Building Emotional Courage with Peter Bregman and Understanding Talent Mobility with Caitlin MacGregor

Taking risks doesn’t always lead you to success, but it will surely help you grow as a leader. One of the risks to take to achieve effective leadership is not just to empathize with your employees but also to tap into your emotions in appropriate ways at the workplace. Peter Bregman, bestselling author of Leading with Emotional Courage: How to Have Hard Conversations, Create Accountability, and Inspire Action on Your Most Important Work, defines what emotional courage is and why it should be a skill leaders must learn alongside confidence, connection, and being committed.


Being an effective leader is about tapping into the potentials of the workforce. To grow is to learn continuously or else the business will hit the plateau. Caitlin MacGregor, CEO and Co-Founder of Plum, knows precisely the importance of revolutionizing the workplace through continuous learning. She dives into the concept of talent mobility powered by the scalability of artificial intelligence and the deep insight of industrial/organizational psychology. On top of that, she shares about the quality metrics they use to center in on who’s going to be successful long-term without bias.

TTL 324 | Emotional Courage, Talent Mobility


We have Peter Bregman and Caitlin MacGregor. Peter is a bestselling author and one of Inc. Magazine’s Top 100 Leadership Speakers. Caitlin is a CEO and Cofounder of Plum. I’m anxious to get to speak to both of them.

Listen to the podcast here

Building Emotional Courage with Peter Bregman

TTL 324 | Emotional Courage, Talent Mobility
Leading with Emotional Courage: How to Have Hard Conversations, Create Accountability, and Inspire Action on Your Most Important Work

I am here with Peter Bregman who’s a bestselling author and one of Inc. Magazine’s Top 100 Leadership Speakers. His book is Leading With Emotional Courage. It’s so nice to have you here, Peter.

Thanks. It’s very nice to be here.

This is interesting to me because of the work I’ve been doing lately. You’re such a huge name in the area of time management, leadership and everything that you work on. I wrote a book about curiosity. A lot of what I dealt with in my research dealt with emotional courage. Everything that you’re writing about ties into what I like. This is going to be fun. In case anybody hasn’t heard of you, can you give a little background on you and how you got interested in this?

What I do is I write, I coach and I teach mostly about leadership. I run a consulting company. I’ve been very focused on leadership for 30 years. I used to lead expeditions, mountaineering, kayaking and climbing. I went from there to consulting. I started my current business about 21 years ago. I’ve been very focused on what enables us to get massive traction on the things that are most important to us. How do we move forward in a way that inspires other people to come along with us? I’ve written four books. I’ve contributed to seven others, all focusing in one way or another on how do we move forward in a challenging life and as leaders in a way that is inspiring to ourselves and to other people? What are the kinds of things that get in our way? It’s funny that you wrote this book on curiosity.

When I think about the four elements that I talk about in emotional courage which is confidence in yourself, connection to others, commitment to purpose and emotional courage. The connection to the other piece is very much based on curiosity. It’s very much based on how do we approach the world and each other with curiosity? It’s one of the reasons I’m not a big fan of things like personality assessments because personality assessments might inform us somewhat about each other, but it kills our curiosity. We should constantly be curious. I remember a conversation I had with my wife. We’ve known each other for many years. At the point of this conversation, we had known each other maybe twenty years. We were walking up this mountain. She was making a very difficult decision. We walked up and down the mountain for one hour. I didn’t say a thing. All I did was listen in the conversation, listen to what her thinking was and listen to how she was approaching it. I nodded a few times. I was listening the whole time.

[bctt tweet=”If you’re willing to feel everything, then you can do anything. ” via=”no”]

At the very end of the walk, I said to her, “Are you interested in knowing what I think?” She said, “I know what you think.” I said, “That’s interesting.” It was interesting for me because I didn’t know what I thought at the beginning of the walk. It took me an hour to listen to her to have an opinion. I said, “What do you think I think?” She told me. What I found fascinating is I said to her, “That’s what I thought twenty years ago when we met.” We had some conversation twenty years ago. Over the last twenty years, I haven’t changed my perspective. It’s hard to stay curious with people that you’ve known for so long and to continue to be open to change. We both had a laugh at that. I told her what I thought, which was very different than what she thought I thought.

It’s funny that you talk about personality assessments. When I wrote my dissertation on emotional intelligence, I became certified to give a few different personality assessments. I had no knowledge of personality or assessing it or any of that before I decided to research the importance of emotional intelligence on sales performance. When I took these assessments, they’re interesting to me. It’s a self-assessment. Should I be that surprised by what I received in my results? I’m not one of those people, “I’m an ESTJ. What are you?” I’m not like that. I thought it was interesting to find out what the opposite type of personalities are of what I could relate to, whether I could measure it or not when I was reading about that stuff.

It got me interested in assessing to some extent, not necessarily personality. It’s good to have a baseline to know where you are, to see if you can improve. On emotional intelligence, for example, it can be improved. In that respect, I’m okay with personality tests. For saying, “I’m this, you’re that. Let’s not do anything with it.” I’m not a fan of that either. What I like about even doing any assessments is that it opens up a dialogue. That’s what we’re both trying to do. In my book, I talk about four factors that impact curiosity. You’re talking about the same things. There are these things. Whether you measure them or talk about them, you need to talk about it.

We have an assessment on our website for leading with emotional courage. One of the things I say is it’s totally unscientific. There’s one question for each chapter. What it all does is it asks you to think about whether you think you’re strong in this or not, because it’s a self-assessment. When I did a self-assessment, it was very early on. I’ll share another story about my wife. It was maybe the first year of our relationship. We were lying around. She had a magazine of some sort with an assessment. She said, “Do you want to take this assessment?” It was a Myers-Briggs type thing. I said, “No, I don’t.” She said, “How about I read it to you and I fill it out? All you have to do is sit there and answer these questions.” I said, “I’m in.” She would say, “You’re at a party. You’d rather talk to one person or you’d rather talk to a roomful of people.” That’s a very typical question. I said, “I’d rather talk to one person.” She’s like, “No way, whole room.” She checked that whole room. That’s part of the issue and part of what’s interesting, which is if someone else took the assessment for you, it would probably look very different than if you took it yourself. She’s right and I’m right. There are elements of both.

TTL 324 | Emotional Courage, Talent Mobility
Emotional Courage, Talent Mobility: Personality assessments might inform us somewhat about each other, but it kills our curiosity.


It’s funny that you said that yours isn’t valid and all that, whatever scientifically stuff. That’s what I did with mine. I went through all the statistical analysis to make sure of this because when you’re in the PhD research community, I was so worried that if I didn’t do that, everybody’s going to go, “Yes.” I think though that those kinds of questions that aren’t researched for validity and all that stuff, all that is so important still. You don’t have to do factor analysis in my mind to determine that these questions are important to ask. They open up this dialogue.

For opening up a dialogue, it’s great. For thinking about, “What do I think about this?” is great. There’s this great research about these couple’s questions. It’s called 36 questions where if you want to feel more intimate with someone very quickly, you start working down these questions. You talk about them together. They’re everything from intimate to not intimate. Having the conversation about what you feel or choices you would make or things like that, predictably makes you feel more intimate with other people by having the conversation. I love that. That’s the right use of a set of questions.

What you’re trying to get at is what I’m trying to get at. That is the bottom line of what helps people be more innovative, more productive and more effective. All the things that people are trying to do in leadership. It’s important to start with what is emotional courage in your mind. If you’re writing a book about leading with emotional courage, we need to know your definition of that.

Let’s do an experiment. Think of a difficult conversation that you’re not having. The conversation that you know you should have, that you feel is important to have, but you’re procrastinating. You’re putting it off. You’re not having it. For the audience, you should do the same. Think about a conversation you’re not having. It’s probably a difficult conversation. Consider why you’re not having it. I’m willing to bet that you know everything you need to know to have it. I’m willing to bet that you’re perfectly skilled at having the conversation. I’m willing to bet that you’ve had time and opportunity.

[bctt tweet=”A big part of emotional courage is the willingness to feel things because if you’re willing to feel it, then you’re not driven by it.” via=”no”]

Why haven’t you had it? The answer is there’s something you don’t want to feel. If you have this difficult conversation, you might have to feel conflict. You might have to feel the disconnection. You might have to feel their defensiveness or your defensiveness if they come back at you. You might have to feel shame or embarrassment if they attack you or you might have to feel what it feels like for them to feel hurt, then you’re going to have to feel bad. If you’re willing to feel all of it, if you’re willing to feel everything, the shame, the embarrassment, the defensiveness, the passive aggressiveness, the anger, the conflict. If you’re willing to feel everything, then you can do anything. That ultimately is the definition of emotional courage, the willingness to feel everything.

You bring up a lot of fear-based things, which we’re tying into why people weren’t curious as well. When you’re talking about feeling things, the opposite of feeling it is being numb. You’re not having any experience in a way. Feeling, you have to have the good and the bad. To appreciate the good, you’ve got to go through the bad to have the experience to know what good feels like in a way. Don’t you think?

I don’t think you should just feel good. I would push back a little bit on even qualifying good and bad or labeling emotions good or bad. It’s more complex than that. I think that you feel all sorts of things. We run a leadership program. One of the things we do is we’re constantly asking the question, “What do you feel and where do you feel it?” If someone says, “I feel sad.” I want to say, “Where do you feel it?” We get confused with being sad versus having sadness. We get confused with being overwhelmed by identifying with the emotion we’re having, where we lose total control versus having the emotion somewhere.

You feel it somewhere. You begin to locate emotions. You realize you’re separate from that emotion. They feel things. There are people who would say, “Anger is a bad emotion.” For most people, anger and expressing anger feels good. It’s why many more people will express anger as opposed to vulnerability or sadness. The feeling of powerlessness is much scarier than anger, which is a feeling of power. It feels good. I would say in terms of the people who are numb to feeling, it’s not that they’re not feeling, in my experience. It’s that they’re not aware of their feeling. They can’t identify the feeling. Even people who are numb to feeling, unless they’re somewhere on the spectrum or they have low amygdala response that basically they aren’t acknowledging the feeling.

TTL 324 | Emotional Courage, Talent Mobility
Emotional Courage, Talent Mobility: Many people are out of touch with what they’re feeling. As a result, the feeling controls them.


They’re not in touch with the feeling. What happens then is those things that you’re calling bad feelings, the feelings like anger or frustration, they leak out in insidious ways. They become passive-aggressive. We all know people who smile and they go, “I’m not angry. What do you mean angry?” Those are the most dangerous people in the world, because they’re completely inconsistent. You don’t know what to expect from them. They could blow up at any moment. There are very few people who are numb. There are many people who are out of touch with what they’re feeling. As a result, the feeling controls them. They become a complete vehicle for the randomness of how that feeling might direct them at any given moment.

As you’re seeing all these things, I’m thinking of people I’ve worked with. I’ve worked with people who have a lot of panic and worry about things. It constantly focuses on all of that. Does this help with any of that? Some people get so into their inner monologue, what they’re telling themselves of what is going to possibly happen that will probably never happen. They think of what ifs and how am I going to handle it. They get so wrapped up that they can’t even enjoy the moments. How do you deal with that?

It’s tough and the obsessiveness of it. I’m a big fan of meditation. I meditate twice a day. I used to meditate various forms. I’ve been doing this one very specific form of meditation. Since I started a few years ago, I haven’t missed a day. I find it incredibly helpful to sit with whatever comes up and recognize like, “I don’t have to do anything about it.” I could feel any number of things and I can hold it. I can let it pass through me. When you become more skilled at feeling things and separating yourself from that feeling a little bit, you could still feel it. It can inform you. You could say, “I’m feeling anxious. Now what?” Now what is the question to ask. That’s an interesting question. I was with someone who is worried about everything. She’s someone in my family. She was worried about this person is eating too much and that person is not eating enough. This person is too lazy. This person is working too hard. She had this very narrow definition of what was okay and everything outside of the definition of what was okay, she worried about.

I was watching her. I used to be more triggered by that. I was watching her in a very un-triggered relaxed way and going, “There is very little usefulness of that kind of worry.” It’s very little. At that point, I was watching that and I made this decision to say, “I’m going to stop worrying. When I watch myself worrying, I’m going to recognize what I have control over and what I don’t. What I have control over, I’ll do something about. What I don’t have control over, I’m going to let go.” It’s that serenity prayer. It surprisingly works. If you can watch yourself or if you can notice yourself worrying like, “I’m worrying, is there anything I can do about that?” If there is, if I can make a phone call, if I could have a conversation and if it’s about me and I could change something, then great. If not, then I’m not going to waste my time worrying about it. Surprisingly, you can shut that off.

[bctt tweet=”If we’re going to wait until we’re not scared to do something, we’ll never do it.” via=”no”]

What I find so interesting is the perception of what’s worth worrying about and what’s not to people. Two people are given the same exact scenario. It affects them exactly the same way. One person is like, “Yeah,” and the other one is climbing the walls.

That’s historically based. It’s about our childhood like, “I worry about money. Do I need to worry about money? Other people in my position might not worry about money.” Instead, “Why do I worry about it? My mother was a Holocaust survivor. Our family grew up very privileged and yet there were a couple of times we almost went bankrupt.” You look at that and you go, “I’ve got a history. That history leads me to worry about money.” That’s the hardest one to let go of and say, “I’m not worried about money because there are some things I could do about it. On the other hand, the things that I can do about it aren’t necessarily the things I want to do about it. I don’t want to take work that I don’t particularly want to do and I’m not passionate enough in order to make a bunch of money. I don’t want to do that, but it’s a little hard to resist sometimes.” The hardest ones are you worry about things that you can control. You don’t particularly want to because the worry itself is not that functional or not that useful. That’s tougher.

That’s where you have to say, “I recognize this as worry. I recognize I can control the outcome.” Here’s a clincher. “This is what I recognized about money. There’s nothing I can do that will satisfy and put to rest my worry about money. Meaning I could make 50 times as much as I’m making and I will still be worried about money.” There’s some element of ingrained upbringing and something that’s part of me. When I realized that I can control it, but there’s no amount of control over it that will satisfy my worry, then you throw your hands up and you go, “I can’t control it because the emotion will always be there no matter what I do.” I have to be willing to feel the worry and make smart decisions that aren’t driven by that worry. I could feel the worry and make smart decisions. That’s a big part of emotional courage, the willingness to feel things. If you’re willing to feel it, then you’re not driven by it. I could feel it.

I was wanting to write fiction. I’m struggling with it because I love writing fiction and somehow I wasn’t sitting down to do it. I was saying to a friend of mine, “I don’t know why I don’t write fiction. I’ve written all these books and yet I’m not writing fiction.” She said, “Why do you think you’re not writing fiction?” I said, “Honestly, I’m scared. I think I’m a bad fiction writer. I’m cliched. I’m not very good. I’m not that creative. I’ve gotten bad feedback. Every time I sit down, I’m scared.” She laughed at me and she goes, “Do you think you should be able to write without being scared?” I thought, “That’s using my own medicine against me or for me.” If we’re going to wait until we’re not scared to do something, we’ll never do it. If I’m going to wait until I feel comfortable with the amount of money I have to not make decisions based on money, then I’m never going to do it. There are certain emotions like, “My experience of this lifetime is that I will experience worry or fear or any sorts of things that will not go away. I better not hold my life up and the expectation that they will go away. I better act in the context of all of those things.”

TTL 324 | Emotional Courage, Talent Mobility
Emotional Courage, Talent Mobility: The sense of self and groundedness, that’s true confidence. The fake confidence, the confidence that competes with you, is arrogance.


You mentioned the importance of confidence. I want to talk about that a little bit because how much is enough confidence? How do you know if you’re confident enough or not enough? Is my confidence level going to be the same as yours and that type of thing? How did you come up with confidence?

The way I mean confidence is the true confidence in yourself. It’s not an arrogance. It’s not a sense of I’m better than you. I don’t care if yours is better than mine. That conversation doesn’t interest me. The sense of self and groundedness that I have, that’s true confidence. The fake confidence that competes with you is the confidence that can’t not know something, which is arrogance. It’s like “I know everything. I’m great. I could do everything probably better than all of you.” That’s not confidence. That’s insecure. The thing that we sometimes read as confidence in other people is insecurity. The confidence that says, “I cannot know things. In fact, there’s a tremendous number of things I don’t know.” If you ask me a question I don’t have an answer to, I don’t have to pretend I have an answer. I could say, “I don’t know.” The confidence that allows us to stay grounded in the face of failure or ambiguity or even success and not lose ourselves. The confidence that can stay with ourselves in the face of various emotions that we have or in the face of an attack or in the face of backstabbing and not lose ourselves to it, that’s confidence. That’s what I mean by confidence.

Confidence that says that you have an essential strength and belief in yourself. You don’t have to name drop. You don’t have to be the most successful person in the world. You can write without thinking it’s going to be great because that’s not why you’re doing it. You can write a great article and then not check if it became number one most popular on Harvard Business Review. That’s confidence. I’m somewhat there. I like checking in my articles and seeing how popular they are, but there’s a lack of confidence there. If you find that it’s number three most popular or number ten most popular or not even on the list, but not the number one was popular and you take that as data, that could be confidence. If you look at it and you say like, “I wanted to be number one.” There’s probably still some good work that you can do around being more confident.

What comes to mind when you say this, I don’t know if you ever saw Christian Bale in American Psycho. He is proud of his business card. He’s so obsessed with how perfect it is. The only thing I remembered about this movie was that a guy next to him has a better one and it destroys him.

That’s insecurity. That’s the definition of insecurity. I said to my kids, because they’re ski racers. They’ve done very well. They’re constantly on a number of areas comparing themselves to other people. It’s hard to be a ski racer and not compare yourself because you literally every race compared to other people. What’s interesting is they’ve gone from racing all these races to then racing regionals. When they make regionals, they make states. Daniel, my eleven-year-old, made the equivalent of state. He usually comes in the top ten. He raced regionals. He did well-enough to make states.

In regionals, he came in nineteenth. I said, “How did you do?” He said, “I’m not so well.” I said, “What do you mean? You made states?” He said, “Yes, but I was nineteenth. I wasn’t even in the top ten.” I’m like, “The racers you’re skiing against are coming from a broader pool of racers. They’re the top racers in each of their regions. You’re competing against a different group of people and to get nineteen out of this set of 80 racers is different than getting nineteen out of your own mountain. When you’re on your own mountain, you’re getting top three.” The thing that I try to teach my kids and this might be a little obnoxious. What I’m saying is there will always be people who are better than you. There will always be people who you’re better than. It’s worthwhile to stop comparing yourself to the people around you and decide what you want and how you can go about getting it as opposed to in competition.

It has to help with connectedness if you stopped doing that.

I can’t connect with you in a certain way if I’m competing with you. We can connect in our competition. Ultimately, if you’re a threat to me, it’s going to be hard for me to sit and relax and be curious about you.

All of these things that you talk about, your confidence, connection, being committed and having emotional courage are something that they all deserve so much special attention. I’m curious what you mean about committed specifically?

Commitment to purpose has to do with both being clear about the larger purpose and context in which you’re operating. Even more important than that, focusing on it. I find a lot of people who were committed to accomplishing things. There are many different things on their list that they struggle with a larger purpose. It’s what do you care about? For me, I went through this process myself. I used to define myself in terms of the outcomes that I’m trying to produce. I help successful people to become great leaders. I know a lot of successful people who are not good leaders. We all know a lot of people who are successful but not good leaders. I know very few good leaders who are not successful. I want to help successful people become great leaders and create stellar teams and inspire their organizations to get great results. That’s where I’m focused. Even as I say that, I could see how that commitment can lead me to spread myself super thin and doing a million different things. I clarified for me that’s the outcome I’m wanting to produce. Who am I? What do I do? That’s where what I said at the beginning, which is that I write, I coach and I teach mostly about leadership.

Being clear about that is my passion. That is where my passion meets my strength, meets a world’s need, in that intersection. When I say that, it’s like, “What percentage of my time am I spending writing, coaching or teaching mostly about leadership?” When I asked that question, it wasn’t a high enough percentage. I started to make changes in order to focus more on that. In order to spend more time writing, coaching and teaching, mostly about leadership and less time on other stuff. Part of the commitment to purpose is the commitment part as much as the purpose part. A lot of people talking about meaning and purpose. That’s part of the general happiness language of do I have meaning in my life, etc. My commitment to purpose is more from a leadership perspective too, which is what are you saying no to? What are you deciding not to do?

Do you have a process for filtering through your choices so that you’re committing to what’s bigger than you? There’s a whole other level of all of this, which I’ll share with you, which I’ve been thinking a lot about. The sign for me of a good book that I’ve written is when I’ve written the book. The more I talk about it and engage with it and teach about it, it grows on me. I began to understand the book more deeply. I begin to understand things I didn’t particularly intend when I wrote it. That’s happened to me with this book. It does not happen to me with all of my books. It’s happened to be primarily with two of my four books with 18 Minutes and this one. One of the things that I’ve realized and this might veer into the realm of stuff that some people don’t like going in the realm of. When I think of spirituality or I think of religion, I’m Jewish, I think of this story and you see this in Christianity also. There’s a story where one rabbi challenges another rabbi to recite the entire Torah, this religious book of Jews, standing on one leg. He goes, “I’ll take on the challenge.” He stands on one leg. He says, “Love the Lord your God with all your heart, with all your soul, with all your might and treat your neighbor as yourself. On these two things, the world stands.”

I would add one to that, which is assumed in the second but not true in our society, which is love yourself, love each other and love something bigger than all of you. Call it God, call it whatever you want to call it, but love something bigger than all of you, love yourself, love each other and love something bigger. I think about this book. That’s what I’m talking about between here and me. There are lots of people who love other people but don’t love themselves. Those are the people who will do anything to please you. They will give themselves up in order to make you happy. There’s a higher proportion of women than men in that category, not scientific, but in my anecdotal experience. What I’m writing about and talking about on people’s radio shows is that this is a leadership book. I believe that anybody can be a leader. It’s about love yourself, love each other and love something bigger than all of you. Have the emotional courage to feel what you need to feel in order to love yourself, love each other and love something bigger. I don’t know that I’ve ever talked about that explicitly except here. As I hear myself saying it, I like it. It’s very true.

You’ve done such amazing work. I know you’re known as a time management guru in all the things that you’ve done. This is one more thing that many people will find so fascinating about your work. It’s called Leading with Emotional Courage. Peter Bregman, you are such a nice guy to do the show. I know a lot of people would want to know how they can get your book. I’m sure it’s on Amazon. Is there any other list of places and things you want to share with anyone?

Thank you. If you go to, if you go to the Resources tab, you can get a whole bunch of stuff for free. You can take that assessment if you’re into that thing. You can find links to the books, read about them and get them wherever you get books.

Thank you, Peter. This has been so much fun. I enjoyed having you on the show.

Thank you, Diane. I’ve enjoyed being with you.

Understanding Talent Mobility with Caitlin MacGregor

I am here with Caitlin MacGregor. She’s built two businesses. She is the CEO and Cofounder of, which combines industrial-organizational psychology and artificial intelligence to help companies hire, grow and retain top talent. It’s nice to have you here, Caitlin.

Thank you for having me.

I’m interested in anything innovation and psychology combined. I had the father of artificial intelligence on my show, Jurgen Schmidhuber. We were talking about some of the potentials of what we’re going to see in artificial intelligence in the future. I’m going to ask you a few things about that, but I want to get a background on you. Can you tell everybody here a little bit more about you?

I built two businesses for other people. I didn’t realize I was going to be an entrepreneur. I was hired as employee number one, Director of Operations and built locally made custom apparel company from the ground up. That was a social enterprise. Somebody sees potential in me and given me an opportunity to build something from scratch that made me realize that that was my unique talent. I went on and built an educational software company in the US. I opened up the US branch for Canadian educational writing software company. That’s when I got exposed to the power of industrial-organizational psychology and how there are over 30 years of consensus around how to predict the future performance of an employee. I got a chance to use that in the business I was growing but through a very expensive consulting process. We saw an opportunity to democratize access to highly predictive data and turn it into software as a service. We started our business helping companies with talent acquisition using predicted data to know who are going to be their top performers. Then we moved into enterprise customers and using that data but in talent management and workforce planning.

I can see why Tom Dub introduced us. I had met him through Dr. Cindy Gordon. She’s into all the predictive analytics and some of the stuff you’re talking about. Some of the stuff that is out there, it’s interesting to look at the assessments and some of the different ways of predicting success in people. When I wrote my dissertation on emotional intelligence and its impact on performance and sales, that was what I was trying to look for with some correlations and find ways to determine what would make somebody successful in sales. I’ve always been interested in the psychological aspect and software creation and all the things you’re talking about. I created a curiosity index, which is called the Curiosity Code Index, which determines the factors that hold people back from being curious, because curiosity is a major factor in people’s success. I’m curious about your level of curiosity. Have you always been that way? What do you think have you seen has helped you be more curious?

TTL 324 | Emotional Courage, Talent Mobility
Emotional Courage, Talent Mobility: Part of continuous learning is gathering information from others and looking at best practices, but then adapting and experimenting on your own unique situation.


There’s an enormous alignment. It’s the same body of research that we’re all pulling from. We’re looking at it from different perspectives or you’re using it for different reasons. It’s very much aligned with what you do and I have tons of respect. In terms of me on a personal level, part of being an entrepreneur and having a high degree of innovation as one of my top three talents, part of innovation is that curiosity. I wasn’t self-aware that I had it until I was in a job that was rewarding and allowing me to try doing it. In hindsight, looking back, being a teenager and into university, any time that there was a gap that I saw, I would fill. From simple things like I was a windsurf instructor one summer and everybody was doing the waterski program and nobody is doing the windsurfing program. I built that program from scratch so that it was getting more people signing up.

To this day, it’s the only remaining part of the program. It surpassed the waterskiing and shut that down and only run the windsurfing even to this day. Everything that I look back and I could see if there was an opportunity to fill a gap to build something, often I was motivated to do it. I wanted to participate in the Model United Nations. I organized 50 university students to sell Krispy Kreme donuts to fund us to go to Ottawa so we could be part of Model United Nations. Before that, there hadn’t even been a club. It’s funny when you look back in hindsight and you’re like, “That’s entrepreneurial behavior.” I studied International Development. I had no idea until I was doing it.

You said something that was fascinating. You said you didn’t realize it until you get a job that was rewarding curiosity. How were they rewarding you for that?

The first job I had out of university and after teaching English in China for a year and again, a sign of being curious, wanting to work overseas and experience another culture which I had already done twice before that. When my first job came, they said, “We have this problem we’re trying to solve.” I was hired to solve that problem, but there was no roadmap. There were no instructions on how to do it. I was given the complete trust and freedom to figure it out. I feel like curiosity, in a lot of the times how it manifested in me, is I’m curious about how we solve it. I’m curious on how we build something from nothing and not being restricted. I wasn’t put in a box. I wasn’t told what I could and couldn’t do. I was given full rein and full freedom to propose and to experiment and try out different things. Lean startup theory didn’t exist at the time. The wisdom now is that when you’re trying to solve a problem, go to the end customer and design a solution in their image.

Because I knew nothing about the apparel business, I grew up wearing second-hand clothing all through high school. I knew nothing about fashion. I knew nothing about manufacturing and supply chain management. The reality is I had to figure it out. I went to the people that would be our customer. I said, “I’ve gone to the mall and found all of the most popular cuts of t-shirts and colors.” I went to a tradeshow and bamboo fabric was hitting the market. I collected all of these examples of what that should be and then I use focus groups. I use the customer’s feedback to find the points of consensus and use that to solve my problem. I constantly was figuring out the solution through continuous learning, which is for me, part of my core value of acumen has been evaluating continuous learning. I’m always trying to figure out how to be better. That’s a manifestation of the curiosity component as well.

[bctt tweet=”To optimize people is to make sure that they’re in a position where they’re leveraging their strengths.” via=”no”]

I’m into continuous learning. As you’re talking about that, you brought up some of the reinventing of the wheel that many people have to do in the workplace because nobody has the answers or they won’t share the answers, which is more frustrating. The learning curve could be cut sometimes, but then again, if you use somebody else’s solutions in their work, sometimes you can be better to come at something from fresh eyes. You don’t have to unlearn all the problem things that they’re sharing with you that they’ve learned. I don’t know which is worse, to have to do it longer to figure it out yourself or to take somebody’s data that’s slanted. What do you think?

It’s a combination. When I was learning about manufacturing, for example, I went out to people that had the knowledge and I learned from them. I had to curate my own education. It’s almost like you’re triangulating. This person said that and that person said that. These were the points that are in common. My situation is different. This is how I can bridge what they were doing to where the solution is. I feel part of continuous learning is gathering information from others and looking at best practices, but then adapting and experimenting on your own unique situation. In this case, it’s a combination of peer support and mentoring is a critical component. I had my monthly CEO peer-to-peer group.

I think about how the membership fees that I have to pay once a year and almost every single monthly meeting, I’m getting my value back. There are ten meetings a year. I end up at the end of the year getting five times the value because I’ve learned about a product that is less expensive than the one I was maybe going to buy. I’ve learned about a headcount that’s more important. I didn’t make a bad hire because I thought there’s a better resource because I learned a company that went through it. I find that the peer part of it is not telling me exactly how to do it, but it’s helping me get the building blocks so that I can figure it out faster myself.

That’s why there are many masterminds and there are many people out there trying to capitalize on helping with peer-to-peer sharing. It can be challenging to know where to get the right information. If you trust the people you were around and the people that you pick as mentors is the key. I’m curious about Plum. I mentioned it’s What exactly do you do? I said a little bit about what you do, but can you go into a little more detail?

When we think about in my case, I didn’t know what is an entrepreneur? I first ran a clothing business, then I ran an educational business and now I’m running software as a service technology business. It wasn’t my past experience and it wasn’t my education of studying International Development that made me successful. What’s helping me be successful are my innate abilities. There’s a model that talks about knowledge, skills and attributes or sometimes it’s talking about attribute or soft skills or talents. Effectively, what Plum is doing is quantifying those attributes, those innate powers that a person has, because those are the most important for predicting somebody’s long-term success. When you look at the most recent numbers on the future of work, they’re talking about somebody that my generation, which I’m in my late 30s, is going to potentially be working for 60 years. People are going to be evolving in their jobs so much. How do you predict what is going to make them successful?

TTL 324 | Emotional Courage, Talent Mobility
Emotional Courage, Talent Mobility: The piece that people are often concerned about is people gaming their personality.


We have been focusing on that missing data. In a universal framework, we found a way to understand the potential and those talents of every individual in the workforce. Be that a job seeker or existing employee and quantify their talents like innovation, persuasion, execution and then also quantify the needs of a unique role. A lot of us in HR are familiar with competency models that often have that skills, knowledge and attributes. We quantify those attributes or talents. The behavioral KPIs needed for somebody to be successful in a given role and then we match. If you know the people and you know the roles, you can then say, “Caitlin is a 30 match for this job that is going to be incredibly repetitive and about structure. I’m 95 match for an enterprise sales type role because I’m high and persuasion and that’s going to be critical.” We make it specific. Everything equal. We keep it up to date and dynamic way. As the nature of jobs changes, companies can quantify their needs and then see their entire employee base and database of job seekers who are the 99 matches or 95 matches for their role.

It’s an interesting thing to try to quantify certain things. I found that very challenging in creating my curiosity assessment. Some things you self-assessed and some things you peer assess, then you’ve got perception in the mix of what you think or whoever is assessing you think of you. How are you keeping that perception out of the ratings? Is that something that you’re finding problematic at all?

We have partnered with one of the leading industrial-organizational psychologists in North America. His name is Dr. Neil Christiansen. He’s a professor at Central Michigan University. He wrote the Handbook on Personality at Work. One of the ways, when you’re looking to assess these talents, is that we measure three things. One is problem-solving. The other one is social intelligence, which is very similar to the EQ you were talking about. There’s personality. The piece that people are often concerned about is people gaming their personality. It is about prioritization. An example would be, what’s most like you and what’s least like you? Do you make friends easily? Do you usually finish what you start or do you generally respect authority? There is no right answer. It’s simply about what are you prioritizing?

Like Key Performance Indicators, KPIs, you can’t have somebody do everything. You need to prioritize what are the most critical behaviors that you need them to do in order to excel in the job. Because the profile is being compared to potentially thousands of job, there is no way of saying, “This job requires me to make friends easily over finishing what I start.” That one profile would be compared to a whole bunch of different job. Using forced choice methodology. People can’t fake it by having a double-blind situation. People don’t fake it. We remove a lot of what makes the data unstable. We’ve removed a lot of that. We have a very high retest reliability score. We have a very strong level of validity that beats out a lot of our competitors in this space because we take the science incredibly seriously.

We can use the self-assessment because of how we’ve designed it that can keep a lot of the problems that you’re talking about at bay. This is not the only data point. This is trying to replace data that isn’t as predictive and hence, it’s against bias. Our studies show that we are four times more accurate than a resume at predicting on the job success. We’re not saying this is the only data mark, but in terms of that long-term success, it will be more accurate than somebody’s name. It will be more accurate than did they go to school overseas or to an Ivy League? Did they work at a competitor or not? As we look for the transferability of talent, especially as the nature of work changes, this data is critical but it’s not the whole piece.

[bctt tweet=”It’s about prioritization. We only have so many hours in a day.” via=”no”]

It’s interesting to look at how to measure some of these things. You mentioned some of the soft skills, some of the personality components and all this stuff. It’s nice to have something that you can give somebody before they get into the company. Once they’re in the company, how are you utilizing your tests and all that to better align people or is this something that you do in the interviewing process?

We started in talent acquisition. The last one was for four years. We’ve been specifically in that space where you have 100,000 job seekers applying for 500 sales roles. We’re using better quality metrics to narrow down who’s going to be successful long-term and remove a lot of the bias. Now where the market pull is and the work that we’re doing with our largest enterprise companies are looking at the problem of the future work where 50% of jobs are going to be replaced by automation and 65% of state students are going to applying for jobs don’t even exist yet. They’re trying to think about if I have 20,000 employees or 100,000 employees, I’m maybe not as concerned about the 20%, 30%, 40% of new people that are joining us. I’m worried about potentially the 100,000 employees, what’s going to happen to them over the next three to ten years? What’s going to happen to jobs that are going to be automated or how do I keep them involved, keep them motivated?

How do I keep them meeting new business objectives? What’s emerged is this concept of talent mobility. How do you take my existing people and optimize them as the business needs change? What we’re able to do is look at what our features called talent rediscovery. You can have Jane that has been a frontend developer for eighteen years and her coding language is starting to become out of date. We can assess as Jane somebody that learns quickly on the job and therefore should be reskilled to be a full stack developer or is Jane better suited to be a technical sales rep or be on the product and innovation team or in operations? We’re able to say for each of those jobs, Jane is 30 match here and 98 match there, a 70 match there and 85 match there. We’re able to allow for that internal talent mobility, which keeps them with the continuous learning, keeps them engaged and keeps them as an asset to the company rather than them saying, “Her skills are no longer relevant and she needs to leave.”

That’s what I’m trying to do a lot with my work because a lot of people are not engaged or they’re going to be displaced. There’s so much that we don’t know what people are capable of. I’ve talked to Olin Oedekoven on my show. He talked about hiring people and did not even knowing what he’s going to do with them. First seeing what he thought they were good at and then designing a job around them. In a way, you’re doing that in a different way by saying, “This is what we figured would be the job based on what we think you would be good at.” Can people change though? If maybe the tedious thing doesn’t bother me now, but in the future after doing it so much. It’s something that bothers me, do we need to keep testing for this?

You don’t need to keep testing for it, 90% of the population after they’ve graduated university and 90% abroad. I don’t have the exact number. The vast majority of the population, their personality and those priorities and the things that, at the end of the day give them a self-sense of self-worth. Those pretty much are stabilized by the time they graduate university with the exception. That’s why there’s a certain portion of the population that will be the exception if they’d gone through a traumatic life event or they’d been working with an executive coach for a year on a particular thing. Ultimately, if I at the end of the day felt fulfilled because I solved a complex problem and I thought about an out-of-the-box way of doing it, that’s going to be the same thing that motivates me when I’m 50. It doesn’t mean that I can’t improve on things. It doesn’t mean that I can’t have a job that relies on another area. I hear my whole career get a sense of self-worth through checking off a to-do-list.

TTL 324 | Emotional Courage, Talent Mobility
Emotional Courage, Talent Mobility: It’s a win-win for the individual to be in a role that is leveraging the strength.


As my job has changed, I had to work on that not being the only way I get a sense of self-worth and to evaluate. If I have to support somebody and unblocked something that’s challenging them and build them up so they can do their job. I need to know frame that as checking off my to-do-list rather than I sent this email that I needed to send by the end of the day. There is training, there is development but ultimately, those are my driving factors. Those are the things that give me a sense of self-worth. I don’t love the time that I’m spending looking at financial models. When I hired a manager of finance who loved being able to create a process around numbers. It fills her up, whereas it drains me. It’s not that I can’t do it, it’s that to optimize people is to make sure that they’re in a position where they’re leveraging their strengths. Everybody wins in that scenario.

What about the people who could have more strengths, but we have never worked with him on that? You’d mentioned testing for problem-solving, critical thinking I imagine and all that type of thing maybe wasn’t taught that much. Do you recommend that we continue to train people in these areas of emotional intelligence, social awareness, all these types of things? Some of those things you mentioned are improvable.

It’s about prioritization. We only have so many hours in a day. Something that would take individual number one to do something and maybe take them ten minutes whereas the second person may take three hours. Do you want to work with the person that’s going to take three hours to do the same task to get them to improve and not the choice? Maybe that’s a good use of time or do you say, “The person that’s taking three hours to do the task, there is a different thing that they can add value on.” Maybe in that case, it’s the relationships they’re going to build. If they spent three hours building relationships, maybe the financial return to the organization is ten times for them feeling value and the value to the company.

If they were building relationships during those three hours’ time versus solving this one problem that the other person is going to solve in ten minutes. It’s simply about do we want to make sure that the person because everybody has some strength, every person is good at something. Do you want to be making sure that you’re leveraging that strength in that time or do you want to be spending that time to work on something that even after all of their training, it’s going to take them 30 minutes to solve that problem? Whereas the other person that still takes ten, even after tons of enhancing development when they could have been spending that time on something else.

I’ve been in a lot of jobs where everybody wanted that same position. Nobody was applying for anything different. There’s always a scale of somebody who’s efficient and could do 100 times more than somebody else. You see a lot of people who are that way of getting more and more dumped on them because they’re so fast and they’re so efficient. Does this help avoid that? You get no good deed goes unpunished at sometimes.

Making sure that there are enough people that are strong doing the things that are needed of them. Making sure that the people that aren’t strong in that, but there’s enough for them to do that. They add value in a different way. I feel like we aren’t always optimizing our resources. That person should not be doing double their work because nobody else could do it. Ideally, there’s two of them that are doing that work. The other people are doing something that equally is important but in a different area in their wheelhouse. You don’t want to have that person who put ten minutes to solve a problem going out and networking for three hours and making no connections whereas that person that’s going out and networking three hours and making tons of connections. There is a strength for everyone. It’s a win-win for the company. It’s a win-win for the individual to be in a role that is leveraging the strength. The reason why we don’t do it enough is that this data was too difficult to get at. It was too hard in the past to quantify everybody so that you understood apples to apples, what value they brought.

It was too hard to understand in real time with the roles needed. It was too expensive because it’s often run by consultants or software that required customization. In 2019, the reason why we can finally bring this data to the forefront is that we know how to do it in an accurate, scalable cost-effective way. Now that this data is readily available, it’s having to change how we’ve been evaluating talent. We have to see that there are new possibilities now that we couldn’t have done it before but now we can. All the research around the future of work has said, “It’s this critical talent like communication, adaptation, curiosity, innovation that are the future. Instead of talking about how we need these, let’s start putting data around it, which comes back to you. The bullets to democratize access to highly predictive data that was locked away from people unless you are maybe at a C level is they brought in a psychologist for the day or very unique siloed situation.

I could see why you love doing what you’re doing because that’s fascinating work and I think a lot of people would like to know more about and you. Is that the best place where they can go to find out more about you? Are there any other links you’d like to share?

If you go to, you will be able to find everything about Plum and sign up for a demo. You can also email,

Thank you, Caitlin. This has been so interesting. I enjoyed talking to you because this is right up with what I love to talk about in terms of personality and assessments. You’re on the cutting edge. Thank you for sharing all that.

Thank you. I appreciate it.

I’d like to thank Peter and Caitlin for being my guests. If you’ve missed any past episodes, you can listen to them at I look forward to the next episode of Take The Lead Radio.

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About Peter Bregman

TTL 324 | Emotional Courage, Talent Mobility Peter Bregman is a bestselling author and one of Inc. Magazine Top 100 Leadership Speakers, His most recent book, Leading with Emotional Courage: How to Have Hard Conversations, Create Accountability, and Inspire Action on Your Most Important Work describes an overlooked – and essential – skill of leading at the highest levels: Emotional Courage. S4a One of the Global Guru’s Top 30 Time Management Professionals for 2018, Bregman is also the author of the Wall Street Journal bestseller 18 Minutes: Find Your Focus, Master Distraction, and Get the Right Things Done; Point B: A Short Guide to Leading a Big Change, and Four Seconds: All the Time You Need to Stop Counter-Productive Habits and Get the Results You Want, a New York Post “Top Pick for your Career” in 2015. Consistently the most-read blogger at Harvard Business Review, Peter’s articles and commentary appear frequently in Bloomberg Businessweek, Fast Company, Psychology Today, Forbes, CNN, NPR, FOX Business News, The Financial Times, and PBS.

About Caitlin MacGregor

TTL 324 | Emotional Courage, Talent MobilityAfter being voted most likely to save the world in her high school yearbook, it wasn’t until Caitlin MacGregor built two businesses that she realized that it meant revolutionizing talent processes to prepare businesses for the future of work. Caitlin became the CEO and co-founder of Plum ( — which combines Industrial/Organizational Psychology and Artificial Intelligence to help companies hire, grow, and retain top talent — so that every business owner like herself could benefit from the predictability and diversity of a talent recommendation engine. Caitlin is passionate about equipping business leaders with the talent data they need to get the right people in the right seats as the workforce shifts in the age of automation.
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