How to Have Difficult Conversations

Feedback is a gift. Here’s how you can give and receive it.

I was devastated by the first negative feedback I got at work.

The feedback came from a mentor-type figure who had taught me so much and supported me both personally and professionally. I saw her as my champion until my manager, surprisingly, told me otherwise.

I felt betrayed. That day, I wrapped up work early and went home to binge-watch Friends. It took me a week to realize that my disappointment might have come from being doubted for the first time in my life.

I was shocked at how naive I was. Then, I told myself, “It’s time to learn about receiving and giving critical feedback.”

A year later, I was on the other end.

While my intuition told me something was off from the get go, I convinced myself to wait until the value gap is so large that we could no longer ignore. I had to let one of my early hires go.

It was my first time dismissing someone, so I consulted my leadership coach for advice. He helped me understand what it would mean for my team and coached me to develop a concise message for everyone.

I want to share some of the key lessons I learned along the way.

How to have difficult conversations?

One of the key LivingOS principles is transparent communication.

Team principles unite a diverse team because people can align their behaviors with your expectation and help you decide who is the right fit for your team, instead of relying on your gut feelings.

This means that I will proactively give feedback to help my team grow. After giving and receiving tons of critical feedback, I want to share some of the lessons with you:

  1. Feedback is a gift: We give feedback because we care and want the person to be better. We care enough to have these hard conversations that are often uncomfortable, so we should be thankful for all the feedback we receive.
  2. Ask for permission: Even though we are doing them a favor, we don’t have the right to give feedback without mutual consent. Thus, we should always seek permission or (even better) coach the person to bring up the issue themselves.
  3. Talk at the same level: Once you get the consent, you need to answer questions at the level they were asked. If you give more than what they are asking, you will make them feel inadequate and waste your energy. You want to be mindful of the receiver’s capacity and elegantly adapt to their needs.
  4. Use the 70/30 rule: Let the other person talk for 70% of the time. Be curious and listen with curiosity. You want to fully understand their perspectives before you make any judgment. Otherwise, you won’t be able to lead them towards effective changes.
  5. It’s OK to not have an answer: You may not know how to respond to certain comments at the moment, and that’s okay. Don’t feel pressured to flesh out all the details at the moment. Just say “Okay, thanks for sharing that. Let me process it, and let’s talk about it later?” One of my decision-making principles is to sleep on all irreversible and significant decisions for 48 hours.

👉🏻Check out Crucial Conversations for guidelines on how to navigate difficult conversations.

In your daily life…

I encourage you to share feelings and have honest conversations with your partner, co-founder, and team every week.

Having tough feedback is hard, but the feedback is meant to help you grow and get better. That tough feedback has exponentially accelerated my growth and given me unique insights into life.

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