The most counterintuitive leadership tip? Leaders, stop doing what you’re good at.

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.

Peldi conceded:

“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.)

Big news: Know Your Company is now Know Your Team 🎉

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).

You can check out the new Know Your Team here.

Here’s why we decided to make this change.

Quick background, first.

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.

“What’s wrong?”

I remember thinking this around this same time, last year, in December.

As I reflected on 2017, I noticed three things:

  1. 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.)
  2. 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.
  3. 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 result is Know Your Team.

Introducing Know Your Team: The new product.

To answer this question, “How do you become a better leader?” we re-imagined our product.

We pulled together research from working with 15,000+ people over the past four years, and discovered that the best leaders do three things exceptionally well:

  • Trust: If you don’t build rapport as a leader, nothing moves forward.
  • Honesty: If you don’t speak the truth to your team, problems fester.
  • Context: If you don’t get everyone on the same page, confusion sets in.

Because of this, we designed Know Your Team to help a leader develop these three skills of Trust, Honesty, and Context.

You can read more about our methodology here.

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.

You can read more about our resources here.

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”….

Know Your Team is for you.

I’d be honored if you gave Know Your Team a shot.

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 claire@knowyourteam.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.)

You have a micromanaging boss. What can you do?

There are 5 reasons your boss is micromanaging you. Here’s how to manage up, and around them.

I’ve heard the phrase, “I have a micromanaging boss,” more times than I can remember.

I heard it again, just last week. This person asked me, “What do I do? Is there anything I can say to a micromanager? How do I manage up?”

Here’s what I recommended to him…

First, identify the reason. (Yes, there is a reason.)

People do things for a reason. No one is a micromanager because they want to be a micromanager. No one hears that word and goes “Oh yeah, I want to be that.” In fact, for most leaders, to learn that we’ve become a micromanager is a sour, disheartening realization that sloshes around in the pit of our stomach.

So, if your boss is micromanaging you, ask yourself, “What might be causing them to act this way?”

Typically, your boss is micromanaging you for one (or several) of 5 reasons:

Reason #1: Worry

Your boss is worried about the outcome of the work and doesn’t think you’ll get it done.

Reason #2: Fear

Your boss’s butt is on the line, and they can’t have you make them look bad.

Reason #3: It’s All They Know

Your boss has only always had a micromanaging boss (or this is their first-time being a manager) — so they don’t know any other way to manage.

Reason #4: Past Experience

Your boss has been burned before by a prior employee who slacked off and didn’t produce results — and so this is their way of compensating.

Reason #5: You 🙂

You’re doing something (or not doing something) that is causing them to overstep and keep a close eye on things.

I want to be clear: These reasons do not excuse your boss’s behavior. Rather, they illuminate that micromanagement is not random, without reason, or out of malice (usually!). When you reflect on what’s driving your boss to be a micromanager, you can better calibrate how to work with them.

Also note that people are complex, and motivations are not neatly categorizable. The reason your boss is micromanaging might not perfectly fit into one (or any) of these reasons I listed above. However, having a hunch —a probable reason for why your boss is a micromanager — gives you wind in the sails to help change their direction.

Second, defuse the reason.

Once you’ve considered the reason behind why your boss might be micromanaging you, now you can take action. You can ask questions and take steps that loosens whatever is causing them to grip so tightly onto you and your work.

Based on what the reason is, here’s what you can do:

#1: If your boss is worried about the outcome of the work… Have a conversation about what success looks like.

Yes, this means defining what metrics or deliverables should be achieved. But equally critical are specific examples of what quality work looks like. “Quality work” is subjective, and as a result, what a leader is most concerned about. To get on the same page about success and quality of work, you can ask your boss: “What’s a previous project I did that measured up to the quality of work you’re looking for? When have I fallen short? What do you think is the best executed project you think the company or team has ever done? Why?”

#2: If your boss’s butt is on the line… Make it clear that you understand the stakes.

Your boss is likely more stressed than usual, and you don’t want that stress to be off-loaded onto you. Ask, “What can I do to relieve any pressure on your end? Is there any reporting you’d like me to do that would help make things more visible or consistent? Is there a crucial stakeholder I’m unaware about who I should consider? Is there a timeline I absolutely have to meet that we haven’t yet discussed?” Show that you’re in this critical situation together, and you’re willing to do your part.

#3: If your boss doesn’t know any other way to manage… Suggest alternatives.

This sounds intimidating, surely, but you can have this conversation in a non-threatening way. How? In your next one-on-one meeting, offer up “working styles” as a potential topic. Then when you sit down to chat, say, “I’d love to talk about our working styles and preferences, and how we each work best. How would you describe your working style and how you work best?” Then after thoroughly listening, ask, “Do you mind if I share mine?” You can also be straightforward and describe what changes in behavior you’d like to see. For example: “Ideally, here are things I’d like to see different. What can I do so you feel comfortable with those changes?”

#4: If your boss is acting based on a previous experience… Draw contrast to how you and this situation is different.

This is probably the trickiest of situations to really defuse well. Ask your boss, “What’s the best work experience you’ve had? The worst?” Then share yours. This will prompt a conversation about expectations and preferences — and what’s influenced those expectations and preferences. It also gives you a chance to learn how to adjust your own actions. You’ll learn that oh, your boss really didn’t like it when their former team member didn’t communicate decisions — and now you know to make decisions extra clear.

#5: If your behavior is causing them to micromanage you… Well, start doing things differently 🙂

This may be hard to admit, but sometimes our own behavior invites someone to micromanage us. We recently conducted a survey of 355 people and learned that the #1 piece of information that managers want to know is the progress that’s being made on a project. So it could be that you might not be sharing enough of the progress you’re making day-to-day or week-to-week. You can get to the bottom of this, by asking your boss: “How can I give you more visibility into my work or decision-making? What part of the job do you think I’m most shaky at?”


As they say, habits die hard. Very hard. You may not be able to kill their micromanaging tendencies completely, nor overnight.

However, you will be able to create some space. It might not be a lot, but it’ll be more than before. Over time, as you build more rapport and history with your boss, that space will grow.

You don’t have to silently absorb the incessant Slack pings or random taps on the shoulder asking, “Have you done this yet?” That’s not the only way to work.

You can have a healthy, productive relationship with your boss. You can help your boss not be a micromanager. Start here.


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.)

Watch our lessons for leaders: The Heartbeat Interview ❤️ with Desiree Vargas Wrigley, Founder + CEO of Pearachute

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: Absolutely.

Desiree: Yeah.

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.

Claire: Absolutely.

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.

Claire: Absolutely.

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.)

Enjoy this interview with Desiree? Check out all our Heartbeat interviews with leaders…

Managing disagreements: How to handle diverging points-of-view with your boss

Six leadership tips on what to do when you disagree with your boss (or another senior leader at the company)

It’s inevitable: You’re going to disagree with your boss. No two people on the planet agree with each other on everything, 100% of the time.

That’s a terrible idea,” you think to yourself, after listening to your boss share a decision she’s come to. “She strongly needs to consider an alternate option.

Yet, managing disagreements at work is tricky — made only trickier if the person you disagree with is your boss. Of all people, you don’t want that person to get defensive or misinterpret your disagreement as an attack. You want whatever thing you’re arguing for to be considered, and hopefully enacted.

The key is to share your opposing point-of-view respectfully — and effectively — so the outcome you’re looking has a higher likelihood of happening.

So, how do you do that? How do you disagree productively with your boss, or another senior leader on the team?

In The Watercooler, our online community for leaders, managers from all over the world suggested taking these five steps when you and your boss disagree:

Peel back the layers of “why”

Start with the assumption that people are reasonable and make rational decisions. Then, ask yourself, “Given that assumption, what would have to be true for them in order to cause them to make the decisions they did?” Are there other priorities they’re managing that you’re not aware of? Are there other stakeholders who have an interest in the outcome that you aren’t considering? Rigorously peel back the layers of their rationale to figure out what those underlying reasons are.

Emphasize the common destination, not the divergent paths.

You’re both on the same team. Remind them of this. While trying to explain your own view, extrapolate the assumptions, beliefs, and values you both have in common. For example, you both care about the team’s success, you both value speed over perfection, you both see X priority to be most critical. What you most-likely differ on is the approach: The strategy to execute, the timeline, the resources, etc. Highlighting the points of agreement re-centers the conversation: While the roads you mapped out are different, you both want to end up in the same place.

Show, don’t just tell.

Evidence is compelling. How can you show — and not just tell — that your recommendation or idea should be taken up? Is there anything that you can work on that directly contributes to the company primary goals and illustrates your point? For instance, one Watercooler member discussed how she started a project without many resources, and eventually recruited people who shared similar views to build her case. It worked — her boss implemented the idea.

Consider: What is the one thing you can fix right now?

When we see a lot of fires, our urge is often to build a brand new fire station. However, in reality, all we might need is to find the nearest fire hydrant to hook up to. If many things are broken and you think you know a better way, avoid the desire to solve everything at once. Focus on just one thing that can be a visible quick win. Connect to the fire hydrant, first. Then, you can better make the argument to build the fire station for the neighborhood.

Ask yourself, “Do we really disagree on core beliefs?”

Sometimes, the gap between the opinions of you and your boss isn’t just a crack — it’s a chasm. It’s much wider and deeper than you initially thought. This is important to pay attention to. If you disagree with a coworker on core beliefs, then the change will be an uphill battle. You’ll want to seriously consider if it’s worth the trouble. And, if it’s not, perhaps it’s not the right company for you to be at. Core principles that you want to be aligned on include: your beliefs around company culture, how managers see and respect employees, the ratio of autonomy vs. control, iteration process, team structure and long-term goals.

Look for an outside advisor or mentor.

A third party can bring objectivity to a disagreement. One Watercooler member recommended how this option is helpful when the conversation becomes circular and isn’t progressing in a positive direction. Having someone fresh can not only be useful to moderate the discussion, but provide new insights that you both may not have considered. However, when doing this, it’s important to set clear expectations, and decide on how to handle the outcome of the discussion. You don’t want the outcome to devolve into office gossip because you “brought someone from the outside in to help.”


These tips have helped orient my thinking around approaching differences of opinion within my own team. I hope they help you too.

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.)

8 ways to avoid your opinion swaying your team too much as “The Boss”

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.

Ask for advice.

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.)

From The Heart(beat) ❤️: Leadership lessons I wished I’d learned earlier

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

Embrace failure.

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.)

11 must-read books for new managers

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:

  1. Managing Oneself, by Peter Drucker
  2. Mindset: Changing The Way You Think To Fulfill Your Potential, by Carol Dweck
  3. High Output Management, by Andrew Grove
  4. Drive, by Daniel H. Pink
  5. Radical Candor, by Kim Scott
  6. Peopleware, by Tom DeMarco
  7. The Manager’s Path, by Camille Fournier
  8. How to Win Friends and Influence People by Dale Carnegie
  9. The New One Minute Manager, by Ken Blanchar
  10. Google’s Re:Work
  11. 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.)

How to prepare for a one-on-one meeting as a manager

The 4 things you should do to make the most out of your next one-on-one meeting.

You’re not prepared. Or at least that’s what employees think when it comes to one-on-one meetings. In a recent survey we conducted of 125 managers and 45 employees, we found 35% of employees believe their manager is only “somewhat prepared” — and 15% of employees think their manager is “not prepared” or “not prepared at all.”

That’s almost half of employees thinking that their managers aren’t as prepared for one-on-one meetings as they could be.

Managers seem to agree. Sixteen percent of managers we surveyed said their biggest frustration with one-on-one meetings is they’re never sure how to prepare or what to ask.

Fortunately, preparing for a one-on-one meeting is neither hard nor time-consuming. Before your next one-on-one, here are the four things you can do (and each takes 10 minutes or less):

#1: Get up-to-speed.

You waste time when you’re not up-to-speed. When you walk into a one-on-one meeting not knowing what the person has been working on for the past month, you squander 10–15 minutes to get caught up on old information. That’s 10–15 minutes that could’ve been spent discovering and discussing new information. Instead, spend a few minutes getting up to speed before the meeting rather than during it. Specifically:

  • Review status updates ahead of time. You’ll save time by not rehashing “What’s the latest on X?” And you’ll better orient yourself on what the focus of the one-on-one meeting should be.
  • Revisit notes from the last one-on-one meeting. You’ll realize there’s an important topic you need to circle back on, or an action item you need to complete. These notes can also help inform the questions you want to ask for this upcoming meeting.

#2: Ask your direct report to create an agenda.

Ask the employee to create an agenda ahead of time with what might be on her mind. You can say or write something like: “Mind kicking-off the first draft of the agenda for our one-on-one meeting? I want to focus on what you want to talk about, first. And then I’m happy to take a pass and add anything else to it.”

By letting her take the lead and initiate the agenda, you demonstrate to her that it’s her priorities that you want to address first. She’s in the driver’s seat, not you.

Then, of course, you’ll want to review the agenda before the meeting, and offer any additions for what you want to talk about.

#3: Clearly define for yourself: What do you want to know?

Yes, you’re asking the employee to write the agenda — but you also want to think for yourself what you want to know. Is there a concern you have about this person’s ability to work well with others? Are you wondering if they feel challenged enough by the work itself? If nothing specific comes to mind, consider these four areas of focus for a one-on-one meeting:

  • Concerns and issues. What potential problems might be bubbling up that you don’t know about, but should?
  • Feedback about work performance. What does your direct report need to be doing differently? How can you improve your own management style?
  • Career direction. How can you help support this person progress toward their career goals? Are you both on the same page for what progress looks like?
  • Personal connection. What outside of work in their life is going on that you want to know more about?

Reflect on these four areas to generate ideas for questions you should be asking, or topics you think should be covered during the one-on-one meeting.

I’d recommend picking one or two of these focus areas, and then brainstorming at least 3–7 questions for each area. You may not ask all the questions (or any!), but they are helpful to have in your back pocket should the conversation lag or veer off-topic.

To help you get started, here are some examples for one-on-one meeting questions in each focus area:

Questions that uncover concerns / issues…

  • “When have you felt most motivated about the work you’ve been doing?”
  • “Is anything holding you back from doing the best work you can do right now?”

Questions that elicit feedback about work performance…

  • “Would you like more or less feedback on your work? Why/why not?”
  • “What’s a recent situation you wish you handled differently? What would you change?”

Questions that help provide career direction…

  • “What’s one thing we could do today to help you with your long term goals?”
  • “Is there an area outside your current role where you feel you could be contributing?”

Questions that foster a sense of personal connection…

  • “Been anywhere recently for the first time?”
  • “What have you been excited about lately?”

I always try to ask at least one question focused on personal connection, and use that question to open up the meeting. This helps break the ice at the beginning of your meeting, and builds rapport with your employee. Without this sense of rapport, your employee won’t feel comfortable divulging anything meaningful — nor will she find the conversation much fun.

For more ideas for questions to ask during a one-on-one meeting, you can visit here.

#4: Calibrate your mindset.

Take a minute to remind yourself: This meeting is not like other meetings. You aren’t running it. Your primary job is to absorb the information being shared with you, poke holes to figure out how an employee is actually feeling, let things marinate, and then figure out when you need to do. You shouldn’t be talking. You should be listening and scanning for the truth.

These four steps takes 15 minutes, maybe 30 minutes at most, to complete in total. That’s 15 minutes — 30 minutes of preparation that ensures your hour-long one-on-one meeting is not an hour wasted. Invest in preparing for your one-on-one to get the most out of this time together.


 

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.)

The leadership mistake you’re likely making? Being nice.

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.)