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How to Repair a Stakeholder Relationship, with Caroline Webb artwork

How to Repair a Stakeholder Relationship, with Caroline Webb

Coaching for Leaders

October 12, 2026

Caroline Webb: Leadership Intelligence Caroline Webb is a leadership coach, economist, and author of How to Have a Good Day, which has been published in over sixty countries.

Speakers Dave Stachowiak, Caroline Webb

TopicsManagementBusinessCareers

Dave Stachowiak (0:00)

Leaders are often called on to repair relationships for the benefit of everybody. When that relationship is a key stakeholder, it's especially important to approach it intentionally. In this episode, the most important steps to help that repair go better. This is Coaching for Leaders, episode 804

Produced by Innovate Learning, maximizing human potential.

Greetings to you from Orange County, California. This is Coaching for Leaders, and I'm your host, Dave Stachowiak. Leaders are born, they're made. In this weekly show helps leaders thrive at key inflection points.

We all have heard some really wonderful advice, conversation, training over the years, mentors help us in so many complex situations, we talk about a number of them on the show. And particularly, those complex situations tend to come up in thinking about how we navigate the relationships with the people we manage, and giving feedback and accountability, of course. And then there's the other direction of managing up, right? Of like how to influence upwards in the organization. And then there's another situation, one that's actually maybe even a bit more common, and I think even in some ways more complex because we don't talk about it enough. And that is, how do you repair and strengthen a relationship with a stakeholder? Maybe that stakeholders appear internally, maybe they're in a partner organization, or maybe they're a client or a customer supplier. When that relationship isn't working as well as it could, what do you do to start today a conversation on exactly where we can begin? And I'm so pleased to welcome a guest expert who's going to help us to do this well and think about this in some wonderful ways. I'm pleased to introduce to you Caroline Webb. Caroline is a leadership coach, economist, and author of How to Have a Good Day, which has been published in over 60 countries. She has been named as one of the top 50 executive coaches in the world by Thinkers 50 and a senior advisor on leadership to McKinsey & Company where she was previously a partner. She is the author of Leadership Intelligence, Science-Back Strategies for Mastering 21 Everyday Management Challenges. Caroline, what a pleasure to have you on.

Caroline Webb (2:18)

Thank you so much, Dave. I'm delighted to be here.

Dave Stachowiak (2:21)

I am delighted too. I'm so looking forward to this conversation. And as I alluded to in the introduction, there are so many complex and difficult situations that come up in leadership, as we all know, and managing up and giving feedback down, of course, are some of the most common ones.

What we don't often have a playbook on is how to handle the situations of navigating stakeholder relationships when they come up.

This is a bit of a different situation in a way, isn't it?

Caroline Webb (2:52)

It is. But people are people, you know, and whatever we think about when we consider our own frailties and foibles and the things that might push our buttons, anyone that we're working with can have their own patterns, their own things that rub them up the wrong way. And if we're going to be the best leaders we can be and the best professionals we can be, we're really thoughtful about how to bring the best out of every single relationship. And that means getting under the skin of what's really going on for the person a lot of the time.

Dave Stachowiak (3:20)

I was struck by two sentences that you write in the chapter of the book on navigating stakeholders. And as the subtitle of the book mentions, there's 21 topics in the book. We're zeroing in on one of them. And there's two sentences that really left out of me. The first sentence is, everyone perceives situations differently without realizing it. And I read that sentence, I was like, okay, you know, I think like most of us recognize that, theoretically, even if we don't necessarily always stop and think about it in the moment. But then there was the second sentence that landed with me even stronger. And you write, people with power tend to find it especially hard to imagine that anyone else sees things differently.

And I'm wondering, what is it that's particularly difficult for people who have power?

Caroline Webb (4:09)

Well, just about every sentence that I ever write is backed up by some set of studies. So I don't write that lightly. There is research that shows that as you accumulate more power, it becomes a little bit harder to put yourself in the shoes of other people around you. And it's not because people who get more senior are jerks. I mean, that's not our experience. That's not what we see. That's not what we feel. It's as you rise up, I guess I have a couple of theories. I mean, one is that the weight on your shoulders gets greater. Maybe it takes a little bit more effort to stop and put yourself in the shoes of other people.

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