Stop being so nice all the time.

“Being nice” can be a crutch to avoid hard choices and uncomfortable conversations. Don’t fall into this trap.

Leaders, stop being so nice all the time.

I don’t mean to sound like an asshole. But when it comes to leadership, it’s true: Prioritizing “being nice” keeps us from being good leaders.

Now I’m not advocating for us to be mean. Disrespectful or dismissive leaders help no one. Rather, I’m calling for us as leaders to loosen our grip on “being nice.” To stop wanting our team to like us all the time. To let go of the expectation that every single interaction with our team should feel good.

Truth is, our team isn’t going to like us all the time. Our team isn’t going to feel good all the time. And trying to be nice to everyone all the time isn’t going to change that. Nor is it actually helpful for your team.

When we’re preoccupied with seeming popular instead of fair, when we optimize for pleasant conversations instead of honest ones — we hurt our teams.

I was reminded of this most recently while I was reading The Watercooler, our online community with almost 1,000 leaders. One manager revealed he was facing this exact dilemma. He was seen as “The Nice Guy” in his company, always complementary, never critical. As a result, he was struggling how to start giving his team difficult feedback — and his team was floundering.

He’s not the only one.

Have you ever found yourself in one of these situations?

  • You avoided giving tough feedback to a coworker… and now the person has made even bigger mistakes than you previously imagined.
  • You didn’t tell someone that you disagreed with them… and now you have to figure out how to course-correct without blindsiding the person.
  • You postponed firing someone… and now have to do damage control for the low morale they infused throughout the team.
  • You said something was “great!” even though it actually wasn’t… and now you have to fix the level of quality for what was produced.

Many of us focus on “being nice” as a leader more than we should. And we pay a price for it.

Hiten Shah, founder of Kissmetrics and Crazy Egg, emphasized this point to me, in a recent interview. He warned that when you’re concerned with being nice all the time, “there’s a level of toxic culture that develops that’s hard to see, especially on a remote team.”

Prioritizing “nice” as a leader is an easy trap to fall into. Being nice fits into our desire for belonging and companionship as humans. We’re social creatures. We want to be liked. Inherently, there is nothing wrong with that.

But “being nice” becomes problematic when it becomes your rudder as a leader. It leads you astray. You lose sight of your purpose as a leader: To help your team accomplish a specific mission. Your barometer for success as a leader morphs from “Are we accomplishing our mission?” into “What does the team thinks of me?

Over time, “being nice” becomes your crutch. It’s a convenient rationalization to avoid hard decisions, uncomfortable conversations, and controversial actions. It’s easier to “be nice” than it is to have tell someone to their face that they’re rubbing a client or colleague the wrong way.

Ultimately, being nice as a leader is selfish. It doesn’t serve the team. It serves your ego. The team is looking to you to help them achieve a goal. And instead, you’re looking to have your decisions, actions, and yourself perceived as positive by them.

A leader is the only person’s whose sole job is help a team achieve the outcome they want to achieve. When you care about “being nice,” you’re essentially saying, “The needs of my team as a whole don’t matter as much as their perception of me as an individual.”

Instead of seeking to be nice, we should seek to be honest, rigorous, and consistent.

Or even better, we can seek to be nice and honest, nice and rigorous, nice and consistent. One of my favorite books, Crucial Conversations, discusses how being nice and being honest are not mutually exclusive. You can be both. The best leaders embrace this duality.

Let’s just stop being so damn focused on being only nice.


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.

The Little Trade-Offs

What seems small to you, as a leader, is not small to your team.

I was running a leadership training a few months ago, when a CEO said this to me…

“I think I know why it’s so easy to become a bad manager, even when we don’t mean to be: It’s because of the little trade-offs.”

I nodded and smiled. I knew exactly what he meant by “the little trade-offs.” I’d made so many myself as a leader, across my own career.

The little trade-offs are the moments when we succumb to what feels most pressing in front of us, at the expense of what our company needs down the road to be successful. We swap “The Thing That Will Help The Team in the Long-Run” for “The Thing That Needs To Be Done Right Now.”

As a leader, we make a dozen of these little trade-offs every week (if not every day!) We negotiate in our heads: “I need to finish this critical project, so I’ll postpone my one-on-one meeting with this employee. We can talk next quarter.” Or, “I need to be heads down on selling to this new client, so I don’t have time to explain the recent company changes. We can announce them later.

“Next quarter.” “Later.”

In the moment, the little trade-off seems like the right one make. Executing on “The Thing That Needs To Be Done Right Now” feels like the top priority. It’s what will pay the most dividends. And when it’s such a little trade-off, how much does it really matter?

Well, here’s the rub: Little trade-offs are not so little. You might make just one or two, in the beginning. But when you’re stressed, busy, and operating on tight timelines, the frequency of those little trade-offs inevitably increases. The little trade-offs you make as a leader become big trade-offs over time.

Consider these seemingly “little” trade-offs:

  • You choose to respond to an investor’s message within 24 hours — but don’t respond to a team members’ email or message for days (or weeks) on end.
  • You choose to be out on the road marketing the company’s new vision to potential customers — but don’t take the time to communicate the vision to the rest of the company.
  • You choose to actively ask a client for feedback and how your product can improve — but are always late to deliver an employee surveys or hold one-on-ones to solicit feedback on how the company can improve.

These little trade-offs say: “I value investors over my team. I value my potential customers over my team. I value my current customers over my team.” These are not little trade-offs. They’re big.

Over time, the little trade-offs reveal your true preferences as a leader and the basic underlying assumptions you hold. It becomes clear who and what really has a hold on you, and where your interest lies. For your team, the little trade-offs you make speaks volumes to them, more than any stirring inspirational speech or pay increase you give. It’s the little trade-offs that they’ll most remember.

No wonder it’s so easy to become a bad manager. Our little trade-offs pile up. Rather than being the exception, they become the rule.

How many more little trade-offs are you willing to make?


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 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 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.

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.

Knock out a quick win

The smallest action as a leader can have the biggest impact.

“I had no idea it mattered so much.”

A CEO said this to me about a year ago. I’d run into him at a conference. As we sat down at lunch together, he shared something that had happened to him recently…

A few months prior, he had asked his team a question through Know Your Team (they’re a happy customer!). The question was:

“Would you like a new office chair?”

The CEO initially thought the question was a little silly, to be frank. Did office chairs really matter? He doubted anything meaningful would come of the question, but he decided to ask it anyway.

Turns out, every single person in the office (they’re about a 14-person company) responded with, “Yes, I’d like a new office chair.”

Not only that, but many of them wrote lengthy, in-depth responses about how unhappy their chairs were making them — how it hurt their lower backs, how it kept them from concentrating and focusing on their work.

“I was shocked,” the CEO told me. “Something I thought was so small, was actually pretty big.”

So he decided to do something about it. The following day, the CEO asked everyone to pick out their own office chairs via Amazon or another site online. The chairs got shipped to the office the next week. Everyone spent a few hours all together during one afternoon, assembling their new office chair, laughing and joking with one another.

To the CEO’s surprise, it became a bonding event. He described:

“That single moment alone — getting people new offices chairs — boosted morale in the company more than anything else I’ve tried. The energy of the office has completely shifted since then.”

He continued:

“I’ve spent tens of thousands of dollars on training programs and all sorts of employee engagement initiatives… and office chairs was the thing that did it?!”

The CEO couldn’t help but laugh. He never expected that acting on something so small would make such a big difference.

But it did. And it makes sense.

Taking action on something small is the single most effective way to increase morale in your company. When you do something that an employee suggests, you’re literally sending the message: “I want things to be as YOU would like them to be.” That’s powerful. Actions truly speak louder than words in this case.

It may sound obvious, but we often forget this as leaders: People share feedback because they want some form of action taken. No one is saying they’d like a new office chair just for the sake of saying it — they’d like the issue addressed somehow. Doing something (even if it is just getting new office chairs) reinforces that you’re listening as a leader, and encourages folks to speak up and be honest with you in the future.

Consider it a “quick win.” No matter how small, it makes a real difference.

Is there something small that was requested by an employee, that you haven’t gotten around to yet? Knock out the quick win.

Is there a decision that you’ve been sitting on, because you didn’t think it was that important? Knock out the quick win.

Employees value responsiveness. They’ll feel encouraged that their words led to action. That momentum will have a positive effect on morale.

Even if it’s office chairs, it’s a quick win. Knock it out.


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.

Close the loop

You can’t just make the call — you’ve got to explain it.

Leadership is about making the call.

Or, at least that’s what we seem to think.

We seem to think leadership is about making the complex decision. As captain of the ship, you survey the seas — what your board is telling you, what your customers are telling you, what the market is telling you, what your employees are telling you — and steer the ship in a certain direction.

Sure, that’s part of leadership.

But the other part is explaining to your crew why you’re headed in that direction in the first place. Making the call is only half the battle — the other half is communicating the call.

We don’t always do this as leaders.

We forget to pull back the curtain and explain why we’re staying the course. We forget to share why we’re not acting on some feedback received. We forget to say how a certain decision came to be.

Leadership is making the call… but explaining the call, too.

Explaining why you’re not doing something — or what I like to call “closing the loop” — is one of the most effective ways to cultivate an open, honest work environment.

You can pose all the questions you want in surveys, have one-on-ones with each of your employees, gather their input at an all-hands meeting… But it’s all moot if you don’t close the loop and say what you’re doing or not doing with it.

If you receive a piece of feedback that isn’t practical or doesn’t align with the company’s direction, tell your employees that. Expose your decision-making process. If you don’t, employees will wonder, “What ever happened to that idea I suggested?” They’ll assume that you’re not open to receiving new ideas, and they’ll hesitate to bring up feedback the next time around.

I remember speaking with a CEO earlier this year, and she told me how she’d hired an external consultant who conducted an culture survey with her team. However, she didn’t tell her employees what she was going to do with the responses, or how it was going to guide any of their leadership team’s decisions. She had the survey deployed. And then, silence on her end as the CEO.

The result wasn’t good. Employees saw weeks go by, and wondered what happened to the survey responses. They felt left in the dark, and confused about what was going on. The CEO eventually heard through the grapevine from an employee that some folks were worried that they were gearing up to fire a bunch of people — which wasn’t true at all!

She had just been so focused on trying to digest the survey results as the CEO and create a plan of action, she’d forgotten to tell her team that’s what she was doing.

Instead, her employees had assumed something completely different when they didn’t hear from her about it.

Not closing the loop was costly for this CEO. She had to do some damage control, and rebuild trust with her team. She had to state clearly: “Here’s how the leadership team is processing the information, here’s how we want to use it, and we’ll let the team know on X date when we move forward.”

Hindsight being 20/20, this CEO wishes she would have better explained her call, instead of just being heads-down and in-the-weeds trying to make the call.

She wishes she’d closed the loop.

Let’s all learn from this.


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.

8 things remote CEOs do differently

If you’re thinking of going remote, here’s what successful remote leaders do…

Earlier this month, I spoke with a CEO who’s looking to transition her company to become remote in the upcoming year. I could tell she was hesitant — perhaps even nervous about it. She’d never run a remote company before.

She asked me:

“Claire, what do CEOs of remote companies have to do differently?”

“Do I need to shift some of my attitudes or behaviors?” she elaborated. “What do I need to do as a remote leader to make sure we’re as successful as when we were co-located?”

I had to pause and think about her questions for a minute.

Even though I’ve been a CEO of a remote company for the past almost four years, I’d never explicitly thought about the difference between what a remote CEO requires vs. what a co-located CEO requires. But when posed the question, I realized there are certain things I deliberately focus on as a remote leader. And, I’ve noticed other CEOs of remote companies focusing on similar things, too.

This isn’t to say that co-located CEOs are a world apart from remote CEOs — it’s just to say as a remote CEO, you cannot survive without doing certain things. You have to do things a little differently.

Based on what I personally strive to practice and what I’ve observed from other CEOs who lead remote companies, here are 8 things that remote leaders do differently…

Write it, don’t say it.

As a remote CEO, I spend 90% of my day writing. Sure, I’m writing blog posts, notes to prospects and customers etc… But I write a lot to our team. I’ll write up our strategy around business development, how we’re doing financially, or a new experiment we should try with marketing. I’ll riff on a new product concept or critique a customer service approach with a co-worker — all in writing. If we were a co-located company, most of this stuff would happen in the form of meetings or chatting someone up by their desk. Or maybe I’d pick up the phone if the person was on a different floor. But in a remote company? You write it out.

“Being a good writer is an essential part of being a good remote worker.” — Jason Fried & David Heinemeier Hansson, co-founders of Basecamp

Jason and David, the co-founders of Basecamp, espouse this in their best-selling book, Remote. But being a good writer is not just an essential part of being a good remote worker — it’s required for being a good remote leader as well.

I’ve observed this firsthand in the way that Jason and David both lead Basecamp, as a company. I’m looped into their all-company Basecamp HQ Project, and I remember being floored when I first saw how Jason wrote up a new idea he was introducing. His written message was crystal clear, well thought-out, and succinct. In other companies, I imagine the same message might get communicated at an in-person meeting — more off-the-cuff, haphazardly, a little all over the place. Here, I saw the power of clear writing as a means to get everyone on the same page, articulate a complex thought, and not waste a bunch of people’s time. Great remote leaders understand this, and utilize writing as a tool.

Commit, don’t dip a toe in.

You can’t half-ass running a remote company. I’ve noticed this in watching other CEOs try to transition their company into becoming a remote company… They only let a select few people work remotely, or they don’t make writing things up a priority, or they don’t make what’s going on in the company accessible to their remote team members. That doesn’t cut it. The remote folks get treated like second-class citizens. Over at Help Scout (a Know Your Team customer, no less!), their CEO Nick Francis says exactly this when talking about their remote culture of 60+ employees world-wide:

“A friend and investor in our company, David Cancel, once told me that you have to choose remote culture or office culture and stick to it, because there is no in between… Trying to optimize for both will likely result in remote employees feeling like second-class citizens.”
– Nick Francis, CEO of Help Scout

Similarly, Help Scout’s Head of People Ops Becca Van Nederynen shared that, “You can’t dip your toe into remote work, it requires 100% commitment.”

At Know Your Team, there’s no way we’d be successful as a remote company if it was just something we tried out part-of-the-time, or only allowed some employees to partake in. Someone, at some point, would have been left hanging. I’ve found being 100% committed to remote work from the get-go has been an advantageous choice to make as a CEO.

Respect the quiet.

Effective remote CEOs understand how quality work happens: People need quiet, uninterrupted time to get things done. That’s how people get into a state of “flow,” which is crucial to thinking creatively or building something from scratch. Remote CEOs recognize this, respect this, and encourage this. Paul Farnell, Co-Founder of Litmus (also a wonderful Know Your Team customer), embodied this when he wrote:

“It’s more important to give employees quiet time than it is to cram them into an open office.”— Paul Farnell, Co-founder of Litmus

This sacred “quiet time” that remote work enables is possibly the biggest reason I personally love being at a remote company, myself. I can’t imagine Know Your Team being co-located and getting even half the amount of stuff we get done today. I attribute the uninterrupted periods of “quiet” time as to why we can be so small as a team (just 2 people!) supporting over 15,000 employees in 25 countries. As a remote CEO, you must embrace and respect the quiet.

Communicate well, communicate often.

Communicating as a remote CEO isn’t just about writing — it’s also about how well and how often you’re communicating. While communication is critical for CEOs who have co-located companies, the importance of communicating well is amplified in a remote company. As Jeff Robbins, founder of Lullabot (another fantastic Know Your Team customer), has said:

“If you don’t communicate well at a distributed company, you don’t exist.” — Jeff Robbins, Founder of Lullabot

In other words, if you don’t say or explicitly communicate something as a remote CEO, your team has absolutely no idea what you’re thinking. Unlike co-located CEOs who might rely on small talk or one-off conversations to gage the pulse of an employee or relay an idea to, remote CEOs must be much more intentional about communicating.

Relatedly, communicating your company’s values becomes even more significant in a remote company. As a remote CEO, you can’t rely on your body language, tone of voice, or physical office relics to communicate values. You have to explicitly state them over, and over, and over. Wade Foster, CEO of Zapier has highlighted this, saying: “You really need to set the values of what your company is going to look like. The high-level things that you care about.”

This sometimes means over-communicating. In her research, Mandy Brown, co-founder and CEO of Editorially and an editor of STET, found that, “Perhaps the most persistent bit of advice I gathered — and in some ways the most counterintuitive — is the need for remote teams to over-communicate.”

As a remote CEO, I definitely default to over-communication. If I’m unsure of something, I ask questions about it. If I’m wondering if a team member understands what I mean, I share greater detail and context. This isn’t to belabor the point or to create extra work for myself or others. Rather, communication is the oil of the machine in a remote company. Without it, things simply won’t run.

Know exactly who to hire: Self-directed, highly-empathetic people.

Jason and David of Basecamp have famously talked about hiring “managers of one.” Other leaders of remote companies advocate for the importance of self-driven folks. Becca of Help Scout has made clear that remote leaders should hire people who are “are mature enough to work well without a ton of structure.” Jeff of Lullabot echoes this in saying, “We need people who capable of thinking about the big picture and self-managing to some extent.”

Here at Know Your Team, we not only seek out self-directed people when we hire — we look for folks with high degree of empathy. People who don’t take things personally, genuinely care about others, and have a deep, intrinsic desire to help. Wade of Zapier describes this necessary empathy well:

“We like folks who have a lot of empathy and are really good, just helpful people because you’re working in Slack and in text all day. You need to be able to empathize when maybe a sentence doesn’t come off quite right, or whatever, you’d be like, oh, I trust that they had good intentions here, this wasn’t meant to be, you know, harsh to me or whatever right. Those are important values that we have that lend themselves well to remote environments.” — Wade Foster, CEO of Zapier

While c0-located companies may value self-direction and empathy in new hires, at remote companies they are an absolute must. As a remote CEO, it’s imperative to discern for these two characteristics while hiring.

Trust your employees… for real.

As a remote CEO, I couldn’t operate day-to-day if I didn’t trust my employees. If someone goes out and runs to the grocery store in the middle of the day… so what? If someone takes the afternoon off to go watch their kid’s school play… so what? In fact, it’s great that they get to do those things, live their life, and get work done too. It doesn’t matter how many hours are being put into the work or when the work is being put in. All that matters are the results — and I trust our employees find a way to make the results happen.

Leon Barnard, a UX Designer and Writer at Balsamiq (another Know Your Team customer we are proud to serve), talked about how their CEO trusts their employees:

“Our founder and CEO, Peldi Guilizzoni, shows a lot of confidence and trust in us. I would guess that we all actually work more effectively than we did in previous jobs where the most important thing was “looking busy” for the boss… Being so distributed, we couldn’t function without valuing trust and autonomy. Peldi doesn’t micromanage. At this point he couldn’t, even if he wanted to.” — Leon Barnard, UX Designer and Writer at Balsamiq

Paul of Litmus put it succinctly: “Trust your team… Work only gets done when you allow people to make mistakes.”

Have a strong, hands-on onboarding process.

Remote CEOs readily acknowledge a key challenge when hiring folks who aren’t all in the same physical place: Getting up to speed as a new employee is key. This means giving new hires the exposure, resources and support they need to be successful. To do this, remote CEOs often focus on having a strong, hands-on onboarding process that’s often partially in-person. Wade of Zapier, explains how they onboard new hires:

“AirBnOnboarding, which when we hire folks within the first month, we actually do like to have them spend a week in person out here in the Bay Area. So we’ll rent an Airbnb, we’ll bring their manager out here, them out here and then spend a week working alongside them.” — Wade Foster, CEO of Zapier

At Help Scout, they give the new hire a buddy — or a new “work best friend” as they like to call it. You can read a wonderful in-depth write up of how they onboard folks here.

Find ways for people to interact who usually don’t interact.

Fostering a sense of connection across the company is a vital part of your role as a CEO — whether you are remote or not. There is literally no one else whose job it is in the company to unite people and ensure they feel they’re heading in the same direction. Doing this in a remote company is admittedly more challenging than in a co-located company where everyone is physically in the same place, bumping into each other, or at the very least, seeing each others’ faces.

Paul of Litmus emphasizes the importance of finding ways to “make time for socialization.” He describes at Litmus how “a few times a year, we have company get-togethers and smaller teams meet in-person more often. Week to week, we get Coworker Coffees, drink beers on Skype, and play video games online. And we invite local employees to the office every Thursday.”

Most remote companies host some sort of yearly or a few-times-a-year meet-up. At Know Your Team, we try to get together at least twice a year in-person. Balsamiq is known for their all-team retreats that focus getting everyone together to have a good time. In addition to in-person meet-ups, Buffer has helped people get to know each other through personality tests, and Help Scout organizes 15–30 minute coffee breaks between randomly assigned team members called Fikas.


Now, there are plenty of CEOs who are not remote that do many of the things above…which is great! However, when you’re a remote CEO, these 8 things become do-or-die. Don’t do them, and it’s likely your company won’t last as a remote one.

When you’re a remote CEO, you can’t afford to not be a good writer. You can’t afford to not know exactly who to hire. You can’t afford to not trust your employees.

If anything, being a remote leader tests you as a leader in all the right ways: It forces you to respect the quiet, uninterrupted periods of time, communicate well, and have a strong onboarding process in your company.

If you’re are considering the leap to become a remote company, keep these 8 things in mind as a leader. I know I’ll be sending this post over to the CEO who’s thinking about going remote, myself 😊


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.