Melody Wilding: 

I bet you find yourself in situations almost daily where you have to make choices that stress you the heck out. You have to decide whether to push back on a timeline even though you know someone will be disappointed. You have to choose between speed and quality when both are important. You have to move ahead with incomplete information because you can’t afford not to.

And the hard part is not just making the decision, you then have to communicate it and manage the reactions. And this is all the more true right now as work is moving faster, AI is changing what we’re doing. You as a leader are expected to deliver when priorities are shifting midday sometimes, and you’re being asked to do more with less, all while keeping everyone around you engaged and calm.

And it’s a lot, to say the least. So I brought in some expert help today. I’m joined by Caroline Webb. She’s the author of the international bestseller, How to Have a Good Day, and her new book, Leadership Intelligence. Caroline is a former McKinsey partner. She is an economist, a longtime executive coach and advisor.

She’s one of the best thinkers I know on how psychology, neuroscience, behavioral science apply to workplace challenges, which is exactly what we love around here. In this conversation, we talk about how do you think clearly when stress and pressure is narrowing your focus? How do you make trade-offs without feeling like you’re failing someone?

How to communicate decisions people don’t wanna hear. She’s going to show you how you build the habits, the structures, so that every hard choice not only feels more manageable, but also gets you a more successful outcome for yourself and for others.

Caroline, I am so excited to have you here on Psychology at Work. Uh, and I think a lot of it is because so much of your work is about leveraging our own psychology, navigating other people’s psychology for maximum performance, so I’m excited to get into this conversation with you today.

Caroline Webb: Thank you. Me too

Melody: Yeah, and I have been a fan of yours, and now we are friends and colleagues, so it’s, it’s quite an honor.

But I can remember 10 years ago when your first book, How to Have a Good Day, came out, and just being captivated by it. Such a, such a elegantly simple title, but such, um, game-changing ideas within it. And at that time, 10 years ago in 2016, this idea of your own wellbeing at work and really being able to drive that was very, um, fresh and was something a lot of people weren’t thinking about.

We were knee-deep in hustle culture back then, if some people remember. But I am curious, because you have, now have a new book coming out, and I would love to hear just a little bit about the trajectory of how did you get from How to Have a Good Day, which has been a huge success internationally, to this new topic around leadership intelligence?

Caroline Webb: Well, they’re really very deeply connected. Uh, they are quite similar in style. They all– They blend science and practical advice and stories, real stories of real people doing their best. Um, and they really germinated alongside each other, to be honest. So How to Have a Good Day absolutely was the book that made it first out of the gate. Um, but leadership was always the, the topic that I focused on as a management consultant. So, you know, when I was, uh, when I was at McKinsey, there was a large part of my work which was about organizational change and effectiveness, and then I would typically work with the leaders to help them build a culture or drive the change that they were trying to drive. And so I always had this interest in wellbeing and performance at work broadly, but also specifically what can leaders do to unlock magic in other people. And so I guess I, you know, I felt that both books were gonna come out at some point and, uh, now when people ask me how long did it take me to write this book, I’ve got a very cute answer, which is 25 years because it’s been bubbling in the background.

And so Leadership Intelligence is very much a companion to How to Have a Good Day, and there’s a lot of, um, uh, of solidarity between the two, I think.

Melody: Yeah. Well, what, what I love about the, the title and the whole philosophy around the book, which I wanna unpack is, in a second, is how… I mean, the word intelligence really suggests that you can be great at delegation and, uh, setting priorities, uh, concise communication, some of those outward tactical skills.

You be, could be great at project management and roadmapping, whatever, but it’s really these, um, invisible relational, emotional, uh, skills that truly make the difference, and it’s that level of intelligence that is hard to acquire. Most people get it by trial and error. So what I really appreciate about this book is, yes, the real stories from people that are very relatable, uh, especially for the, the person who’s going through it.

But also, you, you break the book down into three key strengths of a leader, which are more psychological, and they are making wise choices, inspiring people to perform at their best, and building resilience to up and downs. What made you, out of the whole universe of things you could choose, how did you land on and really say, “These are the three”?

Caroline Webb: Well, a couple of things. So first of all, i- if you think about it, deciding what you do, uh, both in the big and small, uh, of the everyday life of being a manager, and then inspiring people to do it, and then keeping people moving when things don’t go perfectly, you know, that’s a pretty big universe of what leaders need to do.

Uh, and so that’s– that feeling of, uh, okay, good choices, get people rallied around, get people moving, keep people moving, is pretty… It, it felt like it really covered, um, just about everything that I work on with my clients. You know, over the last, uh, 25 years, I’ve been coaching, coaching leaders and managers at all levels, and it felt pretty universal.

And the other part of it is that if you think about what humans do as opposed to what our AI tools do, there is, uh, something really important about even as AI leaps forward in capability, there’s something really important about judgment, critical thinking, the ability to make choices when there isn’t a clear right answer.

So that’s what I call deliberate wisdom. It’s developing the habits that allow you to think clearly about a situation, even if you’ve never seen it before, that is on the shoulders of the human leader of the human team. And intrinsic inspiration is the second big block, and I call it intrinsic because we’re not talking about motivation that comes from, um, outside.

We’re not talking about status and money necessarily, although, you know, important to treat people really fairly. No question about that. But if you’re looking for, um, motivation that lasts and inspiration to do your best work, you wanna look at the intrinsic rewards that the brain, um, the brain’s reward system reacts to. And so that’s that big chunk and, you know, as a leader, it’s you that’s sitting and looking at your team and thinking, “Huh, are off their game. I wonder what’s going on. How do I read this? What is it that I need to do to unlock something fresh in them?” And then the third big chunk is reasoned resilience.

Reasoned because a lot of it, um, comes from thinking about what your interpretation of the situation is. And, you know, again, it’s a human, human leader’s, uh, responsibility to say, “Okay, well, this is really tough, but gonna help us find a way through. I’m gonna lift our sights and our spirits to see a, a path forward, even when it doesn’t look as if there is an easy one that’s, uh, presenting itself.” So there was definitely this feeling of what’s the human intelligence dimension alongside the artificial intelligence dimension that runs through the book.

Melody: Mm-hmm. Yeah. And, um, what strikes me too is that in a lot of these situations, as you were saying, there is this bit of, yes, judgment, but also, uh, r- reading between the lines, having to make, uh, conclusions. Because people may tell you one thing about why they’re not feeling motivated or why they feel confused or why a certain setback happened, which may be different from the real story, and you have to have the skills to excavate that, to explore it, to pressure test it, to do that gently and with diplomacy and tact and respect for the other, other person as well.

So, uh, that actually leads me to, you said a phrase, y- you said something along the lines of being able to analyze or approach a situation even when we’ve never seen it before.

Caroline Webb: Mm-hmm.

Melody: And the person who’s listening, I know you have a lot of people like this in your audience as well. My folks tend to be very, um, very thoughtful, very hardworking, a bit on the perfectionist side, where they wanna get things right.

That’s very important to them. They don’t wanna look bad. They don’t wanna be a burden to others. They get really freaked out about the idea of having to think on their feet because they wanna be prepared. They’re the person who will, you know, wants the talking points, wants to be able to have two weeks before the presentation.

So the thought of, “I have to go into a situation essentially blind and analyze it,” is very scary. So I, I am curious because we know from neuroscience that when we are under stress and the scrutiny that we are under, our thinking narrows, right? Yeah. And I am, um, interested in hearing about from your research and your work with people, what do you see, or what do you see when that happens are the most common traps people fall into, and how do you get out of that?

Caroline Webb: Mm-hmm. Well, uh, you’re right that when we’re under pressure, our perception tends to narrow. It’s pretty narrow already. Uh, I mean, that’s a place to start, which is that whatever is top of mind for us will tend to drive what we then notice next, and there are a number of different names in the research for that mechanism, but, you know, you’ll have heard of some of them: selective attention, confirmation bias, um, default bias, selection bias.

So there’s all sorts of ways that we simplify the way that our brain reaches for information, and that’s because our brain has a limited amount of, uh, bandwidth to notice and then actually also process information. And then, as you say, when we’re under pressure, it, that, that narrowness only gets worse. To my mind, you know, a lot of this happens instinctively. What can you do to manage yourself in a situation where you know you need to see the whole picture and you know you need to understand really deeply what’s going on? And I do think it comes back to habits. The more you can wire yourself in with a few simple questions that you’re gonna remember in the heat of the moment, the easier it is to bring your best, most open-minded self to, to the, whatever meeting or situation you’re in. in, you know, the people I work with, that might be as simple as saying, “Okay, when I start to notice, uh, a certain level of…” May not be anxiety. It might be annoyance. Might be, um, you know, disappointment. When I start to notice some of my cues and tells starting to tell me that I’m perhaps not, you know, being as open-minded as I might, take a step back. I call it ABC routine. Notice, awareness, right? Okay. a breath, that’s the B. And then the C is a centering question to say, “Okay, what really matters here? What do I really wanna notice?” Okay. Now, I can give you a list of 10 questions, 20 questions, you know, uh, but if you can just remember that one question, “What really matters here?

What do I most wanna notice?” going to help to widen the aperture of your perception at the moment where you most need it. And I think just in general, the more you can wire these habits into the way that you do things, I mean, write them on Post-it Notes, put them on your screen. I’ve got Post-it Notes on my screen reminding me to do things. You know, the more you can make these things habitual, the easier it is in the heat of the moment.

Melody: Absolutely. Yeah, just to have that pattern interrupt top of mind, like you were saying. So i- i- it’s sometimes just that one question that even helps you realize, oh, I’m, I’m just falling into that default, right? Where… A- and like you were saying, just helps you generate those, those alternatives. Even if you’re not quite on board with all those al- alternatives yet, the expanding the aperture, I, I feel like when I do that for myself, it has this calming effect of taking away some of the urgency or threat I feel in the moment, which, you know, the emotional and the mental aspects of it really do go hand-in-hand

Caroline Webb: Yeah, so true. And, you know, the whole of the third… Each of the three blocks of the book is based on some really fundamental science, and the whole of the third part of the book is based on how the brain responds to, to threats and potential threats. And the more we see, uh, the, the research move forward on this, the more it comes down to actually it’s what your brain predicts is about to happen more than it is what is actually happening. And so the more you can encourage your brain to see the situation as manageable, uh, maybe even slightly meaningful, I have this little pairing, manageable, meaningful, and the more you can do that for your colleagues and say, “Okay, we got this. All right. What could be going on here? we got this. What could be going on here, and what does that mean we should do, that we can do?” The more you can set that tone, the less likely your brain is to code the situation as a threat, and then you’re less likely to get that narrowing of, of perspective. And so I think there’s a lot that leaders and managers, you know, whether you’re in a formal management role or just, you know, trying to get stuff done with colleagues, the more you can help people feel that situation’s manageable, you’re gonna get better thinking and better perception and, and, uh, creative, um, problem-solving out of them

Melody: Yeah. Well, you saying that, uh, strikes me, it, or reminds me of the idea of emotional contagion, right? And as a leader, yes, you are setting the example, but you also are a steward for the rest of the team’s energy and focus. And so if you are the one leading the regulation charge, people are going to model that, and you’ll put a cap on fear kind of spreading.

And I, I can’t tell you, I’m sure you hear this from your clients as well, just how, um, uh, for example, like right now we’re coming into Q3, and so announcements about strategic plans, what’s getting cut, budgets, all of that is starting to bubble up, and a lot of clients are coming to me and saying the rumor mill is beginning,

realizing that they as the leader need to get on top of not just putting a kibosh on it, like d- do not talk about this, but providing that tempered reassurance around, “We got this.

We will handle what comes our way. I believe in us and our capability. Here’s what we’ve done before.” It just sets the tone for everything else that comes. So that was one thing that stood out. But also, as you were saying, even if you are not, you know, I… There’s… You can be a leader without having direct reports.

I know you believe that as well. And so it strikes me if you’re someone who is in that kind of position, that when you do what you are saying to be, to almost coach others around some of those aperture opening questions, you also show you are calm under pressure, and people relate you with that. So they bring you bigger opportunities ’cause they know you can handle it, and they know you will be the voice of reason, which is great.

Yeah

Caroline Webb: I sometimes call it being a force for good in whatever room,

Melody: Yeah

Caroline Webb: space you’re in, because you’re radiating that sense of, uh, acknowledgement that things are tough, right? So we don’t have to pretend that things aren’t tough, but say, “Okay, what is there that we do know? What is there that we can do? Um, and, you know, what is there that we can bring that is, you know, about our talents and strengths that we can re- we can lean into?” That’s what I call the know be do model of handling uncertainty actually. Um, so, you know, I think it really is, um, something that you can do whether you’re sitting in the chair or just sitting around the table, and you just say, “Okay, what do we know for sure?

All right. And what does that mean we can do?” Mm-hmm. All right. You feel the temperature come down, you’re the one that’s driving that, that, that sort of reorientation towards what’s possible.

Melody: I love that. Know, be, do. That was, that was the three, right?

Caroline Webb: That’s right. That’s right. That’s,

Melody: Excellent

Caroline Webb: in the chapter on managing uncertainty, chapter, chapter 16.

Melody: Love that. Now

Caroline Webb: engraved in my mind, what- the, the title of all the 21

Melody: I, I know how it goes. And, and listen, for everyone who is listening and tuning in, having those little frameworks to grasp onto makes all the difference, ’cause you’re… W- we all have so much coming at us, and so for them to hear “no be do,” that’s what they can go put on their Post-It note after this, right?

And remember, “Okay, I feel uncertain. Let me…” It, it just makes it so much more accessible, so I appreciate all these clever little frameworks. Now, speaking of uncertainty, something a lot of the people who are listening have to do is constantly make trade-offs. They constantly have to, ah, disappoint people or, again, go against their instincts to not optimize for the maximum result, whether it’s they have different competing priorities from different stakeholders, or it’s speed versus quality, it’s revenue, there’s people considerations.

How do you coach and guide leaders through thinking about and making those trade-offs without feeling like they’re failing themselves or, or letting a certain side down?

Caroline Webb: Um, it’s a great question. Um, so first of all, I think, you know, as soon as you start to take on any responsibility, formal or informal, you’re going to be getting the questions that aren’t the easy ones. You’re gonna g- be getting the decisions that aren’t slam dunk obvious. So there’s a little bit of acceptance that I encourage people to say, “Well, you know, you’re gonna get the, the, the trickier stuff, and isn’t that wonderful?

Isn’t that… Solving puzzles, uh, is such a key part of being, being a leader.” There’s, um, there’s a, a leader I admire called, uh, Emma Walmsley, Dame Emma Walmsley, who was, uh, CEO of GSK for quite a while, and she, she said she used to wake up every morning and say, “What horrible problems am I gonna have to solve today?”

And to remind herself, you know, this is, this is the job. This is the job. Now, not all of us are CEOs, and luckily we don’t have s- problems of the scale that, uh, that, that, uh, that she had to deal with. the answer is kind of the same. I think, you know, the answer is a structured decision-making process. You know, now some people say, “Oh, but I wanna trust my gut. I… Why can’t I just trus- trust my gut?” The problem is that gut instinct is very valuable. It’s a huge, um, hugely powerful summary of everything you’ve ever known and seen, but it’s really imperfect because your memory’s imperfect, and that’s effectively w- what it’s drawing on.

And the other thing is just from the research on cognitive science, it just doesn’t stack up. You make better choices when you’re dealing with anything even slightly complicated if you have more of a structured process. And I think a structured process, uh, I call it my ACORN approach. Uh, what I mean is get clear on the aim of the decision.

Why are you making this decision? Uh, what are the criteria for success? What does a good outcome look like? Is it speed? Is it kind of engaging maximum number of people? Is it cost? Is it… Y- y- get on what those criteria are. Then get your options on the table. Make sure there’s more than one. S- options, plural. Otherwise, you might fall prey to default mode, uh, default bias and just go for the easiest one. then you wanna rate them against your criteria, and at this point you’re thinking, “Oh my God, isn’t this like… This is a lot of work.” oh my goodness, it makes decision-making a lot easier. Um, but, and the N is then to next steps.

Okay, what do, what do your scores tell you? It might tell you, you don’t have enough information. It might tell you, “Oh, you were right, but you might need to check yourself a little bit more.” Or actually, gosh, a completely different answer has come out than you expected. And I will say every time I’ve applied this to my personal life, that’s what’s happened. You know, when I’ve thought about a career move or I’ve thought about, you know, um Things like, you know, just deciding whether to put my stuff in storage when moving between the US and the UK. Um, I’ve often found that taking a structured approach actually results in the answer that I was not expecting, and then I have to sit with that. why is it helpful? It’s helpful because it really helps you make the trade-offs, and it really helps to bring people with you because they can see the process that you’ve gone through, and it’s a wonderful process for going through with your colleagues together because people are much better able to get behind decisions where they feel like their ideas have had a fair hearing, and they can see that the process has been fair.

This is, as you know, uh, called procedural justice. as a manager, this isn’t just a good practice for yourself when you’re making choices, it’s a good practice for your team and making it a collective, collective effort

Melody: Hmm. Well, and, and I, I think the, the other thing that, that stands out to me is that then you internalize that structure. You can go through it more quickly, and then soon it becomes second nature. It becomes intuition, right? Yeah, where, uh, that is always… I’m always saying to my clients that what you see is people sort of, they seem like a natural at something.

It is just internalized structures, like you were saying. It’s this pattern they have in their head that they are running themselves through. So I think for s- you know, for someone who is, uh, I don’t wanna say learning this skill, but who is trying to strengthen this skill, just having that, the ACORN model to hold onto, it, it also helps you find your own version of that, right?

To personalize it to you. Yeah

Caroline Webb: And you know what I would say is there’s solid research under every single one of those steps, and if you do any one of them, you’re gonna get a better answer to the research. So you don’t even have to remember all of them. You know, just, uh, just taking on board what feels m- least familiar to you is probably going to give you a bit of a boost in the quality of your decisions

Melody: Yeah. Yeah. Now, when it comes to having to make and communicate decisions, another factor is dealing with other people’s reactions to our decisions, which can, um… You were talking about how our brains predict and are almost anticipating what may happen, and that may block us from making a decision altogether, and sometimes we think people are gonna be upset about this.

I know I’m gonna get complaints, so we hold back from doing something. Or we deliver, uh, bad news or, uh, something people don’t wanna hear in the moment. We get pushback. What do you do when someone reacts emotionally to a decision you make? How do you stay empathetic without completely caving, backtracking to every person’s reaction?

Caroline Webb: It’s gonna depend a lot on the, on the context, you know, were they consulted, were they involved, or is, you know, has this honestly been a little bit dumped on them? Um, but I think, you know, in all cases, you want to understand their perspective, and you want to, uh, show how what you’re doing speaks to that perspective, even if you can’t, you know, fix everything or make them happy in every dimension ’cause, you know, almost always you can’t do that when you’re managing, uh, anything at all complex. Um, I like, uh, an approach called the common ground, uh, technique that I built based on Daniel Dennett’s, uh, write-up of a game theorist called Anatol Rapoport. And, uh, all a lot of preambles say I evolved this, um, from other people’s ideas, it starts with describing the other person’s point of view as if you really like it.

So, you know, someone’s coming to you, they’re really upset, and you say, “I hear you. This is what I hear you saying. Um, you’re really upset because… And that’s because… that’s because…” And the idea is steelmanning, so you’ll… You’re not trying to make their argument sound terrible and weak. You’re actually trying to make it sound like you, you couldn’t– they couldn’t put it better themselves. And if you start with that, and then you do the next thing, which is to list all the areas where you agree, you’ve got a very different type of conversation on your hands because the other person then isn’t desperately trying to telegraph their distress and their annoyance to you. You’re showing, “No, I hear you.

I really hear you.” And the kind of conversation you can have after that is, is a very different type of conversation. And, uh, no, you’re not going to get to a perfect alignment, quite likely, but if you can start with those two steps, you’re gonna get to a sense that you’re at least pulling in the same direction

Melody: Yeah. Yeah. Well, it goes, again, uh, the, a theme here is reducing that sense of threat that both you and the other person feel, right? It’s, it’s so much less adversarial, me versus you, I win, you lose. It’s, it’s more, dare I say, kind of abundant. We can both win. We’re both working towards the same thing.

Cooperative, yeah

Caroline Webb: Yes. Absolutely. In fact, you know, if, if, if the conversation has room to go further, what I recommend people do after that is say, “Okay, well, where are the places we disagree?” They usually feel a lot smaller after you’ve listed all the things that you agree on, and you understand, you know, what shaped that.

So maybe you don’t want to do a massive launch because the last time you did that, um, it all went horribly wrong, and the impact was greater because you hadn’t done enough testing. And maybe the other person had a super successful big launch immediately. And so you, you understand sort of some of the history.

And then the next question is: how could you both be correct? Which is weird when you first see it. You think, “Wow, what does that even mean? How could you both be correct?” Oh, actually, okay, so there could be… You could be right in different situations, or you could be right in different areas or with different groups of people or so on. And then, oh my goodness, m- much more becomes possible.

Melody: I love that question. How, how am I… What was it again?

Caroline Webb: How could both of us be correct?

Melody: How could both of us be cr- that is so good. I love that. I am stealing that for sure. That is so good. Um, Caroline, I, I wanna be respectful of your time. There’s just a few other questions I have for you, and one of them is, all right, we talked about when, essentially when people disagree with you or have an emotional reaction to your feedback, let’s talk about when the shoe is on the other foot, when you wanna disagree with someone.

How can you do that well without, uh, instigating the situation?

Caroline Webb: Well, I think actually if you’re the one that disagrees with someone, you could do worse than just remember those first two, uh, first two steps of articulating the other person’s point of view to show that you really do understand it. You’re not ignoring it, you’re not bulldozing over it. You, you’ve heard it and you understand it, and then to, to list all the places that you agree.

So I, I think those are good both ways around actually. Um, but I also think that, y- you know, this gets to getting very skilled in giving people feedback. You know, if you’ve got a situation where, you know, someone’s done something you really don’t agree with, what’s a really skilled adult, intelligent way to raise that? It’s not to say, really annoyed me,” because you did. It’s to say, our working to me.” intention. specific observation. “I noticed that you invited the client to, uh, the workshop that we’ve been discussing, uh, but you didn’t involve me.” Okay, you gotta be very careful with that because didn’t involve…

Okay, that’s all right. That’s all right. But it’d be very easy to say, “You excluded me,” or, “You, you, you didn’t, you didn’t, uh, you didn’t respect my opinion enough to involve me.” Okay. Well, all right. So you’re immediately getting into interpretations. You have to strip it of interpretation and just do the specific observation and then you say, this is the, you know, invitation stage.

You say, “Okay. Tell me, tell me what was going on.” And then you have the conversation that you need to have. But if you barrel in without setting a clear positive intention and conveying that, that it’s about improving the relationship or fixing an issue, working together really well, and you don’t… You, you make an, what I call, is it interpretation, generalization or extrapolation?

If it is, mm-mm, cut it, and just make the very specific factual observations, what I call factual feedback, and then you’re much more likely to have a conversation that doesn’t put the other person on the defensive

Melody: Hmm. Yeah, it’s so much more changeable than, “I’m sick of you micromanaging me,” or, “This was a terrible idea.” Then you’re just

Caroline Webb: well, it becomes this huge, huge that is very hard to walk back and is very personal. Um, whereas, you know, homing in on specifics m- generally makes it a lot easier to fix the problem as well

Melody: Yes, exactly. Exactly. Okay, Caroline, this, this has been great. I love how much we really focused on decision-making today under pressure, which we all need now more than ever because we have to make more decisions more quickly with more eyes on us, with less information than we’ve ever had before. So this is incredibly useful, and I want to encourage everyone to get your new book, Leadership Intelligence.

Where do you wanna send them to connect with you, to grab the book? What’s the best place?

Caroline Webb: Thank you. Nice question. Um, my website is carolinewebb.co. Uh, that’s .co, not .com. There are a lot of Caroline Webbs in the world it turns out. That’s Webb with two Bs, so carolinewebb.co. If you come there, you’ll find all sorts of information and free stuff, um, to do with my new book. And, uh, you might also find me on LinkedIn.

I’m very happy to, to see people, see people there as well, if you prefer that

Melody: That’s right. And we will make sure all of this is in the show notes as well. Thank you so much for being here with me

Caroline Webb: you. Thank you so much, Melody.