Embracing the awkward

Tips for uncomfortable conversations

A person's success in life can usually be measured by the number of uncomfortable conversations he or she is willing to have.
- Tim Ferriss

I was reminded of this quote today when a friend shared his anxiety about upcoming conversations with customers about price increases.

Although it may not hold absolute truth, this is a maxim that has proven valuable for me. In both my personal and professional life, I can trace some of the most important breakthroughs to uncomfortable conversations.

It’s tempting to avoid difficult conversations, but in doing so we often forfeit opportunities for growth, connection, and service to others. They are necessary hurdles along the way to where we are aiming.

Discipline is choosing between what you want now and what you want most.
- Abraham Lincoln

Tips for Uncomfortable Conversations

Talk in person (or as close to it as possible)

Physical presence, body language, and tone of voice are vital to a productive conversation. If you can’t talk in person, prefer video and then phone. Avoid written communication if at all possible.

Out yourself

Bring vulnerability and honesty to the conversation. Are you anxious? Consider prefacing your conversation with statements like:

• “I feel a bit awkward asking you this…”

• “This is uncomfortable for me."

• “I’m not sure if this will hit the mark but I wanted to share this with you.”

This is both an aid to your own mindset and a powerful human connection.

Pre-Game

Clarify your thoughts by writing them out and/or talking through them with someone you trust. To prepare for tough conversations with colleagues, I’ve found it helpful to talk it through with our company’s HR lead and my boss.

Use a model or framework

There are great frameworks for all kinds of uncomfortable conversations. For example, we encourage people to use clearing conversations, which provide a structured approach to conflict resolution. In negotiation, consider the techniques presented in this Never Split the Difference cheat sheet.

Practice in low-stakes situations

Identify some areas where you can practice and stretch yourself. Check out the comfort challenges that Tim Ferriss suggests for inspiration.

Reflect

Process the conversation by journaling. What went well? What didn’t? What could be improved next time? Anything to follow up on?

Follow-up

If the conversation didn’t go as well as you hoped, try again. Apologize if you overreacted. Try again if your pitch fell flat. If the other person seemed distressed, check in to see how they are doing.