How To Navigate Difficult Conversations

Tom Armstrong
Tom Armstrong

Early one morning in a packed New York City subway car I had a failed attempt at a difficult conversation. That morning the train was especially crowded. I was standing in the middle of the subway car with one arm up on the bar and was being jostled about as the train navigated the century-old tracks. 

The person sitting directly in front of me had crossed their legs so that one foot was sticking out into the packed crowd. Their shoe, which had until then been walking around on New York City streets, was now about a quarter of an inch away from my pleated slacks.

“Excuse me,” I began. “Your foot is sticking out. Please move it”.




“You’re rude!”

You’re rude!”

Mission not accomplished.

When I arrived at our office I spoke to a colleague of mine, Greg Shamie, about it and he suggested that if this situation came up again, and it felt safe to do so, I might try the following:

  • Lean down if possible so you are not towering over the person and soften your expression.
  • See things from their perspective. Consider that they may have gotten on the train earlier when the train was empty and have been so engrossed in their book that they didn’t realize they were sticking their foot at other passengers, or imagine they recently got some bad news.
  • Here’s a sample sentence, “Hi. Excuse me. I don’t mean to interrupt. The train is pretty packed and it is hard for me to stand. Would you mind please just positioning your shoe so that I can move my legs a little more?”

I have taken his advice and it has worked every time (yes, this happens a lot on the train). People want to be treated with respect, even the ones who are being disrespectful. If I approach tough conversations with humility I am much more likely to get the results I seek.

Another colleague of mine, Erika Petrelli, showed me a wheel she created years ago that helps to get difficult conversations on a constructive track. I apply the wisdom I learned from my adventures on the NYC subways with Erika’s Difficult Conversations Wheel and have seen my success rate go through the roof when having difficult conversations at work, including with our biggest clients. Here are the 10 step-by-step guiding questions from her wheel:

  1. Why do I need to have this conversation? What are the facts?
  2. What assumptions do I have?
  3. How have I contributed to this situation?
  4. What outcome am I hoping for? What is the goal?
  5. When and where will I have this conversation?
  6. How might the person react? How will I respond?
  7. What blocks me? What do I need to watch out for in myself?
  8. What else do I need to prepare for this conversation? Whose input do I need?
  9. How would I want to be treated if someone were having this conversation with me?
  10. If it doesn’t work, what next?

When I prepare for any difficult conversation by first asking myself those ten questions I almost always get the results I am hoping for. In the vast majority of the cases the conversation ends with smiles and the relationships become stronger than they were before the issue arose.

By preparing beforehand you are showing the person respect. This alone goes a long way in having conversations that get you the results you need.

But what if they push back? 

A common challenge that managers face when having tough conversations is figuring out how to navigate a situation where an employee is disagreeing or denying there is an issue during the conversation. Classic leadership fails abound here, especially if the manager is certain they are right. We aren’t paid to be right. We are paid to be effective. So righteousness aside, ask yourself, “What is the best path to take to get the result I want?” or “What is the problem I am trying to solve?” and then act accordingly.

We are emotional beings. So when we sit down with an employee who, for example, we know has been showing up late and they insist they haven’t been late it’s hard not to go on defense. When that feeling of moral superiority starts kicking in, it’s time to relax and become curious rather than condescending. 

Having a genuine calm and perhaps even a sense of humor in that moment shows leadership and confidence. Listen attentively and repeat back to the employee what you heard them say to make sure you understood - and to make them feel understood. It’s actually a great opportunity to build trust and they might correct any misunderstandings before you go into mandate mode.

Mark Horstman from the Manager Tools podcast makes a great point about the value of not arguing when a direct report argues against your feedback. He points out that your goal is to communicate to the employee about the future behavior that is needed for them to be effective. You probably don’t need to win the current argument to do that. 

The message has been sent: don’t be late to future meetings. 

Of course, if the employee is late again to future meetings and again claims they weren’t late - you have a whole other issue on your hands, which is beyond the scope of this post. I find this is very rare, however. In the vast majority of situations, the message will be received and for future meetings, they will arrive on time.

There is another advantage to being curious as opposed to digging in when employees push back during a challenging conversation. Quite often there is a reason that feels to the employee as quite justifiable for whatever it is that you are speaking about. 

Sticking to the theme of lateness, I have had employees push back on this because they had a child that was sick frequently, which was making them frequently late. That was important information for me to have and we created a plan based on it. 

In another conversation, I learned that the employee was using an outdated app on their phone for navigating public transportation in NYC. In our meeting, we discovered and fixed that problem. They were on time for future meetings and left our conversation feeling supported rather than humiliated, which is how you build strong relationships with your team. 

I have also examples of talented and otherwise effective employees who pushed back and continued to show up late. At that point, I escalated the process to include a performance improvement plan as this was necessary to clearly and irrefutably establish expectations. But again, this is very rare. I find at least 90% of these types of issues are resolved by using the tools and techniques outlined above.

For further reading, Douglass Stone, Bruce Patton, and Sheila Heen of the Harvard Negotiation Project also did research and wrote a book titled Difficult Conversations: How To Discuss What Matters Most. I am not affiliated with them (or Mark Horstman) in any way, but I do recommend this book for further reading on the subject.

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Tom Armstrong

By Tom Armstrong

Tom Armstrong started with The Leadership Program in 2007 as a trainer teaching leadership skills through the art of percussion. As a professional musician, Tom quickly found that his love for teaching was not limited to percussion. Fascinated by the idea of using the arts as a way to engage youth and adults, Tom began teaching leadership concepts through the arts and grew in the organization to his current position as Senior Director of Programming. He now oversees the successful implementation of programming for over one hundred schools. As a Project Management Professional, Tom also applies his expertise in project management to help businesses achieve their benchmarks for success in all areas of effective management and corporate culture building.