Navigating Difficult Conversations At Work

Sam McAfee
Startup Patterns
Published in
6 min readMar 10, 2019
Photo by Jason Hafso on Unsplash

I used to think it was possible to convince anyone of anything, if you could only explain it clearly enough and provide enough data.

As a young engineer, I would structure most of my conversations that way. I would essentially attempt to “wage” agreement on people. I would arm myself with reams of data. I would prepare for every argument like a battle strategist, imagining every possible scenario and having a plan for what I would do should it occur. People who would “ignore the data” really irritated me. Why were they so frustrating to talk to?!

Even as a senior technology leader, I still went about my conversations with either groups of engineers or direct reports — even my leaders sometimes — as though I were a professor, standing in front of the whiteboard, patiently explaining the key concepts to my students.

Boy I wasted a lot of time, because it turns out that none of that stuff really matters. Humans are not rational and we don’t make decisions using logic. The sooner you realize that, the sooner you will be able to break through in even the toughest emotionally charged work conversations.

This becomes most obvious when there is a real conflict involved. Someone talked smack about someone else’s code. Someone shut down a coworker in a meeting. Somebody didn’t get the raise they were expecting. These conversations put your supposedly rational mindset to the test.

Thinking vs Feeling

Unfortunately for many of us logically-minded types, especially engineers, the latest research in neuroscience strongly suggests that thinking and feeling are actually the same thing.

What?! How can that be, you say? For my entire life, I have been strutting around feeling so superior because I can “control my emotions.” Ha ha, not so fast, my friend!

Take it from Dr. Lisa Feldman Barrett, Professor of Psychology at Northeastern, brain researcher, and author of “How Emotions Are Made.” There is an enormous wealth of information in the book, but I’ll just make a single point here for our discussion. Your brain experiences reality through generating what Barrett calls instances of an emotion. Those instances, say of joy, love, fear, anger, disgust, are whipped up in milliseconds by something called the introception network. Emotions exist in your mind as a set of thousands of statistically probable instances of a feeling (basically, predictions of a feeling) that your brain is estimating that you might feel in the next moment. It then continuously prunes down that set based on real time data coming from your senses until it arrives at a dominant feeling that matches the data. It then uses that validated feeling to make its predictions next time around.

Further, this set of emotional responses to stimuli are not separate from your thinking, or cognition. In fact, according to Barrett’s research, this is thinking! The feelings you feel are part of your cognitive process. It’s an integral part of how you look at the world, and how you interpret it. Whoah! Yeah, I know.

In the field of psychology and behavioral economics, Daniel Kahneman provided significant evidence in “Thinking, Fast and Slow” that our supposedly logical functions in our brain’s System Two are massively overdetermined by our emotionally excitable and fast-thinking System One. And in fact, there has been evidence for many decades in psychology that has suggested a tighter link between how, say, a psychiatry patient feels and how they think about how they’re feeling.

Emotions matter considerably in conflict-rich environments. In negotiations with international terrorists, as described vividly by former FBI hostage negotiator Chris Voss, in his excellent negotiation book “Never Split The Difference”, emotions are everything in negotiation. Voss, who is not exactly someone you’d call touchy-feely, comes right out and drills into readers that the keys to success in successful negotiation is building empathy with your counterpart. He suggests a number of methods throughout the book, including techniques for mirroring back to the person what they just said in order to help make sure they know that you understand their point of view.

We don’t have to go that far down the rabbit hole to make use of this information. Keeping it simple, the way I suggest you think about this is by rejecting from now on the notion that feelings are not part of a difficult conversation. In fact, feelings are the core of the conversation. When you are navigating a conflict in the workplace, either between two other coworkers or between someone and yourself, you will be able to manage the process better if you can show that you appreciate the feelings of all parties.

Build empathy first

The key to managing difficult conversations is building empathy. People need to feel heard before they can listen to anyone else. No doubt you have seen this in action in the workplace. Think back to a time when you witnessed or were part of a tense discussion at work. Do you remember parties vigorously trying to make their case before listening to the feelings of others? How did that approach go over? Not so great, huh?

Remember that one of Steven Covey’s 7 habits of highly effective people is to seek to understand, before being understood. That means, for the most part, shut up and listen. When you find yourself in a difficult conversation at work, try these things:

  1. Choose the setting carefully. Don’t just start having a confrontational discussion in the middle of the office. If there is a difficult conversation to have, it’s best if it is held on purpose and in a way that empowers everyone there. That means at a time and place that all parties agree to in advance, and in a private and comfortable setting. Even the configuration of the room — seating arrangements, temperature, and lighting — can effect how comfortable people feel. Consider as many factors as you can to make a safe space for discussion.
  2. Talk less, listen more. Start out a difficult conversation simply by asking the aggrieved to express their view of the situation. Don’t interrupt, just let them talk as long as they need to. If they get stuck, or slow down, maybe ask “and what else?” Don’t be impatient though. Silence is necessary for helping others feel calm enough to proceed with more details.
  3. Consider the power relations. In any conversation, there will be differences in power. This is especially true in work situations where the organization is hierarchical. Do not discount how overwhelming the feeling of powerlessness can be. Calling it out in the discussion, and getting everyone present to see it and agree that it is there, can make a huge difference in the tone moving forward.
  4. Volunteering over assigning. Do not expect people to carry out any action items that were not their idea, or that they didn’t sign up for. Instead, allow participants at the end of discussion to brainstorm and choose their own takeaway goals or action items they want to accomplish as an outcome of the discussion. Assignments will be seen as an imposition rather than something reconstructive.
  5. Follow up. Don’t just leave people hanging. Especially if you are in any kind of leadership role, even informally, it is critical that team members see you caring about their well-being later on by coming back around to check in on them and their feelings. If there is an open loop that remains unclosed, it will not only bring the difficult conversation back unresolved, it will probably make it worse the second time.

Finally, I would be seriously remiss were I not to say something about diversity in difficult conversations at work. In particular, this is critical when mediating any difficult conversation at work, where it is certain that social categories like ethnicity, gender, class, and so forth have a profound impact on outcomes. In step 3 above, the “power awareness” that I encourage parties to embrace includes all of the ways in which certain groups are less privileged than others, not just the hierarchy in the organization itself. As a white dude in the tech business, a role with considerable privilege, it is my responsibility to regularly get out of my comfort zone as much as possible, and raise the issue of how my privilege might affect others before waiting for them to bring it up. Pretending that aspect of work doesn’t exist will only make outcomes worse when navigating difficult conversations.

Be a better technology leader

Learn to apply these skills in the context of your organization. Check out the Startup Patterns master class on technology leadership. We cover topics like how to discover and pursue your purpose, effective communication, how to manage up to executives, and how to lead change in an organization using influence rather than authority.

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Sam McAfee
Startup Patterns

I train, coach, and develop technology leadership in startups, small business, and enterprise. I write at StartupPatterns.com/blog now, so head on over.