How to have an honest, effective one-on-one meeting with an employee

Here are six ways to get employees talking about what they really feel (and the questions to ask employees for feedback)…

“I can handle the truth. I’m pretty tough, Claire.”

My CEO at the time told me this during our one-on-one about five or so years ago. The year was ending, and he wanted to know what the company could do to improve, how he could improve as a leader — and he wanted to know the truth of what I actually thought.

Yet despite him saying he could “handle the truth,” I couldn’t bring myself to tell it to him.

Truth was, I wasn’t confident in the company’s overall direction. And I was troubled when I learned a few employees felt they were treated unfairly in the company… But it felt futile to mention these things. I couldn’t imagine that our CEO would take my feedback to heart and change anything in the company. If anything, I could more easily imagine that I’d provoke a negative reaction from him. Telling him the truth just didn’t seem worth it.

I’ll never forget that feeling of holding something back — choosing not to vocalize what I was thinking because I felt nothing in the company would change. To be clear: I’m not proud of my silence. Now knowing what I know about giving feedback to a manager, I wish I’d spoken up. Today as a CEO myself, I can only imagine how utterly frustrating it was for him to have that one-on-one with me… and then a few months later learn that I was leaving the company.

Having experienced this, I’ve thought deeply about the one-on-ones I do with my own team here at Know Your Team. I never want a teammate of mine to feel how I once did on the other side of the table. And I don’t want to be like my former boss, blindsided by how an employee is actually feeling.

To encourage honest responses during a one-on-one with an employee, here’s what I keep in mind…

Make empathy your mission.

Every time I have a one-on-one, I have a single mission: to understand how the other person is feeling. Everything else comes second. I don’t use the time to focus on critiquing an employee’s performance, nor do I use the time to get a status update on a project (those are separate, secondary conversations). A one-on-one is invaluable, sacred time to uncover the truth of how an employee is actually feeling.

When you make empathy your mission, the entire landscape of the conversation changes. You start listening more. You start asking more thoughtful questions. You start to level with employees, admitting you don’t have all the answers. Employees notice when an effort is being made to empathize with them, rather than pass judgement or get your own message across. The one-on-one becomes less intimidating to an employee. And when an employee is less intimidated, they’ll be more honest with you.

I’ll oftentimes make my mission of empathy clear upfront during a one-on-one to further diffuse any sentiment of intimidation. For example, I’ll say: “Today is for me to listen and truly understand where you’re feeling on things — that’s it. This isn’t a performance review or status report. This conversation is for me to understand what I can be doing to make this the best place you’ve ever worked.” When you explicitly let your employees know that empathy is your mission, you give them consent to tell you something that they might not have told you otherwise.

Ask questions to uncover two things: tension and energy.

To get to the bottom of how someone is feeling — particularly the negative stuff — I’ll ask questions around specific moments of tension, and specific moments of energy. Specific moments of tension are situations when someone felt angry, frustrated, bored in, etc. Specific moments of energy are situations when someone felt uplifted, excited, and motivated. You want to uncover what these situations have been so you understand how to create more positive situations for an employee that give them energy, and how to avoid and resolve the negative ones that create tension for them.

When you ask someone about specific moments when they felt disappointed, confused, proud, etc. at work, they can reference their emotions to something real that happened, not something ephemeral or imagined. For example, ask the question, “How’s it going?” and nine times out of ten your employee is going to say, “Things are fine” or some other vague, over-generalized response. You’re never going to hear the real stuff. Versus, if you were to ask: “When have you felt frustrated in the past year?” you’re asking an employee about a specific moment, situation, and emotion. You’re forcing them to think in more literal, concrete terms, and giving them permission to talk about how they feel about working at your company (something that doesn’t always happen all too often in the workplace).

Here are some examples of questions you can ask an employee around specific moments of tension so you know what to avoid:

  • When have you been frustrated in the past year? What can I do to help make things less frustrating for you, or get out of your way?
  • When have you felt dejected or demoralized this past year? What can I do to better support you, and make sure that’s not the case going forward?
  • When have you been disappointed with a decision or the direction that the company has gone in the past year? Was there an opportunity you think we squandered? Something you think we mishandled? How would have you preferred we proceeded?
  • When have you been annoyed, peeved, or bothered by me and something I’ve done as a CEO? Why? What would be helpful for you for me to change my behavior going forward?
  • When have you felt bored in the past year? How can I create situations going forward so you don’t feel that way?
  • When have you felt stressed or overworked in the past year? What can I do to create a better work environment going forward so you don’t feel that way?

Notice that when I ask about a specific moment of tension, I follow up with a question about what I or the company can do going forward. This way, your one-on-one doesn’t devolve into a complaining rant, but becomes a productive conversation about how to resolve, avoid, or fix a tension point in some way. This doesn’t mean you need to solve the issue right then and there (very rarely will you come up with a resolution on-the-spot). But a follow-up question about what future action can be taken will get your mind and theirs thinking in a constructive direction.

Here are some example questions you can ask around specific moments of energy — the positive stuff — so you know what to create and do more of:

  • When have you felt excited about what you’ve been working on in the past year? What can I do to provide you with more opportunities so you feel that way?
  • When have you felt most proud about being a part of the company this past year? What can I do to make sure that we do things that continue that feeling?
  • When have you felt most motivated about the work you’ve been doing? What can we do to create an environment so you feel like that more often?
  • When have you felt most “in flow” or “in control”of what you’re doing during the past week or so? What can we do to give you more space and time to feel that way?
  • What have you been wanting to learn more of, get better at, and improve on? How can we here at the company support you in doing that?
  • When have you felt that this company was one of the best places you’ve ever worked? How can I make this place the best place you’ve ever worked?

If this feels “touchy-feely” and not really your style because you’re talking too much about emotions — I understand. Try peppering just one or two questions about a specific moment of tension or energy into your next one-on-one. I guarantee those one or two questions alone will shed more light on an employee’s level of morale, more than anything else.

And, keep in mind that touchy-feely isn’t a bad thing. The way employees feel about their work affect how well they do their work.

Admit what you think you suck at.

When you’re asking employees about specific moments of tension or energy, sometimes the specificity of the question alone isn’t enough to encourage someone to respond honestly. Employees are especially wary of divulging or pointing out something negative, and may need an extra nudge. Why? Because there’s an inherent power dynamic between employees and a business owner. You need to figure out a way to disarm it.

The best way to overcome this power dynamic is to admit what you think you suck at. As you’re asking questions, reveal your fallibility. For example, if you pose the question: “What do you think we can improve on as a company?” and you’re getting a bit of radio silence on the other end, share what you’re struggling with or feel unsure about. You can suggest to them, “I think ___ could’ve gone better… what do you think?” or “I think I could probably be better at __ . Would you agree or disagree?” By showing vulnerability, it gives confidence for an employee to share something that might be perceived as negative.

Explain why you need their input.

One of the keys to making it safe for your employees to be more honest with you is explain why their input is valuable. I often forget to do this myself. But I find that when I do, it shows an employee that I’m not asking questions out of vanity or to “check a box.” Rather, I’m explaining how their feedback impacts the success of the company, and their own career development. Professor Amy Edmondson who coined the term “psychological safety” in workplaces recommends to “make explicit that there is enormous uncertainty ahead and enormous interdependence.” In other words, because the future is so uncertain and there’s much to still figure out, everyone’s opinion and input matters. For instance, you could say something like this to your employee: “Hearing your thoughts really matters to me because we haven’t figured ___ out. There’s so much unknown, and we need your input in order to get to where we want to go.”

Don’t get defensive.

When someone does respond frankly to your question, you’ll want to make sure you do not get defensive. Defensiveness is a killer of an open culture. The minute you get defensive you’re sending the message to your employee: “I actually didn’t really want to hear that.” And the next time you have a one-on-one, that employee isn’t going to speak up honestly. So when someone brings up a tough topic, watch yourself. Do you get testy and a bit defensive? Or do you calmly listen and ask insightful follow-up questions? Your reaction will be their benchmark of whether they’ll feel comfortable bringing up these hard conversations in the future.

Talk less.

Do not try to rebut every comment that is made. Do not give excuses on how swamped you’ve been. Ask your question succinctly. Listen. Take notes. Thank your employee for bringing something up, and say you’ll think on what they said and get back to her or him about it. If you catch yourself replying to an employee’s reply, reel yourself in. Remind yourself that you’ve made empathy your mission. That means you need to talk less. When you talk less, you create the space an employee needs to tell you the truth of how she or he is feeling.


This isn’t easy. Every time I do a one-on-one, I still feel a little nervous when I ask about a specific moment of tension… And I always take a deep breath to keep myself from reacting defensively when they share their answer. Navigating a one-on-one well requires discipline and a dose of courage.

Most of all, it requires a real desire for the truth. What fuels me to seek out honesty in a one-on-one is because I know that seeing the current reality for what it is — how our business is doing, what our employees think of the company — is the only way I’ll build a better company and become a better leader. Without knowing the truth, I’m squandering a chance to move the company forward, or even perpetuating a valuable employee to leave the company.

Holding an honest one-on-one with an employee is one of the few yet most effective ways to get that truth. Let’s double down on doing it well.



P.S.: If you did indeed enjoy this piece, please feel free to share + give it ❤️ so others can find it too. Thanks 😊 (And you can always say hi at @clairejlew.)

Why you should argue with your employees and embrace internal team conflict

Yes, it can feel draining and counterproductive, but here’s why arguing and dealing with team conflict can be good things…

“Did I hire the wrong person?”

I remember thinking that right after I’d gotten into a heated argument with our programmer, Matt, for the very first time.

This was back in 2014. We’d recently hired Matt at Know Your Company (now today Know Your Team.) A few weeks into his time with us, I disagreed with how he was handling our support requests. Matt had replied quickly to a few CEOs… but in my opinion, it was too quick. I didn’t think he’d answered their concerns thoroughly enough. We ended up arguing about what was more important in customer service: speed or quality.

Man, it was frustrating. To feel like your teammate is not on the same page as you. To feel the tug, the push, the pull, the back-and-forth of opinions. We got into it. No yelling or name-calling or anything… but it was an intense exchange.

At the time, I thought: “Uh oh.” If we’re arguing this early on in our time together, maybe this wasn’t going to work out. Were we irreparably incompatible? Perhaps I shouldn’t have even hired him, in the first place?

Then I reminded myself: Arguing is a good thing.

Why? Arguing is a sign that you care. You care enough to have strong opinions about how to make the company better. You’re willing to bring those opinions forward, and battle it out for the best one.

Arguing is how you vet ideas and ensure you’re not submitting to groupthink. Arguing is how you make the best decisions.

In his well-known book, Good to Great, author Jim Collins echoes this sentiment:

“All the good-to-great companies had a penchant for intense dialogue. Phrases like ‘loud debate,’ ‘heated discussions,’ and ‘healthy conflict’ peppered the articles and interview transcripts from all the companies.”

The key is to argue well. To put forth your point not because you want your point to win, but because you want the best point to win. It’s not about ego — it’s about the outcome. You want the outcome that’s best for the company, plain and simple. It can’t be about anything else.

Whew, is this hard to do, let alone remember. When I’m arguing with someone, it can feel negative and draining. My energy feels like it’s just wasting away…

But then I remind myself that what’s worse is the opposite: I don’t want Matt agreeing with me all the time. I don’t want Matt to stifle his thoughts or bite his tongue in exasperation. It’d mean he’d feel like it wasn’t worth the effort to share his opinions. It’d indicate he’d given up and checked out.

Constant agreement is a sign of apathy. When your team is agreeing with you all the time, it means someone doesn’t care enough to bring her or his opinion forward. Someone doesn’t care enough to challenge existing assumptions with a contrarian viewpoint, or to let you know that something is bugging them. She or he will just keep it inside…and it’ll fester, bubble up, and later explode.

That’s when you have a real problem on your hands.

Constant agreement is also an indicator of something deeper at play: fear and futility. If you find yourself in an echo chamber, it’s often because your employees have grown to…

  1. Fear the repercussions of arguing with you. For instance, they’re worried about being viewed as “difficult to work with,” or even are scared about losing their job.
  2. Feel it’s futile to speak up in the first place. If they were to argue with you, they believe you’d simply brush their reasonings aside. So why’d it be worth arguing, at all?

Fear and futility are in fact the top two reasons why employees don’t speak up at work. And so the lack of arguments could be pointing to broader malfunctions in your company where honest conversations are not happening as often as they should.

Pay attention to this. The absence of arguments should warn you that something more is brewing below the surface. Whether it’s apathy, fear, or futility, you should be concerned if your employees are not arguing with you… rather than the other way around.

I’d much rather have an employee who argues with me, than an employee who nods their head, blindly agreeing with me. I’m lucky that Matt is the former.

After all, you’ll never avoid arguing. Arguing is a natural by-product of humans being humans. No two humans are 100% alike, so no two humans will ever 100% agree with one another. Put two people in a room and they will always end up arguing at some point.

Don’t let an argument demoralize you. And don’t succumb to the temptation to avoid it for the sake of saving perceived time and energy in the short term.

The conflict that comes with arguing is worth it. If you want the best ideas to surface and the best decisions to unfold, you have to be willing to face that friction. Embrace the arguing, and focus on doing it well.


How to handle negative feedback we don’t want to hear

Keep this one thing in mind when you’re given negative feedback in the workplace.

What happens when someone tells you something you don’t want to hear?

Hearing something negative about yourself is a hard thing to swallow. Especially when you disagree with it.

I’ll never forget when this happened to me most vividly about four years ago. I sat down to get coffee with a mentor of mine.

To my surprise, she expressed how she was disappointed in my lack of follow-through with two people she had introduced me to. Then she said this:

“Because of that, Claire, you come across as fake.”

Ouch.

I felt my stomach flip. I felt my temperature rise. I knew I had followed up with them. And I knew I wasn’t a fake person. Should I say that? Should I defend myself?

Instead, as silly as it sounds, I breathed in. Then I counted, 1–2–3. And then I breathed out.

I realized that regardless of what I believed to be the truth, what she told me was true to her. And that’s what mattered.

There is always a reason that someone chooses to believe something is true. It’s not as though she (or her contacts) was crazy or delusional. There had to be a reason.

After all, it could be pointing to a larger issue…

Maybe she was right?

Maybe this was a sign that I was taking on too many meetings. Maybe I was brushing people off. Maybe I was caught up in the “go go go, gotta keep moving,” and that I wasn’t investing the time and thoughtful consideration with each person I spoke with.

Maybe I was coming across as fake.

Even though I know I’d followed up with her contacts, that wasn’t the point. The point was that I had a real opportunity to learn, change, and improve. It’s not about what’s true to me. It’s about what’s true to her.

So instead of trying to change her mind — instead of trying to change what was true to her — I decided to try to change my own behavior. I didn’t want to spend energy getting worked up, being defensive. I wanted to use that same energy to become better.

I told her that I was sorry. Really sorry. That I thought I had followed-up. But that it didn’t matter either way. I told her that her feedback caused me to reflect on how I was treating and handling each interaction I’ve had. I was determined to do things differently moving forward.

We’ve touched base since then, and it’s been rewarding to reflect on how much I’ve improved, even just a few weeks after that conversation happened. I immediately started investing more energy and thoughtfulness into every meeting I scheduled, every conversation I had. I meticulously tripled-check my follow-through on things I’ve promised to others. Years later, to this day, her words stick with me.

Looking back, I’m grateful I fought my urge to rebut her feedback in that moment. If I hadn’t, there’s no way I would’ve changed my actions for the better as quickly as I did.

Keep this in mind the next time someone gives you feedback you disagree with: It doesn’t matter if what they’re saying true to you — what matters is that it’s true to them.

The sooner you recognize that, the sooner you’ll benefit from it.

Fun! We’re featured in Glossier’s cover story in Domino Magazine 🎊

We’re in here! ❤️

I’m a big fan of Glossier.

This beauty company’s mission is to democratize beauty, per the words of their founder + CEO Emily Weiss.

I’ve always loved that ethos… not to mention their products 🙂

I wear their Haloscope highligher every day, in fact. So I was thrilled to learn that their CTO Bryan Mahoney wanted to use Know Your Company at Glossier earlier this year. (He’d previously used Know Your Company at Dynamo, a digital agency he founded.)

But what I was most blown away by is that this wonderful customer of ours happened to mention us as part of their cover story in Domino Magazine this month. You can read the excerpt of Glossier’s cover story here:

Hehe “hip happiness-in-the-workplace startup”… We’ll take it!!

We’re honored to play a small role in helping Glossier maintain its fun, fresh company culture — especially as it grows.

Y’all are the best. Much thanks and ❤️!


Looking to ask some of the same questions Glossier is asking in your own team? Give Know Your Company a shot today — it’s completely free for two weeks, and I guarantee you’ll learn something new during that time 😊

New: Free 5-Lesson Course on How to Get Honest Feedback from Your Employees

Short on time? Here’s a handy way to learn the basics of building an open, positive company culture.

Whew, what a three years it’s been!

We’ve spent the past three years observing tens of companies, having conversations with more than a hundred employees and managers, analyzing hundreds of questions answered by 15,000+ people through Know Your Company… All to uncover exactly how to get honest feedback from even the most introverted employee.

From these three years of research, we’ve boiled it down to the basics. We want to share the essentials on what it takes to build an open, honest environment for your employees.

Today I’m launching our 5-Lesson Course on The Essentials of How to Get Honest Feedback from Your Employees. Each lesson is written by me, takes 2 minutes to read, and arrives straight in your inbox every few days.

It’s just what you need to know, and nothing more. So if you’re short on time, it’s the perfect way to learn how to create an open, honest workplace culture.

Not to mention, it’s completely free 🙂

In the course, you’ll learn…

  • Lesson 1: Why employees don’t speak up.
  • Lesson 2: How to create a safe environment for for feedback.
  • Lesson 3: The one word to unlock feedback.
  • Lesson 4: The exact questions you should ask to get honest feedback.
  • Lesson 5: What you should do with honest feedback, once you receive it.

I’ll never spam you (I hate spam with a passion!) and you can unsubscribe anytime.

Ready for your first lesson? Sign up here today


P.S.: Think someone else might benefit from this 5-lesson course too? Feel free to forward this post over to them! 😊

Kill the culture of “nice”: This is how you create a positive work environment

“Nice” can be a dangerous thing when it comes to developing company culture.

Does your company suffer from a culture of “nice”?

A culture of “nice” exists when people do not openly disagree with one another. Employees politely bite their tongues when they have a dissenting viewpoint. No one dares brings up a contentious topic during a meeting. Everyone is hesitant to be seen as “confrontational.”

A culture of “nice” occurs when people have genuinely good intentions, but out of a desire to be liked and to not “rock the boat,” they find it difficult to publicly argue with one another. People are not being fake or superficial — they’re just being “nice.”

Being nice is a positive human character trait. I’m not advocating for anyone to be an asshole, to any degree! But when “nice” defines your company’s culture, it’s dangerous.

A company culture of “nice” dilutes the truth of the current reality. You don’t hear bad news until it’s really bad. You only recognize a problem once it’s festered and ballooned into something serious. Your ideas for solutions are contained in an echo chamber. Your decisions become driven by groupthink.

To discern if your company has a culture of “nice,” here are four questions you can ask yourself as a leader…

What happens when someone messes up?

When someone makes a mistake, do other employees avoid telling you directly? Now I’m not suggesting you encourage “tattle-telling” in a company, but the opposite is detrimental to a company. An unwillingness to acknowledge each others’ mistakes contributes to a culture of “nice.”

How long does it take to let someone go?

How much time passes between the moment you’ve decided a current employee is not the right fit for the company, and the moment you tell them? If it’s longer than a week and you find yourself stalling, you’re guilty of creating a culture of “nice.”

Do people bring up failure?

When is the last time someone (other than you) brought up a marketing campaign that fell short, or a product line that was pulled? If your employees focus only on what’s going well and are reluctant to be critical, they could be engaging in a culture of “nice.”

Do people disagree with you in public?

When you ask for people’s opinion on an important issue, do you get passive head-nodding? Or even complete radio silence? If so, people may not feel comfortable voicing their disagreement, and your company may have a culture of “nice.”

How do you kill a culture of “nice”?

Perhaps you answered a few of those questions I posed earlier in a way that made you think, “Hmmm, we may have succumbed to a culture of ‘nice’…” No worries, you are not alone. Many companies end up realizing they inadvertently sacrifice honesty for the sake of avoiding contentious situations.

Companies that have killed their culture of “nice” slowly over time and cultivated an honest, forthcoming culture in its place, do these four things well:

Communicate that honesty and kindness are not mutually exclusive.

One of my favorite nonfiction books of all time, Crucial Conversations, talks about how our reluctance to tell people the truth comes from the fact that we see honesty and kindness as being mutually exclusive. But, they’re not. It’s possible to be both kind and honest. Communicating this with your team is key. For example, in a one-on-one with an employee you could directly say, “I see honesty and kindness as not being mutually exclusive — so don’t worry about if you think you’re being nice or not… I know you are, if you’re simply trying to be honest.

Model the vulnerability you want to see.

A culture of “nice” often takes hold when the team sees the example set from the leadership team. When managers share only their highlights and accomplishments and never admit where things go wrong… their team will never admit where things go wrong either. If you don’t talk about when you come up short, then the rest of your team surely won’t. Encourage your team to feel comfortable coming to you with their mistakes and shortcomings by admitting your mistakes and shortcomings as a leader, first.

Seek out dissent… and respond gratefully and respectfully to it.

Companies that have killed a culture of “nice” seek out dissent as much as possible. They view conflict not as something that needs to be quelled or immediately resolved — but as an opportunity to grow, learn, and improve as a company. Leaders will ask, “What a devil’s advocate point-of-view to the idea I posed?” or “How I might be wrong in this situation?” They actively challenge their own ideas in front of others. And when an alternative perspective is provided, they listen, thank the other person, and consider what they’ve learned from now hearing a contrasting viewpoint.

Don’t sugarcoat or exaggerate.

When things are going well or when things are going bad, leaders in companies where they’ve killed a culture of “nice” tell it like it is. They try to relay the truth of a situation as objectively and honestly as possible. They know if they inflate something to be more than it is, or skirt away from saying how poorly something was messed up… it helps no one.


Building the culture you want — one where people feel safe to come to you with new ideas, tough situations, bad news etc. — takes time. It’s the by-product of doing things consistently and regularly, day-in and day-out. So don’t expect that your entire team’s attitudes and behaviors will change over night. With time and diligence in doing some of the best practices I described above, you’ll be able to kill the culture of “nice” in your company.

 

How to give feedback to your boss

Giving upward feedback is one of the toughest things to do as an employee. Here are some guidelines for giving feedback to your manager or CEO.

When I was an employee, I felt stuck. I had some ideas about how I thought the company could be better… but I had no clue how to give feedback to my boss at the time.

How could I mention these ideas without it feeling like an attack on him? I didn’t want him to think I was arrogant, assuming I could run the company better than him. And I didn’t want him to become defensive, and brush off my ideas outright.

I was torn about what to do. Comments can easily be misconstrued — and in this scenario, it could cost me any good will with my boss, my reputation in company… and even my job.

I decided not to do anything. I didn’t share my ideas with my boss. I ended up leaving the company later that year.

I’m not proud of my silence. Looking back, I often think: What should I have done instead?

Now almost a decade later, after consuming every article, study, and book I could get my hands on, working one-on-one with companies through a consulting practice I started, and serving with thousands of managers as the CEO of Know Your Team… I know exactly what I should have done to give feedback to my boss.

If you’re an employee and you want to give your boss feedback, here are the lessons I’ve learned on what you can do.

Set up a time to talk

The worst thing you can do to your boss is surprise them with information or create a situation where they feel caught off-guard. Instead, you can send over a note to your CEO or manager to set up a specific time to talk with them.

Here’s something you could start with:

Hey [your boss’s name],

I know how much you care about maintaining a strong culture at the company… I have some thoughts / ideas on that I’ve been thinking on lately! Would you be up for chatting sometime? Perhaps we can grab 30 minutes over coffee next week, when things slow down for you? Please let me know! Looking forward to it.

Ask for feedback about yourself

Another way to kickstart the conversation with your manager is to ask for feedback about yourself. This will help your CEO or manager let their guard down, and realize that you’re not looking to blast them. You’re showing you’re open to a two-way dialogue.

For example, you could write something like this to them:

Hey [your boss’s name],

Lately, I’ve been thinking hard about how I can improve in my role. Would love to get some feedback from you and riff on this together. I’ve also been chewing some ideas about the company that I’d love to share with you too, if you’re open to it! Got time for coffee sometime next week?

Just make sure you’re open and ready to hear this feedback about yourself. In other words, don’t be willing to dish it unless you can take it.

Make your intention clear upfront.

When you do sit down to give feedback to your CEO or manager, begin the conversation by making it very clear why you’re wanting to give them this feedback.

For example, let them know: “I’m saying this because ____ matters to me, and it’s something I could see benefitting the company as a whole. And just to be clear, these thoughts aren’t coming from a place of disrespect or mistrust in you or your ability — I completely understand and accept that this is your thing to have the final call on.”

Another way to do this is by reinforcing what you have in common. You’ll want to remind your CEO and manager that you’re on the same team. “I’m only sharing this because I care about the company culture and am worried about ____, and I know that’s something we both care about.”

Acknowledge that it’s only your opinion

You don’t want your words taken as a critique on your boss’s character. Your words are not a definitive stance on their value as a person — and they shouldn’t be interpreted as so. So you’ll want to reinforce that your feedback is coming only from your personal point-of-view. This will show humility on your part, and encourage them to not take your comments personally.

For example you could say: “Keep in mind this is only my opinion and I could be way off here… I thought you might want to know though, regardless, and I wanted to share these thoughts with you for the sake of transparency.”

One last tip: In preparation for this conversation, I’d highly recommend writing down what you want to say beforehand. (I even do this today as CEO when I give feedback to an employee.) Consider… How do you want your boss to feel after you’ve had the conversation? How can you frame what you’re saying to help them feel that way? Articulating the points clearly to yourself first will help make sure you articulate them clearly to your CEO.

Granted, this all is much easier to do in theory than in practice. I remember all too well how nerve-wracking it was to even consider reaching out to my boss like this. But take that first initial step to schedule the time to sit down with them, and you’ll be surprised at how open most CEOs and managers are to hearing what’s on your mind.

Don’t get too hung up on anticipating how your CEO might react. You can never control another’s person’s reaction. You can only control yourself — what you put out into the world, and your own intention behind it. So focus on that. Fear should never get in the way of you sharing something you think could truly benefit the company.

If the content of what you’re trying to express is worth it, there’s only one way to find out how they’ll react: Speak up.

You’ll never know, otherwise. It’s what I wish I would’ve done four years ago.


We’re hiring a programmer

After our best month of sales ever in December, a new spot on our team has opened up…


Dear programmer who cares about doing meaningful work,

If your dream is to grow a product with a small team that already has its legs under them, and have a big impact on a problem that matters, I’ve got some good news for you…we’re hiring a Rails programmer at Know Your Company.

First, a quick introduction.

My name is Claire Lew, and I’m the CEO of Know Your Company. It’s nice to meet you. My company, Know Your Company, is a tool that helps business owners with 25 to 75 employees get to know their employees better. Companies like Airbnb and Kickstarter use Know Your Company each week to improve their company culture.

Our software was originally built by Basecamp (formerly 37signals) in early 2013. Know Your Company ended up becoming so successful as a product, Basecamp decided to spin it off into its own company. In 2014, I became the new CEO of Know Your Company.

Our mission is to help people become happier at work. We believe this happens when people can communicate openly and honestly at work. As the CEO, this is also my own personal mission. I’ve felt the pain of working in a company where Know Your Company didn’t exist. Since then, I’ve made it my life’s work to help others not feel the same way.

So what’s the job?

You’ll be a one-person product team. As our sole programmer, you’ll be responsible for building, improving, and maintaining Know Your Company as a product end-to-end. We’ll riff on feature concepts together, drawing from conversations you and I have had with customers. You’ll uncover the underlying jobs-to-be-done in the situations they’re facing and ensure the concepts we’ve discussed align with our overall vision for the product. Then you’ll take those concepts from sketches to code to production. What you ship will be used by over 12,000+ employees in over 15 different countries every single day.

There’s no project manager, no design team, and no user research team here at Know Your Company. It’s you and me thinking, experimenting, playing detective on how to help CEOs and employees get more out of the product. No marching orders here either — it’s us together deciding what to prioritize, what to focus on, and what to improve.

You will also serve as the primary technical caretaker of Know Your Company. You’ll be our only line of defense when it comes to the stability, reliability, and efficiency of Know Your Company running smoothly.

We’d bring you on first as a contractor, to make sure you enjoy working with us and vice versa. Then if it was a good fit, we’d bring you on full-time. Eventually, we’ll hire another full-time designer for you to work alongside with. As the company grows, we’d continue to build a team around you. And if things worked out well, you would grow into a CTO role.

We recently brought on a Head of Business Development Jess Singer a few months ago. Thanks to her, we just had our record high number of sales in December. With your help, we’re excited to build on that momentum in 2017.

Together, we’d grow Know Your Company to be a tool that improves the lives of hundreds of thousands of CEOs, managers, and employees every day.

Who am I looking for exactly?

I’m looking for someone who works fast and smart. Someone who is a clear thinker and communicator. You write clean, tidy code. While you don’t consider yourself a pure designer, you have an eye for design. You’re always up for learning and becoming better in everything you do.

You know what it means to hustle. It doesn’t matter what you’ve studied (or if you graduated from school at all), or how many jobs you’ve worked at previously. All that matters is what you’ve built. It’s likely you’ve shipped your own product (or several). You might’ve even started your own business (or several!). Throughout your life, you’ve noticed that where other people have failed, you’ve succeeded simply because you stick with things longer than most.

You’re a problem-solver at heart. To you, there’s no greater thrill than building something that helps other people. You love the process of taking an idea that’s just written on a sheet of paper, and turning it into something real and useful. You know what it feels like to be obsessed with what you’re doing…and you can’t wait to feel that again.

You exude humility. You never believe you have all the answers, and are the first to admit when you’ve made a mistake. You’re always eager to teach or explain something in a way that’s simple and friendly to others. In fact, your day is made when you watch someone’s face light up when something “clicks” for them, or when you surprise them by doing a favor that makes her or his life a little easier.

Most importantly, you believe in the vision of Know Your Company. You’ve personally felt the pain of communication breakdowns in the workplace. Or you’ve previously had a boss who you never felt comfortable giving feedback to. Either way, you’re passionate about what Know Your Company stands for, and how we can help as many people as possible become happier in the workplace.

I want to hire the best person for this role — so it doesn’t matter where you’re located. If you’re in Chicago, that’s fantastic. But if not, no worries. I’m open to working with you from anywhere. (Being in a North American timezone is preferred though, given how closely you and I will work together).

I’d love to hear from you.

If you’re interested in working together, please send me an email at claire@knowyourcompany.com. Tell me a little bit about yourself, share your personal story, and include any relevant work and links. Writing samples are a plus too.

This is a unique opportunity to shape a product from the first floor and up, and to help solve a significant problem. If you’re the right person for it, I’d be honored if we got to tackle it together.

Looking forward to hearing from you,
-Claire Lew
CEO of Know Your Company


If this doesn’t sound quite like you, but someone you might know, please feel free to pass along this post them! And, I’d really appreciate it if you clicked the ❤️ below too… That way, someone who might be a great fit will see this, too. Thank you!

PS: You might recall us hiring for this role a few years ago. Matt, our original programmer and first employee, served this role incredibly well and recently accepted a position as a partner at another company that his friend runs. We’re thrilled for him! And, even though of course we’re bummed he’s leaving Know Your Company, we are excited that this role has opened up to bring in a fresh perspective. Matt will be sticking around a bit to help around with the transition, and even is pitching in to help screen applicants for us. He, Jess, and I look forward to hopefully meeting you 😊

New in KYC: Who agrees with who 👍

The most important decision you make as a CEO is where you choose to put your time and energy. Especially when it comes to receiving feedback — how do you know which opinions in the company are the ones that people really care about, and that you need to do something about?

Today, we’re excited to announce a brand new tool in Know Your Company to help you figure out and focus your attention on what matters most as a CEO. We’re calling it Agreements 👍.

Here’s a small preview of what Agreements👍 look like

Here’s how it works…

Imagine it’s Friday. A few days ago on Wednesday, you asked the question, “Are there any benefits we don’t offer that you’d like to see us offer?” through Know Your Company. The results from that question land in your email inbox. You read everyone’s comments and soak in the responses.

Kurt feels the company is paying too much for the benefits you’re offering. Annie suggests that getting a new laptop should be considered a company benefit. You wonder: What do I do with all this? Is Annie the only person who feels this way about laptops? Or do other people agree with her? How about with Kurt’s comment?

Previously it was difficult to absorb, prioritize, and act on these responses through Know Your Company because you’re left wondering if others are agreeing with what’s being said.

Now with Agreements 👍, you immediately learn who agrees with who, so you can better weigh what feedback is most important to focus on and potentially act on.

Starting tomorrow, your employees will be invited to show if they agree with a co-worker. After each response in the Company Question summary email, you’ll see a link to agree:


Then on Monday, Know Your Company will email you and everyone else in the company a report of who agrees with who:


You’ll notice that everyone gets to see this summary of who agreed with who — not just you as a CEO. We purposely designed it this way because we believe it will encourage employees to be more open and honest in their feedback. When an employee sees that their co-worker “put herself out there” and an overwhelming number of people agreed with her candid comment, you can’t help but feel more confident yourself in speaking up and sharing your own opinion next time.

It’s also a way to engage employees who tend to be a little quieter in your company. These quieter folks might not always write an answer to a Know Your Company question, but they can easily get behind a comment, and feel comfortable showing support rather than having to write out a response. Over time, as they observe more of who agrees with who, they might slowly even feel compelled to start writing more responses in themselves.

As a whole, Agreements 👍 is a powerful new way to help you prioritize what to take action on, and further encourage your employees to speak up honestly in your company.

Now obviously, as a CEO, this doesn’t mean you need to blindly obey what the comment is most agreed with. You’ll make the call on whether not something actually becomes implemented.

But knowing who agrees with who gives you the insights to understand where to focus your time and energy. You’ll now know which opinions actually matter and you should pay close attention to. And as a CEO, that’s everything 🙂


Want to learn what feedback you need to focus on as a CEO? Try Know Your Company completely for free for two weeks today. I guarantee you’ll learn something you didn’t know before about your company… AND you’ll save time and energy as a CEO.


We’re hiring a salesperson

After 2.5 years running Know Your Company as a one-person and then two-person company, we’re ready to bring on teammate #3!


Dear salesperson who cares about doing meaningful work,

If your dream is to help more people benefit from a solution that truly makes a difference, and to do it with a small team that already has its legs under them, I’ve got good news for you… we’re hiring a salesperson at Know Your Company.

First, a quick introduction.

My name is Claire Lew, and I’m the CEO of Know Your Company. It’s nice to meet you. My company, Know Your Company, is a tool that helps business owners with 25 to 75 employees get to know their employees better. Companies like Airbnb and Kickstarter have used Know Your Company each week to improve their company culture.

Our software was originally built by Basecamp (formerly 37signals) in early 2013. Know Your Company ended up becoming so successful as a product, Basecamp decided to spin it off into its own company. In 2014, I became the new CEO of Know Your Company.

Our mission is to help people become happier at work. We believe this happens when people can communicate openly and honestly at work. As the CEO, this is also my own personal mission. I’ve felt the pain of working in a company where Know Your Company didn’t exist. Since then, I’ve made it my life’s work to help others not feel the same way.

So what’s the job?

You will be both an architect and a builder of our entire sales process. Today, we help over two hundred business owners and 12,000+ employees in over 15 countries. Your mission will be to double that.

As the architect of our sales process, you’d start off designing a playbook to sell Know Your Company to more small business owners. You’ll take the two-and-half years worth of data we’ve collected and all the learnings we’ve gained from doing almost 500 demos in-person… and transfer that into creating a repeatable, scalable system.

Then, as a builder, you’d execute on this playbook. You’ll qualify the existing leads we have from our self-signup process and engage them meaningfully and efficiently via email and phone. More than a salesperson, you’ll be a resource and helpful guide for them — showing how they can get the most out of the product, and giving them the information they need to decide for themselves whether or not Know Your Company is the right fit for them.

You’ll do outbound outreach to business owners we believe we can help. This includes building lists, cold calling, cold emailing, setting meetings, doing product demos, and following up. You’ll serve as an advocate of the customer, understanding what objections or issues they raise and relaying it back to the rest of the team. You would also do a bit of account management and support.

We’d bring you on first as a contractor, to make sure you enjoy working with us and vice versa. And then if it was a good fit, we’d bring you on full-time. Over time, if things worked out well, you would grow into a Head of Business Development role. The pay will be competitive and increase based on performance.

Together, we’d help more small business owners get to know their companies again, and improve the lives of hundreds of thousands of CEOs, managers, and employees every day.

Who I am looking for exactly?

I’m looking for someone who is both a strategist and an operator — someone who has designed campaigns from scratch, but also relishes the detail of carrying them out. You work fast and smart. You’re an impeccable in-person and written communicator.

You’re an adept problem solver. While others might shy away from the hard work of digging into something unknown and messy, you aren’t afraid to play detective. You eagerly dive into every nook and cranny to figure out what is working, what isn’t, and why. In fact, you’re driven by the thrill of “cracking the nut” and will hustle your way to a solution, one way or another.

You’re a teacher at heart. You love being helpful to others. Lending a hand to someone who didn’t expect it makes your day. People say you’re one of the most humble people they’ve known. You believe you never have all the answers, and you go out of your way to be forthright, earnest, and compassionate toward everyone you meet.

You can strongly relate to our customers, and build trust with them. Ideally, you would have sold to other CEOs in the past (for instance, perhaps you’ve sold an HR service or product previously) or worked closely with CEOs (such as, you’ve been a CEO coach / consultant before)… But, this is NOT a hardline requirement. You simply have the capacity to genuinely care about and provide guidance to the CEOs we are trying to help.

Most importantly, you believe in the vision of Know Your Company. You’ve personally felt the pain of communication breakdowns in the workplace. Or you previously had a boss who you never felt comfortable giving feedback to. Or you were even a manager who was always the last to know something in your company. Either way, you’re passionate about what Know Your Company stands for, and how we can help as many people as possible become happier in the workplace.

I want to hire the best person for this role — so it doesn’t matter where you’re located. If you’re in Chicago, that’s fantastic. But if not, no worries. I’m open to working with you from anywhere.

I’d love to hear from you.

If you’re interested in working together, please send me an email at claire@knowyourcompany.com. Tell me a little bit about yourself, share your personal story, and include any relevant writing samples. (For example, it’d be great if you shared any “wow” emails you’ve written to potential customers peaking their interest or answering an objection).

In addition, I’d love if you shared a 30-second video of yourself. Nothing fancy, just a little “hello” video that you can film yourself on your laptop. It’s important to me to get a personal feel of how you communicate not just in writing, but in person, as well.

This is a unique opportunity to shape a company from the first floor and up, and to help solve a significant problem. If you’re the right person for it, I’d be honored if we got to tackle it together.

Looking forward to hearing from you,
-Claire Lew
CEO of Know Your Company


If this doesn’t sound quite like you, but someone you might know, please feel free to pass along this post them! And, I’d really appreciate it if you clicked the ❤️ below too… That way, someone who might be a great fit will see this, too. Thank you! 😊