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How to Have (and Get the Courage to Have) Difficult Conversations

Do you keep lists?

I keep a lot of lists. My project list, to-do list, where to go on vacation list. But there is one list that I don’t put down on paper.

It’s the conversations I need to have, that I’ve been avoiding.

And the longer the conversations are on the to-do/not-done list in my head, the harder they are.  They continue to gnaw at me.  

How about you?  It could be a difficult conversation with a direct report. Or a colleague, a friend, a partner. Perhaps there’s something you’d like them to do differently. 

But so often, we don’t take action.  Maybe the issue is subtle, non-egregious, and you can “live with it.” Or, hope it will go away, the person might change spontaneously, or the problem becomes irrelevant.  (Ask me about the story of the Emperor’s horse!)

I encounter this hesitation frequently in my leadership coaching, especially in “polite” workplaces where unpleasant truths aren’t spoken. 

Why don’t we engage in difficult conversations?  Two reasons come to mind:  

  1. We expect that the interaction will be painful, and our self preservation instinct prioritizes current comfort over possible future benefit.
  2. We’re afraid we’re going to screw it up.  

Regarding the first reason, we’re taught that the benefits of holding a difficult conversation outweigh the downsides.  But it is true?  I was curious how people who’d had difficult conversations felt afterwards, and did my first ever LinkedIn poll:

In this non statistically significant sample, half the responders felt better than expected after the conversation.  Only a few wished they hadn’t bothered. 

What benefits could you expect afterwards? 

To the other person: Benefit of knowing what you’re feeling and thinking, because they may sense something is wrong anyway.

To the situation: Possibility of improvement, even  beyond the original topic.

To you:  Inner peace. Well, some relief at least. And the confidence that you can hold a difficult conversation and survive.

Even if the conversation is, well, difficult – contentious, defensive, mutually unsatisfying – there is still the possibility that it will change the future

Regarding the second reason, fear of lack of skill: it feels hard to be expert in difficult conversations, especially if being expert means feeling comfortable and confident each time.  I am personally still a long ways off.  

Yet, there are good teachings and effective frameworks for preparation (see below).  They usually have 3 parts:

  1. Stating your observations as specifically and objectively as possible
  2. Describing the impact of what was done, including how it made you feel, using “I” language whenever possible
  3. Expressing a need or a request.

…and then pausing and giving the other person space to respond.  

I try to remember that imperfect action is better than perfect, unending planning and this helps me move forward even when I’m not sure I’m doing it right.

Courage, as Brene Brown describes it, is doing something vulnerable without knowing how it’s going to turn out.  A difficult conversation certainly falls in that category.  So kudos to you for making the effort.

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