Tips & Techniques for Having Complicated Conversations: P1

When I ask people, Do you like conflict? Do you think that you are “good” at having complicated conversations?, I usually get a quizzical look, or a blank stare in return.

I’m not asking a complicated question, but the answer seems elusive.

Take this for example: I recently polled a group of company leaders about their relationship to conflict. 40% of them said they avoided having conversations specifically around performance management. 63% of them responded that they believe they avoid 1-2 complicated conversations per week. That means that in this group alone, there are roughly 1,500 conversations per year that are not happening.

Simply put: Avoidance is not good for business.

But why then are we so avoidant of conflict?

When we are faced with difficult conversations, we often react from our most basic fear states. Instead, we want to learn how to manage our emotions so that they aren’t managing us. We want to respond rather than react. The kicker is, in order to manage your discomfort, rather than turning away, you have to turn towards your fear.

There are good evolutionary reasons to be cautious. The negative consequences of conflicts may include ruined relationships, uncertainty, isolation, embarrassment, and damaged reputation. Our avoidance comes from our perception of threat and our brains wanting to keep everything nice, simple, and easy. These brains of ours believe that by avoiding difficult dialogues there is a net positive benefit. In actuality, avoidance does the opposite.

Avoiding pain or any kind of stress constricts our behavior and impacts our sense of self, making us psychologically weaker. This short-term solution of avoiding creates a failure to find solutions to whatever existing problems there are. And those problems are NOT going away on their own.

Simply put: You will not, cannot, reach your potential as a leader, public speaker, parent, friend, or spouse without working with the difficult emotions that come up when  facing complicated conversations.

We have to challenge ourselves and our teams to turn towards complicated conversations – we want to get to what I call, productive conflict.

Productive conflict is defined as: An open exchange of conflicting or differing ideas in which parties feel equally heard, respected, and unafraid to voice dissenting opinions for the purpose of reaching a mutually comfortable resolution.

I can’t stress this enough: Productive conflict is important for all team members, and is essential for leaders. Today’s leaders are expected to have good communication and interpersonal skills. Productive conflict is a positive and healthy exchange between people with different ideas and opinions. Instead of feeling attacked, frustrated, or defensive, team members who engage in productive conflict feel heard, respected, and encouraged. Productive conflict leads to a more cohesive team and a stronger plan shaped by multiple perspectives.

Conflict in the workplace, or at home, is stressful… and inevitable. But it IS possible to transform difference and disagreement into positive outcomes.




So let’s get into HOW we do this.

We start by building trust, and creating context. You have to orient people to what you are talking about and what you want to get out of the conversation. Framing the conversation is setting everyone up for success. Creating context includes things like:

  • Create clarity about the goal of the conversation and the agenda.
  • Don’t beat around the bush. Name the problem, complaint, or request.
  • Make sure the time works for both of you.
  • Set a forward-looking, positive tone.


Setting a collaborative tone means you want to understand their world before you explain yours. That’s because the best solutions will come when there is mutual understanding of each person’s underlying interests. You cannot possibly know all the answers, but you can find them together. Define your shared reality, where you agree, disagree, and where there is uncertainty.

After the person has spoken, ask follow up questions, and tell them what you’ve heard. Remember: Conversation is a two way street and what you say isn’t always what gets heard. Reflecting back what you heard establishes that you’ve captured their thoughts and feelings accurately. Paraphrasing helps the other person feel validated and understood and minimizes potential miscommunications. Summarize what you’ve heard to give the person an opportunity to let you know if you’ve understood them or not. If you have not, ask more questions.


In other words, what you are saying is that you’re frustrated.
I’m hearing that you’re confused about this situation…
Did I understand what you were saying? Anything else important that you’d like to add?


This is my first installment on the tips and techniques for having complicated conversations.

Let me know if you have any questions, or if you’ve tried any of these, and how it goes for you. Stay tuned for Part 2.