Advice for having difficult conversations

Everywhere Carmen and I speak people tell us that one of their top challenges is having difficult conversations.

One of the best sources for learning to have difficult conversations is the Harvard Negotiation Project and the book from faculty members Doug Stone, Sheila Heen and Bruce Patton, aptly titled "Difficult Conversations: How to Discuss What Matters Most."

My biggest takeaway from the book is that we can't change someone's mind in a conversation. No matter how skilled you think you may be. Not going to happen.

The purpose of a conversation is to create mutual understanding of an issue so that you can both figure out the best way forward.  In other words, the  goal is to genuinely figure out what's important to the other person and express what's important to us. That's how shifts and change begin to happen.

I encourage you to read --no, devour and highlight -- this book. It will not only make you more effective at work, your personal relationships are likely improve, too.

Until then, here are my book highlights to get you thinking in some new ways.


Biggest mistakes

  • Blaming: it inhibits our ability to learn what’s really causing the problem and to do anything meaningful to correct it.
  • Believing it’s their fault: when things go wrong in relationships, everyone has contributed in some important way.
  • Assuming we know the intentions and feelings of others.
  • Avoiding the problem is one of the biggest contributors to a problem.
  • Not preparing, rushing, catching someone off guard.
  • Not acknowledging feelings.

Important realities

  • Difficult conversations are almost never about getting the facts right. They are about conflicting perceptions, interpretations and values.
  • They are not about what is true; they are about what is important.
  • What happened is the result of what BOTH people did – or failed to do.
  • Difficult conversations don’t just involve feelings; they are at their core about
  • The two most difficult and important things are expressing feelings and listening. (And our ability to listen increases once we’ve expressed our feelings.)
  • When a conversation feels difficult it’s because something beyond the substance of the conversation is at stake for YOU.
  • People almost never change without first feeling understood.
  • Don’t share your conclusions as “the” truth; explain what’s behind your thinking.
  • When conversation goes off track reframe it to focus on mutual goals and issue at hand.



  • What do you hope to accomplish? What’s the best outcome?
  • Is a conversation the best way to address the issue? (Sometimes what’s difficult has a lot more to do with what’s going on inside of you than what’s going on between you and the other person. So a conversation won't actually help. You've got to do some inner work.)
  • Plan a time to talk. Don’t do it on the fly.

How to start

  • Reduce the other person’s anxiety! Don't put them on the defense.
  • Describe the issue in a way that rings true for both sides and is free of judgment, e.g., We seem to have different assumptions and preferences for how to accomplish work we both feel is important.  I wonder whether it’s possible for us to look at the best approaches in view of what we want to achieve.

Explore: their views and yours

  • Listen and explore their perspectives, asking questions, acknowledging feelings, paraphrasing so the person knows you’ve heard them.
  • Express your views and feelings: what you see, why you see it that way, how you feel and who you are. Begin with the heart of the matter for you, e.g., “What is important to me is…”

Problem solve and figure out best way forward

  • Figure out the best way forward that satisfies both of your needs.
  • Talk about how to keep communication open as you move forward


  • What did we each do -- or not do -- to get ourselves into this mess?
  • Can you say a little more about how you see things?
  • What’s most important to you about this situation?
  • What information might you have that I don’t?
  • How do you see it differently?
  • Were you reacting to something I did?
  • How are you feeling about all of this?
  • What would it mean to you if that happened?
  • How do you see the situation differently?
  • Help me understand how you would feel and how you might think about the situation if you were in my shoes. What would you do and why?

Meetings: some counterintuitive advice

Meeting visualOh, the meeting, that time where you hope you can get through your PowerPoint presentation within the allotted time, have everyone love your ideas, and walk out getting exactly what you want. Oh, magical thinking.  Meetings are never that tidy and easy.

Yet meetings are an essential part of introducing new ideas, one reason we developed an entire segment of our video learning program, Be a Brave, Big-Hearted Rebel at Work: Get Unstuck, Find New Perspectives, to this topic, interviewing the talented Brice Challamel, author, entrepreneur, innovation expert, and a master of running meetings.

Some of his recommendations:

  • The worst thing you can do in a meeting: present a fully formed, perfect idea. You’ll be tempted to want to shove the idea down people’s throats, cautions Brice. Instead introduce your idea as a work in progress and ask people for their suggestions, whereby they become your allies and collaborators. The idea will get better as will your relationships.
  • The best way to get people’s support: Ask people what it would take for them to support the idea. And then listen respectfully to their suggestions. If people feel they are listened to, they will listen to you.
  • What ideas people support: Their own. The best way to get people to support your idea is to make it their idea. Again, ask for what they think should be included vs. trying to get them to buy into your version of the idea.
  • How long you should talk: Spend a small time presenting the idea, and leave the majority of the time for discussion about what people heard. This is how you improve an idea and gain support. “It’s important to remember that the purpose of the meeting is to gain allies for later,” says Brice. It is during the meeting conversations that we’re able to do that.
  • What your PowerPoint needs to be: “Keep it as simple as possible so you have room for improvisation based on what’s happening in the room.”
  • When to let go of an idea: “Sometimes it’s better to lose your idea and save the relationships,” says Brice. “You’ll have other ideas, but it may be difficult to repair damaged relationships.”

Learning from the persuasion scientists

BigSmall book coverInfluencing people and decisions is complex, but there’s much we can learn from persuasion scientists. This past weekend I read the great new book, The Small Big: Small Changes That Spark Big Influence, by Steve Martin, Noah Goldstein and Robert Cialdini. Here are some highlights, all based on fascinating research studies that the authors explain in the book.


  • Before a meeting or interview, write about a time you felt powerful and/or adopt a high-power physical posture. “High power” people are more persuasive.
  • Make sure to present your credentials before trying to influence a group. Authorities’ opinions dominate people’s minds, shutting down cognitive consideration of other factors.
  • Focus first on the possibilities and potential of your proposal, as potential arouses more interest than realities. Once the attention is focused on the potential, provide supporting information about the benefits, e.g., testimonial, research data.
  • Admit uncertainty vs. convey over-confidence. A person’s expertise, when coupled with a level of uncertainty, arouses intrigue. As a result --  and assuming the arguments that the expert makes are still reasonably strong -- this drawing in of an audience can actually lead to more effective persuasion.
  • Similarly, consider using a list of “worst practices” instead of “best practices.” People pay attention to and learn from negative information far more than positive information. Also, downside information is more memorable and is typically given more weight in decision-making.

Influencing Decisions

  • Ask people to choose between two options vs. offering just one.  Then influence them to opt for your preferred option by pointing out what could be lost if they don’t select that option.
  • Similarly, people make decisions based on context and comparisons. By first presenting an option that people think is a bit too costly, or one that they might think will take to much time, you can achieve the desired impact of making the target proposal seem even more like the “Goldilocks proposal that it is – just right.
  • Determine whether you’re trying to get buy-in or follow-through. If it’s getting people on board, make the sequence of steps as flexible as practical and emphasize that flexibility when announcing the initiative. If the bigger issue is execution, give the rollout sequence a very structured order and emphasize how, once in place, the program will proceed in a straightforward, uncomplicated fashion.

Forming Relationships

  • Explicitly use someone’s first name more often when seeking to influence them.
  • Identify uncommon commonalities between you and another person, fulfilling people’s desire to both fit and still stand out.
  • When meeting someone for the first time dress at a level that matches your true expertise and credentials. This is in keeping with a fundamental principle of persuasion science – authority. Authority is the principle that influences people, especially when they are uncertain, to follow the advice and recommendations of those they perceive to have greater knowledge and trustworthiness.

Getting Commitments

  • Remind people of the significance and meaningfulness of their jobs, and show how what you’re asking them to do is related to that meaning.
  • To get people to follow through on promises, e.g. I’ll bring up your idea in the executive staff meeting, ask how they’ll go about accomplishing the promise they’ve given to you. This specificity helps them follow through.
  • If you believe that you will encounter resistance with your requests for an immediate behavior change, you might be more successful if you instead ask for a commitment to change at a given time in the future, say three months from know.
  • Appeal to people’s sense of moral responsibility to the future version of themselves.


  • Ask people to submit information before a meeting. This often increases the number of voices that are heard, potentially leading to a greater number of ideas generated. Similarly, ask people to spend a few moments quietly reflecting on their ideas, writing them don, and submitting them to the group. Doing this can help ensure that any potentially insightful ideas from quieter members won’t get crowded out by people with louder voices.
  • The person who leads the meeting always speaks last. If a leader, manager or family elder contributes an idea first, group members often unwittingly follow suit, leading to alternative ideas and insights being lost.
  • If you want to create an atmosphere of collaboration and cooperation, have people sit in a circular seating arrangement.
  • Creative sessions are often more fruitful when held in rooms with high ceilings.

Building your network

  • Just ask! People tend to underestimate the likelihood that a request for help will result in a yes. Plus, those who can help often don't  offer because they wrongly assume their help isn't needed. Why?  Simply because it wasn’t asked for.
  • People who help others but don’t ask for favors in return are much less productive than their colleagues. The way to optimize the giving process in the workplace is to arrange for exchange: a) be the first to give favors, offer information or provide service, and b) be sure to verbally position your favor, information or service as part of a natural and equitable reciprocal arrangement. (“I was happy to help. I know that if the situation were ever reversed, you’d do the same for me.”)
  • Provide explicit thanks and genuinely communicate your appreciation for the favors done and the efforts made on your behalf.