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April 17, 2021

How to Have Difficult Conversations

At various points in our personal and professional lives, we all encounter the need and opportunity to have difficult conversations. They typically involve sharing a frustration, giving critical feedback, working through a disagreement, or making someone aware of how they’ve negatively impacted you or the team. [Go here for a quick caveat about tough conversations]

It can be hard to convince ourselves that having these discussions is worth the discomfort and risk we feel. But—once you’re clear about why you’d like to have such a conversation, and you’ve considered some important foundational prerequisites, you can learn the skills for how to have difficult conversations.

Below are some best-practice strategies and phrases for how to have difficult conversations. These are drawn from a combination of resources, including my work with coaching clients, the Center for Creative Leadership’s SBI feedback model, and Brene Brown’s Dare to Lead method.

Strategies for how to have difficult conversations:

Choose the right moment: Timing can make all the difference in someone’s receptiveness to engage in this type of discussion and not get defensive. Be thoughtful about when to initiate, making sure that:

  • You have sufficient time to talk and won’t get rushed or cut off
  • Distractions are minimized
  • Your partner in the discussion isn’t tired, stressed, or emotionally triggered
  • You both have enough energy “in the tank” – I wouldn’t do it at the end of the day
  • The setting is conducive to a casual, partnership-like dynamic rather than a formal and hierarchical one

Know how you’ll initiate:
Sometimes the hardest part of a difficult conversation is just starting it. It can feel awkward to bring up a touchy topic, especially if you’re not sure of yourself when doing it. I suggest experimenting with these types of phrases:

  • “Hey, I’d like to share some thoughts with you that I think could help us collaborate better”
  • “I want to share some observations and thoughts with you and understand your perspective on them”
  • “I’m curious about something I’ve noticed and want to get your perspective”
  • “I have some concerns I want to share with you and I’d like to get your feedback”
  • “It looks like we have different perspectives about ______, and I wanted to see if you’d be up for exchanging more thoughts about it so we can understand each other better”
  • “I’d like to see if we could reach a better understanding about ______ by sharing more of our thoughts and feelings around it”

Get specific about the situations involved:
If you’ve ever received vague feedback, you know it’s confusing and unhelpful. So, when sharing a concern or frustration, make sure you tie it back to the specific situation or context in which the concern arose, as in “During that meeting…,” or “On that particular project…”

Share observed, objective “data”: One thing that’s bound to create defensiveness is making accusatory or judgmental statements, such as “You’re just trying to be resistant” or “You don’t care enough about this project.” Instead, share observations of objective behaviors you saw or heard. These are free of assumptions of the other person’s intent, but are merely statements that report what you observed through your senses. For instance, saying “I noticed that you didn’t respond to that email,” or “I noticed that you interrupted that person several times.”

Communicate the impact on you: Once you’ve shared the objective observations, you can share how that behavior made you feel. For example, “That made me feel frustrated” or “That’s brought up some anxiety for me.”

Share the story you make up: If your feelings are partially fueled by some interpretations or assumptions you’re making about the other person’s intent, you can voice those while owning that they may not be true. A good way to do this is to start with the phrase “The story I make up about this is…” or “The story I tell myself is…”. Voicing these in this way reduces the chance of defensiveness and gives the other person an opportunity to clarify their actual intentions.

Ask a question to create a dialogue: Once you’ve shared your observations, their impact on you, and the story you might be creating about it, then it’s time to initiate a dialogue to hear the other person’s perspective. Open-ended questions are the best way to start this type of exchange. The most powerful of these start with “what” or “how,” and some examples you could try include:

  • “What are your thoughts?”
  • “What’s your perspective on this?”
  • “What do you think is happening?”
  • “How do you see it?”
  • “What do you think is behind this?”

Listen actively and reflect back:
Once you’ve opened up the discussion, it’s time to listen carefully. Do this by working to keep your attention on the other person and silencing the monologue in your own head. One terrific tool of active listening is to reflect back what the other person said – that means repeating back what you think you heard. In order to do this well, you have to have been listening well. And once you reflect back, it’s a powerful sign to the other person that you were indeed tracking with them and not just thinking of your next retort. This is how a reflective statement might begin:

  • “Ok, so what you’re saying is…”
  • “It sounds like…”
  • “I’m hearing…”

Acknowledge and explore differences, with tact and curiosity:
When an exchange of perspectives is underway, you may still bump up against some differences in viewpoint. One way to help create more mutual understanding is to explore those differences further with tact and curiosity. Sentence starters that might help with this could be:

  • I’m curious about…
  • Tell me more…
  • I’m wondering more about…
  • Help me understand…
  • Walk me through…
  • That’s not my experience (instead of “I think you’re wrong about this/that”)
  • We’re both dug in. Tell me more about your passion around this.
  • What doesn’t fit/work for you about this?
  • I’m working from these assumptions…. — what about you?

Problem-solve together:
After there’s more clarity and understanding about the various behaviors, feelings, intentions, and viewpoints involved, there may be the need to identify a solution or make a decision about next steps. Instead of one person taking control, you can try engaging in joint problem-solving. This is done through using a collaborative “we” approach, and questions that could help stimulate this include:

  • What are our options for finding a resolution?
  • What could we do from here?
  • What are the upsides and downsides of our various options?
  • What would bring us closer to a decision here?
  • What would be best for the team or organization?
  • What are we both willing to do to help?
  • What solution fits best with our overall project goals?
  • What option aligns most with our organizational priorities and values?


A caveat about difficult conversations: the discussions I’m referring to in this article aren’t the same as those that would address incidents of discrimination, racism, harassment, or abuse. Conversations about these situations would require a different approach, likely aided by advice or mediation from professionals in human resources, psychology, social work, law, or otherwise.

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