Claire Lew: The Accidental Bad Manager

In this BoS EU 2019 talk, Claire discusses how no one sets out to be a bad boss, but it’s easy to become one.  After years of research from 15,000+ people and 25 countries, Claire shares the biggest, most counter-intuitive mistakes that leaders unintentionally make – and what to do about them.

Claire Lew is the CEO of Know Your Team – a company that helps companies like Airbnb and Kickstarter and also runs a online leadership community, The Watercooler, with 1,000+ leaders and thousands of conversations on hiring, firing, business growth and more. Claire’s mission in life is to help people become happier at work. She is often cited as an expert on the topic of creating more open, honest workplace environments, and has been published in Harvard Business Review, CNBC, Inc, and Fortune among others.

Learn how to ask your team the right questions, why trust is important, and why being nice can be a bad thing.

also available on the podcast



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I could get used to that. I love, love, love the walk on music. Every time, every time.

Good afternoon everyone. My name is Claire Lew and I’m the CEO of Know Your Team. We are a software tool that helps leaders become better managers and for the past almost 10 years now I’ve spent my working life studying researching writing and speaking on this very topic of ‘how do you help someone become a better leader’. So, I’ve done that in running my own consulting practice, and now today as the CEO of Know Your Team where our tool helps over 15000 people all over the world in over twenty five different countries. Some of whom are in this room, which is great.

We kind of have a weird origin story, though, as a company which I love to touch on before I dive into everything. So Know Your Team – for those of you who might not know – we’re actually a spin off of Basecamp. Tool that’s been mentioned a few times – they make one of the world’s most popular product management software tools and they back in. I don’t know maybe six years ago they were actually my very first consulting clients so they had hired me to help them as leaders the co-founders of basecamp figure out how do we become better leaders how do we create a more open and honest environment and basecamp and then asked me to run this prototype that they had developed at the time then called Know Your Company. So since then I became the CEO of what was then know your company and in the past year or as the year progressed what I realized is while we were originally helping CEOs of mainly small businesses really get feedback. Most recently I found that our software and all the educational writing that I’ve been doing, actually helps managers the most. So new managers, middle managers, managers who just feel like they’re stuck. And so we made a really big change in the business just this past December where we decided to focus purely on helping the people who seem to resonate most with what we were doing and that was with managers. So today though I’m excited to share all the insights that I’ve gained and that our company has gathered over these past five years in working with managers of all different types of companies in all different stages.

Who’s the worst boss you’ve ever had

The biggest question in this process of all the things that we’ve been learning and how to help managers become better is something that I’m curious to pose to you today, which is: who’s the worst boss you’ve ever had? No need to say this person’s name out loud. You can think this to yourself, don’t incriminate anyone here if you might be with that person at this conference. But I’d love for you to just reflect on your career who this person might have been it’s likely that this person was formative for you. Maybe they are the reason you manage and lead people in a certain way. Maybe they’re the reason you left your last job. What we often don’t think about though when it comes to who this worst boss is, is could this worst boss be us? Could we in fact unintentionally, accidentally, be someone else’s worst boss. Let me explain.

Gallup every single year does a study that I’m sure many of you are familiar with. It’s called the Q 12 assessment where. They survey millions of managers in – I believe over eighty four thousand business units – and this is one of the biggest findings that they found in the most recent Gallup assessment which they found that’s 82% of the time companies are choosing the wrong manager. So what they’re doing in most companies it seems is they’re looking at the individual skills and traits that make someone successful in their role and believing that they are going to transfer over well to when they promote them as a manager. Yet that doesn’t happen and the performance isn’t there. And so as a result these folks are in these positions, as managers, as executives 82% the time it’s really the wrong fit. In the same study, again 1.8 million managers involved in the survey, Gallup found that one in 10 managers have what they call the natural talent to manage. Now what they mean by this is Gallup identified five traits that they saw across the most successful leaders; everything around authority, decision making, and now that’s not to say that you can’t learn these skills, but in terms of you having them out of the gate and these skills being inherent to you as a manager. Most of don’t. Only one in 10 of us come out of the gate with this inherent talent with this these five identifiable traits that they recognize.

So given that 82 % of us myself included in this room were chosen for the wrong reasons and that only one in 10 of us actually have the talent to do this job well, the likelihood that we might actually be someone else’s worst boss is actually frighteningly high. And so in many ways this talk is autobiographical in the sense that how do we actually avoid this happening?

How do we act avoid accidentally becoming someone’s worst boss when we don’t need to be when all of us have had worse bosses – we know what it’s like. So, what can we do to just make sure we’re not doing that to other people? So, what I’m going to do is share with you – across the past five years, the over 50,000 people we’ve worked with folks from all over the world are going to share – the insights, the data that we’ve gathered and really pinpoint what are the biggest mistakes that are unseen, that we commit with not without really even knowing, what are the biggest mistakes that we make, in particular the six biggest mistakes that we accidentally make as worst bosses.


So the first is around something that Gareth did a wonderful job in his talk of diving really deep on is around trust. And if any of you were able to see Gareth’s great talk I’m sure you walked away thinking – or maybe you even knew this before – trust is important. Of course. It’s intuitive. I get it, Claire. Trust it’s about team building. Trust is about having team retreats – that was talked about earlier today in holding social events. Building trust is about thanking team members, it’s recognition, showing people that you care. Trust is about being transparent with company information. This is what trust is about.

Something interesting happened, we did a survey this past fall with over 600 managers from folks all over the world, mainly in the tech industry. This is what they said: They actually rated these three elements (or ways of building trust) as the least effective ways. So the retreats that we do, all the money we spend there, the amount of time we spend thanking folks and showing recognition, the conscious effort we put into sharing team information. Those are all beneficial but when it comes to actually building trust those don’t seem to be the greatest lovers. According to these folks. So what did they rank. What did they say about what the most effective ways to build trust were? Here’s what they said. They said showing vulnerability as a leader admitting your mistakes was the number one reason or way to build trust in a team. Second best way to build trust is to make your intentions clear. To say why you’re doing something. And then the third most effective way to build trust, we found in this survey, was to keep your commitments as a leader, to follow through and do what you say you’re going to do.

Now what I find fascinating about this especially the CEO running in my own company is that none of this stuff actually costs money. Saying what you’re struggling with, saying why you’re not going to do something, actually just following through on what you’re going to say. We think about all these complex and fancy ways to build trust and bring consultants and figure out what do we do with this trust problem in my team. And really what is revealing about these answers, is that what trust is truly about, is your intention matching your behaviour. That’s when you trust someone as a leader. It’s when what you say you’re going to do and what you actually do end up being the same thing. So trust it’s not about rapport. It’s not about getting people to like you. It’s not about team building. Trust is intention and behaviour and if we can really register that as leaders, we can avoid that costly mistake.


The second biggest mistake we often find ourselves committing as managers has to do with one-on-one meetings. How many of you in this room might hold one-on-one meetings or attend one-on-one meetings with your staff direct reports? Show of hands. Vast majority if not everyone in this room. That’s fantastic. What’s interesting is – and I’m not going to ask you to raise your hands for this one is totally cool – which is I’m curious though to ask yourself how often do you prepare for those one-on-one meetings. No pressure right. We’re busy. I get it right. Maybe sometimes. Maybe when you can you try. But it doesn’t always happen. That’s fine. I think it’s fine. Right. Should be okay.

Well something really interesting about first of all the effectiveness of these meetings. Great to see that so many people are participating in them because you, along with majority of the managers that we surveyed this fall that was I believe well over 1000 different managers from all over the world, they would agree with you they would say yes they would raise their hand and go what. Claire I do one-on-one meetings. They’re great. They’re so effective. In fact almost 90 % of managers say the one-on-one meetings are positively affecting my team’s performance. Employees would also agree. They would say Oh wow yeah I agree. 71% of employees who answered out of almost a thousand employees said that one-on-one meetings do positively affect my team performance too. Something interesting though about these numbers. You haven’t noticed which is an interesting gap. Seventeen point percentage difference here between a manager’s perceived effectiveness of these meetings versus employees; meaning that the potential for you as a manager to actually be getting more out of these meetings, to make sure that you’re encouraging folks in the right way is there. And it’s actually not as high to what you personally think. And while an employee does think ‘yeah I am getting I’m seeing these as being positive’. There’s almost 20% potential to actually have that be even more. So, why is there this mismatch like why is it that maybe employees aren’t seeing as much of the value or effectiveness as you would like to see in and having their one-on-one meetings.

Interesting. So we asked employees well how well prepared would you say most managers are when they come to the meetings? 76% of employees said oh they’re somewhat prepared at best but most of them are actually not prepared or not prepared at all. In fact of this 40% said that their manager is not prepared or not prepared at all for their one-on-one meetings which goes to say that if there is this gap in how we spend these meetings, how many hours a month, a week alone are we spending in these meetings if there is this gap in the perceived effectiveness that these meetings are having and employees are saying that we’re not coming to them very prepared. Maybe we should prepare for them a little bit. So, this is something that is again seemingly pretty apparent right. But. Preparing for one-on-one meetings can actually be deceptively tricky if we’re not very deliberate about them. So one of the most important parts of preparing for one one-on-one meeting well is actually first figuring out what the purpose of a one-on-one meeting is with your staff. So, what a one-on-one meeting’s purpose isn’t is a status update. So, if you find yourself in your regular one on one’s with your staff where it’s what’s the latest? Give me an update on this. How’s X project going? You’re wasting their time. The purpose of a one-on-one meeting isn’t to get updated on something – I mean you can do that in email. You can do that on Slack – the purpose of a one-on-one meeting is to truly uncover potential issues and get feedback. It’s almost a sacred time where there’s no other meeting where you actually can do that face to face. So, to use it to get caught up on something that you could you virtually use any other channel it’s a waste. So, know what the purpose of a one-on-one meeting is and as you go into preparing for it make sure that it’s not a status update.

The second thing that you can do in preparing for a one-on-one meeting well is to co-author the agenda with your team member and some of you may already do this which is fantastic. And so this is as simple as writing a draft: here are some topics that I think would be helpful, here’s some questions I’d like to ask. So this does a few things, when you do this one you give your team member heads up so they’re not blindsided when you ask them a tough question or ask them about feedback from the company. The other thing that it does is it gives them buy into the actual conversation. So if we want that seventeen point percentage gap to decrease and for both a manager employee to be thinking that this is highly effective then you want that person to be bought into thinking about well what’s the actual content of this conversation. And you can do that simply by just sending an agenda over head of time. And the less critical piece of having an effective one-on-one meeting is making sure you do not ask this question, which is.

How can I help you.

I am willing to bet money – well maybe not real money I don’t know – but I’m willing to bet. That most of you have asked this question before maybe even a colleague maybe to your partner. I’ve asked this question a ton of times. Well I used to ask it up until recently. So in all the workshops that we run with all the CEOs and managers that we work with we actually found in talking with employees on the other side that this question is actually completely destructive because what asking ‘how can I help you’ does is it places the burden of figuring out what you need to do better as a manager on the employee. You’re saying tell me what I should be doing better. You’re not offering help, you’re not offering suggestions, you’re putting all the hard work on the other person. And if you can only imagine as an employee being on the flipside hearing that you might be caught off guard you’re thinking Oh God like I have to tell my boss like what they can do to help me like. How do I make this come across in a way where they’re not going to take it badly. I’m just not going to say anything. So most the time is I’m sure many of you I’ve heard what people will say is “I can’t think of anything right now. We’re good.” I mean how rare is it that someone you ask how can I help you when someone’s like ‘oh let me tell you let me give you like here’s my list right. Please talk to me after the talk if that has ever happened to you I would love to hear about it. No one has told me that yet.

So make sure that you are not asking this question ‘How can I help you’ if you are trying to figure out. How you can help there are tons of other questions to ask and here are a few of my favourites. So one is to simply ask:

what are your biggest time wasters?

And this is an amazing question because what this reveals is obstacles that people have. But usually that they’re not willing to tell you because you’re making it about oh what’s this thing that’s wasting time. It’s not you. This project that you assigned me and you gave me this deliverable right. It’s making it a bit more objective stance distancing this bad thing that they don’t want. So you give them sort of an out to tell you. It’s a great question ask another fantastic question to ask in a one to one meeting is

when have you felt bored in the past quarter or in the past week?

This is really incisive because what it does is it reveals people’s level of motivation without directly asking them are you engaged. Are you happy in your job? I mean again it’s a little too on the nose like people aren’t going to be that comfortable to tell you right away but asking instead Are you bored in the past quarter are you frustrated. Being more specific in your questions reveals a lot more. Another great question to ask and one-on-one instead of How can I help you is to ask this.

What about my management style can I improve

Again you’ll notice the specificity in directly asking for feedback about not just what can I do generally or what do you think about how I’m doing as a manager know this is how can I improve my management style. Gives a whole open field for someone to say well what the way that you happen to share deliverables, you kind of do it a little too late. Like I wish I had contacts no more up front. This question bites that depth of a response. Here’s the thing, these meetings they are high leverage. Right. Most of us in this room are doing them but are we getting the most out of them the most important here is her team getting the most out of them? And if we want to avoid becoming a bad boss we can utilize these meetings to make sure that we’re not showing up just sort of prepared. But truly prepare.


The third biggest mistake that we’ve noticed that managers will unintentionally make is around time. Most of us may think that being busy is good. Means you get stuff done. You’re making it happen. This is good when things are moving. This is good. Busy is good. Or is it? So on a podcast that I run called ‘The Heartbeat’. I had the chance to interview Michael Lopp who’s the V.P. of engineering at Slack also known as Rand’s and he’s something really interesting to me. He said Claire if you’re too busy actually doing the work as a manager that’s actually a huge mistake because when you’re too busy doing the work you don’t actually get to see if two people are having a potential conflict. If you’re too busy doing the work, you don’t realize that you actually need a lot more feedback before that product goes out the door. If you’re too busy doing the work, you’ll actually realize that someone’s about to leave the team. Because the thing is this as a leader what your role is. It’s not actually do the work but it’s to create the environment to do the work and you can’t do that. You can’t help other people do the work if you’re too busy doing the actual work yourself. If you’re adjusting ‘oh this pixel just right here’, ‘oh I’m just going to go and illustrate really quick and just needs to be tidied up’. No if you’re too busy doing that, then you’re not actually utilizing your capacity to help folks do what, honestly, you hired them to do.

So, what should leaders be spending their time on if they’re not supposed to be doing the actual work or even meddling and fixing things last minute. What are we supposed to be doing? So, I posed this question to our online leadership community that we have it’s a part of know your team. It’s called the watercooler and we have over a thousand managers from all over the world who participate in it and shared vice and give suggestions on different issues. And I asked what do you spend your time doing right. And here’s what they said.

  1. The number one thing that across the board that managers said that they spend their time doing or should spend their time doing is recruiting and hiring. And this has been a wonderful theme and we’ve seen a great talk on that during this conference. But recruiting and hiring is so crucial and the number one thing you should be spending your time on as a leader; because where you are going as a team and what you are doing doesn’t matter if you don’t have the right people doing the stuff. So spending your energy and time with deliberate focus on this is key.
  2. The second best use of a leader’s time according to the managers that we talk to is to make sure that you are thinking and considering the long term vision and culture of the team. After all there is truly no one else in the company – or on your team – whose job it is to do this. No one else is thinking about this. This is your job as leader to be thinking about how are we behaving, what is acceptable behaviour. Where is it that we want to go what was it. What is successful to look like when we get there. It’s no one else’s job but us as leaders to be doing that. So that’s where the second biggest piece of our time should be going.
  3. And then lastly as leaders we need to be communicating the direction at all times. Because context is the only way people are going to know what’s good what’s bad. If I go left or if I go right if I stop or if I start. And again who else is supposed to be doing that right. Just us as managers.

So we have to remember as we think about time, if we feel ourselves being a little too busy and too many meetings we’re just a little bit too in the work we have to pause and remember the best leaders actually they choose not to be busy. Don’t take that sign of a full calendar, of tickets being just checked off the list, as equivalents to your ability as a manager remember it’s really and how you are choosing to spend your time.

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The fourth biggest mistake that we’ve seen in managers and one they make constantly without even knowing it’s actually around vision. Also something touched on quite a few times during the conference. So most of us would agree that vision is paramount and typically it better be obvious – why else would we be in this position as a manager or as a leader. In fact vision to us as managers seems so obvious we ran a survey just this past fall around vision and context in particular and we found that people said that it’s actually the most important thing a manager should be sharing and communicating with their staff. And I’m going to guess most of you would also agree with that. Well so if that’s the case, then why is it the case that when we asked through Know Your Team and this is over almost 3000 people we asked, if someone asked you to describe the company’s vision to you, would a clear answer come to mind and almost 30% – almost a third of folks, again almost three 3000 people, answered this – said no.

So it’s like if you’ve a nine person team that’s three people being like no I couldn’t tell you what the vision in the team is. That’s troubling. And it’s troubling for a few reasons which I’ll get into. But let’s hold up for a second because vision before we go any further we can’t think about how to create a good vision or why vision matters if we actually don’t properly define what it is. I feel like vision is possibly the most misconstrued buzz wordy of buzz word words up there with culture and innovation. So let’s talk about what vision is and what it isn’t. What vision isn’t is vision is not mission. Mission is what you do, mission is what. So as Know Your Team, our mission is to build software that helps managers become better. That’s what we do. But that’s not vision. Vision is also not values. So at Know Your Team we think about how we do our work. We think about our values and it’s Simplicity, honesty, trust, passion. Those values, that’s not our vision. Vision is also not purpose. So the purpose for Know Your Team exists is because you want to help managers become better yet that why is not the vision either because what vision actually is, is a place. It’s a destination. Vision is particularly a picture of a better place. It’s where you want to be, and this distinction is important because what our vision is and Know Your Team is it’s a world where good leadership is not the exception.

It’s very different if you compare that statement to oh where software to try and help lead managers become better. Oh this is how we do that with simplicity etc. Now with a crystal clear vision a few things happen. One because we can say okay this is the world we want to create all the sudden a lot of business decisions become a lot more clear. We can say what we actually want to help leaders at all stages because it’s about making sure that good leadership is not the exception. This also means that we better define what good leadership it’s that. That’s got to be a core part of our business. Also a lot of decisions around who we’re serving how we should be serving them becomes a lot easier for us as a manager to digest. And then secondly once we have this clear vision you’re able to actually motivate and bring your team along so much more easier than you could without it. Having that picture of a better place being able to see that’s the world we want to create gets everyone on board and excited to do that so much more than saying oh this is how we’re doing that with these values or this is what our mission is this is what we’re doing. People want to know where. They want to know what that picture of a better place is.

I think one of the best examples of this, I mean beyond Know your team, is think about Apple. Why do people work so hard on the products? Why are they able to create what they create? And you could say Oh Claire it’s their mission, they’re making these simple beautiful products. Their values are simplicity yet beautifully well-designed things. But what is their vision? Their vision is to create a world where we live with incredible simplicity and ease. So what this does is when an engineer is designing and working on a piece of hardware they don’t imagine the mission of Apple they actually imagine the vision; they imagine a person picking up the phone and interacting with that object. They imagine the person pulling it out of the box and their smile that it comes to their face. That’s what’s motivating that engineer, that designer. Not any of this other stuff. And so as a leader and the reason I wanted to really zoom in on this is, clarifying what this vision actually is understanding that it does these two things of clarifying our decisions in the business and then also motivating our team means that we better get it pretty good. We better know what it is ourselves. We better make sure our team knows what it is. That they’re bought on and it. So how do you do that?

How to create shared vision

It sounds pretty hard. Well first of all if you don’t know what the vision of your team is which is actually the majority actually of companies and CEOs and managers that we work with find as you like I know what mission is and I know what our values are and our purpose but I actually don’t know what our vision is. It’s actually first commit to figuring it out. Say that this is going to be something that you talk about at your next all team meeting. Have this be a part of your team’s next deep dive and self reflection.

The second thing that you can do in making sure that this vision is clear and that not in that 30% of your team is not feeling clueless about it is to ask your team about their personal visions because a shared vision across the team is only built by people’s individual visions. In other words where you want to get to as a team doesn’t really matter if each person doesn’t see the value and how and why getting to that place matters to them. So you need to ask individually where do you see yourself what matters to you. Where do you want to be in five years. Personally, it doesn’t even have to do with the team but figuring out what each person’s personal visions are is how you build that greater vision and how you get to that picture of a better place it comes from each person.

And then lastly, creating a shared vision often can come from the interactions that you have with the people who interact with your products and benefit from your work the most. And this is important because we can sort of sit in our offices. Postulating what we think the picture of a better world should be thinking I like this, this feels good. And it can be a whole other thing to talk to people who actually use your products who utilize your service and to realize that the benefit that they’re getting the picture of a better world that you’re creating for them is actually quite different. Hey might even be better than what you imagined. And so if you’re looking for a place to start I figured it out, I’ve talked to my team. Make sure that you go back and you talk to your customers which is also touched on in this conference. Talk to your customers specifically about well how is this actually creating a better world for you? And the more that you can interact with folks directly there the clearer your vision is going to be. Because the thing is this whole concept division now that we’ve hopefully identified it a little bit more strongly it’s not something that just happens. You create it you have to be intentional about it. It definitely is not obvious.


The fifth biggest mistake that we often make as leaders is around being nice. So, I am nice – I promise! I think most folks that I’ve met so far at this conference are like exceedingly nice. I’d like to think that being nice is good.

Patty McCord thinks otherwise. So She was actually referenced earlier today in the talks if you don’t know of Patty she’s a former head of people at Netflix also recently wrote a book called Powerful and in her book she actually said this

“[being nice] often leads to people actually feeling worse.”

What? What do you … what could you possibly be talking about? Well think about it. So when you get when you’re nice when you’re giving feedback. What happens? One of my favourite stories about this by the way is on our podcast we had Des Traynor who’s the co-founder of Intercom. He’s spoken at BoS before and he told me ‘Claire you will love this, it’s a great story. I had a feedback session planned with a colleague so I wrote on a post it note all the things that I was going to say it was a serious conversation. There were a lot of things this person needed to be better at a, b, c wrote it very clearly, put it on my computer looked at the post it note went into the meeting was ready, just ready to let this person know exactly what they needed to do better.’ And then he said ‘and then I came out of the meeting, I felt like the conversation was good and I looked at that post it note and I didn’t say a single thing on the post it note. Not a single thing. I was too nice, too concerned about how I was coming off and that person was feeling good so I completely missed the boat and guess what -that’s another day/week that goes by, who knows maybe months go by, before that person actually knows that their behaviour has to change’ so nice actually sacrifices how that person is going to end up feeling trust me three weeks from now when you actually do tell them the truth and they’re like ‘oh wait why didn’t you tell me earlier?’

Nice also backfires in disagreements. Confrontation is something that many of us don’t like if you’re good at it and you do seek it out fantastic. But for many of us it’s actually something that we find difficult to do as nice people. Which again is a good thing but when it comes to making sure our team is functioning well nice backfires in disagreements it means that we can’t address a point head on. It means that we’re were thinking about the way to frame it instead of just delivering the actual merits. Nice backfires when it comes to firing. I mean I can think about myself personally when I’ve had to fire people where I’ve postponed it, unfortunately, because I’m concerned about being nice. And we all know what happens when someone who isn’t supposed to be a part of the company stays around longer than they should.

And the nice also actually – this is interesting – actually backfires when it comes to praise. Sometimes we can tell someone that their work is good and it’s actually not that good. Sometimes we can tell someone their work is great and maybe it should have been a little bit different. And so it avoids us from communicating the truth and from letting that person really understand what a quality bar of work should be. On our podcast we also interviewed Heaton Shaw who’s a former founder of KISSmetrics. And crazy egg and he admitted this as well. He said

“it’s fascinating because when you optimize for being nice when this becomes the centre of your universe you actually develop a toxic culture [in your company]”

So it doesn’t just even infect that single interaction that you have. But as a leader people learn from your behaviour. So if you’re saying this is good guess what your teammates then going to say to their co-worker oh yeah. That’s good too. It’s good it’s good it looks good. No mistakes don’t worry about it. People learn from that. So your job is as a leader it’s not to be nice. It’s about the outcome. And what we find in fact is that when we do centre around being nice it’s actually because we’re being a little selfish. When you’re choosing to optimize for nice when you’re choosing to be nice over all else which are essentially saying to the rest of your team is I care more about your perception of me than I do about us actually accomplishing the goal that we want to achieve. And that’s selfish. So I’m not now encouraging anyone to get out of here and become an asshole – that’s not what I’m saying. There’s some nuance to this message but here’s it like that’s table stakes. Not being nice isn’t meaning that you have to be evil. Like a baseline, yes. Be courteous, be respectful, and a self reflective person you can be fair right but you don’t have to be likeable you can be honest but you have to focus on being feel good. These things are not mutually exclusive. Honesty and compassion.

So how do you do this more practically. Because I’m sure this isn’t the first time you’ve come across this concept. Let’s get real. Like what do you actually do to make sure that you’re not falling into this trap especially if you have a tendency to be nice and to optimize for being nice. So one of my favourite questions to ask myself as a self check is to say ‘well what is it that my team is actually counting on me for?’ Readjust what the true thing is that you have to deliver on because what you’ll find in asking that question is you’ll realise they are depending on me to make sure we close this client deal. They’re depending on me to make sure we make progress on this on what we said we’re going to do. Like if I don’t fire this person if I don’t give this feedback directly if I’m sugar coating things I’m failing them in this way. They’re counting on me to be honest.

The second question I like to ask is, ’Why am I so uncomfortable?’. Why is it that I have a hard time just telling someone what’s on that post it note should be that hard I wrote it down like what is actually going on here and what we’ll find often if we dig deep enough is it’s fear, it’s the selfishness , it’s the desire to be seen in a certain way and received in a certain way. And the minute we sort of see that it becomes a little bit easier to negotiate with it and go what. Okay that’s a little selfish of me to care more about this person and if they think I’m a cool person or a nightmare or a likable person than actually trying to help the team as a whole.

And relatedly I then will ask myself ‘what’s the worst possible outcome that could come from this?’ because when you actually think about what the worst possible thing could be if you don’t give someone the feedback that they should hear, if you don’t do it, delay on firing them, you realize that the worst outcome is yeah if you don’t do those things. Because then what happens is that person is going to go about their day thinking things are fine and then again surprise. What happens is you set the tone for how disagreements are handled in the company and then people were surprised when you do a complete 180. That’s the cost. That’s the real cost. Not people not liking you that actually might be a best case scenario in some situations. What’s worst case is that you’re not doing what your team is actually counting on you to do in the first place. So, let’s not get too hung up on being so nice all the time.


The last biggest mistake that we often make as managers and leaders has to do with how we think about problems. Oh and there are lots of problems. Problems all the time. Problems all the time. And when someone comes to us with a problem as a manager what do we like to do typically? I know what I like to do or what my sort of knee jerk reaction is roll my sleeves, what can I do. How can I help. Oh. Right. What are the things that I can clear out of the way I’m going to solve this and figure it out. Turns out that’s not what you should be doing at all. So I interviewed Wade Foster from Zapier who spoke I think last year here at BoS in Europe and he told me this when it comes to problems he said:

“when you [jump in and try to solve the problem yourself] you’re actually mistaking your roles. You’ve hired this person to solve the problems. And if they’re unable to solve the problem then you might have hired the wrong person”

What Wade was trying to really hit home here is that your job, like we mentioned earlier, it’s not to be nice. It’s not to be doing everything but in particular your job as a leader is not to be solving the problems themselves which is such an easy tendency to sink into because the reason we often were promoted into this role got into this role is because we were the ones solving the problems. We’re here because we’re good at this and now you’re telling me that I’m not supposed to be solving the problems that I’m not supposed to be doing the thing that I’m good at. Well here’s the thing it causes problems when you yourself as a manager are the ones solving problems you’re the one tweaking that last bit of code you’re the one coming in saving the day on that client call that went awry when you were the person always doing that here’s what happens.

You actually prevent your team from getting any better at solving those exact problems. You stop them from learning because what they notice is they go ‘oh, Claire’s got it. Right. Oh I don’t we don’t we don’t need to go deep on that it’s all good. Someone’s going to come in and fix this for us’. So you prevent your team from ever learning how to become good at those items. And then secondly you slow your team down. Now that your team is relying on you everything gets escalated to you. Every single thing which means you now unintentionally have become a bottleneck. The issues pile up one after the other the other and you’re doing all other sorts of things having one-on-one meetings trying to map out strategy for the long term. And you have all these problems. Creates friction. And these things slow down. So instead rather than thinking okay how can I actually solve these problems quicker faster or better. Ask yourself this: How can I help my team think for themselves? How do I actually make sure that they are the ones learning how to solve these problems better and I’m not the one stopping them from accelerating.

So, questions are often the answers here. So, you can kind of imagine this is Socratic method. That if someone is coming to you with a problem, instead of just saying okay here’s what I think you should do or let me give this a shot it’s actually to ask questions. Here’s a great one – one I’m sure many of you may have asked before – which is
what do you see as the underlying root cause of the problem?

Having the person actually reflect on what is truly the issue here that you need to fix. Another great question to ask instead of solving the problem itself is:

How do you know you will have been successful?

Maybe this person has already gotten there and they don’t even know. Another question:

What’s the most likely outcome?

So understanding the probabilities of all the sets of things that could happen helps that person evaluate that choice and again by asking this question you’re not you’re not solving the problem for them you’re helping them think this through. What have you already tried? Eliminate the options and take them off the table for things that they may have already done. And then actually one of my favourites to ask to help someone solve a problem is:

What do you think would happen if you didn’t do anything at all?

And this is really fantastic for really understanding priorities. What matters. And if a person is perhaps amplifying an issue that shouldn’t be. So, as we think about asking questions instead of just jumping to answers and trying to solve the problem itself. Realize that it’s because you ask these questions to help the team think for itself and to build out its own capabilities instead of your own. As leaders it’s not about us feeling good that we’re the ones solving the problem it’s that we’re helping others figure out how to do it themselves.

So, many of you may be thinking and looking at these slides thinking ‘oh thank you Claire That was Helpful’. I appreciate the reminder. I’ve made a lot of these mistakes in the past, but I’m good now. Like I like I’ve read a lot of this in blog posts. Like it’s good. I don’t make these mistakes anymore well I want to remind you. Of the statistics we saw earlier. Right. That 82% of us in this room were not promoted for the right reasons and that 90% of us don’t have what is seen as the inherent talent to manage. And I remind this honestly again mainly for myself as well because the difference in the gap between seeing these things on slides and reading them and blog posts and actually doing them in practice when you have that one-on-one meeting. When you’ve written those things down on your sticky note when you need to fire someone is quite different. So my challenge to you as much as he may think that these mistakes are mistakes of the past, that you yourself have never made these mistakes. My challenge she was just to ask you are there any that I might be accidentally making. Is it my conception around emphasizing team building and trust instead of thinking about actually intention and behaviour. Is it that I’m not preparing for one-on-one is in my conception of time. I just really like being busy. Or is it that I actually don’t really know or make clear the vision in the company. Am I too nice or do I just try to solve the problems all the time, And I’d like you to just take stock and if you find yourself thinking yes to one of them maybe some of them or even better if you do truly feel like what I actually I’ve graduated and I actually don’t feel like I make any of these mistakes anymore accidentally. That’s amazing. But either way. Seeing these things for what they are knowing that these are accidental mistakes that trust me our worst bosses made over and over is the first and most important step to making progress and making sure that we don’t accidentally become someone else’s worst boss.

So, thank you.

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Mark Littlewood: Thank you, Claire. Some questions.

Audience Member: I’m really interested in this…[inaudible] How do you trigger the awareness of that Blindspot. Particularly in your boss or in your founding partner or whatever. Give us a couple of strategies that you think really work.

Claire Lew: So that’s a really. So the question was ‘How do you help your worst boss realize that they might be your worst boss’ right? And uncover those blind spots. So this is not a cop out of an answer but it is truly one of those hardest things to do because. True identification of a problem starts with the self. It is never imposed from the outside like you can’t actually solve a problem. If you yourself haven’t admitted that it’s a problem. So to have it to have it interjected from externally it doesn’t really work. So then it becomes this weird second level thing. Where it’s how do you help this person realize for themself that this is a problem right. And there’s a lot of strategies.

The biggest is honestly just most straightforward which is that you tell them which I know sounds ridiculous because you’re like Well duh! But most of these problems occur actually just because of the lack of knowledge. Hence the name of my company or your team. Sometimes it is because it’s not getting through but a lot of times it’s just because of the lack of willingness for people which is totally valid, by the way, I’m not trying to play that down and it’s I totally understand why you wouldn’t speak up and there’s a ton of signs around why that is, but, that’s usually not the problem it’s actually just the lack of information right. So that’s. That’s the biggest thing. And specifically it’s in how you tell someone and what you’re telling them. So what happens a lot of times for wide feedback off isn’t received by someone who needs to be hearing it is a few things. One they don’t believe you. So there’s like a credibility issue so you want to make sure that it’s being delivered by the right person. So for example hearing from the employee who is sort of underperforming and you’re hearing that you’re not a good boss from that person. Probably not going to listen to that person as likely as someone on your board. So who the messenger is extremely important. Another thing is in the content of the feedback obviously being as objective as possible. So a lot of times we get into these descriptions of what we think needs to be better because I know I feel this way I am. So it makes me it’s about me it’s about the way I’m feeling versus this is what I notice in the organization. These are the effects that I’ve seen. This is what I know you want to make progress on and you’re not making progress on that you’ve to make it about them. And objectively about the results. And then lastly and this is possibly the most important thing when it comes to giving upward feedback is around intention. Feedback is often most misconstrued because people don’t understand why it’s being given. They assume it’s because you’re out to take a job. They assume it’s because you’re just a nasty person. That’s why you’re telling me this right. So the intention has to be clear. So very very strongly and however you can communicate to say I’m giving you this feedback because I don’t want you to lose your job. Or I care about your personal progress in your career or I know the type of manager and leader you want to be, I know what that is and I don’t think you’re being that right now. And so communicating that care is by far the most important thing. Thanks for your question.

Audience member: Yeah I have a question. Could you talk a little to…

Mark Littlewood: Where is that sound coming from? Hello!

Audience member: Oh it’s a microphone. [laughter] There’s a new technology. Wow trickery and witchcraft

Mark Littlewood: Juju magic! [laughter]

Audience member: Those of us who are in smaller companies. Could you speak a little to the balance in particular on the point of doing your team’s job for them. Those of us who have to play somewhat a supervisory role as well as playing the role of an individual contributor. The balance in there with not sweeping in but

Claire Lew: Sure, so I think, balance is a confusing word because I don’t think there’s true balance right it’s ebbs and flows. And so we’re – as or maybe some of you don’t know we’re a tiny tiny company. So I face it every single day. I’m writing all this stuff about not solving problems but in my day to day I actually have to solve problems right. Just by virtue of the size of the company and so what. I tend to look at it as is ebbs and flows. So there are periods where if you’re having a one-on-one meeting right don’t ask the status update, don’t get in to solve the problem. If it’s not your domain if you’re an engineer and it’s something on design side right that person has to solve the problem solves. So understanding that there are times when you’re wearing that hat. And then in small company of course times where you are going to be the one debugging code or having the conversations with clients. So with all of this actually that I suggested it’s definitely not one broad sweep of anything right. Especially in small companies or for very big companies. All of these sort of your mileage varies accordingly and you want to adjust all the suggestions that I made but I think the most core thing to keep in mind is growth. So if you plan to scale and grow as a company how are you setting a precedent and creating a foundation so that it’s clear what your role is. That your role isn’t to solve problems, that your role is to support and make sure that you’re helping to uncover issues and not in the weeds of the works. How do you set that precedent as a five person company as a 15 person company as a 25 person company before then you get to 30 and you’re like oh everyone thinks that I’m supposed to still be taking care of the code. No I can’t be solving problems at that point Great question. Thanks.

Mark Littlewood: the other mic in the corner.

Audience Member: sorry I think I pressed a button. That was fantastic. So my question is basically towards the beginning of the slides. And you said to touch base with your employees and think about their own personal visions and then generating a vision based on everyone else’s. So what advice would you give if there are a couple of employees who perhaps haven’t expressed such positive visions that make sense?

Claire Lew: So do you mind if I ask a follow up question. So when you mean positive you mean not aligned with the company or that they actually just don’t see themselves progressing far?

Audience Member: Yeah I think a bit of both. Primarily the latter I mean for instance I were like oh yeah we don’t understand how you want to create a 1 billion dollar business or whatever but they don’t understand how that can happen and they’ve been a little bit maybe you just aren’t excited or you don’t understand how that’s even possible but they are a really good employee. They do great work but you’re just trying to figure out whether the mission is.

Claire Lew: Yes well so one thing is to clarify is that creating a billion dollar company would definitely not be a personal vision and I don’t think you were implying that but point being is that whatever you are personally excited about as a manager, as a CEO like what gets you up in the morning might not get folks who are on your team up in the morning right. And that’s okay. So the key with figuring out why identifying what people’s personal visions are so important is because you want to actually do figure out what does get them up in the morning. Right. What is it that they are personally excited about in their career and it could literally – here’s the thing – it could even be non career related. It could be anything absolutely anything and it may not be true. And sometimes it’s hard to recognize because it’s not like in the same degree or you’re like me how could you be excited about that or it’s not even there. And this is possibly one of those frustrating things as a manager is you’re like but it’s not even related to that. You’re like oh come this way.

But it’s not going to happen. Well here’s the thing, as managers we have to have a reality check of as much as we would want it to all sort of be aligned sometimes it’s not. And sometimes that’s okay. The important thing that was to understand the difference because when you can see the difference when you can see that these two people like you said great employees might have personal visions that you don’t really understand how it’s going to tie. Right. They’re not career progression isn’t really that important. they don’t they don’t have the personal growth goals that you thought. That might be okay. But it’s important information to take in because frankly maybe they might not be long term employees in the company or maybe they’re in roles where that might actually not be. Important necessarily at least right now. But I think the important thing is to actually take stock and understand that there are personal visions and not just this grand team vision and that the team vision only exists because personal visions are contributing to it is the important part. So long story short. It’s okay.

Mark Littlewood: Got it. Actually, as it after 3:00, can I ask you to grab Claire in the nicest possible way on the way out. So, Claire thank you so much.

Claire Lew, CEO, know your company
Claire Lew

Claire Lew

CEO, Know Your Team

Claire’s mission in life is to help people become happier at work. She’s adjunct professor of entrepreneurship at her alma mater, Northwestern University and CEO & Founder of Know Your Team, a software tool that helps managers become better leaders. She’s worked with over 30,000 people in 55 countries at companies including Airbnb, Medium and Kickstarter and is often cited as an expert on the topic of creating more open, honest workplace environments. She’s been published in Harvard Business Review, CNBC, Inc, Fortune.

BoS folk love Claire as she’s a brilliant communicator who leaves you with incredibly clear, actionable advice. She’s attended BoS regularly and given two talks: Don’t Be the Last to Know, on why leaders are often the last to discover something and what to do about it; The Accidental Bad Manager on the biggest mistakes managers make and how to avoid them. You can watch them and more here

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