Master Difficult Conversations

Difficult conversations are a fact of life. The release is delayed. Someone on your team is not performing. You’re not hitting your numbers. Or the ever-present conversation for PM’s — you can’t prioritize a request from a stakeholder. Mastering difficult conversations is essential to being an effective communicator, and critical for product managers who want to rise as leaders.

In the Unseen Battles Podcast that my friend, Parul Goel, launched this week, I shared my story about one of the most difficult conversations that I’ve had: telling my manager that I was pregnant. You can hear more details about what happened and my thoughts on maternal bias and the gender gap on the podcast, but the key takeaway here is that I didn’t expect the conversation to be a big deal, so I didn’t prepare for it, and it didn’t go well.

Unseen Battles Podcast, Episode 1

After that experience, I’ve thought back to that meeting a lot. How could this difficult conversation have gone differently? Over time, I’ve reflected on that meeting and others, and learned what makes difficult conversations effective. I’ve incorporated all of the learnings into the R.A.R.E.R. framework.

Master difficult conversations with the R.A.R.E.R. Framework

RECOGNIZE if the message that you need to deliver will be a difficult conversation

Simply being aware that a conversation has the potential to turn difficult will enable you to better prepare for the conversation. In the example that I shared about telling my manager that I was pregnant, my mistake was underestimating how he would react to my message. If I had expected this to be a difficult conversation, I would have prepared differently by jotting down key points that I wanted to remember to touch on or brainstormed ideas to mitigate his concerns. Instead, I was blindsided and forced to improvise on the spot. Try to think ahead and identify what outcome you need coming out of the difficult conversation.

ANTICIPATE how the other person will feel upon hearing your message

Imagine how you would feel if you were the one receiving the message. As you do with features that you build, put yourself in the shoes of your “user.” You can deliver the same message to different people, and have it be received very differently. Here are some questions to ask yourself:

  • How well do you know the other person? Their reaction will be easier to guess if you know the person better.
  • How important is your message to the other person? Their reaction will be stronger if it’s important to them — such as if it impacts an issue they care deeply about.
  • Is the message a surprise or have your communications been building in this direction? Their reaction will be stronger if it’s a surprise.
  • How much does the other person trust you? Their reaction will be stronger if the other person has not built trust with you.

RESERVE time for the other person to voice their point of view

Deliver the message as clearly and concisely as you can. Don’t make it into a Shakespearean monologue. Instead, pause. Let the empty air space invite the other person to share their reaction. As they talk, listen actively to understand:

  • Are they sharing new information?
  • Are they bringing up any points that you had not thought about?
  • What do they need to get out of this conversation?
  • On which points do your views converge? Where do your views diverge?

EXPLAIN your point of view

Acknowledge what the other person said. Now, share your reasoning. It’s important to help them understand your thought process, but also to show that you were listening to them. You can do that by highlighting points of convergence or referencing new information that they have brought to light.

RESOLVE jointly to the path forward

Close the conversation by steering the meeting towards the plan to move forward. What can you agree on? Are there next steps that require further action? Do you need resources or support from the other person? Make sure the conversation ends with you achieving the outcome that you needed from it.

You can use the R.A.R.E.R framework (Recognize, Anticipate, Reserve, Explain, Resolve) as a template for your difficult conversations. To grow even further, you can take your communication skills to the next level by journaling about your difficult conversations. How did you feel during the conversation? What went well? What would you have liked to have gone differently? Through practice and reflection, each conversation will get less difficult than the next and you may find yourself transforming into the most rare of all zebras, the coral and green striped master communicator. 😊

I write about once a week about topics like product management, design thinking, becoming a better leader, and personal branding. By subscribing to my newsletter, you’ll get these insights emailed right to your inbox every time I post.

Friday Flashes is a series of quick one-minute videos that introduces a topic of reflection for the week. Each prompt is product-focused and ties back to one of the ten disciplines in the Product Decagon.

The Productive Product Manager is a guided journal that combines the weekly reflection with weekly review and other goodies. You can see the inside of the journal in the Friday Flashes announcement video. Don’t worry — the journal is not dated, so it’s ok if you don’t start at Week 1.

Lauren Chan Lee is a product leader who enjoys writing about the connections between product principles and everyday life. Learn more at: