Looking for a new job? Don’t be boring

The best advice for someone who’s on the job hunt this new year

“Don’t be boring.”

When I asked Amanda Lannert, CEO of Jellyvision, what advice she had for people who are looking to get a job, that’s the answer she gave.

As a CEO of a rapidly growing 400-person company, soon to be 500 people, Lannert has done her fair share of hiring.

“It feels like companies hire people, but in fact people hire people,” she explained. “By and large, recruiters are bored. People play it safe. They commodify themselves into just a bullet-point list of skills and experience.”

By not being boring, Lannert pointed out how you’ll catch a recruiter’s eye, and make yourself much more likely to land that initial phone call or interview.

At the same time, it’s also a great way to assess the fit of the role for you, as a prospective employee. When you show who you are as a candidate — what you value, what environment you work best in — and don’t get a call back, that company may be saving you some time and energy.

How do you not be boring? Here are five things to try:

Focus on the cover letter, not the resume.

At Jellyvision, Lannert shared how they place supreme emphasis on the cover letter. “There’s nothing more refreshing than seeing someone who takes a chance to be incredibly human in a cover letter or an outreach, to put themselves forward,” she says.

This means language that’s real, down to earth — not stiff, business jargon-y, and cut from some googled job site template. As someone who’s reviewed thousands of applicants for jobs for Know Your Team, I’d often set aside an application when the person would start their cover letter with, “I’m interested in X role. Please see my resume attached.” Everybody writes that in their cover letter — focus on saying something different.

Show, don’t tell.

A few years ago, a friend of mine wanted to land a job at Trunk Club, a company he’d been dreaming to work for some time. The only problem was that they weren’t hiring at the time. I suggested that he show them what he had to offer the company — not just tell them. So my friend whipped up a 50-slide PowerPoint presentation detailing ideas, suggestions, and projects for exactly how he could improve their online presence and user experience. He did the work of showing how he’d be an asset to the team — not just telling. Lo and behold, they created a role for him and offered him a job.

Get creative.

As a CEO myself, when I was hiring Know Your Team’s first full-time programmer several years ago, I’ll never forget how one applicant wrote me a poem — yes, a poem — perhaps 20 lines long that described who he was and why he desired the role. While we didn’t end up selecting him (he lived outside the United States and we required that the person live stateside), I remember that application so vividly even years later. He took a chance, got creative, and stood out from the 400+ applications we received in the first 72 hours alone. He was far from boring, and it worked.

Demonstrate you want this job, not just any job.

Another way to not be boring is to make it clear: “I want to work here, nowhere else.” This past year, when we were hiring for our Chief Technology Officer role, someone took the time to build a custom software application, just for Know Your Team. He’d replicated the Know Your Team software to the best of their ability, using what he’d gathered from screenshots he’d seen online. His intention was to demonstrate that he was technically up to snuff for the role.

My greatest takeaway was that it showed he wanted to work here, and nowhere else. I was impressed by him wanting this job, not just any job, and that caught my attention.

Sound like yourself.

Perhaps most importantly, you should make sure you sound like yourself. Don’t try to write a poem if you’re not good at writing poems. Don’t try to be funny in your application if you’re not funny. Be thoughtful in portraying the truest version of yourself — not what you think the employer wants to read.

If you’re concerned about how to do this, the key is simply to take put a little time and care into your application. Don’t rush your writing your cover letter. Think about how you can thoughtfully show who you are and what you can bring to the company. When you pour considered thought and energy into something, your true self will come through. Being not boring is about being yourself, more than anything else.

Keep this credo of “Don’t be boring” in mind, as you apply for a job. Dare to be different, and stand out from the sea of bullet-pointed list resumes and bland cover letters. The less boring you are, the more memorable you are. And the more memorable you are, the more likely you’ll land the job you want.


Claire is the CEO of Know Your Team – software that helps you become a better manager. Her company was spun-out of Basecamp back in 2014. If you were interested, you can read more of Claire’s writing on leadership on the Know Your Team blog.

This article was originally published for Inc.com.

How transparent should you be as a leader?

Two things I’ve found helpful to consider when trying to decide what to share 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.


Claire is the CEO of Know Your Team – software that helps you become a better manager. Her company was spun-out of Basecamp back in 2014. If you were interested, you can read more of Claire’s writing on leadership on the Know Your Team blog.

This article was originally published for Inc.com.

How to tell if a CEO is worth working for

If you’re looking to leave your company to work for another, you’ll want to consider this.

A few months ago, someone asked me for advice about potentially leaving one company to go work for another. He was curious what factors he should consider before making the decision.

He’d already vetted the role, the company, and the offer itself — all important aspects to consider. But I told him, in my opinion, the most crucial thing to vet is the CEO.

If you’re about to join a new company, you must figure out:

“Do I believe in the CEO?”

No company is successful with a CEO who can’t communicate, who can’t get everyone on the same page, who can’t hire well, and who can’t chart out a vision.

Personally, I remember interviewing at one of my first job out of college, and I remember it being really hard to tell if a CEO is “good” or not.

Plenty of CEOs sound like they’d be a good CEO. They’re charismatic, they’re articulate — but does sounding like a good CEO really make it true?

After almost four years of researching and observing hundreds of CEOs, I’ve learned to ask these four questions to discern whether or not a CEO is a good CEO:

#1: “When have you had to sugar-coat the truth — or avoid telling the truth — to your team?”

How a CEO answers this question reveals her barometer for integrity. Your CEO might laugh and say, “Oh, all the time,” a little too flippantly — signaling that she intentionally misguides employees habitually. On the other hand, if a CEO is too hesitant to admit anything substantial, that’s a red flag as well. It’s likely she’s holding something back. Ideally you’re looking for a CEO to level with you and admit in a nuanced, considerate way when she’s chosen to not be transparent with the team, and why.

#2: “What do you think is your own greatest leadership blindspot?”

This is a take on the classic, “What do you think your greatest weakness is” question — but with a twist. The word “blindspot” implies that the CEO has a weakness she might often overlook. So her answer to this will reveal her self-awareness. Does she have a hard time giving you a straight answer? Or is it clear that this is something that she’s thought a lot about, self-reflected upon, and perhaps even talked about with peers or an executive coach. If it’s the latter, it signifies that this leader has the humility and self-perceptiveness you’re looking for.

#3: “What does ‘success’ for the company look like to you?”

This may seem like an unassuming question to ask — perhaps it’s one you’ve asked the CEO already. However, we often don’t listen closely enough to the answer. If all the CEO is focused on is “winning” and “making money” and “dominating the competition” in her answer, I can guarantee that’s 100% what the work environment is going to revolve around. On the contrary, if she also talks about creating a sustainable, healthy culture, and making sure people feel fulfilled, challenged and supported in their jobs — you can bet that the work environment is going to reflect that. The answer to this question makes is crystal clear what a CEO’s priorities are.

#4: “What would an employee who’s left the company say it’s like to work for you?”

This may feel like a tough question to ask you prospective CEO — especially if they haven’t hired you yet. But it potentially is the most important question. The answer to it demonstrates how cognizant the CEO is of how they’ve treated employees in the past, and how willing they are to admit if they’d haven’t been the ideal leader. Be wary of CEOs who say only positive things, as it shows their refusal to recognize their shortcomings, or failure to understand how their own leadership behavior may have driven the other person away.

If you’re worried that asking these questions — particularly the last one — might offend your prospective CEO, that in itself is a sign that the CEO might not be who you’d hope for. The best leaders welcome tough questions, and will be impressed by your desire to better understand how they lead.

If anything, asking these questions will make you look better in their eyes. And, it gives you all the information you need to decide if they’re a CEO worth working for.

Claire is the CEO of Know Your Team – software that helps you become a better manager. Her company was spun-out of Basecamp back in 2014. If you were interested, you can read more of Claire’s writing on leadership on the Know Your Team blog.

This article was originally published for Inc.com where I write a column on leadership.

Managers, screw the Golden Rule

Don’t treat employees the way you want to be treated. Here’s why.

“Treat others the way you’d like to be treated.”

This is The Golden Rule we all learned growing up. As a manager or CEO in a company, you’d think it would make sense to follow it too. Managers should treat their employees the way they’d like to be treated, right?

Not quite.

In a recent interview I did with David Heinemeier Hansson (DHH), the Creator of the popular web framework Ruby on Rails and Chief Technology Officer at Basecamp, he shared this insight: You shouldn’t treat other people the way you want to be treated because the other person isn’t you.

The other person has different preferences (beliefs, ideas, and experiences) and is going to react to a situation differently than you. You might think something is reasonable or fair, but that’s you thinking that, not the other person. You cannot assume that the way she would like to be treated is the same as the way you’d like to be treated.

David admits to being guilty of this as much as anyone, saying that when he does this, “I’m trying to be empathetic to my own mirror image, which is not actually a very good definition of empathy.”

In fact, it’s self-centered in many ways to assume that if you treat others the way you’d like to be treated, other people will like it too.

One of the most memorable examples for me of this is when I talked with another CEO a few months ago. He told me how his company had implemented an unlimited vacation policy recently. In theory, he thought it was going to work great. It’s what he had always wanted when he’d worked at other companies himself — unlimited vacation, what could be better?

But then something interesting at his company happened: No one in his company took vacation. Maybe a day or two off here and there, but people took less vacation with the unlimited vacation policy than they had in years before.

I was a little shocked when he first told me this. What went wrong? The CEO learned is that none of the employees wanted to be seen as “the slacker” or “letting the team down.” Everyone else was afraid of taking vacation, so no one went on one.

After realizing this, the CEO replaced the unlimited vacation policy with a requirement that people take at least two weeks off of paid vacation during a year. It’s not what he would have necessarily wanted, but that’s not the point. If you’re a great manager or leader, you shouldn’t be operating from the point-of-view of what you want, you should be operating from the point-of-view of what others want.

Instead of practicing The Golden Rule and assuming other people are just like you, what should you do?

The answer is deceptively simple. Ask.

Ask your employees what type of vacation policy they’d prefer or what work environment they’d like to be in. Here are some examples of things you can specifically ask:

  • How do you prefer I give you feedback? In-person or in writing?
  • When you are most productive in a day? During the morning or the afternoon? Or even at night?
  • How much social interaction is important to you? Should we plan more team-bonding outings or have more regular company lunches?
  • How often would you like to get together for one-on-ones? Once a week, once a month or once a quarter?
  • How would you like to recognized for your work? Do prefer verbal praise in front of others, or more privately? Are small gifts or tokens of appreciation a good way to signify gratitude?
  • How much direction or context do you like before kicking off a project? Do you need space to gather your thoughts initially, or do you like having a lot of suggestions from me upfront?

Don’t just assume their answers are the same as yours. Ask, listen, and then act accordingly. The Golden Rule need not apply.


Claire is the CEO of Know Your Team – software that helps you become a better manager. Her company was spun-out of Basecamp back in 2014. If you were interested, you can read more of Claire’s writing on leadership on the Know Your Team blog.

This article was originally published for Inc.com.

How to prepare for a one-on-one meeting as an employee

Many managers say flat-out that their biggest frustration is when employees are not prepared for a one-on-one meeting.

Yikes, really?

Over the past four years, I’ve heard countless of managers, CEOs, and business owners say a version of this to me:

“During a one-on-one, I’ll ask a question and there’s silence on the other end. Or they’ll use it as a complaining session and it’s clear they haven’t been thoughtful about what feedback they’re offering. The lack of preparation just kills me.”

As an employee, this may be somewhat surprising to hear. We often underestimate how vexing it can be for a manager when we don’t come fully prepared to a one-on-one meeting.

I know I didn’t prepare for any of my one-on-ones, six years ago, when I was an employee. Out of fear, anxiety, and a bit of dread for what the conversation was going to be like, I pushed my impending one-on-one meeting out of mind. I didn’t think about what I wanted to say in the weeks (and days) leading up to it. “Was it really worth putting in the energy to do so? Nah…” I thought to myself. So I decided against it. As a result, when my boss asked me, “What do you think could be better in the company?” my answer was vague and not meaningful.

In the moment, it felt like the safe and comfortable thing to do. But truth is, I only hurt myself. I bungled my opportunity to influence real change. And, I only further frustrated my boss, who was perplexed that I seemed dissatisfied but never vocalized my concerns outright.

Eventually, I left the company. But I dearly wished I’d approached those one-on-one meetings differently — with less passivity and more positivity. I wish I would’ve seen those one-on-one meetings as an opportunity instead of an obstacle. I wish I would’ve seized those one-on-ones as a moment to engage and dig deeper with my manager, instead of using them to create distance and fester in apathy.

In the six years since being an employee, now as a CEO myself, I’ve since learned the power of preparing for a one-on-one. It’s not just managers who should be preparing for them, but employees too.

Knowing what I know now, here’s what I wish I would’ve considered when preparing for a one-on-one meeting with my then boss…

Share what’s been most motivating to you.

Managers crave to know what they should be doing to help you do your best work. After all, a manager’s ultimate job is to create an environment that enables you to tap into your own intrinsic motivation. During your one-on-one, make sure you share what tangibly has been most motivating to you while at the company: What’s been your favorite project? Who was someone you really enjoyed working it? Why was what you were working on so invigorating to you?

Reveal what’s been draining and demotivating to you.

As an employee, it’s always tough to bring up a critique of the company— especially if it’s about your own manager’s habits and actions. You’re worried it’ll be misinterpreted as “complain-y,” that your manager will take it personally, and that it could affect your career progression. Or perhaps worst, you’ll put in all the effort of sharing your feedback and nothing will happen. While all of those scenarios might be possible outcomes, what we must remember is that if we don’t talk about it, our managers will never know about it. The little things — whether it’s your manager interrupting you during meetings or always asking you to stay late — add up. They gnaw away at your ability to feel energized about your work. If you don’t say something, then who will? When you do speak up and vocalize tough feedback, look to approach the conversation with care, observation, fallibility, and curiosity. It’s a hard, delicate path to travel. But it’s a worthwhile path if you want your work environment to become better.

Explain how you want to stretch and grow.

Your one-on-one with your manager is your chance to let her know how you’d like to be further pushed and challenged in your role (or outside your role). Take time to reflect on what you’d like to improve or work on professionally. Perhaps it’s something more broad, like learning to be more patient and strategic in your thinking. Or maybe it’s much more about gaining a specific skill, such as becoming a better writer. Suggest potential projects for how you’d like to grow in those areas, and see if your manager has any ideas around it. Ask your manager for advice on what books, classes, or people you should be talking to help you pursue the greater learning you’re looking for.

Highlight what you’re grateful for about the company, work environment, or how your manager has treated you.

Giving feedback during a one-on-one isn’t just about zooming in on the bad. It’s the perfect time to point out the good, especially the good things your manager has done or said. Think about what your managers does that your previous manager at another company never did. What are the things you want to make sure she knows you don’t take for granted? Be specific, and say thank you. Not only will it help boost the morale of your manager (who needs the positive support, as being a manager can be a thankless job in some ways), but it helps guide your manager to double down on the things that you appreciate.

Consider what’s been confusing or concerning to you in the company.

Are you concerned that the company is growing too fast, and losing some of its original culture? Are you confused why the company decided to change its vision midyear, when things have been going so well? Consider leveling with your manager about what uncertainty is weighing on your mind during the one-on-one. It’s much more challenging to try to bring it up those questions outside of a one-on-one meeting — so take advantage of the fact you have dedicated time to discuss bigger questions about the state of the company with your manager.

Suggest one thing you see as your greatest shortcoming, and what you want to do to actively compensate for it or improve on it.

During your one-on-one, your manager is bound to share some constructive feedback in an area you could get better. While intimidating at times, it’s a good and helpful thing — and something to prepare for. To help make the conversation easier for you both and to show that you’re actively looking to improve, offer some thoughts yourself about moments you wish you would’ve handled differently. This could come in the form of goals, such as, “I want to find ways to ask more questions when interacting with customers,” or observations of areas you want to strengthening, such as, “I have a tendency to rush some of my projects, and I want to find ways to focus more on quality instead of speed.”

Prepare 3 to 4 questions to ask, to help you better understand how to focus your efforts going forward.

In case your manager doesn’t ask questions that cover everything you’d like to cover, you’ll want to have a few questions prepared. Here are some examples of questions you can ask that’ll help you better understand how you can improve as an individual contributor, and help your manager understand what she can be doing better as well:

  • Do you see any untapped potential in the work I’m doing? An area you think I could be pressing a bit harder in or exploring deeper?
  • What’s been frustrating or confusing about working with me? Where do you see the greatest opportunity for me to improve?
  • What’s the biggest challenge you feel you face as a manager? In what ways can I be helpful in overcoming or facing that challenge?
  • What worries you most about the team?
  • What are you most proud of the team having accomplished?
  • In what ways have I saved you time or made your job easier? What can I be doing to do more of those things?
  • Where do you see the team or company a year from now, and what I can do to help make sure we achieve that vision?
  • What are the biggest challenges you foresee the team or company facing in the upcoming year?

This may feel like a lot. I might recommend taking 30 minutes or so to reflect on some of these items, and even writing out some questions, yourself.

But keep in mind that the more you put into a one-on-one, the more you can get out. While a thirty-minute or one hour meeting doesn’t seem like much, it’s an opportunity to create a better relationship with your manager, to improve the work environment around you, and be plain happier in your job.


Claire is the CEO of Know Your Team – software that helps you become a better manager. Her company was spun-out of Basecamp back in 2014. If you were interested, you can read more of Claire’s writing on leadership on the Know Your Team blog.

How to influence culture when you’re not the CEO

“Culture starts from the top,” it’s often said.

But is that really true?

Surely, it is easier to influence company culture when you’re at the top. As a CEO, founder, or business owner, people are already looking to you for example and guidance around what’s important within the team. (I wrote a bit about how you can influence culture as a leader here.)

However, being a leader in the company is not required to influence company culture. If you’re an employee or a middle manager and you’re frustrated with the status quo in your company, all is not lost.

Culture has nothing to do with what your job title on your business card says. It has everything to do with your beliefs, words, and actions as an individual.

Culture is made up of people after all — people who decide what artifacts, espoused values and beliefs, and basic underlying assumptions are true for a team. Any one person can influence culture, not just the CEO.

Regardless of what position you hold in the company, here are few ways you can create an environment for the culture you want to take form:

Model what you’d like to be true of your team.

Let’s say your CEO isn’t great about being responsive to emails and showing that she’s listening. If responsiveness is something you think should be a part of your company’s culture… the question is, how well do you respond to your own emails? When in a one-on-one or a meeting with your team, do you yourself do a good job yourself of listening to and responding to others’ requests? Look at yourself, first and foremost, as a starting point for the kind of company culture you aspire to have.

The power of modeling what you’d like your company culture to be is two-fold: (1) You make it known and visible what can be improved. And (2) if things start going well and your colleagues are really loving what you’re doing, someone — the CEO, founder, or business owner — is going to notice. She’s going to say, “Hmm maybe we all should start doing what you’re doing.”

In other words: Show what you’d like to better in the organization — don’t just wait for it to happen.

Dissent is a responsibility.

If there’s something you think could be better in the organization that the team should adopt to improve the culture, speak up. As an employee, dissent is a responsibility. Voice it respectfully, especially when the opportunity to give feedback presents itself. For example, in your last one-one-one meeting, when your manager or CEO asked you what could be improved, did you share a thoughtful answer?

Culture can only be intentionally shifted if it’s intentionally talked about.

It’s important to do this in private — no leader likes to be “blasted” in front of the company about what you think she is falling short of. (You can read more about how to give difficult feedback to your boss here.)

It’s also important to share your suggestion in the context of the team — and not just your own individual interests. For instance, it’s easy to say that you think the culture should be more open, especially around financials, because you think it’d help you better negotiate a raise. But instead, if you can share why transparent financials would help everyone on the team feel more bought on to what the company is trying to accomplish, the likelihood of others embracing what you’re looking to change increases.

Give space, grace, and gratitude to leaders.

It may take time for the rest of your company to catch on to how you’re trying to influence the company culture for the better. You may even get questions or resistance for why you’re doing things a certain way. Don’t be deterred. Understand that change takes time — especially cultural change, not to mention change that happens from the bottom up. Understand that your leaders are juggling many priorities, and that it may take repeated action for them to take note.

You can also thank your leaders in the meantime for the things they do that already reinforce and support the kind of culture you desire as an employee. There’s a lot of talk of the importance of employee recognition — but manager recognition is just as important. Leaders aren’t thanked very often, so it goes a long way to help solidify the culture you’re want to have, when you show appreciation for the things you already think are headed in the right direction.


Influencing culture from the bottom-up, and not just the top-down, is possible. Though, it may be more difficult and take more time to manifest, it’s an important route to seek as an employee or middle manager. If you can slowly yet steadily put energy behind shifting the culture, you not only make things better for yourself, but for others as well.

As an employee or middle manager, a better company culture can start with you.


Enjoy this piece? Read more of Claire‘s writing on leadership on the Know Your Team blog. And, check out Know Your Team – software that helps you become a better manager.

How to influence company culture

“How do you actually influence company culture?”

This is the big, hairy question I often get asked by CEOs, managers, and employees alike. The other week, I posed it at the end of my most recent piece, The Culture Cliché.

In that piece, I shared how the fundamental, core element of culture are our basic underlying assumptions. That is, the things we actually believe — but might not always say or outwardly show — are what determines our company culture.

As a result, the key to influencing culture is tapping into those basic underlying assumptions: Listening to them, responding to them, and acting according to them.

But what does that tangibly mean? Can you affect or influence others’ basic underlying assumptions, to begin with?

Yes and no.

Yes, basic underlying assumptions can be affected.

But no, they can’t be outright changed. You can’t manipulate someone else’s basic underlying assumptions. Employees are not malleable objects for leaders to shape. Each person has her own intrinsic, worthwhile desires and beliefs — and that’s not for you as a leader to try to mess with.

Instead, what you can do is to focus on creating an environment where employees can choose to shift their basic underlying assumptions in line with what feels right to them.

Let’s talk about what this practically looks like.

There are three parts to creating an environment where the kind of basic underlying assumptions you want — and ultimately, the kind of company culture you want — can come into fruition:

Personal accountability

You must model the behaviors and basic underlying assumptions you want to be true. One of the greatest shortcomings of a leader is wanting others to do something when she doesn’t practice it herself. For instance, a manager often doesn’t admit her own weaknesses, but expects employees to be upfront and forthcoming about mistakes that happen in the company. See the disconnect? Whatever basic underlying assumptions you desire to be deeply rooted in your company, you must exhibit those basic underlying assumptions yourself, first.

As the leader, you should be the living embodiment of the basic underlying assumptions you want your culture to have. You should be consciously and intentionally speaking and acting in a way that shows people, “This is important to me.”

Consistency

Your desired basic underlying assumptions won’t be made true unless they are consistent. Basic underlying assumptions are solidified when you act consistently upon them.

Say you want honesty and transparency to be a basic underlying assumptions within your company’s culture. You decide to hold an all-hands meeting every month where you cover high-level financials, company goals, accomplishments, and answer employees’ questions. Seems like it’d be an effective initiative to establish that honesty and transparency are a basic underlying assumptions within the company.

But here’s the missing piece: Is it consistent? Do you hold those all-hands meetings every month, regularly? Or has the frequency of those meetings tapered off so now it’s every 2 or 3 months…or just whenever you remember to have them.

If it’s the latter, you’re falling short of creating an environment where those basic underlying assumptions can be strengthened.

Consistency determines whether or not this tenet of your culture is fleeting, or here to stay.

Richness

Being consistent alone in how you demonstrate your basic underlying assumptions isn’t enough. You must think about the richness of how you’re communicating these basic underlying assumptions. Are you using a variety of channels, means, and mediums to show that this is something that’s important for the team to embrace and embody? Or are you just relying on one?

For example, it’s not enough to just hold the all-hands meetings and assume that’s the only way to foster honesty and transparency within the company. Consider that some people might not feel comfortable speaking up in front of the rest of the company… so you’ll want to make sure you’re also doing one-on-ones. But don’t also merely assume that a one-on-one is enough of an opportunity for someone to speak their mind. Perhaps that person doesn’t always feel comfortable directly addressing that particular manager. Make sure you provide other opportunities for your employees to speak up, be it at group lunches, coffees get-togethers, CEO office hours, or an all-company survey.

The richness of how you communicate, the varying formats and mediums, helps dictate if the basic underlying assumption is truly what it should be: foundational.

Now this is no grand formula by any means for creating the culture that you want. Shaping a company’s culture and tapping into a team’s basic underlying assumptions is more art than it is science.

But consider these three elements — personal accountability, consistency, and richness — in how you’re upholding the basic underlying assumptions you want to make more real.

Pick one, commit to it, and see progress build over time. Slowly, but surely, you’ll see the difference.


Enjoy this piece? Read more of Claire‘s writing on leadership on the Know Your Team blog. And, check out Know Your Team – software that helps you become a better manager.

Cereal Day

Something as small as breakfast cereal– yes, cereal — can improve employee engagement. Here’s why.

The executive director of a prominent nonprofit called iMentor Chicago reached out to me the other week. Her name is Halleemah Nash.

“A question I asked my team a few months ago really caught me off guard,” Nash shared with me.

“I thought it was honestly kind of a silly question — something I’d never answer myself, personally. But I thought, ‘Oh what the heck, let’s ask it and see what happens.’”

The question was:

“What’s your favorite breakfast cereal?”

She asked this question to her staff, expecting nothing much to come of it.

The opposite happened. Almost every single person on her staff responded — enthusiastically, humorously. It got the whole office talking, laughing, joking with one another.

Nash took notice. She saw the collegiality it spurred, and wanted to encourage that positive spirit even more.

Once a month, she decided to plan a “Cereal Day,” when she’d bring in everyone’s favorite cereal. She had “Cereal Day” take place on the day of her team’s monthly strategic planning meeting — no doubt a tough, intense day for the staff.

Her staff absolutely loved it. Nash was stunned. “Who knew that cereal would get people pumped for a strategic planning conversation,” she wrote to me candidly in an email.

While it’s endearing to think that breakfast cereal is “the thing” that flips a switch for a team’s employee engagement, there’s something deeper going on here. Nash’s “Cereal Day” works as a means to boost her team’s morale for specific reasons.

Here’s what we can all learn from it as leaders:

Great leaders bring levity to a team, not just the load of work.

Let’s be real: Work feels serious a majority of the time. Everyone’s busy, there are deadlines flying around, a thousand decisions to be made — it’s easy to get your head stuck in the weeds of work. We all need a break, at some point.

Nash understands this, and so intentionally chose her strategic planning meeting day as the day to hold “Cereal Day,” as a result. She knew how in moments of stress or intensity, people do better work when they can step away, have a laugh, and just lighten up a bit.

As a leader, yes, it’s your job to press the gas pedal to make sure folks are focused. But you also want to give people permission to be people — to have fun, be silly, be expressive. Don’t get frustrated if you notice your team members cracking jokes during a meeting. Don’t be bitter when an employee takes an extra long lunch with a co-worker. Take it as a sign that they might need that levity. Like Nash, if there is a particularly tense time of year, use it as an opportunity to bring lightness to that meeting or season.

Great leaders find a way to connect everyone, not just some.

“Cereal Day” was effective at bringing together Nash’s team because, frankly, it’s unlike a lot of other team-bonding events: It involved everyone. Think about it.

At a happy hour, typically the same folks congregate and talk to one another. During a one-on-one coffee conversation, you only get to know that one particular person. It’s rare to have moments in the company where everyone gets to interact with everyone else — but that’s what “Cereal Day” did. Nash’s “Cereal Day” is the antidote to the silos that pop up in organizations.

Take an honest look at your own company’s current team-bonding events and see if they’re a common touch point for everyone, or just for some. You may be accidentally reinforcing the silos in your company you’re working so hard to dissolve. You may have to get creative — or even better, ask your employees about their personal tastes and interests — so you can tailor company outings, events, and activities to be a shared, common touch point for everyone.

Even if it’s about breakfast cereal — the fact that it’s something everyone can participate is what matters.


Whether you try to engage your employees as a leader with cereal or not, that’s totally up to you. But “Cereal Day” is an important reminder for us as leaders that employee engagement isn’t just about the big, grand gestures of extending vacation time or big pay raises.

True employee engagement is about caring enough to ask even the seemingly small, trivial questions to your team — and paying close attention to the answers.


Enjoy this piece? Read more of Claire‘s writing on leadership on the Know Your Team blog. And, check out Know Your Team – software that helps you become a better manager.

This article was originally published for Inc.com.

Exciting! We’re launching The Watercooler

An online community for leaders looking to become better

“How do I become a better leader?”

I’ve spent my entire working life trying to answer that question. The answer, unfortunately, has never been very clear. I found books to be one-sided, conferences require you to be there in-person, and mentors who I trust not always available (nor do they always have the experience or answers I’m looking for!)

So we built “The Watercooler” — an online community for founders, CEOs, owners, executives, and managers to talk candidly about our struggles and our successes. No matter where you live, no matter where your company is located in the world, we now all can support each other on the path to becoming better leaders.

Who The Watercooler is for

  • Business owners who don’t have the time (or have never been interested) in attending leadership seminars, but crave thoughtful discussion around how other folks think about leading teams.
  • Managers who are having a tough time transitioning into their new role, or feel like they haven’t learned any of the “leadership stuff.”
  • Founders who’ve been hiring quickly, and scaling and managing a rapidly growing team is starting to feel overwhelming and a little perilous.
  • People who believe that great leaders never stop learning, and continually ask themselves: “How do I become a better leader?”

What we talk about at The Watercooler

At The Watercooler, we chat about things like…

  • Company culture — Organization structure, goals, employee handbook, values, mission.
  • Individual performance — One-on-ones, feedback, reviews, career growth, check-ins, promoting people.
  • Hiring & Recruitment — Best practices, salary range, job description, interviews, hiring committee.
  • Tough Conversations — Inappropriate behavior, body odor, harassment, firing people, conflict.
  • Benefits — Healthcare, 401ks, paid time off, flexible hours, equity/options, profit-sharing.
  • Remote Companies — Challenges of building a great remote environment.

And more: Growing the business, product strategy, work-life balance, social events.

Who makes up The Watercooler Community

At The Watercooler, we value leaders who have a shared commitment to becoming better — those who come from a place of humility and honesty. Upholding those qualities are important and is the only way we can ensure an open dialogue on sometimes tough and personal topics.

As a result, we have a strict review process for members. You can either be referred to The Watercooler by a current member, or you can apply for membership here.

About two weeks ago, we invited current Know Your Team account owners as part of a private beta… and it’s been amazing to see the conversations, honest insights shared, and helpful advice exchanged in only 14 days. We’ve discussed topics like “how to let someone go” and “how we run our all-hands meeting” and “how to create fairness between locations in a distributed company.”

With 130+ folks who joined our initial private beta, here’s what a few folks have told me about The Watercooler so far:

“The Watercooler has become one of my internet pitstops, providing a daily dose of inspiration on how to build great businesses, straight from those doing it every day.” — Sean Conner, Managing Director of Marketing at Guerrero Howe

“It’s easy to feel isolated in leadership. The Watercooler is a daily reminder that we’re in this together and can help each other.” — Chris Powers, Director of Engineering at Sprout Social

“I’ve only been signed up a couple of days and already I’ve found some good ideas that I’m implementing, and some inspiration for things I’d like to do.” — Chris Lilley, Director at Black Pepper Software

How much The Watercooler costs

The Watercooler is just $20/month to join (or $200/year if you’d like to save 15%). This is to cover our maintenance costs and ensure we have a high-quality, moderated community.

Hope to see you at The Watercooler!

As a CEO myself, reading the threads in The Watercooler has been energizing. It’s made me feel like, “Phew, I’m not alone!” and helped me think through my actions and thought-processes on certain topics. I’d love to include you in the conversation. And, please feel free to share it with friends and colleagues who you think might benefit and add value to the community.

I look forward to learning from you at The Watercooler. See ya there!

Apply for membership to The Watercooler today.

PS: Please 👏 this post if you’d like others to benefit from The Watercooler. Thanks so much (and please say hi at @clairejlew!)

The Culture Cliché

If you’re looking to shift your company culture, it starts with understanding what culture is in the first place.

“Culture” has become the ultimate buzzword these days.

Everyone wants to “improve their company culture.” I see the word frequently littered across the headlines of countless of articles, book titles, and conference talk topics. Leaders also seem to talk about it all the time: CEOs say company culture is their first or second most-important priority as a leader.

Yet for as much we seem to talk about it, do we really know what culture is?

If we want to influence our company culture, we have to start with a keen understanding of what culture actually is.

What is company culture, really?

“Culture is the way we do things around here.”

You may have heard this before. It’s how prominent organizational consultants Terry Deal and Allan Kennedy defined culture in the 1980s. Culture is the thing you can’t necessary touch and feel — it’s the invisible binds and unspoken rules that enforce “how people do things around here.”

However, this definition can be insufficient at times. “The way we do things” feels awfully vague and amorphous, especially when it comes to thinking about how to intentionally create a company culture we’re proud of.

As a result, our attempts to influence culture get muddled. We conflate culture with surface-level relics, confusing culture with “Things To Make People Feel Good.” Think ping pong tables and happy hours and free lunches. Sure, those are part of “the way we do things” — but it doesn’t explain why you’re doing those things. Culture includes that why.

Let’s take a look at culture a few levels deeper.

Three levels of culture

Edgar Schein, another prominent organizational scholar, defined culture as having three levels:

Artifacts

This is the level of culture closest to the surface. Artifacts are things you can see, touch, smell. Ping pong tables, happy hours, and free lunches. It’s also the office layout, the logo rebranding you just did, and your company holiday party. This is typically what we think of when it comes to company culture.

Espoused values and beliefs

One level deeper are your espoused values and beliefs. These are the things you think you believe and say you believe. It’s the mission statement you wrote together as a company, the code of conduct that’s in your employee handbook, or the six core company values your CEO talks about during your all-staff meeting.

Basic underlying assumptions

This is the final, core layer of culture. Basic underlying assumptions are the things you actually believe. For example, at Know Your Team, we have a basic underlying assumption that we must be honest, regardless of the personal cost. So when we made a big mistake a few years ago, we proactively shared it with our customers, even it meant risking losing them. Our basic underlying assumption steered our decision-making and how “we do things around here” — ultimately, driving our culture.

Our basic underlying assumptions are the foundation of culture. If we can influence our basic underlying assumptions, we can influence culture.

Why this matters

More often than not, there’s a misalignment between this final layer — the basic underlying assumptions — and the espoused values and beliefs and artifacts. The things you actually believe, versus the things you say you believe and the things you do to show it.

Perhaps the most glaring case has been Uber. A company that no doubt had artifacts as “proof” that they valued their employees — lavish office parties and state-of-the-art offices. A company that had 14 cultural values it touted, including that employees should “be themselves.” And yet the basic underlying assumption persisted: Win at all costs, by any means necessary. We saw this in countless of examples of questionable ethics and sexual harassment issues ignored. At its core, Uber’s culture was rooted in this aggressive, toxic mindset — and that manifested in how they treated their people, regardless of what superficial artifacts or espoused values they trumpeted.

If you’re looking to truly shift your company’s culture, you have to zoom in on this last and final layer: Your basic underlying assumptions. What you truly believe — not always what you say or outwardly show — is what drives your company’s culture. This should be your focus as a manager, CEO or employee.

Changing your company culture is not about just changing the artifacts. Getting beer taps installed in the kitchens doesn’t make your culture more friendly. Nor does building an onsite gym mean your culture all of sudden cares about employees’ health and well-being.

Changing your company culture also isn’t about just changing the espoused values and beliefs. Saying at all-company meetings, “We believe in honesty and transparency” or writing “We believe in diversity and inclusion” on your career website doesn’t automatically make those things true.

Changing your company culture is about tapping into the core beliefs of each individual, understanding what their basic underlying assumptions are, and creating an environment where those can be listened to, brought together, and reacted to.

How do you exactly do this? That’s a whole ‘nother topic I cover in a separate piece here.

Until then, I hope we can take a minute to look past company culture as not a cliché — but an opportunity to use it as a precise, perceptive lens to examine how to make our organizations better.

If we can understand company culture, we can improve it.


Enjoy this piece? Read more of Claire‘s writing on leadership on the Know Your Team blog. And, check out Know Your Team – software that helps you become a better manager.