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Hard Conversations: Why you need them, and how to have them. – A response from a reader

What's one of the most overlooked (yet powerful) leadership skills? Proficiently delivering bad news. Hear why one tech executive wished they read Joanna's advice about "Professional Gut Punches" sooner.

This week we’re going to hear from a reader of all my ponderings. He reached out after reading my article about Professional Gut Punches and the role of true leadership in hard conversations. After the ensuing email back and forth, and a delightful phone catch-up (we hadn’t spoken in probably 8-10 years), I asked him if he’d share his experience with the rest of us. So this week’s lesson in leadership is brought to you by a brilliant, kind and empathetic leader. Chris, the story is yours.


A few weeks ago I received a very timely email, don’t you love it when that happens? Recently I was reflecting on a particularly challenging time in a previous job and how it has informed my style of handling bad news ever since, and along came an email titled, “Hard Conversations: Why you need them, and how to have them”. 

I will admit, my first reaction was a raised eyebrow at needing hard conversations. You see, there was a time in a previous job where I had received not 1, but 3 Professional Gut Punches or PGP’s for short (check out the original article here). I definitely didn’t feel like I needed any more hard conversations then, nor do I relish them now. And yet there it was in this email, “Every day, plenty of moral, kind-hearted leaders like you are throwing PGPs at their team members.”

For the first time upon reading that I gained perspective and was able to put myself in my previous manager’s shoes. Most importantly, I was able to reflect on the one PGP that had kept me up at night back then and how I had handled it. You see this particular “no” from my manager had impacted my team. All I kept thinking at the time was I didn’t want my team to feel as disheartened and frustrated as I had upon hearing the news. 

At the time I had to come up with a better course of action, but where to even start, delivering bad news is so difficult. I focused on telling my team in a way that didn’t feel like a PGP to them. It was a Wednesday and I had until the team meeting the next week to formulate my plan. The luxury of this sort of time I know most people won’t necessarily have, but the steps are the same regardless of the time you have.

  1. Really calm down and give yourself a beat to react yourself. You can’t deliver news to your own team in a constructive way if you are still reeling from the bad news. For me, this meant viewing the situation in my manager’s shoes as best as I could and seeing how I could make this better for my team.
  2. As Joanna said in her original article, consider how your audience will receive the news. In my case, this was a potentially exciting new project for the new year that was now being put on the back burner due to other priorities and resourcing. 
  3. Formulate the best “why” that you can. For my team, I didn’t want to rely on “Management said no”, it deflected the blame and also felt flimsy. I decided to go with a straightforward why: “In the new year our priorities are changing from what we had originally thought, and so we needed to review the projects and align to those new priorities. For now, this project will be a lower priority.”
  4. Practice delivering the news with someone – this was hard as many of my colleagues would know the news before my team, so I decided to go with outside help. In this case, I recruited my husband, and some wonderful women I had met via a professional networking group. I received some good feedback about my tone, and the words I was using – I even had one wonderful woman inform me that my poker face, or lack thereof, was betraying me. This practice was invaluable and I encourage you to find someone to help you.


Then it was time to deliver the news, and I replayed the main talking points over and over again, to quote Joanna’s article again, “It’s not the disappointing news itself that leaves the person devastated beyond recovery, it’s HOW the news is shared that makes that lasting impact.”

Overall, the conversation went well, my team was upset of course and had questions and a variety of responses. I wish I had Joanna’s advice to take a pause if I needed to and think about my answers. Regardless, in one case I took a question away to find out more. 

Afterward, a senior member of my team whom I had worked with for many years came to talk to me. This was their way of processing bad news. They were often quiet during the delivery and then needed to talk afterward. In the past, these conversations had been hard, emotional and lengthy. Instead, this time they were calmer, the team member had a few thoughts on ways we could incorporate new ideas to map to the new priorities, and the conversation was very constructive. Was it the new approach and the way the bad news had been delivered? Time would tell. I could only hope my first attempt at delivering bad news in a better way lessened the impact on my team. I have been using this approach ever since.


A couple of thoughts before I let you go.

  1. Did this example and the results make you pause again about how you might shift how you’re delivering bad news?
  2. Put yourself in the shoes of one of the team members. How much would you want to work for a manager who thinks like this? I know I would. 

Lastly, I want to confess something. The author of this article was a woman, not a man. Surprised? I used the “he” pronouns to anchor your mindset on purpose. I wanted to see if it would change how you read the story. Now I’m not saying it couldn’t have been a man who responded this way. Interesting factoid – I get more responses from my articles from men than I do from women. I did it because I was curious about the answers to this next set of questions:

  1. Would you have read it differently if you’d known this was a woman’s story and not a man?
  2. Think about how you answered the question I asked earlier about if you wanted to work for this person. Would it have made any difference had you been aware of the presenting gender?

There are no wrong answers here. Just observations and curiosity and honesty about how we react to everything we’re exposed to. This is why I write:

We’re thinking beings and it’s our thinking, our observations, our curiosity, our empathy that make people brilliant. I’m just here to help you go “Hmmm, now that’s something to think about.”

Until next time.

PS. I’d love to hear from more of you about what you think of these posts. We’re always looking at your comments and ideas. And yes, if you’re brave enough we’d LOVE to have you have a voice here too.

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