Today, our guest is Claire Lew. She is the CEO of Know Your Team and this is Work Minus Bad Managers. Hi, Claire. How are you?

Hey, Neil. I’m doing great. Thanks.

Very excited to talk with you. You are a bit of an expert in the realm of management. So, I want to ask you to introduce yourself and tell us how you got so passionate about management.

Sure. So, for folks who aren’t familiar with our work, like Neil was saying, my name’s Claire. I run a software company called Know Your Team and we help managers avoid becoming a bad boss. And I was inspired to embark on this whole journey and start this company because about eight or so years ago I had a terrible boss, and for those of you who are listening, this is surprisingly maybe not a unique experience, something that maybe you can resonate with. But I had a really bad boss and I was really conflicted about what to do at the time because it was a very small company and I didn’t know. Well, do I tell him? Is there anything different that would ever change? I found it just to be this immensely frustrating problem where I had no right, first of all, even telling the CEO how to change but if something were to be different, could it be from internally or would there need to be some external force that would help this person become the leader that they wanted to be? And so, I decided that the solution was likely the latter.

So, I left the company and ended up first starting a consulting practice working with CEOs to help them get to know their companies better and see their blind spots. And my first client was actually a company called Basecamp, and some of you may be familiar with that company. They used to be called 37signals. They make project management software. They serve, I believe, over 15 million people worldwide and the CEO of Basecamp was actually my first consulting client. And so, I did this consulting project for them and then ironically enough, they also, Basecamp, happened to be building their own software product to help them solve this issue of getting better feedback and becoming more self aware as leaders and that was actually what was then called Know Your Company and today is Know Your Team. So, what ended up happening is that Know Your Team was actually spun out from Basecamp as its own separate, not just product, but separate company, separate LC, everything. And Jason Fried, the CEO of Basecamp, asked me to run the company. And so, we split ownership 50-50 and we spun it out. It’s completely separate and I’ve been running the company today called Know Your Team for the past five years it’s been now.

That’s a great story. I love that. Are you still in touch with your old bad manager? Do you send him thank you notes every once in a while saying thank you for letting me start my own company?

No. It’s one of those things where it is truly been my biggest inspiration for the work that I’m doing today in the sense that it was such a tough situation, it was such a sensitive time. I mean, here’s the thing. I was really young. I was 22, 23 and to feel like I had any audacity to tell my boss, who’s at least 15, 20 years my senior, what he should be doing, it didn’t really feel like my place. And not only that, but I wasn’t also confident in knowing what could be better. And then lastly, even if I did share what I felt like could be better, at the time, I didn’t think anything was going to change. And so, in fact, this sense of futility, and I don’t know if we’ll get a chance to talk about this later on the podcast, but futility, studies have shown, is actually the biggest reason for why employees don’t speak up at work. It’s not that they’re just scared.

So, it’s not like I was just fearful that this person who I respected was going to think ill of me. And I was, right? But even more than that, the reason why I didn’t tell this boss, and today even, don’t share all the things of all the things that I felt could have been better is unfortunately because of this sense of futility and feeling as though if something’s not going to be different then you don’t give the feedback because that is the reason for why you even want to give that feedback in the first place. And so, for leaders, as we think about how do I create an open, honest environment? How do I make sure I don’t become like Claire’s boss, who has no clue that everyone in the company thinks I’m running the company terribly? How do I make sure I don’t become like that? Okay. Well, overcoming futility and making it really clear that if someone’s going to say something to me, that something’s going to be done about it. That was the biggest thing.

Let’s get into some of these topics. You’ve written a lot of things. I’m going to base a lot of my questions around one article you wrote about nine leadership mistakes you make. In that article, you cited a statistic that says only 1 in 10 managers possess what they describe the natural talent to manage. So, how did we get into this problem where it seems like you start off with something you do really well as a performer and then automatically if you’re good at performing, well, obviously you’re going to be good at management? Where did that disconnect start and why is it perpetuated now?

So, the study that you’re referring to is something that Gallup ran I think back in 2016 where they literally… and it’s an annual study that I’m sure folks who are listening are familiar with I believe. It’s the state of the workforce study that’s done with over a million people across over 84,000 business units. They do it almost every single year and what Gallup identified was what they saw as the 12 inherent traits that good managers who are successful tend to have. And what this means is and it’s things like clear decision making, empathy, just traditionally what you would think of is a good manager. This isn’t shocking insights by any means. But what they found that was really, really shocking is the fact that folks who were promoted into the role of manager, one, usually did not have these traits or skills out of the gate. So, like you said, only 1 in 10 of folks who are managers actually possess these skills out of the gate to become a good manager. It doesn’t mean you can’t learn them. But coming out of the gate, you don’t have this.

And then the second statistic in the study that was just mind blowing is that 82% of the time managers are promoting the wrong people, or companies, rather, promoting the wrong people. So, what this means to your point is that, okay, here we have individual contributors who were so successful in their roles getting promoted off the wrong skill. So, to now circle back, that was just a lot of context there, but to really pinpoint on your question of how did we end up doing this, well, to be very frank, I think the biggest reason is because leadership in itself for what it is to be successful as a leader is actually very nebulous and ill defined in our society. So, if you look at academic scholars and the way that they define leadership, there are literally hundreds of definitions on leadership. Scholars cannot agree on a single definition of leadership.

There’s this scholar I think his name’s that Ralph Stogdill who wrote in 1974 he ran this big study and he wrote this statement that I thought was hilarious which is he said that you can find about as many definitions of leadership as the number of people who have attempted to define it. So, the reason why that’s so problematic is if you don’t have a clear definition for what it means to be a good leader, obviously then the metric or the indicators for what it means to be a good leader are all over the place. You don’t really even know what you’re looking for because we can’t even agree on what it means to be a good leader. So, that’s one of the biggest reasons that in companies it’s so easy just to promote the folks who are doing and succeeding really great as individual contributors but then realizing, oh, my gosh, we’re promoting them for things that they’re really good at as individual contributors but that doesn’t necessarily translate into leading others.

So, what’s the take away in this? Well, as senior managers who are promoting these folks, can I clearly define what it means to be a successful leader in our organization? And most probably speaking, even though there are, like I said, hundreds of definitions, you go back to Aristotle when he started defining leadership and then from there on out, but despite the fact there are hundreds of definitions around leadership, the most coherent definition that I would say that spans most is the fact that a successful leader is someone who does two things. One, they’re able to create an outcome that wouldn’t have existed if that person hadn’t been able to get other people on board. So, this whole idea is that teams exist because you can do something beyond just an individual doing that thing. So, a leader is someone who can help get that done. And then the second thing is that the most successful leaders are ones who create the best environment for people to get that work done. So, it’s not necessarily about direct control or influence but it’s about creating that environment for people to get that best work done and then to accomplish that outcome.

So, that being said, it’s like, okay, well, let’s first define it really well. The second reason for why we end up in this place is it’s really hard to measure identify those skills. It’s like wait, what does it look like for a leader who’s really good at creating an environment, or a potential leader? What does that actually tangibly look like? We don’t track for that really well. So, for example, listening skills or the ability to ask good questions or the ability to be consistent. Consistency is something that’s not really looked at when we look at promoting folks. So, those are the two biggest reasons is that we don’t define leadership very well and we don’t identify and track what it means to be successful when we do promote those folks.

Would you advocate for people management to be just a specialty that someone can develop and just is brought in because this person has studied it, they know what they have experience and practice in it instead of just being a default, “Hey, we need somebody to be the manager so just throw the hat at somebody.” And what implications are there for that in terms of salaries and cost structures? What would be the best way to structure an organization?

I’m of the belief that leadership can be learned. So, this is the reason why I started Know Your Team is because I don’t think as much as there are inherent traits that you can have out of the gate and that only 1 in 10 people have them, you can develop these skills, you can develop the capacity to understand what makes a good leader and then become better. I’m an optimist. I can’t imagine a world where we just say folks who already have spent the time in the past and who have the established expertise are the only ones who can do this. I think you can only imagine our society being successful in every single way if you think anyone can learn this stuff if they want to. This isn’t for the sacred few who are plucked out and who decided to go through formal training or school, or like myself who spent their working careers. So, to answer your question, Neil, no, I don’t think you need to go hire a “people management expert.” Also, I don’t even really know what that means, to be frank. And I don’t mean this to diss anyone who calls himself that but I think, like I was saying, when you really think about what the definition is of what it means to be a successful leader, someone who’s able to get a result that wouldn’t have been possible had it just been one person alone and then someone who was able to create an environment for people to do that. Okay. You don’t technically really go to business school to do that. You can’t really read a book to do that. And again, this is why we created Know Your Team is because we believe that there is a methodology that exists to do that but it looks a lot different than what is traditionally seen. So, I have to believe that you can learn this stuff.

I think your product is almost like a management school in itself just with real life experience, you’re having somebody to help you along and think through it as you go through. I think it’s a really great tool for that.

Thank you. The whole hypothesis behind it, and I’ll admit we’re learning as we go, we really started focusing on helping managers become better. I mean, we’ve done it over the past five years specifically for CEOs but more recently it’s been really in the past six months to a year where we’ve really focused on new managers. But what our hypothesis is is that you need first a foundation of knowledge. This is how any person becomes an expert whether it’s in becoming an expert tennis player or becoming an expert chef, you have to know what a forehand is and a backhand is and a serve and a volley. You have to have the foundation. So, we have these online guides. Then you have to be able to apply what you’re learning. So, you can’t learn how to play tennis by reading a book. You can’t learn how to ride a bike by reading a book. You’ve got to go out and do it. And so, then we have software tools to help you apply that stuff. And then you need a community of support. So, like in tennis camps or like when you go to cooking school, you’re not just in isolation. You’re working with others. You have a coach. You’re getting feedback. And so, we have an online community of managers. And so, that’s the hypothesis. It’s the ecosystem of education software tools to apply what you’re learning and then a community of support that can help you learn. And like I say because I refuse to believe that you are a born leader. I just refuse to believe that. I think leaders can be made.

One of the colors of the thing you talk about is the one on one meeting. In any kind of a management relationship, talking to somebody, sitting down with them face to face and really talking through some things. But for one, we just need to do that. A lot of people just don’t do that and that’s the first problem. But the deeper one is, okay, what do you actually discuss in those times? What are some common fallacies that people run into in these one on one meetings and how can I get out of them?

So, one on one meetings from the over thousands of managers that we have using Know Your Team, over a thousand managers we have in our online community that we call the Water Cooler, and here’s the other thing, I run this podcast called The Heartbeat where, as you know, I interview all these leaders, and the thing that always comes up as the highest leverage tool that a manager can use is these one on one meetings. And so, for the folks who do them, yeah, they can be useful. And we did a large study with almost 3,000 people just this past fall where it said over 80% of managers believe that one on ones have a positive effect on team performance. So, there’s this broad consensus that these are helpful. Now, the potential though for this to be even more helpful is huge. So, for example, when we asked employees the same question, how helpful do you think one on ones are?, they answered at a less degree of positive impacts. It was closer to 70%. Actually, it would been less than that because the difference is about 17 percentage points. So, the point being is employees feel like, okay, you’re asking me to come in, have this one on one meeting for 30 minutes or an hour, and man, I’m not getting as much out of it as my manager seems to like to think.

So, we identified this gap, and so, to your question, well, what can you do to close this gap and to make one on ones more effective and to live up to the fact that some managers seem for some reason to being having, really like I was saying, having this be the most high leveraged tool in their organization. So, in the survey that we ran with almost 3,000 people, what we found were a few commonalities. So, one is preparing for them just in general. So, the majority of employees said that their managers were either not prepared at all or only somewhat prepared when they came to meet with their manager. So, the first thing for a manager, if you’re listening to this, is just prepare. Well, what does that mean? So, one is to have an agenda. But one of the best practices that we learned in talking to thousands of managers and running the survey is to co-write the agenda with your employee. So, you can write a quick draft and then send it over to your employee to add. And so, that way they’re bought in on the conversation and it becomes a dialogue and not just I’m just going to talk at you.

The second most important thing is to make sure you really understand what the purpose of this time is. So, it’s not a status meeting. It’s not a status report. So many managers that feel like they don’t get a lot out of one on ones will say, “Oh, yeah, it’s because I end up using it just to catch up on stuff.” So, knowing what people are working on, what’s the latest, don’t use that or don’t talk about that during your one on one meeting. The one on one meeting is truly, and this is what we collected from the survey, the number one purpose folks said is to uncover potential issues. It’s to get feedback. It’s not to figure out something that you could literally ask via email or slack. So, don’t use one on one meetings as a status report.

And then the last thing, so in addition to actually preparing and co-writing an agenda and not making it a status report, the last thing is to ask specific questions. So, the most common question that is often asked in a one on one that is truly just sort of a waste and I think it’s a terrible question. And I’m guilty of asking this question, by the way, myself, is how can I help you? This is the worst question that you can ask your employee in a one on one meeting. How can I help you? It’s typically asked at the end of a one on one meeting. You’re going through anything and you go, okay, is there anything I can do to help you? So, the reason why this is a terrible question to ask even though your intent might be good is because you are placing the burden of what could be better about the working relationship you have with an employee, you’re putting that burden on the employee. You’re putting them on the spot asking them to catalog amongst the entire year’s worth of progress and work and things what you as a leader should be doing better. So, you’re making the employee do the hard work of figuring out what you should be doing better. You’re putting them on the spot to do it. It’s a really counterproductive way to figure out actually how to help someone. There’s that. The other thing you’ll notice is what do people typically say 9 times out of 10 when you ask them?

Nothing. It’s fine.

Yeah. Exactly. They go, “I think it’s pretty good. I can’t think of anything at the moment.” And it’s because they didn’t have time to prepare, or like I was saying, it’s this huge cognitive burned on the spot just to reflect and pick something out. There’s this intimidation factor of you’re telling your leader what they should be doing better, again, on the spot. And it’s a very broad question. It’s like, well, do I talk about the weird thing you said to me during the meeting last week? Do I talk about broad strategic initiatives for the quarter? What level of granularity are they asking for feedback here? And so, the question is way too broad. So, instead there are so many better questions that you can ask during a one on one meeting than how can I help you, and I mean, literally like hundreds of better questions.

And you have a lot of those on your site so I’ll encourage people to check those out and also obviously inside the software, too. We get the same answer when we talked about diversity and inclusion that a lot of times those who are in a privileged position to ask other people what do you want me to do? How should I help with that? It’s really not a very helpful question in that situation either. Is that a good parallel?

Yeah. I mean, I think you could extend it even broader beyond. I mean, here’s the thing. It extends to any situation where you have a power dynamic at play, like when you have a one up, one down relationship, like when someone, whether it’s in the case of diversity inclusion, has historically held more power, that’s a one up, one down relationship. And so, to ask the person who’s one down, how can I help you? It’s just completely unhelpful because that power dynamic exists. And in the workplace as much as we as leaders don’t want to maybe acknowledge it or admit it. We like to think there’s no hierarchy. Well, there is because you’re paying someone to do something.

Absolutely. And really, that should be your job as a manager to look over the results of the one on one to see everything and to be able to see clearly how you can help somebody. That’s what you’re being paid for, too, anyway.

Exactly. I mean, different people will ask, well, what do you say instead, Claire? Well, what you can do is you can actually suggest specific things that you could do and say what do you think? Is this a good idea? Would this be helpful? Actually do the hard work yourself as a manager to offer suggestions of ways you think could help rather than just sitting back, kicking your heels up, and just asking the employee to do the hard work of saying how can I help you. And like you were saying, we have hundreds of questions, whether you follow me on Twitter or read our blog or use our product, of other questions you can ask in one on one meetings.

So, if you get one on one meetings down, nothing else is good as a manager, you don’t focus on anything else, you just focus on trying to get good at one on one meetings, how much of a bump are you going to get in terms of how good of a manager you’re going to be?

Like I was saying, just refer back to what almost 3,000 managers seem to say is that almost 90% of them said that it has a positive effect on their team performance. So, by a certain degree of magnitude, you can expect to become better just by doing that alone.

Excellent. There’s so much else I wanted to talk to you about, too. You have the three pillars of good management. We’re talking about trust and context and honesty. But I’ll have to let people look that up on your blog and get into that because a lot of good thoughts to share there. Claire, where can people go to find all this information about you?

So, I highly recommend checking out our blog if you found any of this information useful or you’re thinking, wait, I want to read more up on the survey that they ran or best practices around trust or one on one meeting. So, that’s knowyourteam.com\blog. We also host a podcast where we talk about everything A to Z from leadership and I interview leaders I respect the most and so you can also check that out on our blog. And then, of course, you can visit our software. It’s called knowyourteam.com and we actually have one on one guide and tool to help you put all the recommendations that I talked about into practice and to get ideas for questions, etc., we have agenda templates. So, definitely check that out. And then lastly, if you’re just curious of, well, how can I just learn more of what Claire’s been reading or writing, etc., Twitter is a great way to keep in touch. I’d love to do hear from you there. So, that’s @clairejlew is my Twitter handle.

Fantastic. Well, Claire, thanks a lot for coming on the show and sharing your insights with us. We appreciate it.

Yeah. Sure thing. Thanks so much, Neil. This was fun.