How to Master Difficult Conversations

A person’s success in life can be measured by the number of uncomfortable conversations he or she is willing to have. — Tim Ferris

Have you ever avoided a conversation that you know that you needed to have? Has a desire for comfort taken you off the direct path to achieving your goals?

Or even worse, have you ever had the difficult conversation, and then felt you came out worse as a result?

As a Product Manager, you are likely to face more difficult conversations than people in other positions. Examples include stopping work which no longer aligns with top priorities, giving feedback to others, negotiating roadmaps, and apologizing when you dropped the ball.

Mastering “difficult conversations” gives Product Managers superpowers. You get confidence to advocate for new product ideas, drive changes in how your organization functions, and are enabled to lead your group.

I would argue that if you are not having difficult conversations, it is likely that you are avoiding them!

The book “Difficult Conversations” is one of the most thorough books on the topic. Here, I attempt to give you a bird’s eye view of the ideas, with some expert commentary based on my experience as a Product Manager, and as a coach and teacher at Intentional Product Manager.

Why are difficult conversations difficult?

Difficult conversations have three layers:

  1. The “What happened” layer. What’s the story here?
  2. The Feelings layer. Uncovering how you really feel.
  3. The Identify layer. What does this say about me?

Dissecting difficult situations is like peeling an onion with three layers. Caution: sometimes you will cry :)

Photo by Erda Estremera on Unsplash

Let’s dive deeper into each of these.

The “What happened” Layer

The stance that makes conversations go wrong is “I am right, and you are wrong.” Being right feels good! We all want to be right.

The core reason why we get ourselves into this state is that we have more information about ourselves than we have about the person we are engaging with. We know our actions and our intent; on the flip-side, we only know what they did, and try to deduce their goals based on their action.

More so, we make our deduction based on what suits our pre-conceived notions best.

To overcome this limitation, you must use the “And” stance. The “And stance” is that both stories are right.

Their story is right.

So is your story.

How can that be?

How can two conflicting stories be right?

They can be right because when you argue and have conflicting stories, the argument is not about what is right or true. You are arguing over what is essential.

Here is a situation I faced once. I got feedback from a colleague that my presentation was sloppy.

I looked through the presentation, and there were three grammatical errors.

At the same time, it was a deck of thirty slides which told a complicated story very clearly and led to an important proposal being accepted.

Now, who was right? Me or my colleague?

My colleague was telling a story based on the fact that there were errors. I was telling a story based on the fact that the deck got the proposal accepted.

The conflict that arose was about what was more important in that situation.

However, we had quickly resorted to the “I am right” stance without realizing that we were arguing really about what was more important in that situation.

There are two ways to get through the “what happened” complexity of conversations.

The first way is to disentangle the impact of the action from the original intent.

I felt that they were trying to nit-pick. My colleague’s intent was likely to help me improve; in some sense, mentoring me to have the same level of polish in presentations that they did.

I understood this only several months later. I could have saved a lot of brooding had I had the wisdom to understand this sooner.

The second way is to map the contribution system.

The change in mindset that you need to make is not to get caught in the blame game. The blame game tries to pin one party as the root cause of the conflict.

The contribution system brings a mindset that both parties contributed to the situation. You have to acknowledge that one of your actions contributed to the case, and so did your partner’s actions.

When you begin the conversation by acknowledging your contribution, your partner is more likely going to reciprocate. They will probably recognize their contributions.

The Feelings Layer

Feelings are at the heart of difficult conversations. We try to avoid them because they are uncomfortable to express. But unexpressed feelings cause resentment, anger, and frail relationships. Ignoring emotions is NOT a recipe for constructive conversations.

There are three steps to expressing feelings in difficult conversations.

The first is to get better at uncovering your feelings. Some feelings tend to hide other, more profound, more relevant feelings.

An example of such a feeling is anger. Anger can hide several emotions, such as sadness, shame, regret, and guilt.

So you must take a step back and do two things:

  1. Reframe feelings to be something you are experiencing vs. who you are. For example, don’t say you are angry. Say that you are experiencing anger.
  2. Second, question what might be behind this emotion? Are there other ways you might describe how you are feeling? Here is a useful reference.

The second step is to realize that you can negotiate with your feelings. Your feelings are the outcome of your thinking. You can challenge your emotions by negotiating with your thoughts.

Here is another example. I experienced envy when a particular performance review did not go as expected for me when I saw others get glowing reviews, bonuses, and promotions.

I had to negotiate with my feelings to have constructive conversations during that performance review. I had to look for patterns in other people that had done well in their discussions.

I had to ask, “What’s the story I am telling myself?”

The story I was telling myself was that I sucked. I was worthy of only being rated as inadequate.

The more positive story was, I had misdiagnosed what it took to be successful. I negotiated envy into a feeling of curiosity, a sense of determination. It took work, and I had to make sure that I was following this:

“The first principle is that you must not fool yourself — and you are the easiest person to fool.” — Richard Phillips Feynman

But I ultimately was able to have better conversations about the performance review because I had taken time to negotiate with my feelings.

The third step is to describe these feelings carefully to your colleague without venting. An example of a bad reaction is you say to your colleague, “you are so self-absorbed.” That’s a judgment. The way to reframe that would be to describe what you are feeling, which is “I felt that my opinions were not paid attention to.”

This way of expressing your emotions doesn’t guarantee that your partner will do the right thing, but it’s a much better starting point.

Sometimes, feelings will be too strong for you to deal with on their own. It’s likely then that the conversation has somehow triggered questions about identity.

So read on.

Photo by Kyle Glenn on Unsplash

The Identity Layer

The last layer of a difficult conversation is the “identity layer.” The identity conversation is where you might start to worry about what the conversation says about you.

There are three core identity-related questions that we ask ourselves:

  • Am I competent?
  • Am I a good person?
  • Am I worthy of love?

It takes practice to figure out when your mental state has gotten itself to this place. One trick that works for me is to rate — on a scale of 1 to 10 — if the conversation has raised these fundamental identity questions.

Over time you can start to see patterns, and begin to recognize when your identity triggers are causing you to lose balance. The wider the gap between what you believe to be true and what you fear to be accurate, the more likely you are to lose balance.

You might discover the primary question in your life. And there might be a tendency to classify this as the dark side of the force. Resist this temptation. There is no dark side to this force.

To regain balance, try these things:

  1. Use the 10/10/10 framework to gain perspective on your situation. Ask yourself: Will this matter in ten minutes? Ten months? Ten years?
  2. Get help. You might need a therapist or a coach, or just a friend acting in one of those roles to get past identity-related questions.

Mastering Difficult Conversations

Now that you understand what makes difficult conversations so complicated, lets’ start to dig deeper into how you might master these discussions.

The three things you must do to make difficult conversations successful are:

  1. Begin from the third person
  2. Listen more intently
  3. Speak for yourself with clarity

The Third Person

Being able to tell the story in the third person is the first superpower. I compare it to teleportation.

The third person perspective is the story that an impartial observer would tell.

Imagining in the third person is bound to be unfamiliar at first. The most useful tactic for me is actually to write it down as a story. If I teleported into an observer’s body, how might I tell the story and integrate both viewpoints, I can write the story in the third person.

Writing in the third person gives you space to have a broader point of view and the distance to express it somewhat more objectively.

Listen Intently

Next, you must listen more intently. Intent listening can give you the superpower of mind reading.

A related framework I teach in the Intentional Product Manager foundations class is called SOAR. SOAR stands for:

  • Make Space
  • Observe and validate
  • Ask
  • Repeat and confirm

Speak Up With Clarity

Lastly, you must be able to assertively state your story, without aggression and without getting defensive. Speaking up with clarity gives you the superman strength to start to influence.

You can lead your colleague if you can speak with clarity. If you model the behavior of assertiveness with openness, the more likely it is that your colleague will state their story.

But above all, you must realize one thing. That most of us prefer to be with people who speak their mind. We trust them. We feel confident in them.

You are doing your colleague a service if you expressed yourself clearly.

And you are doing damage to the relationship if you are bottling thoughts, feelings, and emotions.


If you are interested in learning more about “difficult conversations” I highly recommend you read this book.

The skill of navigating difficult conversations well can help you influence, negotiate, and lead. You can become a 10X better product manager if you dedicate yourself to mastering this skill.

As you start to get better, you might even start looking forward to difficult conversations as a place to practice your skills.

You must peel the three layers of the difficult conversations onion: what happened, feelings, and identity.

And you must get better at them by practicing your skills, beginning from thinking in the third person, of listening intently, and of expressing your point of view assertively but without blame.

Mastering Difficult Conversations gives you Product Management superpowers. Use them wisely.

I hope you enjoyed the article!

If you liked the blog post, you will love my free course “How to be an outstanding Product Leader without working insane hours.” Go ahead, enroll now!

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