Leadership Expert Caroline Webb: How to Have a Good Day (backed by science!)
Season 1 Episode 6
The science of a good day is also the science of a better future.
This week’s episode of How We Future with Lisa Kay Solomon features Caroline Webb: leadership coach, behavioral science expert, McKinsey Senior Advisor, and bestselling author of How to Have a Good Day.
Caroline’s work sits at the intersection of neuroscience, psychology, and practical leadership. She shares how we can prepare for chaotic times and gain agency by understanding the ways our brains handle uncertainty, stress, and decision-making.
You’ll learn:
Why attention is your most precious resource
A simple three-part framework (“Know. Be. Do”) that helps leaders navigate chaos
How naming what you’re feeling instantly reduces stress
Why imagining a future scenario trains your brain to respond better in real life
Why realistic optimism, not blind positivity, is the mindset leaders need right now
This conversation is a practical, hopeful guide for anyone trying to lead with more clarity, calm, and positivity. Caroline shows that the skills we need to navigate the future aren’t abstract. They’re learnable, repeatable, and rooted in how we manage our minds today.
Links from the show:
Learn more about Caroline and her projects on her website
Buy the book: How To Have a Good Day by Caroline Webb
Take Caroline’s LinkedIn Learning Courses: Science-based Habits for Modern Leadership and How to Have a Great Day at Work
Link to HBR Chapter: Guide to Dealing with Conflict by Caroline Webb
Even more resources from Caroline Webb to help you thrive!
🎧 Listen now:
▶️ Watch now:
📖 Read now:
Lisa Kay Solomon: I’m Lisa Kay Solomon, and this is How We Future, where I talk to some of my favorite changemakers about shaping tomorrow starting today.
I’m so excited to welcome my friend, Caroline Webb, to How We Future. Caroline is a leadership coach, economist, and author of the international bestseller How to Have a Good Day, a book that blends behavioral science, neuroscience, and everyday wisdom to help us all thrive at work and in life.
I first came across Caroline’s work during the pandemic, and it was exactly what I needed at that time. Her ideas about how to focus our attention, reclaim agency, and bring a little more joy into even the most complex days have stayed with me ever since. Today, Caroline shares practical ways to manage stress, lead with realistic optimism, and find meaning even when life feels uncertain. She talks about how focusing on what we can control changes everything and how small daily choices can ripple into better leadership, better days, and better futures. I’m so grateful she joined me for this conversation. Here’s Caroline.
Caroline Webb: I’m delighted to be here. Thanks so much.
Lisa: I’ve been a big fan for a long time. We are part of a shared authors group, so we’ve gotten to know each other. I have to say, I really dove into your work. It was almost like the heavens opened up and it was delivered to me at the right moment during what I would call peak pandemic. I have this great vivid memory of doing one of the few things we could do at the time, which was take walks outside. I was listening to this brilliant conversation with you and Scott Barry Kaufman, another colleague and friend of ours. It was like one of those moments where it was like, “This is what I need to hear at this moment.”
Everything you said was just the reminder of how to be intentional about my attention and how to figure out how to do more with what was available to me versus not. I’m a huge fan and I’m excited to talk to you about all of that and more. Maybe we should start with where some of those ideas came from, which was your first book called How to Have a Good Day. Maybe we’ll start there and talk about how did you come to write a book called How to Have a Good Day?
Caroline: Obviously, I’m having a very good day right now. [laughs] That’s not the origin story of the book. I got interested in how to use behavioral science, behavioral and cognitive science to help people thrive at work. A long time ago, I actually had a first career as an economist, and then I went into management consulting and I was doing a lot of work on leadership and on organizational change.
I saw time and again how a little bit of understanding about the brain could help people tweak the way they work to give them more productivity, for sure, but also well-being and, dare I say, even some joy. What I noticed was that also using a little bit of neuroscience and psychology and behavioral economics made it a lot easier for people to accept that it might be worth trying to behave a little differently at work to get more of all of those good things. That’s where it emerged.
I was using this in my coaching work. I was using it in my training and teaching work. Eventually, a client said to me, “Where’s the book that takes all of this and writes it down?” I thought, “Oh, maybe there’s a place for a book that actually shows people how to practically apply all of this stuff to have better days.”
Lisa: I love that description because one of the things I experience in your writing and your work and, of course, the conversations that we have is I think you are a brilliant strategic toggler where you can take big concepts that are backed in science and have rigor behind it and then translate them into very actionable bits.
Certainly, that’s throughout the book where you have chapters and you talk about things that make sense to so many leaders around how do they prioritize their time, how do they think about resilience, and it’s very directed. It has that both-and feel to it of like, “Yes, I’m going to help you and I’m going to shrink the change and give you some guidance on how you can do that right away.” Was that something that has always been part of your practice?
Caroline: Absolutely. I think everybody is busy, everybody is stretched. A lot of the advice that’s out there requires people to create whole systems and put a lot of effort into re-engineering how they live their lives. That’s not realistic for a lot of people. We might have space for one small change in how we run our days.
I’ve always been interested in what’s the highest leverage points of intervention that are going to make the biggest difference. That’s where science helps because if you understand, oh, actually, if you do this, then it’s going to have an outsized effect. The way that your brain works, then that, to me, has always been a tremendous unlock.
Lisa: I think it also helps that you come to this work from many years working at the highest echelons of strategy and consulting. You were a partner at McKinsey for many years and got fascinated with leadership, almost, I don’t want to say by accident, but it sounded like it was not intended to be your main job and to take this route. You were doing some exploration to make you better at being a partner at McKinsey and then had a moment where things shifted for you. I wonder if you could talk about that transition for yourself.
Caroline: That’s certainly true. Actually, the time I first got interested in leadership goes back earlier in my life. I was working in Central and Eastern Europe because I had that first career as an economist. I was doing work on behalf of the British government to help with the transition from communism.I fell in with a group of students. They were former students in Prague who had led the peaceful revolution, the Velvet Revolution in Czechoslovakia as it then was. That was mind-blowing to me. I was 21, 22. They were the same age.
I was very proud of having led this society or run this little thing at university, at college. Then they’d actually run a revolution. This blew my mind because it helped me realize, oh, leadership isn’t about seniority or age or status or job title. It can be something you step into at any age and any stage. That was very inspiring to me. It took me a while to get back to that and realize that was the topic I really most wanted to work on.
When I went from working in the public sector to McKinsey, I did have an inkling that I really wanted to work on leadership. Then when I was there, it became clear after a couple of years this was my jam, this was really what I wanted to work on. I did then get certified as a coach, which was quite early in this coaching world. Then realized, “Oh, okay. I specifically want to be a leadership coach. This is clearly what I want to do with my life.” Writing allows me to coach people at scale, let’s say, so I love that too.
Lisa: It’s a great combination. Oh, gosh, what an incredible experience to have early on. Talk about how, in future, to see 20-somethings changing the direction of their country. One of the things, at least, I’m trying to offer in this conversation series and podcast is this idea that there are no they that’s going to tell you how to do it, particularly in moments of high volatility and change.
Often, you are the they. [chuckles] You often buy the like, “Wait a minute, I’m living in a place right now. This is not how I want to see the future. There’s a big gap. What can I do? What can I try?” The courage to do it, not necessarily knowing if you’re going to be successful. How extraordinary to have that up-close view of that change and transition so early on.
Caroline: It gave me a huge sense of the agency that’s there if we look for it and if we’re willing to take it. It’s not an exaggeration to say it changed my life to see that. I’m still in touch with many of them now, and it’s fascinating to see what they’ve gone on to do.
In general, it helps me help my clients, help my colleagues, help my friends and my family focus on what they can change, focus on where are those points that they can control. It can be sometimes just in the way that they hold themselves and how they show up in a situation. It can be in the small things that you actually do control. There’s a lot there usually. It can sometimes feel like there isn’t when you feel very done to by what’s going on in the world. There’s always plenty that you can take control of.
Lisa: I know. What always amazes me is that we don’t spend a lot of time focusing on that or practicing that. I remember writing an article pretty early on into the pandemic talking about leading, learning, and living through a pandemic. Part of it was, though, what can you control peace? We’re just not as practiced at that.
I think as the world feels like it’s speeding up, the gift of reminding people that we can actually slow down and notice more and pay more attention and do something with that I think is so critical. I think that’s what you do so brilliantly at the highest levels in your leadership work. It matters for all of us, for sure, but leaders are often in a position where they’re making choices that have impact on their teams, on their organizations, on their cultures. There is a larger lever if they’re able to embody that, too.
Caroline: Absolutely. We get a lot from neuroscience on why it’s so important to look at what you can control. Uncertainty is deeply stressful for the average brain. It’s highly taxing. It means you have to cogitate and compute all sorts of possible futures. When you don’t have Lisa in your back pocket, that’s hard work. [laughs]
The more that you can reduce the cognitive load by focusing on what’s certain and what’s known, then the more you can use your small amount of mental energy and attention for the things that really need it and really need you to do that cogitation. As ever with all of these things, there’s a good scientific reason why this kind of approach actually works.
Lisa: Are there certain questions, either reflective questions? Again, going back to this idea of a big idea, focus on things you can control versus what you can’t, and then the integration and application into our lives. When you’re working with leaders, are there some go-to questions to help people to start to pay more attention to the fact that all the things happening are not the same, not necessarily the same quality, that there are some things you can influence over and some things that you can’t?
Caroline: Yes. I actually remember it myself by know, be, do. What are the things we know for sure? There’s often more in that than you think. Sometimes when 20% of a situation is uncertain, it colors everything. Often, there’s a lot that we do know for sure.
We might not know what the outcome of a decision is, but we might know when it’s going to happen. We might not know when it’s going to happen, but we might know the process that is going to unfold. There’s more often in the things-we-know bucket than we sometimes immediately think, or at least until the leader gets a team to sit down and say, “Okay. What are all the things we know for sure?”
Then there’s the Be buckets. There’s who are we, what do we stand for, what has been true about us that will still be true in the future, what are our values, and so forth. That really is powerful when you’re facing into a challenge. It can also include strengths and talents and experiences.
Then the question of what are we able to do, and that’s where it gets to, what are the things we might be able to choose ourselves to do in a difficult situation? I find with those three questions, which are what do we know for sure, who are we, and what is there that we can do, that’s the rubric that really helps leaders when they’re sitting down with their teams in the midst of chaos and crisis. It gives everybody a sense that they can move forward, even if not in an ideal world.
Lisa: It’s so valuable. I’m so thrilled that we’re going to be able to offer that to folks listening to How We Future. It reminds me a lot when I’m trying to help leaders and students learn the difference between what they can influence and what they need to maybe reframe or think differently of in order to put their attention intentionally towards the right areas, is this idea of paying attention to strong ideas loosely held, having a strong opinion about something, but you can be open to new ideas because it’s dynamic, it’s ambiguous, and strong values strongly helped. That, you can control.
I often say to leaders that if they have done their job in really creating a clear mission statement and strong values, that’s your superpower because that’s the stuff you can go back to. That can create a rubric that’s clear amid a context that’s changing so dynamically.
Caroline: So true. So true. I bet people are very lucky to have a chance to do that with you. If anyone is listening to this and thinking, “I don’t know what my values are,” there’s another simple question you can ask, which is what do we want to be known for? If you want just one question, that is a way into that big topic.
I think you also raise a really important point about attention. That’s the currency of our lives, is where our attention goes. We have much less of it than we tend to think. Our conscious attention is very limited. Both for leaders for themselves, but also in how they lead their teams, being deliberate and intentional about where do we want to put our attention. It will otherwise be scattered by whatever is coming through the door.
You can end up feeling like the proverbial headless chicken very, very easily unless you’re really intentional about saying, “Leaving aside all the things we don’t know, what matters most today is that we communicate really well with our customers or whatever it is.” That clarity of where attention should be going is such a gift when you’re in a team that’s being led by a person who knows how to do that.
Lisa: I love that. It really creates a grounding for people because let’s face it, the world does feel, at any given moment, that it’s spinning in all these different directions. My colleague, Scott Doorley, has a great term. He talks about we are living in a never-up-to-speed environment, which is the acronym, NUTS. “It’s NUTS,” he says. Our little puny nervous systems are not able to handle. He says, “Our nervous systems are nervous.” I think that’s so true that we’re not prepared, we’re not practiced.
That’s why I think one of the gifts of your work is to be like, you don’t have to do this alone. There’s some knowledge and science we have from behavioral economics, from neuroscience. Not all of this has to be into the wilderness.
Now, the way you apply it is going to be appropriate for your context. That will take some work and application, but you don’t have to invent all of it. I think this idea of really being able to go back to some of those core questions, say, “What do we want to be known for?” By the way, side note, I think that’s a futurist question. I’m just saying. When you say, “What do I want to be known for?” what you’re saying is, what do you want to be known for at a future point in time? Then come back to say, “And then therefore, how does it inform?”
Caroline: The neuroscience behind why that’s calming when you’re dealing with chaos is that what you’re doing is distancing, which is a well-established psychological technique to get some distance from a situation. It drops as a state of threat in your brain. We can do that by saying, “What would my best friend say to me?” That’s distancing and putting yourself in someone else’s shoes. I do really like the power of the future as a place from which you can think more clearly. Thank you for inviting me on your podcast about the future. [laughs]
Lisa: Thank you for giving me the technical term for why scenarios are so powerful because they allow for distancing. They often say one of the most vague, broad pieces of work was for South Africa when it was moving from apartheid to a more democratic government. Adam Kahan, among others, created these mount floor scenarios. One of the things, it’s hard to fight the same way you would about this present day as you would about the future. You just gave me this gift that there’s this distancing that can be so powerful, so thank you for that.
One of the ways I know you talk about your work and how you approach, which really is resonant for me, is this idea of realistic optimism. I want to talk a little bit about that phrase because I think that really does embody a lot of what we’re trying to offer in How We Future and in the conversations and in the resources that I’m working hard to provide is to not be Pollyanna, not be so optimistic that you’re like, “No, it’ll all be fine,” but also not to say that we are helpless either. That there’s this way of approaching this moment with some realism and a sense of hope. I just think the way you talk about that is so powerful. I wonder if you could talk about how you came to that and how that plays out in your work.
Caroline: How I came to it is a really good question because I remember writing in a school yearbook when I was 17 that my life philosophy was realistic optimism. I wonder where that came from. I think it came from a sense that there was possibility in the world, but there was also challenge. I’d not been to an easy school from 11 to 16. I was pretty tough, and yet I saw that it was possible to rise from that and to do something with my life.
I think from an early age, there was this duality, this sense of, okay, things are tough. It’s back to the question of where’s my room for agency? Where’s my room for influencing the situation? I think if you start to look for that perspective, then it becomes easier to see, yes, you acknowledge that things are difficult because if you don’t, actually, psychologically, it’s really hard. If the situation is really hard and everyone is just saying, “No, no, everything is fine,” you feel gaslit in our current language. That’s what we would call it now.
If you acknowledge, “Yes, this is what’s going on and this is difficult, and here’s where we can take steps to move forward.” I think I saw the power of that early in my life. Then I saw it again and again once I was looking for it in the professional realm as well.
I saw how different it was when a leader did the realism bit as well as the optimism bit and how much more powerful it was than if they just said, “We’re going to do great,” versus, “Here are the things we’re wrestling with. I believe in you. I believe in us. This is what I think we can do.” Obviously, I think anybody listening to that, you say, “Actually, I would believe the second leader more than I would believe the first.” That’s what I’ve seen again and again.
Lisa: I think particularly powerful when it can be grounded in purpose, when it can be grounded in values as opposed to some abstract idea. I think you are really naming something to look out for that I know for me as someone that tends to be very enthusiastic about possibility to not go to a place of toxic positivity where you are, as you were saying, not quite gaslighting, but just not really being authentic about the challenge. I think it is what I would say this both-and is what I get from a lot of this.
Caroline: Exactly.
Lisa: Hard things are possible and let’s not overlook or minimize that they’re hard. Let’s do what we can.
Caroline: Again, there’s a deep truth that comes out of the science here, which is that affect labeling, and this is actually more from the psychological research, labeling the emotion, labeling how you’re feeling actually reduces the grip of the emotion on you. If you’re in a meeting and things are getting a bit sticky, that’s why it can feel so much better if someone says, “Gosh, this feels hard, doesn’t it?”
Calling it out, if you do it without drama, if you just name what’s going on, it’s a very, very effective way of reducing some alert that people’s brains are trying to telegraph, and then that allows you to move forward and think about what happens next. There’s almost always some kind of really fundamental thing about how people’s brains work that then explains why common sense actually [laughs] is common sense. In this case, it’s perhaps not so common sense to do the acknowledgement, not just the optimism.
Lisa: I think when you acknowledge it, you’re also saying, “Wait, there’s data I can pay attention to.” I’m not acknowledging it and therefore I’m weak and can’t do it. I’m acknowledging it so that I have more to work with.
I really appreciate, Caroline, in your work that you name stress as a real condition of the human experience. There’s too much of it that leads to dysfunctional anxiety. To not name it and not practice how we deal with it and to understand that all of us deal with it differently is critical and particularly critical for leaders. I wonder, could you share a bit more about specifically that area that I think a lot of people are feeling right now, which is this pervasive stress or even anxiety about the things out of our control and how we could learn to do maybe a more adaptive job? [chuckles]
Caroline: Sress, as many people listening will know, is not all bad. There is a degree of rising to a challenge that actually is really healthy in how we go through life and work. I think when we talk about stress, what we mostly mean is negative stress, where it’s turning into something that feels unpleasant and is triggering a threat response.
More and more, I think we understand there are three components to the kinds of situations that generate a defensive stress response. They’re negative, of course. Otherwise, what’s the problem? [laughs] They are unpredictable, so you’ve got this uncertainty, and they’re demanding. If you had something that was negative and something that was uncertain, but it wasn’t that big a deal, whatever. It’s the combination of being demanding, unpredictable, and negative that actually ends up creating this stress response.
That then gives you, quite quickly, okay, what can I do to find the positive? We’ve just said we don’t want to be polyannarish. Can we find something that is meaningful, that gets us back to, as you were saying, gets us perhaps back to things we care about, things we value, things that are meaningful to us. Unpredictable, okay, so can’t necessarily make the unpredictable predictable. Can’t make things that are demanding easy, but you can focus on what is manageable in the situation. I feel like we keep on coming back to the same point.
All of the stress management techniques that work are effectively doing are reconnecting you to your sense that you can find meaning and manageability in the middle of the noise. One of the things that people might be thinking is, “What about meditation and breathing and stress and sleep?” The reason that helps is it helps your body feel like, “Oh, I’ve got this.”
Your brain is taking signals from the quality of your physical state and your health. The better rested you are, the fitter you feel, the more your brain says, “Everything seems to be under control. I’m going to interpret this situation as manageable. That’s why the physical side of things is part of this question of how do you make stress feel meaningful and manageable even when it feels hard.
Lisa: That contributes to having a good day. I joke, but I’m serious about it. When we think about what do we really care about, we care about not necessarily delivering on our KPIs or whatever they are, although those are important. We care about the connections we have, the quality of our life, our health, our relationships with others.
I think that what you’re sharing is an opportunity to do some context framing, maybe some perspective shifting about how do I think wider about this so I’m not so in that moment of reacting to whatever is coming my way. I have larger reservoirs to pull on. As you were saying, my body is even ready to pull on it. Really thinking with a much wider systems lens, I think, is so powerful.
I just want to say one of the things I also appreciate about your approach is that it is interdisciplinary. It’s not just one way of going about it. You’re like, “Here’s why we understand our bodies work this way when it encounters something unpredictable.” I think that’s incredibly helpful. First of all, it validates, hey, if you’re feeling your heart palpitating or you’re sweating a little bit, not just you. [chuckles] Not just you. It’s a biological evolution of telling you that you’re alive. I just think that’s such a helpful way.
Then to think about once we understand that, then we can practice it. I’m a big believer that we get better at things we practice. What I often say to people is, “Listen, I was not born learning how to give a great presentation or do an Excel spreadsheet. It’s okay. If I’m not born practiced at handling this level of complexity, it doesn’t mean I’m a failure. It just means I’m under-prepared or I have an opportunity to get better at it.”
Caroline: There’s a phrase I learned from Ben Zander, the conductor. He used to teach his musicians, when they made a mistake, to throw their hands up in the air and say, “How fascinating. What can I learn from this?” I’ve now worked with hundreds of leaders, probably thousands of leaders I’ve used that phrase with. Sometimes it comes back to me. I’ll get a message from someone saying, “This was a ‘how fascinating day.’” [laughs]
Lisa: I love it. What a great reframe. How fascinating because that says we’ve learned something. I think that one of the most powerful things we could do is learn how to learn forward. So much of what you offer is an opportunity to not stay stuck. Say, “Wait, how else could we interrogate this? What else is happening?” How fascinating also reminds me, we had an earlier guest, Dan Klein, who teaches improv at Stanford. He plays an improv game called Oh, Good! Like practicing, whatever you get. Oh, Good. Same kind of thing. It just changes your whole posture.
Caroline: I love that. I’m going to steal that. Oh good.
Lisa: There’s another piece of this too that I want to dive into around our posture towards uncertainty in the future being one of abundance or possibility or one of scarcity and reaction. So much of what I try to do in my classes or experiences or even conversations that I design is to not only get to a better idea, but also to help people feel like they’re building the capacity to be comfortable in the ambiguity.
To say, “I have a choice here. Am I going to look at this and react or am I going to pause,” as we said, pay attention, “and reframe?” I wonder if you could share a little bit about your experience with helping leaders move from a reactive or narrowing state to a more abundant being state.
Caroline: It takes practice. I love that you’re emphasizing that. Any new practice takes a little bit of work to have it feel habitual. The first thing I always start with is self-awareness because there are certain tells that we all have when our brain and body are working in concert to put us in a state of alert. We are all a little different. Yes, for most of us, our heart rate will rise. For most of us, we’ll notice our palms get a little sweaty if we start to feel stressed. It’s a little different for everybody.
Getting people to tune into, when was the last time you were super stressed? You think about, what do you think you would have noticed had you been watching you? What do you remember? Might have been a phrase going through your mind. What do you notice about your physical state? Actually, people can usually home in on it. They might say, “I’m not sure. It might be this.”Then the homework is to go and notice because it’s rare that there’s a week that doesn’t have a moment of some stress. Just starting to pay attention to that. Honestly, that is the first step.
Then the second step is to label, as I said, what you’re feeling and say, “Oh, I noticed that I seem to be a little stressed. The internet isn’t working very well today, and I am concerned about that.” Just even labeling that will drop the state of alert so that you can think more clearly. That’s probably where I start with just about everybody.
Then I also get people to tune into which types of situations tend to push their buttons. I talk about cues and tells. The physical stuff might be tells and then cues are specific hot button situations. You know that you’re meeting with someone who will always talk over you, and it really pushes your buttons. Okay, well, that’s actually a really useful thing to know because you can get yourself ready before going into the conversation and do some mental preparation about how you want to react. Take a beat, take a breath, put your feet on the floor when he or she starts doing it.
I think that might sound fundamental to people. Most of us need to recalibrate that stuff every few years because we do change. To know what your cues and tells are is the foundation for managing your stress effectively, I think.
Lisa: It’s so powerful. Again, dare I say there’s a little futuring happening there to imagine the scenario and to try to then rehearse it. Sometimes they say better rehearse the future than be blindsided by the present. This notion of like, “Hey, if this happens, then I might respond this way if this happens.” Now, of course, we can’t predict, but at least it’s not the first time. The first time we want leaders navigating ambiguity is not peak pandemic. That doesn’t mean that we should put undue stress on our systems, but we should practice when the stakes are a little lower. I think that’s so valuable.
Caroline: Yes, really nicely said. I’d also pull out, once again, that there’s a bit of science that sits behind this, which is that when you rehearse in your mind a situation, you notice is it going to be potentially a roadblock and you rehearse in your mind, “How am I going to react to that?”
You’re creating some of the same neural activity as when you actually then go into the situation. That’s why behavioral science research on implementation intentions, as this is sometimes called, what I call when-then, because that’s easier to say. [chuckles] When this happens, when I’m interrupted, then I will take a breath and I will smile and I will remind myself that this is a frail human that I’m dealing with who has their quirks and I have mine too. Back in the room. [laughs]
Lisa: When-then, that is brilliant. We could all use, I think, a little bit more practice in when-then. I remember early on when I started to facilitate groups and teams around conversations that had some high-stakes elements to it and unknown variables, so two things that I think get us hyped, we did some work around Chris Argyris’ ladder of inference. Oh, that was just a huge eye opener in how quickly people jump to a conclusion without, what I hear you say, slowing down and thinking about, “What am I noticing? How could I be more curious about what’s happening versus jumping to a conclusion that I get stuck on?”
Caroline: Absolutely. I love what you’re doing there. You’re helping people come up with a different story. That doesn’t mean, for example, the person who’s interrupting me, it doesn’t mean they’re not annoying, but to go quickly to, “They’re awful. They’re an awful person. They’re an evil person, even.” That’s a story we tell ourselves. Actually, to catch yourself and say, “What might be a different story?”
It’s not that you’re going soft on the person or the situation. What you’re doing is you’re loosening, back to your point about lightly held, you’re loosening your attachment on one possible interpretation of the situation. That then allows you to de-stress a little and then think more clearly. These mental tricks to increase your mental flexibility and your ability to see possible stories helps you in so many different ways, not just problem solving, but also managing yourself through uncertainty.
Lisa: I appreciate that there’s a real attention to what you can do in the moment. I sometimes think about these as micro moments that can lead to macro movements. This idea, if we practice in the small-- well, first of all, when you’re a leader, sometimes people then, “Oh, that’s a good practice. I’m going to learn from that.” You’re modeling. There’s a piece about the muscles growing together. Then it gets better if you start in those moments. I think that is so powerful and, again, a reminder of what we can do versus being overwhelmed by the stuff that we can’t.
Caroline: So true.
Lisa: Are there things that you do in your day to set yourself up for having a good day? Are there rituals or reflections or just things you incorporate?
Caroline: Oh, my goodness, absolutely. I had a filter for the last book for How to Have a Good Day, which was I wouldn’t put anything in if I didn’t do it myself. I needed to shorten the original draft. That was a very helpful filter because there was some stuff that I might advise other people to do, but if I wasn’t doing it myself. Okay, maybe I hadn’t run into that specific situation or whatever, but that was a solid bar, so I can vouch for what’s on the page.
I will say probably my favorite technique, the one that I almost always use whatever is going on is the end-of-day review to say, “What went well and what can I learn from the things that didn’t go so well?” That’s a really rock-solid habit for me. Even as everything else changes, even as the country I’m living in changes, it’s really guided me through. I sit on the couch at the end of the day with my husband and do it. Although I have sometimes had a formal journal, it doesn’t have to be using an app or a journal. That’s probably the most powerful thing out of everything.
Lisa: Oh, that sounds like a fantastic feedback loop. I sometimes ask when I’m in interviews, one of my favorite questions is, tell me about a good day, just to learn about them. It’s like everything has gone well, you’re thinking, you’re reflecting at the end of the day, what has happened? It’s very telling.
Caroline: One of the reasons the book was called How to Have a Good Day was I did the same thing. Great minds. We hadn’t yet met. Whenever I started a consulting project, when I was doing big organizational change work, working with a top team on driving some strategic initiative, I would actually go in and my interviews would start with, “What’s a good day for you? What’s a bad day? How could you get more good days?” Sometimes my colleagues used to say, “Where is the rest of the question?” I said, “Trust me, this is all we need.” [laughs]
Lisa: I love it. Sometimes the best question is the one that is most simple in that way. I did not quote this. I think it’s Oliver Wendell Holmes around finding simplicity on the other side of complexity, which that question does, which I love. Caroline, I know you’ve been working hard on a new book for leaders. I wonder if you can share anything about the research you’ve been working on or what you’re excited to bring to the world next in this new book.
Caroline: Thank you. That’s a lovely question. Yes. I’m working on a playbook for leaders that takes a similar approach to How to Have a Good Day in that it blends science and stories and strategies to give really, really practical advice on how to deal with everyday situations. It’s structured around 21 very common leadership situations from how do I find out what’s going on to how do I make a good decision to how do I set direction in a really inspiring way. That’s how the book is structured.
I’m very hopeful that it’s going to be a one-stop-go-to book for leaders because a lot of books go very deep in a specific area, difficult conversations or whatever. I really want to create a book for busy leaders who can only really have one book to hand and they can go to it again and again. That’s the idea. Then I’ll send people off to the more detailed specific books in a reading list. I think there’s a little bit of a gap for that sort of general leadership guide, and I’m hoping to fill it.
Lisa: I cannot wait. I cannot wait because it is. That, I would say, is really leaning into the use cases of what happens in our everyday. I think that’s going to be so powerful. There are so many times where I think, “Gosh, have we just expected people to be really good at setting direction for their team or running a team meeting?” Why don’t we slow down and actually [laughs] help people learn how to do that?
Dan Klein and I, that I was talking about earlier, I remember we were watching this beautiful exchange of gratitude from a group we were hosting from New Zealand. It was beautiful, filled with Maori traditions and honoring and music and song. We were like, “We could teach that, how to be grateful, how to introduce someone, how to be thankful.” All these things that we take for granted and just be like, “This is how you can elevate everybody in this way.” It sounds like that your book is really going to be just a tremendous asset for leaders that are expected to know, but maybe really don’t.
Caroline: Thank you. I really hope so. It reflects the topics that come up most in my coaching work with people of all ages, but even those well into their 50s and 60s. I hope that it’ll be a book for everybody. Anyone who’s in any kind of leadership role, even if it’s not a formal one like the students in Prague.
Lisa: Well, you are a gift to so many, helping them how to have a better day and helping them learn how to future with humanity, which I just think is so critical in this moment. I just wonder as we close out, Caroline, is there anything that you’d like to share for our listeners about just how they can think differently about how we future, about how they can future?
Caroline: Well, I do have a website and I have a bunch of resources on that website that are free. I’m very delighted to see people come and download them and use them. That might be a place to start. My website is carolineweb.co. That’s .co, not .com. There are lots of Caroline Webbs in the UK. It’s a very common name. [laughs] Not so common in the US, but it’s very common in the UK. Carolineweb.co. Yes, absolutely. There are a bunch of things there. You can search by topic and you can search for resilience, for example. You can search by a keyword of uncertainty, and you’ll get some help, I hope.
Lisa: Oh, absolutely. We will definitely put that in the show notes and we’ll do some continued digging ourselves. I just want to thank you so much for taking time amid the final stages of this new book and for doing what you do to help more people. Have a good day. I think it is essential, it is foundational. We don’t talk about it enough. I cannot wait to share your work with more people. Thank you so much for being here.
Caroline: Thank you so much, Lisa. This has been tremendous.
Lisa: What a gift to spend time with Caroline Webb. I learned that having a good day isn’t about everything going right, it’s about noticing what’s in our control. Here’s a practice you can take away from this conversation. Before you close out your day, take a minute to reflect on two questions Caroline offered. Number one, what went well? Number two, what can I learn from what didn’t? It’s a small ritual that can completely change how you end your day and how you start the next one.
If this conversation resonated with you, take a moment to share it with someone who could use a bit more calm and clarity in their leadership. Or leave a rating or review for How We Future. It helps new listeners discover these conversations and join our community of curious, optimistic changemakers.
I’m Lisa Kay Solomon. Thank you for listening. Here’s to more good days ahead.