In one of my favorite quotes from Tim Ferris, he says “A person’s success in life can be measured by the number of uncomfortable conversations he or she is willing to have”.
And oh how true I have found this to be!
Early on in my career, I would try and avoid uncomfortable conversations. I felt that I should just suck it up and deal with whatever was going on.
Once I started supervising other people, I had a completely different perspective! Lots of uncomfortable conversations were needed to:
1. Communicate clearly what my expectations were
2. Give feedback (as is expected from a manager)
-and-
3. Have my people’s backs when they needed me. I had to speak up and be an advocate for the people that work for me!
Having uncomfortable conversations as a supervisor helped me, in turn, to be more ok with advocating for myself.
At this point in my career and life, I have to say that I actually enjoy having uncomfortable conversations. I know that if I’m starting to get those butterflies in my stomach I’m on the right track. I’ll only feel better, be more productive, and have better outcomes and understanding on the other side of that conversation.
So here’s what I’ve found works for me in my approach with uncomfortable conversations:
1. If I’m feeling emotionally charged, I’ll take as long as it takes to calm my mind.
2. I think about why this is important (to me personally or to the goal we’re trying to achieve).
3. I think about how to deliver my message with compassion, since the ultimate goals is to have a productive outcome, not to flatten the other person.
4. I think about what my ask is, or what my desired outcome is.
5. Then I go do it.
When I’m nervous, that’s my cue that I need to have that conversation. When it feels like there’s a lot on the line, like there’s potential for me to mess it up, that’s when I push forward because that means it’s important.
And when I’ve had that conversation, I’ve never regretted it.
What uncomfortable conversations do you need to have?