What’s the Breakthrough Conversation you need to have?

We’ve all been there.  Avoiding getting into a conversation with someone for fear of a bad outcome.  It’s a common leadership performance trap.

We tell ourselves:

“Maybe things will get better if I just wait longer.”

“I’m waiting for the ‘perfect’ opportunity to share what’s on my mind.”

“I can’t see this turning out well no matter I approach it.”

But whether we’re avoiding telling a direct report that the way they dress is inappropriate, informing a colleague that their approach to the business is interfering with our department’s success, or asking a neighbour to stop mowing their lawn at 6am on Saturday mornings…the issue doesn’t go away (and it may even be getting worse the longer we wait.)

Why do we avoid difficult conversations?

  • We don’t want to be uncomfortable.
  • We want to be liked.
  • We worry that we may make the situation worse.

On that last point…I’d prefer to forget the times I’ve spoken up without thinking it through first, because we really CAN makes things worse!  But the good news is that, if we handle it well, a “Breakthrough Conversation” can not only make things better but it can also improve our relationship with the person we’re talking to. Having the courage to speak up will also help our credibility.

In my last article on providing feedbackI promised I’d share my tips on turning a difficult conversation into a positive “Breakthrough Conversation”…

Take a moment to consider…Who do you need to have a challenging conversation with? 
How can you apply these tips to make it a Breakthrough Conversation?:

What assumptions are you making about the person or the situation? For example, are you assuming the other person already knows how you feel about the situation?  Or that they’re being intentionally disrespectful?

An interesting thing about assumptions is that they can FEEL like they’re facts, but they’re not.  Once we’re able to let go of our assumptions that are making us feel judgmental, defensive, angry, etc., then and only then can we show up at our best.

Our very worst conversations are often fueled by negative emotions…So identifying those emotions can help ground us and increase the chance of a positive outcome.


What do you want to get out of this conversation?

More importantly, how do you think the OTHER person can benefit from having this conversation?  For example, receiving honest feedback could support their career growth, or learning about how they’re frustrating others can help them shift their impact.

We really are doomed if we head into these conversations with only our agenda on our minds.  It’s much more powerful to be open to finding alignment between both our and their agenda.


Planning an Opening to “launch” the conversation sets us up for success.

The keys are to:

  • Share the facts in a clear way – not too hard, not too soft.
  • Let them know you’re seeking a positive outcome
  • End with an open-ended question

And in the case of providing feedback to a direct report, you may wish to incorporate the “SBI-Question” approach I shared in my last article.

Here’s an example of an Opening:  “Pat, I’ve noticed that you tend to interrupt others around the table in our team meetings.  I’m concerned this is causing other people hold back from sharing what’s on their mind. I’m confident we can figure this out together. What are your thoughts on the matter?”

Another example is: “Terry, I know you want to be valued as professional.  I’m concerned that the way you dress doesn’t convey that message. What can we do to ensure you’re not inadvertently sending the wrong message?”

If the stakes are high, I sometimes run my Opening by someone else to get their input – you may want to try that, too.


Once we’ve shared our perspective, it’s time to get into conversation…

Things it can be helpful to keep in mind:

  • Be genuinely open and curious to hear their perspective on the situation.
  • Ask open-ended questions, listen to understand, and work collaboratively toward a positive outcome.
  • Focus your questions on achieving the “win/win” goals (from point #2, above.)

Ensure you’re both clear on what was agreed to, and collaborate on some next steps. And acknowledge the other person for working with you on creating a better future.

Now, it’s time to have your Breakthrough Conversation!   Wishing you much success and I’d love to hear how it goes!

And if you or someone you know would like to get into conversation about transforming your leadership, team or organization, let’s connect!