Making Difficult Conversations Less Difficult

“We have difficult conversations” is one of Lessonly’s values. It is an incredibly important ambition for our team. When done well, difficult conversations foster psychological safety and give our team a significant competitive advantage. In life and work, there are many valuable conversations that are easier left unsaid. These are the difficult conversations we need to be having—they help us address the tension and conflict that might otherwise keep us from doing better work.

People on the Lessonly team appreciate this sentiment, and time and again, when they are privy to—or the driver of—difficult conversations, they find value in them. However, I’ve learned that “we have difficult conversations” is a difficult concept to teach, and is even more challenging to put into practice.

Most of us have lived our lives without much guidance for how to process tension or conflict, let alone directly address it. Seeing no better way, we prefer to cross our fingers and hope the feeling passes or the situation resolves itself. Oftentimes, neither thing happens.

In all the literature I’ve seen on the topic, conflict avoidance does have a place, and it’s when the conflict is momentary. For example, if a perfect stranger passes you on the street and says something rude to you or your friend, you should keep walking. Here’s why: If you’ve never seen the person before, it stands to reason you aren’t likely to see them again. Letting it go and continuing to walk ends the issue.

Non-momentary conflict, though, should generally not be avoided. If it has the potential to fester and divide, it should be discussed. But in order for people to talk about issues directly with others, they need to learn how. So I’ve been hunting for guidance, asking my teammates and mentors if they know any good methodologies for difficult conversations. My favorite so far is Nonviolent Communication. My colleague Casey recommended it to me, and I can seriously say that it is changing my life.

I am going to write a four-part weekly note on this idea. This is part one: the introduction. In coming weeks, I’ll share:

  • New ways to think about tension and conflict
  • How we tend to share our evaluations instead of observations, when the latter is way more useful
  • How the nonviolent communication methodology works

Ideally, this series will help us all understand one another better and give us tools to work through tension and conflict before they rot our baseboards—or our relationships and teams.

Would love to hear from you about the role of tension and conflict in your workplace. As always, feel free to email me.

Until next week,



This is Max’s note—a weekly message from Lessonly’s CEO about learning, leadership, and doing Better Work. Sign up below to subscribe via email. No spam, we promise!

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