Books for software engineers and managers

Difficult Conversations

Difficult Conversations

How to Discuss What Matters  Most

by Douglas Stone, Bruce Patton, Sheila Heen

Engineering Manager

How strongly do I recommend Difficult Conversations?
9 / 10

Review of Difficult Conversations

Difficult Conversations is a top read for everyone, providing pragmatic tools and techniques for improving both our personal and work lives.

In a work context, I think this book and the approaches discussed are particularly important for engineering managers of people because we’re often faced with difficult conversations around individual performance, delivery schedules, and project priorities.

For guidance more specifically on negotiations, check out Never Split the Difference.

Difficult conversations are mostly about feelings, not  facts

When you’re having a difficult conversation, it’s easy to focus on facts.

Facts are objective. If you can agree on the facts, surely you’ll arrive at similar conclusions, right? Well maybe not.

That’s because difficult conversations are fundamentally about feelings, not facts.

I once had a difficult performance conversation with an engineer and thought it best to establish the facts up front. Whoops. 90% of the subsequent conversation focused on facts. Who said what, who did what, blah, blah, blah.

Focusing on facts can lead you down a very pedantic, nit-picky, and ultimately unproductive path. People can sense when the wall of facts is building against them or a gotcha is on the horizon. That’s when they either fight like a dog in a corner or tune you out.

The second time around, I change things up to use this feelings-first approach. I started by describing what I was feeling and experiencing. What the impact of their behavior on me was. Then I encouraged the engineer to do the same. This feelings-first approach led to a much more productive conversation.

Map the contribution  system

Engineering managers like feeling prepared. We pride ourselves on planning the details. So we rightfully prepare for difficult conversations.

Foremost, we prepare a list of problems. Usually problems contribute by the other party, often an underperforming engineer or failing partner.

If they just fixed these things, we’d be squared away, right? Now we have a solution. Excellent. This concludes our preparation… but it shouldn’t.

Focusing blame on the other party is fundamentally a disempowering position. You’re at the mercy of them changing.

You also need to look at the ways you contribute to the problem. One of the biggest ways managers contribute to underperformance is by avoiding the difficult conversation. So give yourself some credit for at least remedying that underlying issue.

But likely your contributions also span day-to-day interactions both with that employee and with other employees. Culture is what you celebrate and tolerate, so consider the implications for your underperforming employee.

Don't jump to problem  solving

Difficult conversations feel awkward and stressful.

In response, we try to alleviate tension by jumping to problem solving. Big mistake.

Before hopping into problem solving, you need to ensure that the other person understands how important this conversation and issue are to you.

Communicating this importance is a necessary precursor to solving the problem, so don’t rush it.

Stop trying to control  reactions

When delivering bad news, you’ll be tempted to control or mitigate the other person’s response. It goes like this:

“Sorry, we have to let you go. But don’t worry, I’m sure you’ll get back on your feet in no time. Plenty of software companies are hiring and I think you’re a great engineer, but right now it just wasn’t working out. I’m happy to be a reference for you.”

Of course, you have good intentions. But more fundamentally you’re just patching over the awkwardness, often by blabbering on with cushiony language.

Instead, just sit with it. Let the person react. This conversation is as much about you as them and they deserve space.

Ask the other person to paraphrase  back

Teachers and trainers call this a “check for understanding.”

Even when you think you’re crystal clear, ask the other person to paraphrase back what you’re saying. For instance, if you’ve just explained how their behavior makes you feel and the impact on you, explicitly ask them to tell you what they heard.

In other words, don’t assume alignment or understanding. Confirm it.

Also, be a little careful about how you request the other person to paraphrase back. This is about you making sure you’ve communicated your experience and feelings well, not about them parroting back to you something they don’t believe in.

Difficult Conversations