Playing to your strengths as a leader doesn’t make you a good boss – in fact, it can make you a bad boss. Here’s why.
Of all the tips to be a good manager, “leaning into your strengths” has got to be one of the most frequently cited.
“Do what you’re good at. Focus on your strengths.” That’s the conventional advice we all receive. There’s no shortage of StrengthsFinders assessments and personality tests urging us to triangulate which strengths we should zoom in on.
However, I recently had a conversation with Peldi Guilizzoni, CEO of Balsamiq. His insight on this topic turned my head sideways… in a good way. Peldi asserted:
“Doing what you’re good at hurts the team.”
Huh? Let me explain.
Peldi admitted to me that he’s good at getting stuff done. He makes things happen. He thinks he’s killing it. But as a CEO, 10 years in, should he really the one doing all the doing?
After a decade running his business, Peldi noticed he’d created an environment where his coworkers were depending on him to get things done. If he takes a vacation – he leaves them hanging. If he has to be out for a week – they’re stuck.
“What I realized is that I should stop myself from doing things I’m good at — which is so counterintuitive — and instead, focus on delegating training and making sure that everybody gets good at doing those things.”
Doing what he was good at was hurting his team, not helping.
I could relate.
I’m good at communicating. So I do it internally. A lot. I write-up about what we’re doing, why we’re doing it, a new approach I’m thinking about, a new concept we should try… But, when I take a step back, it’s a bit too much. We’re a tiny, two-person company. For our size, all that communicating is overkill. I could easily spend some of that same time somewhere else in the business and have it be more meaningful.
For both Peldi and I, our predisposition became a preoccupation. We’re good at it, so we automatically assumed it was good for our team.
Whenever you’re good at something, you don’t objectively assess its effectiveness as you should. You apply less of a discerning eye. You know you’re good at it, so you figure the more you do of it, the better.
But as with anything, repeated actions without rigorous judgment become lazy and reckless. And naturally, they have unintended consequences.
Now avoiding this pitfall is hard.
No one is going to stop you. Rarely do others have the temerity to stay, “What you’re good at is bad for the team.” Plus, doing what you’re good at is fun. It’s inherently satisfying to flex your strengths. Who wants to not feel that way?
So, you have to ask yourself: Are your actions feeding your team, or your ego?
Focus on what you’re good at, and the team never becomes good at it themselves. Focus on what you’re good at, and you never see things for what they really are.
Resist viewing your strengths as the only way to make the team strong. Resist falling in love with the short-term results of doing what feels good to be doing.
Pause. Don’t be so busy. Take stock. Why are you doing those things? Because you like doing them? Because you’re good at them? Or because it’s the best way to move the team forward?
Find someone who will tell you the truth. Your co-founder, your coworkers. Ask them if what you’re doing that you’re good at is really helping move the team forward.
This truth-seeking takes 10 minutes to do. Start today. And stop doing what you’re good at, all the time.
P.S.: If you did indeed enjoy this piece, please feel free to share Thanks 😊 (And you can always say hi at @clairejlew.)
After four years, we’re launching a new product, business model, and company name. Here’s why.
We’ve always been a bit weird.
We’re a two-person company serving 15,000+ people who use our product in over 25 countries. We’ve generated almost $2MM in revenue to date, have been profitable since Month 1, and every year since. We’ve never raised money from investors, or taken out a bank loan. (And, we started out as a tiny prototype that Basecamp spun-off.)
Today, we’re doing something weird, again.
We’re launching a new product, business model, and company name.
We’re now Know Your Team — software that helps managers become better leaders. We give you educational guides, tools, and a community of support to help you avoid becoming a bad boss.
Know Your Team costs $65/month per manager (or $600/year).
If we’ve never met before, hello! I’m Claire, CEO of Know Your Team. It’s nice to meet you, albeit virtually.
Our original software, Know Your Company, used to be focused on helping business owners with 25 to 75 employees get to know their company better. We charged $100 per person, one-time, for life.
We generated $1MM in cumulative revenue in a little over two years. We helped tens of thousands of people at companies like Airbnb, Medium, Kickstarter. And not just at tech companies, but law firms, marketing agencies, retail stores, and even a few churches.
When we surveyed customers, 94% of employees said Know Your Company helped them feel more connected to their coworkers, and 85% of CEOs said Know Your Company positively impacted their company culture.
Yet as 2017 was winding down, we noticed our sales becoming flat.
I remember thinking this around this same time, last year, in December.
As I reflected on 2017, I noticed three things:
Our online community for leaders took off. We’d launched our Watercooler community in October 2017, to help managers learn from each other. More than 200 people signed up for it in the first month. (Today we have almost 1,000 members.)
Our writing about leadership took off. The writing I’d been doing on our blog increased our organic traffic by 3X in a month’s time. It would go on to increase by 20X over the next six months.
Our software sales went down. Our sales, however, did not increase. Not 20X. Not 3X. In fact, sales were fairly flat in 2017, if not dropping during some months.
Seeing the discrepancy between our audience and our sales, we scratched our heads.
Yes, Know Your Company was helpful as a piece of software. But for who?
When we got started back in 2014, we focused on selling to business owners. But by the end of 2017, our audience had evolved. After some digging, we learned that our 20X increase in traffic were mainly managers at companies of all sizes.
We had a mismatch. Our audience was managers, but our software was for business owners.
Our audience was asking the question, “How do I become a better leader?” But our software, Know Your Company, wasn’t answering that question.
In fact, no one was doing a good job of answering that question, “How do I become a better leader?”
Sure, you can read books, but they lack practical application. Trainings are expensive and one-time. And man, making mistakes and learning trial by fire is awfully painful.
I searched high and low for a good answer to, “How do I become a better leader?” I couldn’t find one. So we decided to build our own.
The best way to learn anything is to go do it. The second best way is to practice doing it. So with Know Your Team, we combined theory with practice. You can’t become a better manager by just reading books, or just by using software tools, alone. We built Know Your Team to include 3 complementary resources, to be used together:
Guides — Written guides on leadership, based on data, with 50+ chapters on topics such as one-on-one meetings, giving honest feedback, building trust, and more.
Toolbox — Dead simple software tools to help you run effective one-on-one meetings, ask for feedback, get high-level team updates, foster rapport, and more.
Community — Online support from 1,000 other managers from all over the world, where you can discuss tough situations like firing, hiring, and more.
And, we’re not done! We’ve got loads of ideas for more guides, more tools, and more resources that we’ve already started working on creating. There’s so much to be done to help people become the leaders they’ve always wanted to work for.
Changing our business model.
For new customers who sign up for Know Your Team, we chose a new business model. Know Your Team costs $65/month per manager to purchase. As a monthly subscription, this makes it easier for managers to swipe their credit card without having to ask for permission from their boss.
Previously, our one-time pricing model had been useful to get us to profitability quickly. For example if you had 19 employees, we charged $1,900 one-time. We were essentially collecting the lifetime value of the product upfront.
But over time, we noticed our one-time pricing model becoming a big barrier to sales. A business owner had to justify a $2,000 or more expense to their finance department, to their investors, and to their leadership team.
Now that we’re selling to managers, there was no way a $2,000 product was going to feel accessible to them, even if the cost was only one-time. We wanted Know Your Team to feel like a “no-brainer” purchase for folks who might not have access to the company’s budget. So we moved to a monthly subscription model.
Building Know Your Team with two people.
We spent six months building Know Your Team. This meant designing and coding new features, writing 50+ chapters on leadership for our guides, and constructing a new billing system, new onboarding system, and new marketing site… All with just two people.
Every piece of copy, code, and illustration you see is something our CTO Daniel Lopes or myself created. (We did this while maintaining our current product, doing customer support, writing blog posts and pursuing other marketing projects.)
This is a big move for us. As a bootstrapped company, we don’t have piles of cash stacked up, in case it doesn’t work. We don’t have investors to run to if we get stuck in a bind. (In fact, we have $140,000 in the bank, to be precise.)
But, the change feels right. Since I’ve been running the company in 2014, this launch, today, is the most energized I’ve felt.
Why the weirdness?
Admittedly, our approach is weird.
You might be wondering, “Why are you making things so hard on yourself, Claire? Why not raise some money to make this change? Take out a bank loan or open a line of credit? Hire more people? Buy yourself more time?”
Those are not bad ideas. We considered them. And who knows, maybe we’ll pursue them in the future.
But for right now, the short answer is: I don’t want to.
When you run your own business, you have to remember why you wanted to run it in the first place. What you want. Not what others want.
In business (and in life), we’re addicted to pattern-matching. We snuggle into where the grooves are carved, where the tracks have been laid — not necessarily because we want to — but because they’re just there.
For me, I got into this whole starting-a-business thing because I wanted to do it on my own terms: Small in headcount, big in impact, independent, profitable. Life is short. Why build a business any different from your vision for it?
Of course, you shouldn’t mindlessly listen to your own din, in isolation. You should carefully choose who to listen to. The only people I want to listen to are our customers, current and prospective: Employees, managers, leaders, CEOs.
The minute you take on investors, accept money from a bank, put people on your board — you change the people who you’re listening to.
I don’t even want to listen to Jason and David, the founders of Basecamp (and Know Your Team board members) 🙂 We’re lucky that Jason and David want us to do things our way, too. We disagreed on some of the strategy of the roll-out of Know Your Team, but they were very supportive of us choosing to ignore their advice. (I’ll write more on this perhaps another time…)
If you have the luxury to choose who to listen to, choose intentionally.
Is Know Your Team for you?
You might be one of those people I want to listen to.
If you’ve spent late nights googling things like, “how to be a good manager” or “how to run a team meeting” or “how to delegate well”…
If you’ve bought carts of leadership books on Amazon, desperate to avoid beginner manager mistakes…
If you’ve ever thought to yourself, “I have no idea what I’m doing as a manager”….
If there is anything else — truly anything — I can do to help you become the leader you always wished you worked for, I’m here. Feel free to email me at email@example.com or ping me on Twitter at @clairejlew.
I look forward to hearing what you think. I’ll be listening to you.
On the journey with you, -Claire
P.S.: If you did indeed enjoy this piece, please feel free to share so others can find it too. Thanks 😊 (And you can always say hi at @clairejlew.)
As a second-time founder who’s scaled a business to $5MM+ annual revenue and appeared on SharkTank (getting an offer from Mark Cuban along the way), Desiree shares her biggest leadership lessons on identity, team dynamics, and growth.
Every two weeks as part of The Heartbeat ❤️, I asks one question to a founder, CEO, or business owner I respect. This week, I interviewed Desiree Vargas Wrigley, Founder + CEO of Pearachute. Watch & read what she has to say here…
Claire: Hi everyone. I’m Claire Lew, and I’m the CEO of Know Your Company. Today, I am honored to have someone who I admire, a good friend of mine. I have Desiree Vargas Wrigley, who is the founder and CEO of Pearachute, which is this amazing platform that helps anyone who has kids drop into any class that they want. I think it’s yet a brilliant idea and she’s really built and grown the company. Before that, was the founder and CEO of GiveForward.
Something really cool that Desiree was also telling me about was they’re actually now offering Pearachute as a great work park. So something you can actually give your parents who are parents to help them, yeah, just really engage and feel connected with their kids. So anyhow, Desiree, it is so amazing to have you here and to be able to ask you this one question about leadership.
Desiree: Thank you for having me, I’m excited to see you.
Claire: Thanks. Okay, so you don’t know the question in advance, so brace yourself. Here’s what I’d like to ask and here is what I’ve been asking CEOs and founders who I respect, which is: What’s one thing or it can be several things, you wish you would have learned earlier as a leader?
Desiree: That is a big question. Early on someone gave me this advice but I didn’t know actually how to internalize it until later. So I’m going to start with … I’m going to make it a two-part.
But the first one was that don’t beat yourself up too much when things go wrong, but also don’t take too much credit when things are going right. Because a lot of times there are things that are happening as a leader and as a company that are out of your control.
As much as you want to believe that you are driving everything, external forces really do have an impact and great hires of course make up … as terrible hires sometimes make an impact. At the end of the day, like yes, you are the one holding the bag as CEO, but it’s never all your fault or all your credit. It probably sounds obvious, but I think in the early days I really thought if I work harder or if I think smarter I’ll be able to solve this problem all the time. Sometimes there are really just outside factors and you have to learn how to navigate them and kind of remove ego from the scenario to be able to just really perform.
That’s one, and then … Two, figuring out what kind of leader I wanted to be. I think a first founder, a mistake that a lot of us have which is tied to my first part of the answer is that you are so closely identified with the business that you’re creating because it came out of your brain. It’s literally like your brain child and you are convincing people to come and work on it with you, and convincing people to invest in it. It is so closely tied to how you feel about yourself. So the ups and downs can be … You know, have a really big impact I think on your mental state but also on your quality of leadership.
The more you can remove your sense of self-worth from the performance of your business, the better your business and your leadership will be.
You’re able to see more clearly kind of where your baby is ugly or why certain things aren’t working. So just kind of having that level of knowledge and reflection, being able to separate yourself. One other thing that allows you to do well as leader is that when people underperform, it’s not that they are kind of violating this promise to your baby, but it is instead an opportunity to coach them and help them grow into a better version of themselves. All for the kind of same North Star as opposed to taking care of this child that you are giving them access to.
Claire: Wow. No, I can completely relate to that answer, having now sort of my third company and I think it is a hard lesson to learn Desiree. I think this idea that you separate your identity from the business. I mean, how do you do that, first of all, and second of all … Or maybe I should actually ask the second part first. When did you learn that? Like did something happen? Whether it was when you were starting and running GiveForward, whether it was when you were starting GiveForward, whether it was when you were starting and running Pearachute, where you realized, “Huh, I think I’m equating my sense of self too closely to the business and it’s actually having negative effects.”?
Desiree: Yeah. For me, it was a series of things that helped me fully, fully realize the separation. You know, bringing in a co-founder early on meant that I had to of course share the vision with someone else. But I think if I’m being honest with myself, it still always felt like mine and I was letting him in. Which is not a great way. We’re still good friends and we overcame I think the challenge in our partnership. But if I’m being really kind of just honest about how I treated things in the beginning, I think as you bring in senior team members, starts ruling some of your ownership over that control.
So in a way you kind of give up a little bit of that identification, tiny bits at a time. But truthfully for me, when I decided to step away as CEO and bring a new CEO. It’s not honestly something I would recommend to most people, it’s a very challenging way to do that, to separate yourself. A much healthier way is through coaching and through maybe therapy, reading, I don’t know, a combination of things.
I ended up working with an executive coach for a while who like helped me make a lot of progress and understand kind of my role within the vision, as opposed to being the creator of the vision.
So I don’t recommend getting a new CEO as a way to do it, I think there’re other ways. But sometimes it does take something daring like that to force yourself and then there is a grieving process, no matter how you do it. Because you are separating a piece of yourself and it’s not a divorce in any way, shape, or form, but it is retraining your brain to think about yourself and your value differently than you did before. It’s so liberating.
Honestly, this time around with Pearachute, I get to look at Pearachute as something that is on its own. I actually think truthfully being a mother has helped me do this that much more because I have two boys that I’ve birthed and then a step-daughter also.
My role as a parent is not to dictate who they become, right? But to help put them on this journey for success and to give them the foundation and the resources that they need to be their best selves. That’s true about a business too.
So you know, the analogy does continue, but one that is less emotionally aggressive I think, which is: If you treat your company as this being that has his own life, and its own identity, and its own brand – you create the resources and the support system around. It’s just such a much more relaxing place to live and you still want them to do well. You still need them to get into college, you still need all those things to happen but you’re not … It’s not the same as your own personal value.
Claire: Absolutely. What then are you doing differently with Pearachute in this approach? Is it a mindset, is it in conversations you’re having with your senior leadership team, has it affected your hiring? Like curious, given that you’ve learned, “Okay, I can’t be as emotionally aggressive.” what are you doing differently then with Pearachute to sort of set those boundaries?
Desiree: Yeah, I’m doing so many things differently. Definitely hiring.
I hire a lot more for the individual athlete role.
I think if I’m being honest with myself, before, I hired good people that I thought would be good at the job, but this time I’m looking for efficiency, and a lot of creativity, and a strong level of autonomy. Because this time around I just have so much more trust and I sometimes feel sorry for some of my earlier team members because I just didn’t know how to trust them with the vision.
This time around I have that clear understanding. So people can achieve so much more obviously when you are willing to kind of give them that freedom to explore and make mistakes.
Of course, they fail and recover from those failures, and wow you, right? So creating room for that within my team is really important to me. Because of that, I often think we get more done with our eight or nine people than we did with our 40 that we had before. Just because people are able to be really, really focused.
I am so much better at clearing a path towards creating time blocks for people and making sure that they have enough time to do their work. Where in the past I think we really jammed meetings because there needed to be a lot of communication.
I think if you’re transparent and constantly doing a great job of reinforcing vision and the kind of ways you’d attack toward that end goal. That you don’t need to do as much real-time collaboration because people have a clear idea of where we’re all headed. It’s more about checking in with each other and confirming priorities, and then kind of getting back to work.
Claire: Absolutely. Yeah, and I mean, I think there’re so many CEOs and founders who I talk with who struggle with this, right? Like you start a company, you’ve been kind of killing yourself over it and now someone else is going to start to do your job. So being able to sort of release that and just be a lot more hands-off. It takes a certain amount of discipline but it sounds like that’s really paid off and been the difference for you, between the two companies. Yeah, that’s amazing.
Desiree: For sure and I’m actually very practical with my team too. A lot of their roles right now are a jack of all trades, wearing many hats.
So I remind that our job is to build this company to be big enough that you kind of earn the right to either hire your boss or hire the person to take everything off of your plate that you don’t love or aren’t the best at.
That really, like that is the sign that we have gotten there, is being able to also then relinquish some of the things. Sometimes it’s things that you do love that you have to relinquish. But I think if you’ve got into the culture, it creates less kind of territorial-ism and more of a willingness to like let peoples’ skills flow into the places that we need them the most. As opposed to like this is my silo, that’s your silo.
Desiree: Which is something also that we did not as well in the first startup.
Claire: Totally. I mean, what you’re describing Desiree is the struggle that has come up so often in these conversations, which is a struggle with ego and a struggle with … again, like almost a sort of possessiveness. Which is very related to the very first thing you said, which was kind of the first answer you gave around what you felt like your biggest lesson was. Which is that it can be very easy to feel like when things are going really well, it’s all you, and then when things bad, it’s all you.
So tell me a little bit more about that founder mentality or … You know, I don’t know if you want to call it a syndrome, I don’t know if you want to call it sort of a blind spot, right? But why do we get stuck thinking that when things are really good, it’s all us, and things are really bad, it’s all us, and what are the dangers of that? Like how has that affected your journey as an entrepreneur?
Desiree: Yeah. So a very specific example of this for GiveForward was … So we were a crowdfunding company, coming of age when Facebook was coming of age. We launched before Kickstarter but Kickstarter’s massive rise definitely helped elevate all of crowdfunding, right? So we falsely believed that because we were investing in SEO and paid search, and we had this great channel for distribution through Facebook, that the growth that we were seeing was entirely of our own doing. That we were figuring it out, we had the secret together.
Then it took the Facebook algorithm change to knock us down really big. We didn’t realized that we were growing on top of the growth of other giants, and that while we had been intentional in how we spent, we didn’t perfectly know how to find our customers. Our customers are very hard to find. The best friend of someone with cancer is a hard target, absolutely. But this time around, I have a better understanding of what kind of external factors can be contributing to growth.
At the same time, I’m more much laser focused on what are the measurable things that I can do within kind of our economics to create efficiency there. So that I can predictably know that when I put $50,000 into marketing, I’m going to get X numbers of customers out. So I think that comes with experience just in general and success. So now our user growth feels much more earned because I had that other thing to reflect on. But I’m also very aware that I am now sitting in a company that is targeting mostly millennial parents and only 20% of them have started having children. So there’s this massive group, that’s 80%, that is about to have children.
I will assume that our growth and rise to power will be because of what’s happening within these external forces. You know, paying attention to both I think helps to remember that like it’s not … Everything that you’re doing is not perfect and something that works now obviously might not work again in a year. But it’s when you’re in the middle of crazy growth, it’s hard not to pat yourself on the back and say, “Look how amazing we are. We’ve done all these things right.” The truth is, a lot of it is about timing.
Claire: Yes. I think that advice is worth its weight in gold. Because I don’t think you learn it until you get burned by that situation and you realize, “Huh, I think we made a lot of assumptions.” I guess, what advice do you have for founders and CEOs to be rigorous about not assuming that it’s all you? It sounds like from your perspective, the analytics, the level at detail that you’re looking at, like you were saying the metrics are really key. But is there something also you’ve embedded in your team, are there sort of systems you place in Pearachute? Curious just about advice you would give to other founders to do that well?
Desiree: Yeah. It’s so tempting, right? To find this path that works and double down. So yeah, that is an element, of course, with any level of growth. But for me, I am very aggressive with my team about diversifying acquisition. That paid search is great, or any kind of paid ads are great, until the cost of acquisition gets so high that you have a ceiling and you can no longer spend to affordably acquire your customers depending on your LTV.
So we have been conscious of the pieces of acquisition and since the very beginning knowing that, of course, there’s a viral component to the business, there’s also a direct, which is a little bit harder to manage or influence. We need to be working kind of equally on all parts, because at the end of the day, full reliance on one channel has very high risk of creating really expensive customer acquisition down the road.
Desiree: So I would say just constantly diversifying, yeah.
Claire: Again, I think everyone who is watching this will be taking notes and writing that down. Desiree, thank you so much for sharing.
I’ve been learning a lot just listening to you. Like I said, you’re someone who I’ve always really, really enjoyed hearing about your experience in building and growing companies. So thank you so much. I know everyone who is watching has really appreciated your thoughts too. Thanks.
Desiree: Thank you for having me.
P.S.: Please feel free to share + give this piece 👏 so others can find it too. Thanks😄 (And you can always say hi at @clairejlew.)
You’re likely making these 4 leadership mistakes as a leader. Here’s what to do instead to become a better listener.
You’re not listening, as leader. You think you might be — but it’s highly likely that you’re not.
Think back to your last one-on-one meeting. Be honest: What percent of the time did you accidentally zone out during your direct report’s answers? Were you distracted by an impending meeting with an unhappy client? Were you trying to guess your direct report’s motives, and running through past one-on-ones with them in your head?
I don’t blame you, quite frankly. As leaders, we’re trained — and rewarded — to multi-task, rapidly context-switch, and think in parallel. We’ve got a firehouse of tasks, team dynamics, goals, customer requests that we’re juggling… How else are we supposed to weather the storm?
However, listening requires an opposite motion. Listening lives in silence. In stillness. You need to focus purely on the person you’re listening to. Not analyzing the response as they speak, not anticipating the next sentence, nor brainstorming ourselves what we’ll say next. Not thinking about the next meeting, the next phone call, or, hey, lunch is in 40 minutes.
The only way we’ll truly understand what the other person is trying to say is if we’re zoomed in on listening, in that moment.
When we do, listening becomes a powerful lever. A great listener gains knowledge that’s overlooked. They hear the tone of disappointment in an employee’s voice and discover that person is not happy on the team. They recognize that an employee has been having revealing conversations with a customer, and they finally understand why a customer isn’t satisfied with a particular part of the product. It’s knowledge only found in the nooks and crannies — you have to pay attention closely in order to spot it.
Not to mention, when you listen well, you show empathy and build trust in a way that’s more genuine than any office perk or team social event.
So how do you know if you’re a good listener — or a terrible one? Here are the 4 most common mistakes leaders make that reveal they’re not a good listener. Read on to see if you’ve been unintentionally committing any of them…
Mistake #1: You keep your phone on “just in case.”
Yes, emergencies do happen. But keeping your phone on during a meeting and having it buzz is enormously distracting for the other person. Countless of employees I’ve spoken to have mentioned how disrespectful it feels for their manager to have their phone go off — or worse, to be texting during the meeting. A recent study revealed that smartphones are distracting, even when we aren’t looking at them. So, what’s the solution? Just put it away for the meeting to be present as much as possible. If you do have to take a call or are expecting an important message, simply let the other person know so they’re aware, or reschedule the meeting.
Mistake #2: You assume people want your two cents — so you give it immediately.
As a leader, you’re often looked to as the expert. And, well, you are the expert most of the time. So it’s common to want to jump right in and help your team by providing the answers, or share how you’d attack a challenge. However, that eagerness to lend a hand can backfire. Rushing in with your opinion can crowd out any room for your team to share their opinion. I’ll always remember my interview with Laura Roeder, founder and CEO of MeetEdgar. One phrase Laura rigorously used with her team was: “Make this decision without me.” This gave her team the space to figure things out on their own, share their honest opinions with her — and helped her listen, not just tell.
Mistake #3: You only ask one question, before moving on to the next topic.
How many questions do you typically ask a direct report? Just one, then on to the next item? Or do you try to follow-up each topic with at least two, three, or more questions? Whether it’s during a one-on-one meeting, a Zoom video conference, or in a Slack message, the best managers frequently ask follow-up, clarifying questions — both about themselves, and their colleague. They ask, “What isn’t clear?” or “What am I not explaining enough?” Additionally, when their team members speak, they ask questions such as, “What do you need to make X happen?“ or “What can I take off your plate to help you do X?” The more clarifying questions you ask, the more listening you’ll do.
Mistake #4: You rarely ask yourself, “What’s my mood right now?”
We all have bad days. It’s inevitable. To make sure you can listen to someone well, it’s important to be aware of your current emotional state and to optimize for it. Not a morning person? Schedule your meetings in the afternoon. Just got out of some crazy traffic, or rushing to get all your tasks done before the weekend? Consider rescheduling — not avoiding — a tough conversation. The other person will be relieved that you asked if they don’t mind chatting with you once you’ve had time to take a breath.
If you’ve found yourself thinking, “Oh man, I’ve definitely done a few of those recently” — no need to get down on yourself. We all have been guilty of them, myself included. My hope is that in pointing them out, they no longer float under the radar. With awareness comes a small change in actions. We can all lift the veil that we’re all not as good listeners as we’d like to be. If we want to be better leaders, it starts with knowing what work we have to do 🙂
P.S.: If you did indeed enjoy this piece, please feel free to share + give it ❤️ so others can find it too. Thanks 😊 (And you can always say hi at @clairejlew.)
A good manager knows their opinion can influence their team sometimes TOO much. Here’s how to compensate for that.
When you’re a manager, something interesting happens: You mention an idea off-hand, and all of sudden, it becomes a priority. You casually ask a question out of curiosity, and all of sudden, everyone scrambles ASAP to get you an answer.
As a leader, your opinion matters. But sometimes, it can matter too much. You can unintentionally sway team members by stating your opinion prematurely. Or, you can accidentally quell perspectives that are critical for you to hear.
How do you keep this from happening? One of the managers in The Watercooler, our online community with almost 1,000 leaders, kicked off this conversation recently. Below is a summary of the insightful, practical replies.
Here are 8 ways for you to compensate for your opinion weighing too much, as “The Boss”…
Assign others the task of disagreeing with you.
Force the hand, and create a safe space for someone to disagree. For example, in a meeting with ~5 people, you might pick someone and say, “The four of us seem to be saying the same thing, and I’m making it your job to disagree with us regardless of how you actually feel. So if you’re forced to play the role of the disagreer, what’s your argument?”
Give someone less experienced a chance to speak first.
This helps prevent folks from just shutting down and saying, “Yep sure, what that person said.” Even if the person is way off the mark in their opinion, it either signals you should spend more time working with them, or it causes the team pivot on the original idea after hearing others. One Watercooler member mentioned how he was recently listening to Great at Work and a high performing example company followed this practice: Most junior employees shared their thoughts first, most senior shared their thoughts last.
Have the person with the strongest opinion speak last.
A strongly-held viewpoint can drown out any potential for diversity of thought to emerge. So have the person who has already thought about an issue and formed a strong opinion speak last. This is also helpful because they’re the least likely to be biased by what everyone else says.
Ask others what they think before jumping in with your own thoughts.
One Watercooler member shared that he’ll often send people a link to a story, article, idea, etc. and ask people, “Thoughts?” to see what he gets back. This helps provoke thoughts from other people, in an unfiltered way, before you insert your own.
Ask everyone to explain their thought-process, not tell you their opinion.
This keeps the people with opinions — but perhaps more trivial reasoning behind them — from dominating the conversation (and wasting everyone’s time). In addition, understanding how someone is coming to a conclusion is sometimes just as valuable, if not more, than the conclusion itself.
Use phrases like “you’re the expert.”
When talking to people about areas that they’re a specialist in, affirm that they are the person who has the required knowledge and expertise. This helps make it clear that your view isn’t any more correct than theirs.
When you say to someone, “I need your advice,” you can open the door wide to getting useful feedback from your direct reports. The statement both indicates openness to fresh ideas, as well as a clear request for that person’s personal viewpoint.
Admit what you’re unsure about or struggling with.
Try saying something like, “I’m pretty sure I know the direction I want to go, but I want to be sure I haven’t overlooked something important. Will you review this with me, and poke holes in my idea?” Or “I’m having a tough time figuring this out…” It leads to a very different dynamic. Even if you end up sticking to your original plan, people are more likely to feel respected for being asked to help vet the idea. You’ll get valuable input, regardless.
If you want your team to be making the best decisions, making sure your opinion isn’t driving all the decisions is important. You want people to be honest, to bring up what they think could be better, and to point out what they think is wrong. Try one of these 8 ways to help foster that openness in opinions. Your viewpoint may unintentionally sway others, as a leader — but it doesn’t have to.
P.S.: If you did indeed enjoy this piece, please feel free to share + give it ❤️ so others can find it too. Thanks 😊 (And you can always say hi at @clairejlew.)
Here are a few of my favorite leadership tips from CEOs, founders and executives featured recently in our Heartbeat interviews.
Every two weeks, I ask one question to a founder, CEO, or business owner I respect and share it on The Heartbeat ❤️, our bi-weekly newsletter on how to become a better leader. The question I always ask is, “What’s one thing you wish you’d learned earlier as a leader?” Here’s what some of our recent interviewees had to say…
Leaders don’t need to know it all.
Rob Walling is the co-founder of Drip, an email marketing automation software company that we in fact use a Know Your Company. What does Rob wish he’d learned sooner? That it’s okay for leaders to ask questions. He says:
“I wish that I had learned that I didn’t need all the answers as a leader. [I hire] people that are better than I am at something, and then when a problem comes up I can look around the room and say, ‘I don’t know. What do you think?’” — Rob Walling, co-founder of Drip
Aynn Collins is the Director of Talent Strategy at MailChimp, the world’s largest marketing automation platform with more than 900 employees. Aynn’s advice to her younger self is to understand that failure is part of growing as a leader.
“Embracing failure and understanding how you learn and grow from those failures is what I would tell people to learn early in their career. They can own failures, talk about them, debrief with your team on…and not try to just make everything shiny and pretty. Because we know business and leadership is not always perfect, and shiny and pretty.” — Aynn Collins, Director of Talent Strategy at Mailchimp
Forget the org chart.
Dan Mall is the founder of SuperFriendly (a design collaborative that’s worked with clients such as Apple, Time Magazine and ESPN) and CEO of SuperBooked (a software application that helps people find creative work). For Dan, he wishes he’d known that an organizational chart isn’t the end-all, be-all of business.
“The leaders aren’t the ones at the top. They should be the ones at the bottom. They should be the one supporting everyone else…They need to be able to see everything. They need to be able to support people. So, I wish I would have learned the idea of servant leadership, which is becoming more and more popular now.” — Dan Mall, founder of SuperFriendly and CEO of SuperBooked
P.S.: If you did indeed enjoy this piece, please feel free to share + give it ❤️ so others can find it too. Thanks 😊 (And you can always say hi at @clairejlew.)
New to the whole “manager” thing? Get your feet wet by checking out these 11 most-recommended leadership books.
Congratulations on your role as a new manager! You’re likely feeling 80% excited… and 20% terrified. That’s completely normal 🙂 Becoming a first-time manager is intimidating. You’re about to start flexing skills you might never have had to use before.
Folks who were once your peers are now reporting to you. You’re now included in more high-level leadership meetings. Your entire focus in what you do has shifted, too: Your ultimate responsibility is no longer to just get your own work done. It’s to ensure the success of your team’s work.
So, how do you start getting into the mindset of a good manager?
I asked almost 1,000 leaders on The Watercooler, our online community for managers, what helped them transition into their first managerial role and the majority of them said reading has helped guide them into the leader they are today. Here are the top 11 must-read books that have helped them become better managers and leaders for their teams:
Unintuitive Things I’ve Learned about Management: Part 1 and Part 2, by Julie Zhuo
Big caveat here, though: Becoming a good leader requires much more than just reading books. Much of what you’ll learn is through experience: Trial and error, talking to your own team, and talking to other leaders who’ve been in your shoes before. Books are merely a primer to give you a foundation for what it takes to be a good manager. These 11 books are a good start.
Do you have any books missing from this list that helped you transition into a managerial role? I would love to add it to our must-read list. Let me know in the comments or on Twitter at @clairejlew.
P.S.: If you did indeed enjoy this piece, please feel free to share + give it ❤️ so others can find it too. Thanks 😊 (And you can always say hi at @clairejlew.)
Why being nice as a leader backfires — and what to do instead.
Leaders, stop being so nice all the time.
I don’t mean to sound like an asshole. But when it comes to leadership, it’s true: Prioritizing “being nice” keeps us from being good leaders.
Now I’m not advocating for us to be mean. Disrespectful or dismissive leaders help no one. Rather, I’m calling for us as leaders to loosen our grip on “being nice.” To stop wanting our team to like us all the time. To let go of the expectation that every single interaction with our team should feel good.
Truth is, our team isn’t going to like us all the time. Our team isn’t going to feel good all the time. And trying to be nice to everyone all the time isn’t going to change that. Nor is it actually helpful for your team.
When we’re preoccupied with seeming popular instead of fair, when we optimize for pleasant conversations instead of honest ones — we hurt our teams.
I was reminded of this most recently while I was reading The Watercooler, our online community with almost 1,000 leaders. One manager revealed he was facing this exact dilemma. He was seen as “The Nice Guy” in his company, always complementary, never critical. As a result, he was struggling how to start giving his team difficult feedback — and his team was floundering.
He’s not the only one.
Have you ever found yourself in one of these situations?
You avoided giving tough feedback to a coworker… and now the person has made even bigger mistakes than you previously imagined.
You didn’t tell someone that you disagreed with them… and now you have to figure out how to course-correct without blindsiding the person.
You postponed firing someone… and now have to do damage control for the low morale they infused throughout the team.
You said something was “great!” even though it actually wasn’t… and now you have to fix the level of quality for what was produced.
Many of us focus on “being nice” as a leader more than we should. And we pay a price for it.
Hiten Shah, founder of Kissmetrics and Crazy Egg, emphasized this point to me, in a recent interview. He warned that when you’re concerned with being nice all the time, “there’s a level of toxic culture that develops that’s hard to see, especially on a remote team.”
Prioritizing “nice” as a leader is an easy trap to fall into. Being nice fits into our desire for belonging and companionship as humans. We’re social creatures. We want to be liked. Inherently, there is nothing wrong with that.
But “being nice” becomes problematic when it becomes your rudder as a leader. It leads you astray. You lose sight of your purpose as a leader: To help your team accomplish a specific mission. Your barometer for success as a leader morphs from “Are we accomplishing our mission?” into “What does the team thinks of me?”
Over time, “being nice” becomes your crutch. It’s a convenient rationalization to avoid hard decisions, uncomfortable conversations, and controversial actions. It’s easier to “be nice” than it is to have tell someone to their face that they’re rubbing a client or colleague the wrong way.
Ultimately, being nice as a leader is selfish. It doesn’t serve the team. It serves your ego. The team is looking to you to help them achieve a goal. And instead, you’re looking to have your decisions, actions, and yourself perceived as positive by them.
A leader is the only person’s whose sole job is help a team achieve the outcome they want to achieve. When you care about “being nice,” you’re essentially saying, “The needs of my team as a whole don’t matter as much as their perception of me as an individual.”
Instead of seeking to be nice, we should seek to be honest, rigorous, and consistent.
Or even better, we can seek to be nice and honest, nice and rigorous, nice and consistent. One of my favorite books, Crucial Conversations, discusses how being nice and being honest are not mutually exclusive. You can be both. The best leaders embrace this duality.
Let’s just stop being so damn focused on being only nice.
P.S.: If you did indeed enjoy this piece, please feel free to share + give it ❤️ so others can find it too. Thanks 😊 (And you can always say hi at @clairejlew.)
What makes a good leader? Look at how you spend your time.
Time is the one constant we are all given. No one gets more or less of it than anyone else. As leaders, it’s how we spend our time — what we choose to prioritize, and what we choose not to do at all — that reveals what’s important to us, and determines our team’s outcomes. If we want to figure out how to be an effective leader in the workplace, we must start with examining how we spend our time.
As a CEO myself, I’ve personally wrestled with this. I’ve had weeks where I’ve had fires to put out, meetings to show up to, business development calls to make, interviews to hold… Before I know it, the week is over, and I’m looking back at it thinking, “What the hell just happened? Where did my week go? Is that really where I wanted to spend my time?”
As a result, I decided to pose this question, “What’s the best use of a leader’s time?” to our online leadership community, The Watercooler, with almost 1,000 leaders from all over the world. The answers were remarkably consistent. Based on Watercooler members’ responses, there seemed to be three areas that leaders should focus their time on…
Recruiting + Hiring
Your team’s success hinges on the people you choose to hire. Surely, this is an obvious statement — and yet we forget about our role as a leader to drive these efforts. As a leader, you should be thinking strategically about who you want to contribute to your culture and help get your company to where you want it to be. What kinds of non-negotiable values must they have? What diversity of ideas and backgrounds should they have? Then, you should actively work to attract and recruit those folks to your organization. How are you showing that you run a company worth working for (e.g., your company’s marketing, you speaking at conferences, etc.)? How often do you meet new people outside your network, to connect and passively recruit folks who may be great to work with in the future?
As a leader, you also set the standard for what matters when hiring: the skillset, the values, the experience. You say when it’s time to hire — and when it’s not. Naturally, depending on the size of your company, you may have a hiring team helping you out with this. But regardless, your voice in this process as the leader is essential. It’s too important for you not to be spending your time on it.
Considering your team’s long-term strategy, vision, and culture
Admittedly, focusing on the long-term view of the company is hard to do. Especially, when there seems to be so many immediate needs for the company to take care of…and, when we’re not so sure about the long-term view of things, ourselves! But thinking about the long-term strategy, vision, and culture of the company is critical because, well, no one else is doing it. Literally, it is no one else’s job in the company to be thinking about the long-term, be it six months, a year or two out, or ten years down the road — other than you, as the leader. In particular, considering the long-term vision is paramount, because a company’s vision is where the most fundamental source of motivation for your team is derived. If you’re not spending time designing and adjusting a long-term vision — a picture of a better place — people won’t be motivated to do work to help get the company there.
Communicating the direction to everybody all the time
Communication is the easiest thing for leaders not to do. After all, it’s quite a repeated, draining slog to keep saying the same thing over and over again. Despite this, many members of the Watercooler emphasized that you cannot communicate enough as a leader. Why? You can’t expect your team to know anything unless you communicate it. And, depending on the size of the organization, it usually takes some time for a message to sink in or a for a decision to be thoroughly explained. Knowing what’s going on and where a company is headed is how people do their best work. People can’t perform well without the context and information to do so. If you’re not constantly communicating what people should know, the context isn’t there and people can’t do their best job.
These three areas are what our Watercooler members said are the best use of a leader’s time. But how about for you? Do you find yourself spending time in these areas as a leader… or not?
As the founder + CEO of a company serving over 75 million people worldwide, Kathryn shares her biggest leadership lessons around trusting your gut and decision-making.
Every two weeks as part of The Heartbeat ❤️, I asks one question to a founder, CEO, or business owner I respect. This week, I interviewed Kathryn Minshew, Founder + CEO of The Muse. Watch & read what she has to say here…
Claire: Hey, everyone. I’m Claire Lew and I’m the CEO of Know Your Company. Today I am absolutely thrilled to have with me someone super special. I have Kathryn Minshew, who’s the co-founder and CEO of The Muse. You’ve probably heard of The Muse if you’ve ever been on a job search because they actually serve I believe over 75 million people in helping them navigate their careers, which is pretty phenomenal. Kathryn is someone who I’ve definitely looked up to in the industry. Just been a big admirer of your work. I know you recently published a book called I think it’s “The New Ways of Work.”
Claire: Excuse me, “New Rules of Work.” Just so excited to be able to ask you this one question about leadership.
Kathryn: Wonderful. Thank you so much for having me. I’m really excited we’re able to do this too.
Claire: Cool. Well, all right, Kathryn, here’s the question, it’s what’s something you wish you would have learned earlier as a leader?
I wish I would have learned to trust my instincts. I started The Muse when I was 25, seven years ago. Because I was so young, I was conscious of my inexperience, I sometimes I let other people overly influence the decisions that I made because it felt like I was so new to starting a business.
Kathryn: As I look back, my instincts actually served me pretty well. Sometimes I trusted them and it was absolutely the right decisions. There were other times when I overruled them and went against my better my better judgment and I regretted it. I think on top of just the trusting your instincts, obviously I’m not the first person to give that advice, but I also think when you’re a leader and particularly when you’re the CEO of a company, a startup, at the end of the day, everything that goes wrong or that doesn’t work out, like you bear the ultimate responsibility for the success or failure of initiatives, of the business, et cetera.
I think when things don’t go wrong but you made that decision at your call, it’s hard, but you can live with that because you made the wrong call. We all make the wrong call. When something happens, if there’s a failure and you knew better, you overruled your own instinct, you let someone else make a decision that really you felt deep in your gut probably should have gone differently, I think those for me are the hardest mistakes to live with. Ultimately, I would rather trust my instincts, make the calls, and deal with the results good and bad.
Claire: Absolutely. I’m over here sort of nodding my head laughing because I’m like, “I can totally relate,” having started running Know Your Company when I was 24. I don’t think there was a bigger case of imposter syndrome. When that happens, I think there’s something to be said about being young, whether it’s being a woman or whatever it is, or a feeling as though you need to take in other people’s opinions for whatever reasons that there are. I think in a world where as a CEO you are inundated with advice all the time, there’s no shortage of articles or hey, video interviews about advice, it can be very easy to sort of get pushed one way or another.
For folks who are watching this, would you say that there’s a spectrum of decisions in which they should sort of rely on that instinct? I mean in what situation do you feel like that’s the way to go? For example, do you feel like it’s when the decision is really big, is a really tough one to make, do you feel like when … What if it’s not your expertise, right? Just to push back. Someone might be watching this and going, “Well, Kathryn, what if it’s not within your expertise? Do you still go with your gut?”
I mean for you, what have you learned? Was there a specific situation or how do you sort of process how you make those decisions? Threw a few questions there at you.
Kathryn: Yes. First of all, I think getting better at making decisions, particularly small decisions, is something that I am actively working at right now.
Because as you build a company, especially if you’re trying to do something that no one’s ever done before, you are calling countless problems, you’re making countless decisions, and that can be exhausting. First of all, I’ve tried to get better at dividing decisions into two categories.
There are smaller decisions. This also includes maybe big decisions, but ones that are reversible. If you choose course A but you realize pretty quickly it’s not right, can you just choose course B instead.
These decisions I try and make quickly. I often try and delegate. I think that you can get bogged down as a leader in over analyzing these decisions, which I have definitely been guilty of, but I’m working to just ensure like, “Okay. How big is this decision? What are the impacts of getting it wrong? Can we change our minds?” If the answer to those three is sort of a green light, then try to make it quickly and move on. The other types of decisions I think are the sort of bigger, thornier decisions. To me, I think it depends.
Is this a guiding light or a principle’s decision or is this a sort of structural or tactics decision? I’ll give you an example. This is a metaphor I’ve been thinking about recently. I don’t think it’s a particularly good one, but it’s the best I’ve got, which is in the early days of starting a business, you’re almost an explorer. Think sort of Lewis and Clark. You’re charting the wilderness and you have an idea. You have a small team, but ultimately you’re deciding where to go. At some point, you find sort of your product market fit, your sweet spot, and then you start building a town.
You can be an explorer with great instincts and some level of training or very little training to some extent. But if you’re building a town, you may want to actually bring in like plumbers and electricians and people that have deep technical expertise.
For things like that, I would empower those people. Let them make decisions. Let them really lean into their skillsets because you hired them for a reason, right? It’s not necessarily your job to know how to be a better electrician than the person you’ve hired to help build your town.
Kathryn: But when it comes to sort of principles, the core ethics, the values, the big picture direction questions of how that town comes to be, I think is where you can’t delegate because I think those are the most weighty, and they’re also the ones that are hardest to undo.
People talk a lot about building culture, but changing culture is very hard. I think understanding where decision falls and how sort of irreversible it is is a really important tactic for deciding whether and how to delegate or when you need to just make and own that decision.
In fairness, I get a lot of advice.
When I was earlier in my leadership journey, people often mistook my interest in their advice for, “Oh, well, don’t just do what I tell you to.” I’m like, “Don’t worry I won’t.” I really appreciate and enjoy hearing different perspectives, and it’s an ingredient to my own thinking that ultimately produces a sense of what the right answer is likely to be.
Claire: Absolutely. I do like the explorer analogy because I think what we often forget as CEOs is as an explorer, your role is to say, “Hey, here’s the kind of town you want to be. Here are the things we want to stand for. Here are the kinds of people we want to attract,” et cetera. You could take this metaphor in a lot of ways. I think your point about the tactical decisions to getting to that point, you might not always need to be relying on your instincts and you can delegate those decisions, et cetera, and rely on expertise to carry them out, but there’s something to be said for making a stand.
It makes me think of this quote, what you’re talking about, is “What hill do you want to die on?” For the decisions that are irreversible, those are the ones you want to make sure are with your core. One thing that you alluded to is this idea of taking in people’s perspectives as an ingredient to building out your own perspective. What advice do you have for entrepreneurs, leaders, managers who are trying to enrich their perspective, who are trying to develop a better gut instinct? Is there a way to do that?
Kathryn: I think there is.
Firstly, I try and speak to at least three different people for any big decision or any area where it’s newer to me and I’m learning. In particular, it’s not just any three people.
One of those people, I like to find someone who is very similar to myself. Let’s say it’s a big fundraising decision or some sort of CEO strategic decision, I will specifically look for a woman CEO who potentially has had somewhat of a similar years of experience before starting a business. It doesn’t have to be spot on.
Kathryn: This is helpful because sometimes people … When I was fundraising for The Muse in the early days, there were not a lot of women fundraising. I got a lot of really well-intentioned advice from them and a lot of it just didn’t work. The first time I really started talking to other women who had raised, I was like, “Oh, their experience is a little more relevant in this because there’s a factor about fundraising that makes a difference,” particularly in 2011–2012. I hope that’s changing. TBD on whether it is fast enough.
Claire: I’m with you.
Kathryn: But anyway, I would look for someone whose experience was similar. On the flip side, I also like to make sure that one of those people is someone whose experience is very different and whose perspective is likely to be very different. I have an old friend, someone that I love talking to about business issues, who could not be more different in a lot of his leadership styles. He’s a very aggressive leader. I mean he’s known for in sort of the entrepreneurship ecosystem for big, bold, offensive, controversial bets, and yet he’s a phenomenal resource because I have a little bit more of a collaborative style.
And yet sometimes I think that this is the sort of playing field available options and he’s like, “Yeah. Also, you could over there or over there,” and it widens my understanding of what decisions are possible and what factors someone totally unlike me would consider. I think that’s a really useful element of developing your gut as well is spending time and developing deep relationships with people who might have a totally different approach or perspective. Then the third person is kind of just someone I think might have expertise or relevant something to share.
It’s less particularly important, but I think getting both the sort of near term perspective and the far away.
Then usually if it’s a big decision, I try and sleep on it at least one night because sometimes it’s like it’s putting all the ingredients in the sort of cocktail shaker of your brain. You shake it up. You let it settle and then in a day or two it becomes clear what you want to do.
Claire: Absolutely. No, I think that’s invaluable advice and something that I’m going to be taking away and thinking about how can you sort of set out those differences and opinions to be able to form your own and then give yourself the time to let it percolate and have whatever pours out of that cocktail shaker to be really good instinct.
Kathryn: I’ll add one other thing, which I’ve been trying to do more recently, which is vision retrospective.
Kathryn: I think to the question about developing a gut, it’s not only important to practice making better decisions, but also after the decision has been made, whether it’s a couple days, a week, three months, looking back and thinking, “Why did I make that decision the way that I did? What were the factors that influenced me? Am I happy with how it turned out? If not, what additional information or insight?”
I think you have to be nice to yourself. Like you’re not going to make all the decisions well and sometimes you’re like, “You know, it would have been great to know that, but I had no idea.”
That’s fine, but sometimes you can realize patterns like, “Oh, I was too loyal to this idea or this principle. I was blind to this thing. If I just asked this person’s perspective or if I have done this type of diligence, I would have uncovered the information that might have changed my mind.” That’s incredibly helpful because you learn those skills and they translate to better decisions in the future.
Claire: That’s invaluable, invaluable advice. I think everyone who’s watching this is going to be thinking, “All right. How am I going to be developing my gut instinct better and leaning on that maybe a little bit more in the bigger decisions?” Well, Kathryn, thank you so much again. It’s been an honor to be able to have this conversation. I know folks who are watching have learned a lot.
Kathryn: Well, thank you so much for having me. I really enjoyed it, and I look forward to hopefully doing this again some time.