wonder and awe.

Watch my LinkedIn Live conversation with executive communications coach Jared Dickinson on the Art of Uncomfortable Conversations.

If you found this note helpful, I would love if you could forward and share it with someone who needs the inspiration today.

Executive Coaching and Leadership Development


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