#572: Practical Courage Skills Every Lawyer Needs, with Jim Detert

Episode Notes

Transcript

Zack Glaser:

Hey all, I’m Zack and this is episode 5 72 of the Lawyerist Podcast, part of the Legal Talk Network. Today, Stephanie talks with Jim Detert, a professor at the University of Virginia’s Darden School of Business, and author of Choosing Courage, the Everyday Guide to Being Brave at Work. They explore why it’s so hard to speak up at work, how fear and physiology trip us up, and how we can build practical courage even when it’s uncomfortable or risky. But first I’ve been thinking about contras, like you do those sneaky words that mean they’re opposites, the English language is full of them, even though some sources say they’re rare, they’re really not. In my mind, like Ravel, that’s one of my favorites. It can mean both to tangle up or to untangle or sanction, which might mean permission or punishment, right? Then there’s dust trim seed left. I mean that means what remains or what departed.

There’s clip fast oversight. I mean, we’re getting a lot here, right? Then there’s the legal ones. Lease and rent are perfect examples. Are you the one granting use of property or are you the one receiving it? I guess it depends on which side of the deal you’re on. My favorite though, because I was a creditor’s rights attorney, is probably garnish because in one sense it can mean to take something away, obviously in kind of the legal sense, but then you can also garnish something, a plate. It can mean to put something on something as well. So context is everything, and quite frankly, in our contracts, in our leases, and we don’t always have context, so this is a good reminder that in law clarity matters because even when we think we’re being clear, our words might be doing double duty. So maybe go back and see what your leases say. Maybe go back and see what some of your contracts say. This might be a good time to go. Make sure that you’re being clear. Well, now here is Stephanie’s conversation with Jim Dieter.

Jim Detert:

Hi, I am Jim Detert a professor at the University of Virginia’s Darden School of Business. I write on topics related to leadership, why people speak up or don organizations, and the trouble that causes and what we can do about it to help ourself and others be more competently courageous. It’s good to be with you today,

Stephanie Everett:

Stephanie. Yeah, thank you for being with me and I’ll just give you a little shout out here quickly. I have your book right here, choosing Courage, the Everyday Guide to Being Brave at Work. Just that kind of hits you the idea that we need to be brave at work. What kind of led you to write about this

Jim Detert:

In the year 2025, including in the law space? Of course, that’s completely self-evident, right? But considering I decided that a while back, it is probably worth an explanation. I teach primarily practicing managers, so executive MBA, part-time m mba, so working professionals, many in leadership or management roles, and what I observed over time is that while people were happy to learn tools to put in their managerial toolkit or just let’s just say their interpersonal tool for tough situations at work, what they really ended up saying over and over is, it’s great that we’ve learned all this stuff, but in reality, when those important moments come, I don’t think I’m likely to do it. And in part it’s because I’m afraid and I don’t overcome that in part though, because that fear comes from lack of actually knowing the particular kinds of skills for those high stress moments and having practiced them enough. And so really my desire to work in this area came from the combination of continuing to have those experiences where people were saying there are issues from just performance problems to interpersonal treatment problems to unethical or illegal issues that I wish I was more capable and more willing to speak up about. When I looked at, well, what’s out there on that topic, I was disappointed to see there actually wasn’t very much good advice, and so I made that a mission to work on that.

Stephanie Everett:

Yeah, it seems to me a lot of people are familiar with Kim Scott and this idea of radical candor and it’s like, yes, I want to do that at work. I want to be that person that can be candid with my team and have those hard conversations. And then when it comes time to doing it, and I know with even the clients that I work with, it’s like we almost are paralyzed by the fear. It feels really hard and scary to even start engaging in those tough conversations.

Jim Detert:

It does, and I think that one of the things I learned early on is that if you’re going to help people in this domain, you have to actually just start with sort of some myth busting. I mean, I think we see courage in a lot of inaccurate ways. We somehow think it’s this innate sort of born property that a few of us have, but most of us, we think it’s some set of skills and abilities that are unique. It’s not true. I mean, I have looked for personality and background nationality. There is no such thing as sort of a courageous disposition as Kim Scott and others have. There are people who are more likely to have a fight response than a flight response in those situations, but frankly, most people who fight are just as unskilled as people who flee. And so if your goal is to be skilled, then you have to learn new skills and practice them, whether it’s if you will, to fight better or to just speak up more.

So one myth is just it’s not some magical thing. It’s in fact a skill It like any skill, you only get better through practice if you want to play the piano, if you want to play a sport, you don’t watch a video on it or read a book or just think about inspirational quotes. You’ve got to get out there and practice. And the same is true here. And then I realized, well, okay, even if you convince people it’s not innate and that they need to practice, you also have to then teach them concrete things because there are related myths. I can’t do it because I’m afraid. Well, I think Scott Peck got that right a long time ago. He said, the absence of fear is not courage. The absence of fear is some kind of brain damage. Reasonable people are worried in work context about career consequences, about social consequences, about psychological consequences. So this is not about not being afraid. This is about do you learn how to overcome your fear skillfully?

Stephanie Everett:

No, I love that,

Jim Detert:

And that’s what I’ve been trying to help people do.

Stephanie Everett:

And so what are some first steps that you could help us with if we’re like, okay, I know I need to engage more and have these, we’ll label ’em harder conversations. Maybe that’s unfair. Sometimes I feel like for me, I try not to put too many labels on the conversation ahead of time. I think that builds up the anxiety in my mind that it’s going to be hard or it’s going to be, that’s my mindset going into it. And then sometimes I get into it and we engage and then it’s a lovely conversation and I have to tell myself, wow, that wasn’t as bad as I thought it was going to be.

Jim Detert:

That’s a particular example of one of the three areas we work on. So I would say, Hey, if you want to start moving in the right direction, you have to realize that the barriers are essentially physiological reactions in our body, how we end up feeling. They’re cognitive, they’re how we think, and what you just said is an example of that and how we think both before those conversations and then how we behave, what we actually say and do both in the moment and then after. One of the reasons I actually think it’s worth working on these three sets of skills is that 80, 90% of people when I work with them on, okay, set a specific goal, do some practice scripting that actually practice the conversation. In my work, I tend to use trained actors and have people do one-on-one simulations of very particular conversations they want to have, and most of the time I’d say 80, 90% people say When I did that work and then just did it, it was significantly better than I thought.

Now, sometimes it wasn’t great, but even when it’s not great, it’s usually better than we believe it will be, and I think we know the basic reason for that. It’s a very well established fact in psychology that just this phenomenon we say bad is stronger than good. If you think about our survival journey as a species, it made a lot of sense that our brain evolved to overestimate risk. I mean, you can jump 10 times thinking there’s a snake, and if you’re wrong all 10 times you’re still alive, but if you don’t jump once and there is a snake, you might be dead. So the brain evolved to overestimate risk, and so one thing we will commonly do is we will tell ourself the worst possible version of what’s going to happen. And so that itself, that’s one part of the cognitive bucket. So one is stop telling yourself anything about how it’s going to go and just focus on that. It’s important for you to do it. Others are to think about other mindsets. Too often we get stuck in a performance mindset. I got to have this conversation, I have to be perfect at it, and I have to achieve this outcome

In many cases rather than a performance outcome. It’d be better to just have a learning out orientation to say, look, I actually don’t know how it’s going to turn out, and even if it goes poorly, I will have a lot more information after the conversation than I did before, and I’ll be in a better position to act going forward. Sometimes people say, well, what if they say they won’t talk to me or they yell at me or say, well, you have more information now than you did about how you’re going to approach them next time or whether this is the right place for you to work. So I think this performance versus growth or learning mindset really matters. We also know from the stress literature, a situation is a situation you and I could have to go into the same meeting, so that context is objective.

You however, might go into that meeting with what’s called a Stressless threat mindset. You might be going in saying like, God, my career’s at risk. Oh God, I’m going to blow it. Oh, this is going to be a disaster. I might go into the same meeting saying, this is a real opportunity for me to learn how to have these situations go better or I’ve been working on new skills. This is a chance for me to show them. So it’s the same objective context, but research is now showing that whether we frame stress as a challenge or a threat doesn’t just affect how we show up in the situation. It also affects long-term health outcomes. We used to think like, oh, people die from too much stress. And I think more and more we’re learning that actually it’s not the objective amount of stress or challenge in people’s lives. It’s this mindset we have around stress that creates a lot of illness.

Stephanie Everett:

Yeah, no, I love that. As someone who, I mean, I feel like I thrive on stress sometimes, so I like that I just have to all be bad. I can feel that for good.

Jim Detert:

I mean, let’s face it, in what high performance context is there No stress. Stress is enhancing when it’s appropriately managed.

Stephanie Everett:

So if we could shift for just a minute, because let’s say I’m like, okay, this is going to be my learning opportunity and I’m going to approach this with that growth mindset and do all the things, but now I get into the conversation, I struggle getting in, getting it started and shifting to, okay, Jim, I need to do, I set it up and say, I got to talk to you about something and it’s not easy for me, but I got to just get myself through it. Am I allowed to kind of give a disclaimer at the beginning or what’s the best way to kind of get going?

Jim Detert:

So I think there are some different views and not a lot of evidence around this. I think though many people tell themselves a story that sort of a start with fluffery, then get to the point and then end with some this like, well, Stephanie, we’re here to your performance. I want to tell you, you did a lot of great things this year and we really liked this, this and this. And then after diddling around with that for 10 minutes, I tell unfortunately this year, blah, blah, blah, you’re getting this bad performance rating because of this, right? But then I make sure to end with, but everybody loves you and we’re all committed to you, and I think this creates all kinds of problems. I mean, sometimes people walk out of meetings like that not actually having heard that there’s an issue or a problem. They got focused on the front and the back.

Sometimes people just are irritated and angry that you wasted time being round about. And I actually think that in many cases what we describe as that’s nice to the other person is actually just a self-serving way of hiding the fact that we’re afraid. And so we are smooth gliding in for ourselves, not for the other party. I prefer actually just getting to the point, and I think to more specifically to your question, I think it’s appropriate and helpful to sort right away. If we were going to have that kind of a meeting, I think we could sit down. I could say, hi, how are you? You could answer. I could say, look, I want to be honest. I think this is going to be a challenging conversation. I might say, I don’t think this is, I’m guessing you’re not going to love this, and I want to be honest, I’m not looking forward to this either.

It’s really important though that I be honest with you because I care enough and I respect you enough to not evade the truth. And I think in some cases if the conversation, for example, doesn’t have to happen, you also might say things like, is this a good time for you to have this conversation? Does this work to talk about this now? But I think for me, if the purpose of a meeting is ultimately X, then starting with a bunch of A and B and turning to Z, I think actually at some level that’s a sign of our fear. It’s not actually about kindness to the other person.

Stephanie Everett:

I love that advice that resonates. I wonder if we could really shift gears also curious. And so I wanted to ask you about right now we’ve been talking about being courageous maybe in a personal situation, relationship at work. So maybe a coworker is kind of the context we’ve been talking about, but I also think we’re at this interesting time. So I got kind of excited about this when your book really got me thinking about where do I need to show up and be brave in a different sense at work. So I don’t know. I’m going to go to a place where I feel like this is me being brave asking you hard questions. Because right now, if we look at what’s happening in our world, which it’s just hard not to, I can say objectively that lawyers are being labeled targeted. Some are even losing business for doing their jobs.

When I first was reading your book, it was coming out that immigration attorneys are really doing a disservice to their clients or somehow to the country, I think is how they tried to frame it. When we know they are representing their clients to the letter of the law, they’re doing the hard work. And so it also occurred to me that when we talk about being brave at work in our world right now, it’s important that we maybe dive into how should we or should we do we need to be brave as a profession and sort of stand up in a different way and be, I think because leaders and business owners are afraid to speak out, do we just not say anything and duck our head and see what happens with all of the atmosphere is so charged right now that I just really wanted to ask you about that.

Jim Detert:

Yeah, it’s a great question and I appreciate it because I think honestly in the broader environment we’re in today, in the US s we can talk about, well, what about that difficult conversation with your peer, your subordinate? But to avoid this kind of elephant in the room is in a sense un courageous. So it’s a great question. And by the way, the question you are asking is the same question I’m asking, and all my colleagues are asking in higher ed, the same sort of let’s say attacks, concerns. I mean, welcome to our world too, right? Yeah, fair. Very similar. And I think in the work I do with for-profit corporations, even ones you would think are more independent, let’s say from federal government, it turns out that I think one of the things we’ve learned in the last six months, two years, that we are in a hugely sort of interconnected, interdependent world, and there are very, very few of us, no matter what sector we’re in that aren’t at some level with local, state, federal government.

And so this question applies to all of us in a way it has not maybe or not to the same degree in the past. And my own view on it is that we are at sort of an existential point of saying not just like, well, how do we speak out amongst ourselves, but in what instances and in what ways do we need to speak out as let’s say individuals, as organizations, as law firms? So in your context, in your listeners’ context, it’s what do I as a lawyer personally choose to say and do then for the firm, it’s what does the firm choose to say and do? And then for the profession as a group of folks who have taken an oath to the profession, what are we bound to do? And I don’t pretend to know the answer for every individual, every firm, every, but if you’re asking my opinion, my opinion is that there are professions I believe that have oaths to certain principles, certain belief systems, certain missions in the case of law, certain professional oaths that to be unwilling to speak our truths on behalf of those is a form of cowardice.

It doesn’t mean I can’t understand why it’s happening. I think there are very real consequences. I suppose all I would say about that is that the basic definition of courageous action is to do a worthy or noble thing despite some real or perceived risk. And so if people are going to say, well, I would speak out if it wasn’t so risky or would do this or that if I wasn’t afraid, well then I would say, but then you’re basically saying, I would want to credit myself for courageous action when it’s not courageous anyway.

It is potentially costly. I find myself thinking often about something Patrick Lencioni wrote a while ago, he wrote an article called Make Your Values Mean Something. And he said, most organizations, they believe they have a set of core values. So if I look on any law firm or certainly any company, I can easily find the mission of the firm and then I can find we believe or our core values, every organization has it. And he said, those are actually aspirational values. Those are things you hope would be true or you would like to tell people are true. He said, though, the real test of whether those are core values is if somebody says to you, tell me a time when it costs you something significant to defend the value, you should be able to immediately give an answer. And if you can’t, then it’s just an aspirational value, right? You’d say, we would like to be committed to, but if you can’t point out pain, you suffered, it’s not really a core value. And so I suppose, I’m not trying to duck the question.

Stephanie Everett:

No, it’s

Jim Detert:

Because I think it’s a crucial question, but I do think all of us right now should be asking ourselves the question, yeah, I’ve spent X number of years in this profession claiming that my core values were X, am I willing to actually endure any cost for those values at this point in time?

Stephanie Everett:

And for me, because I’ve been dealing with this personally too, and just thinking about it and talking to clients about it, and part of the equation feels very real. It’s like, am I going to cost my team? Am I going to cost my company business or possibly impact my team negatively? Are there going to be blowback or consequences to me speaking out? And so in a way it’s like, I don’t know if the right word to say in tricking ourselves, maybe that’s not, but I feel like people are kind of trying to frame this around this obligation to speak out and feeling like they also are the protectors in case a business owner, their team, I’m responsible for these people’s payroll, and if I do something that has negative, it’s one thing to say, okay, there’s going to be negative consequences to me, but what if I impact them and their families?

Jim Detert:

I agree. And I think I went through exactly that calculation a few months ago thinking about an article that I was going to publish and that calculus I went through, and it was kind of enlightening for me in that I think that I had thought implicitly or consciously for a long time that this cost benefit around am I courageous enough to do X despite some risks? The risk was largely about the self. Would blowback come on me? Would I be criticized this, that, or whatever? Would I lose opportunities? And I think in the environment we’re now talking about whether it’s law, academia, whatever, there is a very real reason to say, well, no, no, no. Let’s say I’m more than willing to have the blowback on me, but do I want to see federal funding for cancer research cut at my institution, for example? I think that’s not in itself a rationalization.

I think that’s very real. If you’re in a leadership position in particular and you realize that what you said can easily and perhaps will be taken to reflect the firm’s position, it’s a reasonable caring thing to try to calculate. I think where I have come personally, again, I’m not saying this applies to every person or law firm. Where I have come personally is to realize that there’s also a short term and a long-term dimension. In the case of higher ed, for example, I would argue that perhaps beyond any other thing, the fundamental reason a university exists and should have a privileged place, if you will in society, is to explore truth in the service of progress with the safety to go wherever that takes you, and then the safety to publish and educate people on that truth. I mean, if you look back historically, I mean the harm that came to people for daring to say the earth is not flat or what have you, that in a sense is the core reason that we should have this thing called higher ed. If we should have tenure. It’s the reason we should have that. And if for too long, too many of us said, well, if we continue to speak truth to live that mission of the university, oh, they’ll take away this funding or that funding or whatever. At some point in time, the issue of whether we had this funding or that funding for a given program would sort of become moot because our entire broader reason for existence would be gone.

And I think there’s a parallel in law and other professions where you can make a very recent calculus about not wanting to do harm to others, paychecks, employment, the firms, blah, blah, blah. But if at some point there are bedrock principles of what it means to have our legal system, our justice system that are undermined by everybody caving, then this short term it’s reasonable is still undermining the ultimate purpose of the profession.

Stephanie Everett:

I think we need to be willing to engage in those discussions. Even just having that discussion and going through that analysis is probably worthwhile so that we can get to an informed decision instead of just immediately saying, well, I’m not going to go there. That I think that’s what the first step. And you talk about building your courage plan, and maybe that’s kind of the first couple of steps that someone can take is be willing to really think and listen and not just immediately come to a conclusion, but engage with it. See where you go.

Jim Detert:

Yeah. Because again, if we say our brain’s tendency is going to be happy to land on a safe seeming solution, so it’s both logical that we would end up feeling confirmed and comfort and also that it might be correct in the shorter term to say, Hey, let’s not do or say X, Y, z without pushing ourself to say, but let’s play this out five or 10 more years, and if this continued down this path for five or 10 more years, then what would be the purpose of us anymore anyway? Or where would we have landed anyway? And I think you had to push yourself that extra step. Again, I don’t presume to know what or tell anybody else what the outcome of that should be, but I think it’s a worthwhile addition to the contemplation.

Stephanie Everett:

And maybe as we kind of start to wrap up here, you do talk in the book about, I think I got it right, like a courage plan, right? Is that

Jim Detert:

Courage ladder a plan? Sure. Ladder,

Stephanie Everett:

There you go. How we can start to take some steps to be more courageous. And so would love just your thoughts on what that could look like for the people who are listening today and they’re like, okay, I get this and maybe I need to engage more or differently and get beyond the fear and all the things that I’ve told myself that are holding me back. What are some initial steps people could take this week? What would you tell ’em to do?

Jim Detert:

I mean, one thing I would say is it’s different for everybody. I mean, I’ve seen thousands and thousands of people’s courage ladders by which I simply mean thinking about a physical ladder where each rung on the ladder is successively more challenging or frightening for you to do. And to literally lay out some specific behaviors from this makes me a little bit uncomfortable to like, wow, this feels completely incapacitating now. And really sort of put them in graduated levels of difficulty and then to start taking action at the lower levels. And the logic of that is simple. If I decided, oh, I’m going to run a marathon, that’s a goal. I’d like to run a marathon, but right now I’m not in very good shape. I haven’t been running well. If I go out and try to run 10 miles tomorrow, one of two things is going to happen. If that’s what I decide to start with, one, I’m just never going to leave my house because it’s too intimidated. I know I can’t do it, it’ll be miserable. Or two, I’m going to do it and I’m going to be so hurt that I’m going to stop doing that because I’m only going to confirm how crazy nuts that goal is.

So a much more reasonable first step would be to say, I’m going to try to do a mile where I maybe only slow jog a third of that mile and very slowly build. And I think the idea of a courage letter is similar, which is if you’re saying, Hey, I need to learn how to control some of my physiological reactions better or some of my thinking patterns differently, or I want to try out some new communication tools, well do that by starting at some conversations that aren’t terrifying that are like, yeah, I’ve been putting that up, but I could do that. Because they give you practice with a chance to have some success that motivates you to keep climbing. If you start with the most difficult, A, you’re likely to just not do it, and B, it’s not likely to go well, that will only confirm for you courageous action is stupid. What are some common things that people literally, for many people, it’s things like saying no to meetings after five or 6:00 PM or on the weekends it’s asking off of or not going to meetings that actually are not important to me or delegating and letting go of things that are not true priorities. It’s walking away from some business opportunities because it’s worth money, but it’s a misfit in a lot of other ways.

It’s asking a colleague to change a minor, not hugely conflictual issue, and those are the kinds of things that you can get some practice with before you sort of, again, it’s different for everybody, but for most people’s stuff like, I need to tell my boss, I think our strategy is completely off track and going to derail us, or I need to ask a high status peer to stop disrespecting women by saying.do. I mean, you can imagine that is as you escalate in the sort of power of the person you’re dealing with or the degree to which you’re talking about behavior that is of a larger magnitude ethically or strategically or interpersonally and appropriate, those get harder. So the idea of what can you do by building ladders? You don’t have to start there and if that’s all you think of, you’ll just probably not start. So get something more manageable on your plate and do that and then learn from it.

Stephanie Everett:

Love it. Say no to that client. That is a bad fit. Say no to that meeting after five that those are so easy and simple. I love those and something we all need to be doing. So that’s a great place to start.

Jim Detert:

And going back to right where we started, those are the things that when you do, you start getting reps with going, oh, that was nothing like, that was not so bad. That was not, you need to get that to start overriding that other thing that’s constantly floating around in your head about how terrible it’s going to be.

Stephanie Everett:

Yes. Awesome. I know when I read your book, which is again, is Choosing Courage, the Everyday Guide to Be Brave at Work, I immediately, I don’t even think I got past chapter one before I was actually reading it when we were on vacation, so I was sitting by the pool and my family looked at me. They were like, what’s wrong with you, mom? I was just staring into space because I was like, oh my gosh, it just hit me. I’ve been avoiding this conversation with somebody at work for a really long time and I was like, I got to go back and dig in and have that. So definitely it’s a great book. It gets you thinking, but then also gives you some, like you said, those little steps that you can take to kind of start to get there to flex that muscle and dig in.

Jim Detert:

That’s right.

Stephanie Everett:

Alright, well thank you for being with me today.

Jim Detert:

Thank you for having me. Be well.