The Anti-Mentor: How a bad boss influences our leadership style

Having a bad boss shapes our leadership style more than we realize – for better and for worse.

Who’s the worst boss you ever had? Your answer to this question matters. It influences your leadership style in more ways than you think.

For myself, I can answer that question, “Who’s the worst boss you ever had?” almost immediately.

He’s someone I’d worked for coming out of college, after I’d started my first company. You’ve likely met a variant of him before: One of those leaders who looks you steadily in the eye, and with complete conviction and charisma, articulates a beautiful vision of the future the two of you could create together.

Back then, I nodded my head, convinced.

He then turned around… and he didn’t follow through on what he’d promised. He played favorites. His mood temperamental, at best. Ask a question, make a suggestion, offer a new idea – and he appeared irritated that you dared to speak up.

He wasn’t a bad person (he was a lovely person, in fact.) But having him as a boss showed me exactly the kind of boss I didn’t want to become. I took his template of leadership and whittled my own – a relief carving in opposition to his.

This worst boss of mine is what some would call an “anti-mentor.” Far from the person who you aspire to be like, they are who you avoid emulating, at all costs.

To this day, my “anti-mentor” influences my actions as a leader. For instance, I go to great lengths to be immaculate with my word. I’ve witnessed firsthand how destructive it is to say one thing and do another, as a leader. I strive to be unabashedly fair and consistent, because I’ve noticed how much instability and low motivation an unpredictable leader injects in a team. And, to this day, I’m highly conscious of creating an environment that encourages people to share divergent opinions. I’d seen what happens when the leader expects honest feedback to come to him – he never hears it.

When I reflect on my own leadership style, I realize that the bad bosses I’ve had influenced me more than any good boss I’ve had. Seeing what you don’t want to be like is more powerful than what you do want to be. The push is greater than the pull.

Psychologist Frank Oser calls this “negative morality” – learning from mistakes is markedly more powerful than learning from successes. However, you don’t necessarily need to experience the mistakes yourself to feel its impact. In the book The Moral Advantage, William Damon explains how the people he interviewed often cited the “anti-mentor” for shaping their values more than any other positive example or role model.

In this sense, an “anti-mentor” is a gift. My experience with my worst boss was a clarifying force. It helped me understand what I valued as a leader and as a person. Resistance shapes you. When know what you’re against, you more firmly know what you’re for.

At the same time, “anti-mentors” have unintended, adverse consequences when you model your leadership style in reaction to them. You can easily – and unknowingly – overcompensate. For example, my worst boss was never sensitive about extenuating life situations of his employees. If someone’s kid was sick, if something tough was going on in life, it was, “Well, that’s too bad. Can you get this done ASAP?” As a result, with my own team, I’m exceptionally generous about the time someone can take off. Sure, that’s good in the right doses… But I think in the past, I’ve been too liberal with it. There are people I’ve worked with who’ve taken advantage of my overly generous tendencies, and left our team worse off.

Most commonly, I talk to many leaders who have a problem being too nice because of their “anti-mentor.” Their former boss was as asshole and they are scarred by that experience. But inadvertently, now as a leader themselves, they lean the other way too far. They can’t bring up hard conversations with their staff. They have difficulty firing people who needed to have been let go months ago.

Whether or not you’re positively or negatively influenced by your “anti-mentor,” the critical thing is to realize that you are influenced by this person, to begin with.

Ask yourself: Who is the worst boss I’ve ever had? Then reflect. In what ways are you consciously or unconsciously reacting to your experience with this person? Are those reactions to this person – your “anti-mentor” – helping your team? Or, are they hurting?

Your worst boss is with you in more ways than you think.


The 3 most effective ways to build trust as a leader

Based on data from 597 people, the best ways to build trust as a leader aren’t what you think they are.

How do you build trust as a leader? The answer seems intuitive enough.

For many of us, we hold company off-sites and run team-building activities. Informal lunches, monthly social get-togethers, and one-on-one meetings are part of how we build trust at work.

We also thank our team publicly and give employee recognition for a job well done. And, we strive to be transparent with company information during all-team meetings.

These are among the most popular ways to build trust because they work… Right?

Wrong.

To my surprise, in our survey we ran this past fall with 597 managers and employees, these three ways to build trust were in fact viewed as the least effective by employees.

Specifically, these were the 3 least effective ways to build trust as a leader:

Company retreats + team-building activities.

Only 1% of managers and employees who responded to the survey said that this was the most effective way to build trust. This is fascinating, given the amount of money and energy many companies spend planning company off-sites and team-building activities.

Thanking your team and giving recognition.

Only 4% of people said that this was the most effective to build trust in a team. While this shouldn’t imply you should never thank your team, it goes to show there’s more to building trust than doling out compliments.

Being transparent with company info.

Only 10% of managers and employees stated that this was the most effective way to build trust in a team. No doubt that transparency is important in a company – if you want your team to be able to make the same decisions as you, they need access to the same information as you. But when it comes to building trust, perhaps it’s not as effective as we’d imagined it to be.

Now, just because these methods are not viewed as “most effective” for building trust at work doesn’t mean you should stop doing these things, all together. Rather, they may accomplish other worthy goals in the organization. (For example, being transparent with company info is helpful for alignment in a team.)

So what is most effective when it comes to building trust?

From our survey, here’s what 597 managers and employees said were the most effective ways to build trust:

#1: Show vulnerability as a leader.

Twenty-eight percent of people said that being vulnerable and admitting your shortcomings as a leader was the most effective way to build trust. For both employees and managers in the survey, they remarked how being vulnerable with your weaknesses and mistakes demonstrated empathy: The more empathetic someone was, the more likely they were to trust them. One person in the survey in particular remarked how their manager “needs to show more empathy,” and that “morally he is probably a good person but there are some times when it’s unclear if he actually has empathy due to challenges expressing it.”

#2: Communicate the intent behind your actions.

Twenty-six percent of people said making your intentions behind your actions clear was the most effective way to build trust. This makes sense, given that intent is such a primary part of the definition of trust, to begin with. Communicating the intent behind your actions means being open about why you’re saying something, and why decisions are made – including your decisions to not act on something. Be opaque about why you’re changing your mind, or fail to express why you’re giving feedback to someone and it can wreck havoc on your work relationship.

#3: Follow through on commitments.

Eighteen percent of employees expressed that simply following through on commitments was the most effective ways to build trust. This seems to be especially powerful given that we found that 48% of employees believed that the company has been all talk and no action on something lately – and 28% of employees said their manager has been all talk and no action. Similarly, 61% of managers believed that their direct reports had been all talk and no action on something lately.

In short, trust is not rapport. Trust is not team-building. It’s not about getting people to like you. And it’s not about getting people to just “feel good” about you or the company.

Trust is your intentions and your behavior. It’s making it clear why you’re doing something, being honest about it, and then following through with it.

You can hold as many company retreats as you’d like… But if you’re not vulnerable during those moments, your team won’t trust you.

You can be congratulatory with your team every week… But if you don’t follow through on your commitments, your words ring hollow.

You can share company financials far and wide… But if you don’t reveal your intentions about what you’ll do with that information, your team will be skeptical of you.

Align what you do with what you say. Your word and your action builds trust. Nothing else does.


PS: If you’re looking for a helpful system to build trust more authentically, you may want to check out Know Your Team – our software to help you become a better leader. In Know Your Team, we give you tools and resources specifically around building trust so you can put much of what I shared here directly into practice. Check it out here.

How transparent should you be as a leader?

Two things I’ve found helpful to consider when trying to decide what to be transparent about with my team – and what to keep to myself.

How transparent should you be as a leader?

This is a question many leaders struggle with — including myself. Do you share financials with the company? Or how about salary? How open should you be about why someone was fired?

From open-book management to making compensation public within the company, the concept of transparency in the workplace is more popular than ever.

Understandably (and rightfully) so. As a concept, transparency makes sense: If you want your team to behave the way that you would behave, they need access to the same information that you have. And, the more transparent you are, the more you’re likely to build trust within your team.

But what about the unintended consequences? Can transparency backfire? Do you inadvertently cause panic in a company when you reveal what the monthly burn rate is? Do you encourage resentment from more junior employees when you reveal how much senior employees in the company are making?

As a leader, how do you decide what to share with the rest of the team and what not to?

A few months ago, I spoke with the insightful Des Traynor, Co-founder of Intercom, on this topic. For Des, deciding how transparent he should be was one of the hardest lessons to learn as a leader. And as a CEO myself, I couldn’t agree more.

In our conversation, Des shared with me two things to consider when deciding how transparent you should be in your company:

Transparency requires context.

“The key thing people forget in transparency is it’s not about opening up the Google Drive and making sure that everyone can read everything,” says Des. “It’s about transparency of context as well.” Many of the CEOs who are a part of our leadership community in Know Your Team, The Watercooler, echo this sentiment as well. One CEO remarked how he had shared revenue numbers once, and “things had gone sideways with individuals who just don’t understand or appreciate all that goes into starting and operating a business.”

In other words, the negative reaction came from the lack of context about the revenue numbers. What that CEO wished he would’ve done was share more context. If you share revenue numbers without context of monthly spend, people start wondering, “Where’s all that money going?” So for example, at my company, we share revenue numbers, within the context of also our profit margin and expenses — so it’s understood how revenue supports our business as a whole, and not just “here’s the pile of money we’re making.”

Transparency is a spectrum.

Transparency isn’t all or nothing — things don’t have to be either completely open or completely a secret. Des emphasizes this, saying, “I think it’s worth having a critical threshold to decide what’s actually good for everyone to know, what’s not a secret but needs context, and what actually genuinely might be a secret because you don’t want everyone panicking about something.” Transparency is a spectrum, and if you indiscriminately just make everything 100 percent public, you could be wasting people’s time, confusing them, or causing them strife. Everyone has a capacity of information, and overloading folks with every detail of what’s happening in marketing, support, design, engineering — it can be too much. As a leader it’s important to ask yourself: In what cases is transparency appropriate and helpful, and in what other cases is it distracting or a burden? Are you being transparent, just for the sake of being transparent, or are you truly trying to help people make better decisions, and feel a greater sense of trust?

At the end of the day, transparency is truly a positive force. When it does backfire or causes fallout, it’s often because a leader hasn’t often taken the time to consider these two things: Transparency requires context, and transparency is a spectrum.

As you think through what you should be transparent about in your company, keep in mind these two things. Hopefully, they’re things you won’t have to learn the hard way.


This article was originally published for Inc.com.

What makes a good leader? Leadership is your product, not your identity.

The minute you stop tying your leadership so closely to your identity, you become a better manager.

Your leadership style is not your identity.

You are not your leadership style. In order to be a good leader, you must internalize this. As much as you might self-identify with being an “empathetic leader” or a “decisive leader”, you’ve got to let these notions go.

This is not an obvious truth because leadership feels inherently personal. The adjectives we use to describe our own leadership style might be the same adjectives we use to describe our own personality or disposition: Calm, patient, deliberate, compassionate, rational…

But the minute we fuse our identity to our leadership, we cling to it – and it blinds us.

I was recently reminded of this when I interviewed Desiree Vargas Wrigley, CEO and founder of Pearachute. She emphasized to me:

“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.”

Desiree admitted how, as a leader, it’s easy to cement yourself as “a certain kind of leader” – and you fail to see problems for what they are, because of this.

For example, if you see yourself as a “motivating leader” but an employee isn’t performing up to par, it’s tempting to feel frustrated. You might think to yourself, “I’m doing everything I can over here to be supportive… How can this person be flailing?”

Or, if you consider yourself a “fair leader” yet a team member implies you’re playing favorites, their critique feels like a personal attack. “Wow, I’m a fair leader, and they really think they’re not getting their chunk of the pie?”

In both situations, you view your own leadership as static – it’s the other person who needs to change. You shut the door on collecting more information, evaluating the situation objectively, and the possibility that there’s something better you could be doing.

The closer we tie our sense of self to how we lead, the harder it is to improve.

Instead, can you view your leadership as a product – not an extension of your identity?

With a product, you welcome feedback, you experiment with what works, you see it as a work-in-progress. With a product, you take a step back every now and then to reflect if it is indeed working.

You’re not incredulous if it’s not working for some folks. You’re not personally offended if some people don’t seem to like it. You adjust, test, readjust.

If anything, when leadership is your product, you’re excited for your leadership to evolve, and get better.

Otherwise, your leadership is self-righteous. “This is just the way I am” or “This is just how I’m wired” become the default mode of thinking.

The most important thing your leadership should be doing is serving your team – not your sense of self. Is the way you communicate, make decisions, handle conflict, set direction helping my team get closer to what they all want to make happen?

Leadership is a tool to help your team achieve the outcome it wants. It’s not a precious thing, in itself, that needs to be held on high.

Our leadership isn’t an outward expression of some grand inner personal philosophy, gilded in gold. Our leadership isn’t a foundational core of who we are, set in stone.

The more you relish in self-identifying as a “certain kind of leader,” the less responsive you become to the needs of your team and how you can become better over time.

The more you separate your personal identity from your leadership, the better leader you’ll be.

Building trust in teams: What and why?

How do you build trust in a team? First, let’s understand what trust really is and why it matters.

Who do you trust?

The first people who likely came to mind were your partner, your family, and your friends (hopefully). 

How about your boss? Your coworker? It’s harder to say. 

A 2016 study conducted by Edelman surveyed 33,000 people in 28 countries. From it, they discovered: One in three people don’t trust their employer. And only 24% of employees in this study believe their CEO exhibited highly ethical behavior.

In our own Know Your Team survey this past year of 597 managers and employees, we found that folks were slightly more trustful of one another: About 8% of employees said they rarely or never trust their manager. That’s almost 1 in 10 employees not trusting their manager. 

Why defining trust matters

Whether 1 in 3 employees or 1 in 10 employees don’t trust their managers – both are significant occurrences. Especially given the amount of time we interact with our coworkers, and the projects and outcomes that are on the line, it’s startling.

Are we really spending all this time with people we don’t trust? Should we be doing anything about this?

To answer those questions, we first have to define “trust” clearly. Misconstrue what trust actually is, and you spend time on the wrong things. Get it right, and building trust gets easier.

What trust is NOT:  Likability

We often equate trust with likability. We think, “This is a nice person” or “This is the kind of person I’d want to hang out with on weekends”… So we trust them. 

However, that’s only part of the equation. 

Consider someone in your company you don’t trust. You might like her. She’s affable, genuine and definitely tries her best. But trusting her with a high-profile project? You hesitate – she hasn’t shown the track record you need to feel confident. You don’t give her the big project because, honestly, you just don’t trust her enough.

So you if you want someone to trust you, it’s not enough that they like you. It’s not enough that they think you have good intentions. They’ve got to think you’re capable. They’ve got to think you have what it takes to prove something through. 

You might think someone is a good person – but you don’t trust them to actually get the work done. You need both.

This is an important distinction because many leaders accidentally optimize for likability as a means to build trust. They try to “be friends” with their direct reports, thinking it’ll mean their team will trust them more.

If we can internalize that trust is not likability, it causes us to not fall into the trap of trying to please everyone around us. If we want to build trust, there’s something deeper we have to access.

So then, if trust isn’t likability, what is it?

What trust IS: Intentions + Behavior

In a 1998 paper, Denise M. Rousseau suggested this definition of trust:  “A psychological state comprising the intention to accept vulnerability based upon positive expectations of the intentions or behavior of another.”

In short, trust is two things:  Intentions and Behavior. It’s people’s perception of who you are, and their expectation of what you can do. 

The 4 Cores

Stephen M.R. Covey defines trust in his popular book, “Speed of Trust,” similarly to Rousseau. To Covey, trust is the belief in who the person is, and a belief in their abilities – a person’s “Character” and their “Capabilities.” Covey then further breaks down trust into what he calls “Four Cores”:

  • Integrity – This means being honest, walking the talk, and being congruent with what you believe. You can’t trust someone unless you believe they have integrity. When someone is assessing your integrity, they’re wondering, “Do you have values I align with? Are you a good person?” 
  • Intent – This is your agenda or mission. Your team must trust your intent before they can trust you. A person sizing up your intent will wonder, “Are you thinking about yourself, or others, in this situation? Do you have the short-term, or the long-term in mind?”
  • Capabilities  – This is your talents, attitudes, skills, and knowledge. When someone is determining whether or not to trust you, they’ll consider, “Does this person have the expertise to do this job as well as they say they can?” Based on our survey, we found that both managers and employees most question their each others’ capabilities (26% of employees said this, and 36% of managers said this).
  • Results – This is your track record, your performance. You can’t be trusted unless you’ve shown results in some way that you can be trusted to follow-through. When you ponder about a coworker, “What has this person done that proves I can trust her?” you’re seeking results.

Warmth + Competence

Another related lens for understanding trust is described by organizational experts Amy J.C. Cuddy, Matthew Kohut, and John Neffinger. They revealed the two elements needed for a leader to be trusted were “Warmth” and “Competence” – with warmth needing to come first. 

According to their research, when you project strength too quickly, people have a harder time trusting you. They explain in Harvard Business Review, “Before people decide what they think of your message, they decide what they think of you.”

These perceptions of warmth and competence are powerful: “Insights from the field of psychology show that these two dimensions account for more than 90% of the variance in our positive or negative impressions we form of the people around us.”

How do you show warmth and competence? Cuddy and her research partners detail how warmth can mean positive body language, affirming words, generous actions, and even a smile. Competence can be projected similarly through body language (such as standing up straight), your past track record, and the actions you take going forward.

Like Covey, Cuddy’s research and explanation of the requirements for trust echo Rousseau’s definition of intention + behavior. Trust is all about who people think you are (warmth), and what they think you can do (competence).

Getting this distinction straight helps lay the groundwork for you to build trust in your team. You can now understand why someone might distrust you. Perhaps you haven’t defined your intent clearly enough. Perhaps it’s because of your past behavior. As a result, most importantly, you now can start to think how you can build trust in your team.

The clearer understanding we have of trust and what it really is, the clearer path we have to our teams trusting us more.

The Mindset Shift: How to become a good new manager

Are you a first-time manager? Of all the management advice for new managers, embrace this one, first.

Image for the mindset needed to become a good new manager

Don’t be fooled: Becoming a new manager is deceptively difficult.

No matter how many leadership books you’ve read or conversations you’ve had with mentors – the transition to becoming a manager is precarious.

Talk to any leader, and they’ll affirm this. “I was a terrible manager when I first started,” most will say. Myself included!

This is because the change required to be a good boss isn’t apparent from the outside looking in. You’re not truly aware of the change that’s needed in the role, until you’re actually in the role.

So what change do you need to make as a new manager? From 15,000+ people we’ve surveyed through Know Your Team and thousands of conversations with managers in our online community, the #1 consistent insight folks have shared is this:

Becoming a new manager isn’t merely a change in what you do – it’s a change in how you think.

When you become a manager, your responsibilities change and your daily schedule changes. But it’s your mindset that changes the most.

The biggest change in thinking, as a new manager, is that your best work is not you doing your best work. Your best work is creating an environment for others to do their best work.

You don’t think about, “Am I moving fast enough?” Instead, you now contemplate, “Am I removing obstacles so my team can move fast enough?”

You don’t consider, “Do I know the answer to this?” Instead, you ask yourself, “What am I doing to help my team become experts and find the answer?”

Becoming a good manager starts with how you think, not what you do. Shift your mindset, and the actions follow.

This shift in mindset, while seemingly obvious, is both substantial and hard to internalize. What previously indicated “success” for you as an individual contributor doesn’t indicates success anymore.

No longer do you pat yourself on the back when someone says, “Great work” or “I love what you did here”. As a manager, the small bump of validation happens when someone says: “Now I understand,” “Thank you for listening,” or “I’m excited to work on this.” The small wins change when you’re a manager.

This shift doesn’t happen overnight. We have to disregard the prior experiences of we were rewarded for as an individual contributor. We have to reconfigure our default settings of behavior that got us to where we are now.

But if you can embrace this mindset shift as quickly as possible, your ability to become a good manager exponentially increases.

You don’t have to wait til you’re in the thick of everything, as a manager, to know what you must change.

Now you know: You must change your thinking, first.

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 leadership 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, and actually internalizing this counterintuitive leadership tip, 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.

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.)

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 in Know Your Team, 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.)