In this episode we explore how leaders navigate overwhelm and uncertainty while sustaining connection, learning, and forward motion. We discuss practical coaching habits — listening with empathy, pacing conversations so people are ready to move from grief to rebuilding, and using foresight to prepare for multiple scenarios. We examine how leaders balance human connection with technology adoption, when AI can augment basic coaching and when human wisdom and intuition remain essential. Listeners will leave with concrete prompts for empathic conversations and steps to coach change into their teams.
Andrea Chilcote brings three decades of executive coaching and organizational development experience as founder and CEO of Morningstar Ventures. She synthesizes frontline leadership work with research on post-pandemic needs and has written What Leaders Need Now to capture practical guidance for turbulent times. Andrea helps leaders build resilience, improve team cohesion, and align development practices with strategic change. Her focus on listening, empathy, and pragmatic foresight models the coaching mindset we recommend for sustaining engagement and catalyzing recovery.
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Transcript
Welcome to lead with a coaching mindset, a podcast where every conversation sparks new ideas on how the best leaders unlock their followers potential. I am Dr Damian Goldvarg, and I am here to inspire you to become the best leader you can be. Be sure you subscribe and rate us. Let's jump right in. Today. We have with us, somebody very special. I had the opportunity to meet Andrea when we were working on my book. She was one of the reviewers of my book, and she gave me feedback and helped me to make a stronger book. So Andrea, I really appreciate you doing that for me. I also had the opportunity to be a guest in your podcast, so you are having a leader. For many years, you have been working with leaders with many years like me, coaching, training, and in our conversation, we have a lot in common. We think I like it in many different ways. So welcome to our program. And let's start by asking you, in your experience, what do you see currently as a leader working with other leader. What is in people's mind? What are the current challenges?
Andrea Chilcote:Oh Damian, the current challenges is that there are so many challenges. People are overwhelmed. It's not one thing. It is uncertainty. It is overwhelm of an uncertainty you know, you client to client, they're either going through layoffs, or they're going through some kind of acquisition that can be very positive, or they're going through AI implementation, and they don't know what that means for the future and how they're going to do work. Everyone is going through some kind of change, and often it means that their jobs are changing and they don't have time. They think they don't have time. It appears they don't have time to do the things that leaders do, that we think leaders do, right?
Damian Goldvarg, Ph.D.:Yeah, I am with you. I hear the same challenges. Interestingly, the word uncertainty is what I resonate a lot with. I hear that a lot. What skills do you need to navigate that uncertainty? And you hear people talking about resilience, ability to adapt, and I believe, also foresight, being open to looking at the future. So how do you navigate this uncertainty, not knowing a lot of information, not knowing what is going to come, and then at the same time, spending time and energy the exercise or looking toward the future and what can come and how we can prepare for different scenarios.
Andrea Chilcote:Yes, something that struck me when you re emphasize the word uncertainty. I was helping a group of very senior leaders prepare to talk with some folks that were going to be left after a layoff, and you know, you've been through this, you know, that's the the the most difficult thing after the letting go conversations, and they they were preparing for the coaching that they were going to have to Do, and I talked to them about the importance of just having, you know, empathy conversations, just asking people how they were feeling and letting them express how they were feeling. And one of them asked a really genuine question. He said, So how long do we keep asking people how they're feeling? How do we know when we stop that and move on to conversations about rebuilding and conversations about what's next and help them get some ground under them and and I said, Well, you do that when They're ready. And how do you know that? Well, you pay attention. You pay attention to what they're saying and what they're doing, and you don't move on until they're ready. And that's how they get ready and and it's such a simple thing to us, who are coaches, but leaders as coaches have to experience that, and
Damian Goldvarg, Ph.D.:it's interesting that many leaders believe that they are empathetic and they listen to to their colleagues. But in my experience, it's a curve like that. Some are great, most are in the middle, and there are some that are not very good at all, and still they think that they are good problem. But I do believe that first being empathic and listening is not something that all leaders find the time to do. So it's about how you prioritize in this mindset. Of as a coach, understanding that people need to be heard and understood, and just being willing to buy your time and listen, because we always tend to get defensive and explain why things are the way they are, versus just ask for people's experiences, feelings, and then, as you said at one point, okay, now we need to move on and how we start looking at what needs to be done and also engage people from a collaborative stance, engaging them in what they see as possibly scenarios and possible next Steps to rebuild, really like that word rebuilding something that can be something completely new and different. What also produce uncertainties? So it's like, it's not easy. Let's say it's bringing requires a lot of resilience and willingness and trust. How can you trust the leader, I believe. I don't know what your experience but when colleagues trust their leaders, it's easier to do this exercise, it's easier to have conversations about their experiences. It's easier to talk about the future. But what is your experience about that?
Andrea Chilcote:It can't be done without it. And you know, so if you're going, if you're in this kind of environment, and you don't have that, you're starting from a really difficult place.
Damian Goldvarg, Ph.D.:And how do you see technology? And you mentioned that before, like, for people who are in the United States, and we have a global network, and people listening to us from all over the world, what happened in the United States affect United States, but many times, affect many other countries too. So like Andrea had a colleague from Australia, from Sydney, say, Oh, I'm tired to keep continue listening to the news about your president. It's like, okay, not. It's like everywhere in the world paying attention to what happened in the United States. And so what happened politically, I said, I think that sometimes is affecting people, is distracting them. Some people feel angry or sad or have emotions about it. And then there is this, not only what happened politically and socially worldwide, but also technologically, how AI is affecting the work of everyone, including us as leaders, as coaches, as trainers, some of the work is also being done by AI. So what is your experience about embracing technology and the role of leaders on that? Yeah.
Andrea Chilcote:So, ah, gosh. I see, I see such a mixture in organizations. I see some organizations who are taking it slowly, methodically, business, looking at really single business use cases, taking it through a process, trying to make it, apply change methods to it. Then I see other organizations who think that it's the it's the solution to everything, and some leaders within technology, in those organizations that say this is a disaster waiting to happen, because it's not the solution to everything. It is a technology, just like the internet was a technology years ago, and we had to learn to use it, but it was a technology, and we still needed the people around it and the leadership around it to learn how to use that technology. So I think there are a lot of people who are afraid of it, not because it's going to take their jobs only, I think there's that, but I think there are a lot of people afraid that strategic decisions aren't being made well around it. But I think that's true of any new technology, so I but I think that adds to the uncertainty that we talked about when we started. That's one more thing. That's one more really big, noisy, expensive thing on people's minds.
Damian Goldvarg, Ph.D.:Have you seen or met any leaders who are effective at doing that, embracing technology in an effective way, to inspire people around them to incorporate that in their jobs?
Andrea Chilcote:Yeah, I have, I have, I have in, in a, I'd say, medium sized organization, where the leaders can can impact the senior management team and have them. It's not perfect by any means, but can have them understand the strategic impacts and understand. Understand what it's going to do and not do and and minimize the risk. Now it's not there's not been enough time to test it all the way through, and I certainly don't have the span. I know that it's being used in other organizations. I got a customer service reply this morning, and it said, I'm going to forward your request to a human who can give you more information. And the human actually replied within about an hour. And I thought, This is really good. This is really good. So I don't work with that company, but I'd like to, right, so I don't have an example like that, but something's working there, because it was really good. And, you know, it was a merchandise company, it was shoes.
Damian Goldvarg, Ph.D.:So it's interesting that, in my experience, is leaders need to first embrace it, because they if they don't do it, you're going to be very difficult that anybody else follow that. And sometimes it can be a request or some something that HR may want to start. And then leaders find themselves that they have to do things they may not want to do in related to embracing technology, and many times, is because it required time, investing, time to learn it. So this is one of my experiences, that for some leaders, they experience overwhelmed. They had to come up with result, and they feel okay, I don't have time to really learn this, so Okay, I will delegate to somebody else, but they are not doing it themselves. So it's challenging to want other people to do it when they are not doing it themselves. So how you find time? How you make it a priority? And that's exactly what you said at the beginning about being a strategic have to be part of the strategic perspective of how they're going to be working and why it's important for the future, and how investing time in training and learning it's key for that success. So that's a that's a mindset I think that is challenging to switch like we're talking about coaching mindset as a mindset that needs to be developed. Not all leaders, again, find the time to coach their people. Sometimes they hear, I don't have time for that, and what did they cost? So that's, I think, the something for leaders to pay attention to what they may be missing if they are not investing some time on coaching, on building skills around technology basics. And it's also there are generational issues too here too, with your experience around that, like different generations respond differently to technology.
Andrea Chilcote:Well, that's a whole, a whole thing. I want to, I want to just reinforce what you said about a coaching mindset this organization that is doing some some things really well. They don't look at this as, oh, it's AI. It's a scary AI. It is a another technology, and it's change management. It's change and so what do we do when we have a change? We coach it through, and managers have to coach it. Managers have to embrace it and coach it. And is it perfect? No, no, but that is the way they have to do it, the the way you're suggesting, and that's what they're that's the method that they're using, absolutely and I don't you think generations help us with this one, because Millennials and Gen Z's embrace the technologies in in ways that some of the other generations don't.
Damian Goldvarg, Ph.D.:iends who have kids at around:Andrea Chilcote:Well, they definitely want relational connection. Yes, yes.
Damian Goldvarg, Ph.D.:So when you go to the other extreme, and when you don't embrace technology, but when you shall depend on technology, and you start missing is like going to the other extreme, yes, it's not about not embracing. Next technology, but just depending on it, to the extent that you let go of relationships or the humanity in some way and how to find the right balance, that's something else for for leaders to pay attention to. It's like you have one extreme and you have the other extreme, and probably none of the extremes are good.
Andrea Chilcote:Yeah, I don't think that we're going to go to an extreme personally with with AI, but I don't know. I don't have a crystal ball.
Damian Goldvarg, Ph.D.:So what will be an extreme for you? Like when you think will be an extreme with AI? But what will that look like?
Andrea Chilcote:Well, you know, we're both coaches. I don't think we're going to have, I don't think, I don't think AI is going to replace our roles. Let's take it to the leader, the leader coach. I don't think that's a role that AI could or should replace. Maybe it could, but I don't think it should. I think there's other things that that can be done in organizations that I don't think that would be a role that that should be replaced. What do you think
Damian Goldvarg, Ph.D.:that's a good question. I think that that humanity and that contact, that relation, that build that trust for people to want to follow their leaders and to be inspired by them. I don't think that can be replaced with AI. And at the same time, they need new research that came out couple of weeks ago, there was a conference in New York about technology from Columbia University, and they have done some research about AI, and they were showing how in some companies, they are using AI to replace some of the leadership functions, including some coaching. So we have to see what these researchers what are the outcome they are starting and I do believe that there is a space for technology and AI to replace some of things that may not be able to be done by leaders. But again, I agree with you that the contact and the relationship cannot be replaced, and I do believe that there is a lot of value on that now, if they did not for whatever reasons, the leader is not able to spend time with their collaborators. Maybe that is a better option than nothing. Between nothing and virtual bots to get some guidance, coaching suggestions. I think that that may be a better choice than nothing at all, but I will always privilege the relationship in coaching, in leadership. I don't think nothing can replace that.
Andrea Chilcote:Yeah, they're creating this emotional intelligence function, and they can respond to tonality and word choice and that type of thing. And, you know, knowing that we were going to talk about this today, I had a I had a client. Just now I spoke with and she, just by coincidence, she she was telling me about something that happened in between our our meetings, and she said, You know, I want to tell you there was a question that you asked me and and by the way, her background is, she is a coach herself. She's a psychologist, and she is also a senior executive who's very involved in AI in her organization. And she said, I want to tell you that a question that you asked me was pivotal, and it caused me to make a decision that will impact the rest of my life, and I want to thank you for that, and here's what I did. And she told me about what she did. So we got to the end of our meeting, and I said, I want to ask you a question. May I share? Oh, I personally want to ask you, would do you believe that AI, an AI Coach, could have asked you that question? And she said, Oh my gosh, no. She said, you knew the moment based on your experience, based on your intuition, based on all of the factors of the conversation of the history with me, you know, knew what to ask at what moment, no, and that's where I say it can't replace and that's just my position.
Damian Goldvarg, Ph.D.:So, yeah, I think that I agree with you that human context cannot be replaced intuition, the wisdom, let's say, the wisdom that came with experience and the intuition. In the moment, and that connection that cannot be replaced. And at the same time, I think that for some company that are hiring now platforms to provide coaching to people, basic coaching, I think these platforms are going to replace some of the work of, let's say, some beginning level coaching. I get that, and the benefit will be that more people will benefit from that, and if they can be trained to ask questions and make people think versus telling them what to do.
Andrea Chilcote:Bravo. That can
Damian Goldvarg, Ph.D.:be different. Sometimes I ask chat GPT to ask me questions, to think things. So instead of telling me what to do, I say, Okay, I have this challenge. Ask me questions to make help me think about this, right? Yeah, and yeah, we'll not get that question with that wisdom, yeah, and we were talking here. But I get some basic help that many times is helpful. You know, it's kind of bad enough. I agree with you that wisdom, that intuition, that connection, that cannot be replaced. And Andrea, some people would rather work with AI than with other human being. So, so you we want to think, we want to people want to talk with another human being and connect and but I do I get to learn that some people will just benefit from not having to talk to another human being. So, yeah, yeah. I think there is space for for everything. I don't think that AI will replace coaching in general, but I do believe that some basic functions of coaching may be replayed for some technology, including AI, so we need to start wrapping up. Andrea, anything you want to share before we go? Any tips or any suggestions for people who are listening to us. How would you like to wrap up?
Andrea Chilcote:Well, I think that they should read your book, because coaching right now with what people are going through. You know, one of the things you shared on the podcast, my podcast, the Gallup global workforce survey, had just come out with a 21% employee engagement and deplorable manager engagement, and that is only going to get worse if we don't keep people engaged during this time. And we started by saying, leaders need to be having conversations with their teams, with people on their on their teams, and you give all of the components, and not only the components, but aligned with the ICF competencies. So it is. I've recommended it to so many of my clients, and I think you that that is a really important thing for people right now and to make the time to do it.
Damian Goldvarg, Ph.D.:Andrea, thank you very much. I really appreciate your support, your comments. And by the way, Gallup came up with another study last week where they show that AI, what we covered today in this podcast talks, that when leaders are involved and engage and enroll. Models, people are also engaged and participate, and when they don't, when they really don't. Do that they don't. So if people are interested. Came up with some research demonstrating what we covered today in our podcast too, and I wrote to the post about that also in LinkedIn. I use that information for my post for two days, so everything is aligned. Great to have you here. Thank you for joining us. I know this is not our last time having the conversation, so I hope you come back to our program soon.
Andrea Chilcote:I'd love to thanks so much for having me. Bye, bye.
Damian Goldvarg, Ph.D.:Thanks everybody for listening to us. We hope that we continue listening and our next session in two weeks, we continue discussing issues related to our book, lead with a coaching mindset. See you then. Thank you for listening to lead with a coaching mindset. I am thrilled you have shared this time with you. Don't forget to subscribe and give us a rating. Stay tuned for more episodes. Keep growing and see you next time.