How to Have Difficult Conversations

The first time I had to fire someone, I was in my mid-30’s. I had just taken on my first managerial role, and the very first directive I received from my boss (who had been managing the team before me) — was to fire Jim, one of the senior members of the team. Jim was at least 20 years older than me, and in another city. I made arrangements to fly to meet him, my heart heavy and my nerves jangled the entire trip.

I sat in the oversized conference room sitting face to face with Jim, and within 10 minutes, I had fired him. He was incredibly professional- even kind. His parting comment to me was “tell the boss he is a coward for making you fly here to do this- he should have done it himself”.

Unfortunately, since that time I have fired many, many more people for many different reasons. I have also had incredibly difficult personal and professional conversations — as most of us eventually will, on a wide variety of topics. Jim’s reaction always stuck with me- his poise and grace under pressure, as well as his undisguised venom towards my boss for sticking me with the difficult task.

I have had a lot of time to think about how to deliver, and also receive, hard messages. Here are my thoughts:

1) As mentioned in this post, you can’t beat “speaking the truth with love” as the best foundation from which to build the delivery of a message. It can be painful to share bad news- but if you start from a place of finding the courage to speak the truth, with as much caring about the other person as possible, it will set the conversation off in the best way possible.

2) Don’t beat around the bush. If there is something that needs to be said, just say it. It may feel cold to just get to the brutal reality — particularly if a job (or a relationship) is being terminated. But there is no glossing over that will make the message easier — just say it. As Colin Powell once said “Bad news isn’t wine. It doesn’t improve with age”.

4) Don’t be like my boss who made me fire Jim- sticking someone else with your dirty work is just low. Take responsibility and own your decision.

5) Prepare. If you are giving life changing news, make sure you are clear on what you want to say. I am a fan of writing it all down. If I don’t write it down, I have a tendency to go over and over and over in my head what I am going to say (even to the point of dreaming about it). Writing it down gets it out of my head and lets me evaluate it in black and white.

6) Know when to listen, and when to end the conversation. If a decision has been taken that is non-negotiable, prolonging the discussion can just make the other person think there is hope. It may make you feel better but making sure they know that there is no hope, if that is the truth, is far more kind.

What about when receiving feedback? There is a really good book called “Thanks for the Feedback, the Science and Art of Receiving Feedback Well”, by Douglas Stone. He makes the point that most people think they are great at giving and receiving feedback, but shockingly the people they give feedback to, aren’t good at receiving it, nor are the people who give them feedback good at giving it. The human condition summed up — lack of self-awareness is unfortunately most common around the topic of feedback.

So, how to receive feedback well?

1) Listen. Really listen and try to hear what is being conveyed. Imagine (even if it isn’t true) that the person giving you feedback is speaking the truth to you with love — and try to hear it through that lens. I once had a boss who yelled and swore when giving feedback — so many people dismissed the message because of the delivery. The reality was that the content was often insightful and valuable, if you could listen through the distraction of how it was communicated.

2) Ask real questions to clarify, and also try to understand if this is a conversation, or if this is a lecture or directive. No point in getting your hopes up if there is no hope. If you don’t know- ask.

3) Just because you get feedback, doesn’t mean you have to agree with it. Be professional and respectful — and then take the pieces that you feel serve you and discard the rest. Note that if you are always getting the same feedback, there may be something to it, so take note. We all have flaws, and we are not obligated to fix every one of them. So be thoughtful and selective about how you want to accept, and then address, the feedback you receive.

Life is a process of learning and growth. If we are lucky, there will be times that we will receive useful feedback that can help us to develop into a better incarnation of ourselves — if we choose to hear it.




Advisor, Mentor, Speaker, Writer. Fintech and Commodities Professional. Wife, mother, grandmother and devout Catholic. Views expressed are my own.

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Catherine Flax

Catherine Flax

Advisor, Mentor, Speaker, Writer. Fintech and Commodities Professional. Wife, mother, grandmother and devout Catholic. Views expressed are my own.

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