August 5


Challenging Leadership Conversations: How to Tackle the Hardest Part

By Sara Canaday

August 5, 2021

business leaders, career, career success, communication skills, emotional intelligence, leadership, leadership skills, professional success

I’ve been intrigued in recent years by the number of experienced leaders — many of them strong communicators — who have told me the same thing: The hardest part of having tough conversations is getting started. 

Maybe you need to address a serious performance problem. Deliver bad news. Find a compromise during a heated argument. What’s the very first thing you say?

Ahhhh, yes. The door-opening, tone-setting words that tee up a potentially prickly discussion. For better or worse.

Here’s an example. Imagine you have been invited to a meeting about an important strategy that will directly impact your team’s work, but you don’t agree with part of the proposal. The way you initially express that disagreement will determine how your opinion is received and, in many cases, how the situation is resolved. Consider these starter options:

“While I agree with you on (common ground), have you considered (your point of view)? 

“I understand your point about (summarize the common ground). I’d like to explore what you mentioned about (the topic of concern).”

“I see it differently. May I tell you why?”

“I can see that you’ve put a lot of thought into this. Would you be willing to consider an alternative?

“Given the importance of this project, would it make sense to explore other options?”

Now, when it comes to handling challenging conversations, I’m not a proponent of a “one size fits all” approach. Every situation is unique. But when I’ve offered the leaders in my virtual courses some tools like these to help them get started—to kick off those tough conversations—they are always relieved.

That’s why I set out to develop a new resource called Taking Charge of Your Leadership Conversations, and I’m excited to announce that it’s now available as an online course through LinkedIn Learning.

Here’s a sample:

The course highlights 10 of the most common, high-stakes moments that can catch leaders off guard and fumbling for the right words. Instead of providing general advice or vague theories, I equip leaders with the exact language they can use to neutralize tense moments and set (or reset) the tone of a critical interaction.

If you are interested in increasing the impact of your leadership conversations (particularly those in the less-than-pleasant category), I invite you to check out this LinkedIn Learning course. And if you have some of your own tried-and-true phrases or questions for starting difficult conversations, I’d love to hear about them!  

In the meantime, stay safe and continue learning.

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Until next time,

Sara Canaday

About the author

Sara began her journey working full-time while she earned an MBA. As she climbed the ladder of corporate America, she repeatedly observed a surprising phenomenon: the most successful people weren’t necessarily the ones with the highest IQ or best job skills. She recognized instead that career advancement was much more closely linked with how people applied their knowledge and talents — their capacity to collaborate, communicate, and influence others.

Today, Sara is happily fulfilling that commitment as a keynote speaker, author, and executive coach. These venues have given her the opportunity to mentor and support thousands of people in diverse situations, inspiring many of them to move from insight to action with dramatic career results.

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