What’s Worse than a Difficult Conversation? Avoiding One.

In leadership roles, the most important work often happens in the least comfortable spaces. Handled well, risky and confrontational conversations — especially those that surface awkward facts or get to the source of organizational tensions — can improve how we relate to each other, help organizations get a better grip on reality, and enable leaders to make better decisions.

Yet while we tell ourselves that these conversations are tough because we don’t want to upset the other person, usually the squirmy feeling we’re experiencing has less to do with our counterpart and more to do with our own unconscious anxiety about not being able to handle the conversation well. Overcoming these anxieties and having the tough conversations anyway is one of a top leader’s most difficult challenges — critically needed yet chronically hard to do.

For advice on how to handle it better, I turned to executives who have conversations on some of the trickiest topics in an organization: trust on teams, organizational restructuring, and addressing underperformance. By definition, these kinds of conversations require you to get out of your comfort zone. You may even feel like you’re betraying former loyalties to past products, old ways of working, personal affiliations, or previous professional identities.

I found that four elements make the difference. First and foremost, in my own experience and with the executives I’ve talked to, is a shift in mindset from seeing difficult conversations as a hurdle to seeing them as a resource. Difficult conversations can actually strengthen personal bonds if you handle them well.

To learn more about the other 3 elements of handling difficult conversations, read Deborah Rowland's full article here on HBR.org.