How to Start a Conversation You’re Dreading

I anticipated that the conversation would be difficult.

Shari* and I had worked together for many years, and I knew she was expecting me to hire her to run a leadership program for one of my clients, Ganta, a high-tech company. But I didn’t think Shari was the right fit for Ganta or, frankly, for the role of running the leadership training. In fact, I had become increasingly critical of her recent performance, though I hadn’t mentioned anything to her about it yet.

That was my first mistake. I should have said something before it got to this point.

So why didn’t I? I’d love to claim that it was because I liked her, and I didn’t want to hurt her feelings. Or because I hoped things would get better without my intervention.

And while those things were true, there was a deeper truth: I was afraid of the cringe moment.

Do you know that uneasy moment – right as you’re saying something that feels risky, but before the person responds? That’s the cringe moment.

In other words, I delayed speaking with Shari because I was afraid of how I would feel giving her the negative feedback: awkward, uncomfortable, and maybe even unreasonable.

But I couldn’t avoid it anymore. And because I had waited so long, the conversation promised to be even more awkward and uncomfortable. And now that she was getting a more extreme message with no warning, I would feel – and appear – even more unreasonable. The cringe quotient had gone up.

The day of the difficult conversation, I felt anxious as Shari came into my office. We shared a few pleasantries and then I began. I told her that I knew she wanted to run the leadership program at Ganta. I talked to her about the complexities and challenges of the leadership program and of Ganta in general. And I spoke with her about my frustrations with her recent performance. She asked me questions and I offered explanations and examples.

I did such a good job avoiding the cringe moment that, 30 minutes into the conversation, I still had not clearly communicated to Shari whether I was firing her or hiring her. My build-up was equally appropriate as context for either.

Finally, she did it for me. “So,” she asked, “Are you saying that you don’t want me to lead this program or you do?”

Now that I’m aware of it, I see my own behavior in leaders everywhere. Standing in front of the room, one senior VP slowly constructed a case to close a business. But he never got to his conclusion as people began debating unimportant details related to his argument before they even knew where he was headed.

In another case, a CEO sat in a meeting of department heads with the intention of telling them she was creating a new position to which they would all report. But she lost them as she spent the first 20 minutes giving context to a decision she hadn’t yet announced. As one person later told me, “All of the context was lost on me as I was trying to guess what she was getting at. It was a complete waste of time.”

The intellectual reason we build a case, or give context, to a difficult decision before announcing it is because we want to convey that the decision is well-thought out, rational, and an inevitable conclusion to the facts. But since the listeners don’t know what decision is being made, they have no context for the context and it all feels meaningless.

The emotional reason we give such long introductions to hard decisions is because we are procrastinating. We’re delaying the cringe feeling.

But this delay is counterproductive; it only stretches and deepens the discomfort of everyone involved.

The solution is simple and straightforward: Lead with the punchline.

What should I have said to Shari? “Thanks for coming in, Shari. I am not going to have you run the leadership program with Ganta, and I’d like you to understand why . . . ”

The senior VP should have started by saying, “I have come to the conclusion that we should close XXX business.”

And the CEO should have opened her meeting with the department heads by declaring “I have created a new Senior Vice President role, reporting to me, who will oversee this part of the business.”

After those openings, people will be interested in hearing the rest. Or, they may surprise you with instant agreement and there may be little more to discuss.

Here’s what I’ve come to realize: I almost always overestimate how difficult it is for the other person to hear what I have to say. People are resilient. I’m usually more uncomfortable delivering a difficult message than the other person is receiving it.

Next time you have a conversation you’re dreading, lead with the part you’re dreading. Get to the conclusion in the first sentence. Cringe fast and cringe early. It’s a simple move that few of us make consistently because it requires emotional courage. At least the first time.

But the more you do it, the easier and more natural it becomes. Being direct and upfront does not mean being callous or unnecessarily harsh. In fact, it’s the opposite; done with care, being direct is far more considerate.

And it doesn’t just reduce angst, it saves time as well. Shari wasn’t happy about not running the program at Ganta, but she understood why and accepted the decision quickly. Much more quickly than it took me to introduce it to her.

*Names and some details changed.

This article was originally published on the Harvard Business Review


  1. Linda Wearne says:

    So absolutely true – something I realise I have done regularly without really being aware of it.

  2. Joseph Sullivan says:

    This is one of the best “leadership lessons” I’ve ever run across. It applies to everyone, everywhere — in our families, schools, workplaces. I will share this article with my son, daughter, and associates. Good work, Peter! BTW – I am “guilty as charged” too. — J.R. Sullivan, New Hampshire

  3. malaika says:

    Yes! totally agree! As long as we are kind, gentle, and compassionate, being direct and honest is the best!

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