Preparing to Have a Difficult Conversation

What to do when it’s time for some tough talk

By Ken Norton

7 min read • Nov 17, 2022

Ken Norton

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[Comic book scream: Aargh!!]

Frequently, a coaching conversation orbits around a difficult conversation: everything from firing an employee, confronting a disrespectful co-worker, delivering tough feedback, to having a heart-to-heart with a co-founder. Sometimes procrastinating or avoiding the conversation is the source of persistent anxiety. Or the client is aware that the conversation must happen but doesn’t know how to prepare. At other times, the client is picking apart a discussion that occurred in the past, looking back with regret on how they might have handled it differently. Often, something is being unsaid that needs to be said, and the difficult conversation is meant to bring it to the surface—you might hear me call these “Name the Elephant” moments.

Some years ago, when I was at Google, an engineering director held in high esteem reached out to me to talk about one of my PMs. He wanted to share some first–hand concerns and some frustration that had bubbled up from his engineers. He was precise, to the point, and constructive. He started the conversation by taking an interesting third-party perspective on the problem, almost as if he was a wise observer noticing what none of the parties could see. Even though he had some hard to hear feedback for me on how I could handle the situation better, his framing was constructive and blameless. We had a fruitful conversation that strengthened our relationship and only increased my admiration of him. I left that meeting wanting to learn how to do what he did.

I soon discovered that Google offered an internal course called “Having Difficult Conversations,” run by the company’s outstanding internal learning and development team in conjunction with the Harvard Negotiation Project. I immediately signed up and, several months later, took the class. It was fantastic. A version of the class is occasionally offered through Harvard and the creators also wrote a book called Difficult Conversations: How to Discuss What Matters Most.

In the class, we were taught to prepare for difficult conversations by walking through a series of steps. I’ve since streamlined them down to five. The book and the course go into much more detail and address the mechanics of the conversation itself, but today I’ll focus only on the “how to get ready” part.

1. What Happened

What are the indisputable facts? Where does your story come from? Theirs? What might their intentions have been? What have you contributed to the problem? It’s vital to carefully consider the facts from the other party’s point of view.

Example: “My CTO kept interrupting me during product review to disagree about our release dates. It got pretty heated.”

2. Explore Your Emotions

What emotions are present? Name them (e.g., frustrated, scared, angry) and identify where and how you feel them in the body (e.g., tightness in the jaw, twisting in the belly). What is behind these emotions? Do you choose to allow, accept, or appreciate them?

Example: “I’m frustrated. My fists are clenched, and my heart rate is elevated. I’m also worried. There’s a lump in my throat. I’m frustrated at the CTO for attacking me and worried that our relationship is going off the rails.”

3. Ground Your Identity

What’s at stake for you? What story that you tell about yourself might be getting triggered? (This section will sound familiar to anyone who read my previous newsletter on how to receive feedback: identity triggers abound there too.)

Example: “I see myself as a competent, level-headed product leader who always has their finger on everything going on. Disagreements about the timeline made me look weak, unprepared, out of the loop, and might undermine that identity.”

4. Check Your Purposes

What do you hope to accomplish? Is a conversation the best way to do so? What happens if you don’t raise the issue and let it go? What values of yours might be relevant?

I can’t begin to tell you the number of times I’ve gotten to this point and realized the conversation the way I’d contemplated it wasn’t going to serve anyone except myself. Frequently, I would notice that my sole purpose was to unleash some pent-up anger. “I’m mad that this person made me feel bad, and I need to get it off my chest.” With my own coach, I’ve developed more emotional intelligence. I’ve learned to acknowledge and release my feelings, making finding a more constructive purpose and advancing to the next step considerably easier.

Example: “After I process my emotions, I see that my main purpose in having the conversation is to repair our working relationship. Collaboration and fun are important to me and to the success of the team. But I also need the CTO to understand how their aggressive approach was hurtful.”

5. Write the “Third Story”

First, describe the problem from your perspective. Then, try to explain the situation from the other party’s perspective. When considering their story, try to understand who else might be influencing their point of view or actions behind the scenes. In the fictional example of my CTO, they might have been protecting their engineering team just as I might have been influenced by the CEO’s relentless pressure to launch this quarter. Go back and forth until you’ve fleshed out the two stories.

Now, try to tell the third story, the invisible story that a keen observer might tell. This is the most powerful part: It can be almost magical. Imagine this story coming from a neutral, disinterested bystander, like a mediator. This story includes both the parts that would ring true for both parties and the difference between the stories—the whitespace formed in the middle. This gap between stories isn’t right or wrong, or better or worse; it’s just the difference. (During our in-person training, we practiced by physically moving between three chairs placed in a triangle.)

If you’d like, you can also try to tell the third story by taking the perspective of the relationship itself. This is a relationship coaching technique emerging from family systems theory and can be a tricky concept to get your head around at first. It’s applicable to relationships of any size, from individuals and teams to entire organizations. As an example, imagine a married couple. There are the two partners, but also the marriage. The marriage is its own entity, greater than the sum of its parts, and shaped by forces beyond the two people (such as their jobs, inlaws, children, or the home environment). It can almost seem to have its own knowledge and understanding. Try to step into the relationship. What does it see, what does it know that the individuals do not, and what story might it tell if it could speak?

Triangle with three corners labeled My Story, Their Story, and Third Story

When you enter the conversation, you begin by describing this third story, then sharing your purpose, and finally inviting the other party to partner with you to solve the problem. Here’s an attempt at an opening based on the third story with that CTO:

“I’ve been thinking a lot about what happened between us in yesterday’s product review. I came away feeling frustrated, and I suspect you did as well. It seems like we have two different standards for what constitutes launch-ready and we’re each unhappy with the other’s approach. I worry this dispute has undermined the positivity and trust that exists in our relationship. Our partnership is important to me and I wonder if we might talk about that? I’d like to better understand what was happening for you, how you felt about the meeting, and I’d also like to share what I found upsetting.”

Throughout the conversation, you’ll need to listen to their perspective, share your viewpoint, and reframe as necessary. Here’s the thing: the third story isn’t an excuse for you to back down. You’ll need to express yourself with clarity and power, taking a stand for yourself. If you don’t fully express yourself, you’re not leaning into the relationship. This is a critical point because the “see both sides” framing can make it easy to self-sabotage by ceding your own perspective. Remember: it’s a third story, not a complete surrender to their story.

This technique isn’t an easy button. One of my “aha!” moments from the course was the understanding that productive conversations will still be a grind. This is especially the case when the other party argues from a place of blame or emotion and is slow even to consider the third story. If the conversation is too painless, one of the parties might have prematurely ceded their perspective in a way that won’t be productive for the relationship over the long term.

The conversation will probably be uncomfortable, but you can see how beginning with the third story helps it off to a more productive start. One thing that wasn’t obvious at first and only opened up from the third story was the recognition that we each have different quality standards around launches. I have the opportunity to invite the other party to partner with me in figuring that out. From there, we’ll begin to explore their story and my own, express my viewpoints, and hopefully advance to problem-solving mode together.

Further Reading on Difficult Conversations

Ed Batista, a fellow executive coach, wrote about preparing for difficult conversations, including some overlooked facets such as location, timing, and physical space.

Adar Cohen, a conflict resolution expert, has another approach that emphasizes “moving toward, not away from the conflict,” acting as if you know nothing about the situation, and staying quiet (especially in the beginning).

➤ Marshall Rosenberg’s classic and influential book Nonviolent Communication is always a handy resource to have by your side when it comes to this topic.

➤ Brené Brown tackles tough conversations in her book, Dare to Lead (here’s a recap). I love how Brown returns again and again to values. How might you best honor your values during the discussion?

Originally Published: November 17, 2022

This article was originally published to my private newsletter exclusively for executive coaching clients and alumni

Ken Norton is an executive coach who works with product leaders. He spent more than 14 years at Google where he built products used by more than 3 billion people.