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

After four years, we’re launching a new product, business model, and company name. Here’s why.

We’ve always been a bit weird.

We’re a two-person company serving 15,000+ people who use our product in over 25 countries. We’ve generated almost $2MM in revenue to date, have been profitable since Month 1, and every year since. We’ve never raised money from investors, or taken out a bank loan. (And, we started out as a tiny prototype that Basecamp spun-off.)

Today, we’re doing something weird, again.

We’re launching a new product, business model, and company name.

We’re now Know Your Team software that helps managers become better leaders. We give you educational guides, tools, and a community of support to help you avoid becoming a bad boss.

Know Your Team costs $65/month per manager (or $600/year).

You can check out the new Know Your Team here.

Here’s why we decided to make this change.

Quick background, first.

If we’ve never met before, hello! I’m Claire, CEO of Know Your Team. It’s nice to meet you, albeit virtually.

Our original software, Know Your Company, used to be focused on helping business owners with 25 to 75 employees get to know their company better. We charged $100 per person, one-time, for life.

We generated $1MM in cumulative revenue in a little over two years. We helped tens of thousands of people at companies like Airbnb, Medium, Kickstarter. And not just at tech companies, but law firms, marketing agencies, retail stores, and even a few churches.

When we surveyed customers, 94% of employees said Know Your Company helped them feel more connected to their coworkers, and 85% of CEOs said Know Your Company positively impacted their company culture.

Yet as 2017 was winding down, we noticed our sales becoming flat.

“What’s wrong?”

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

As I reflected on 2017, I noticed three things:

  1. Our online community for leaders took off. We’d launched our Watercooler community in October 2017, to help managers learn from each other. More than 200 people signed up for it in the first month. (Today we have almost 1,000 members.)
  2. Our writing about leadership took off. The writing I’d been doing on our blog increased our organic traffic by 3X in a month’s time. It would go on to increase by 20X over the next six months.
  3. Our software sales went down. Our sales, however, did not increase. Not 20X. Not 3X. In fact, sales were fairly flat in 2017, if not dropping during some months.

Seeing the discrepancy between our audience and our sales, we scratched our heads.

Yes, Know Your Company was helpful as a piece of software. But for who?

When we got started back in 2014, we focused on selling to business owners. But by the end of 2017, our audience had evolved. After some digging, we learned that our 20X increase in traffic were mainly managers at companies of all sizes.

We had a mismatch. Our audience was managers, but our software was for business owners.

Our audience was asking the question, “How do I become a better leader?” But our software, Know Your Company, wasn’t answering that question.

In fact, no one was doing a good job of answering that question, “How do I become a better leader?”

Sure, you can read books, but they lack practical application. Trainings are expensive and one-time. And man, making mistakes and learning trial by fire is awfully painful.

I searched high and low for a good answer to, “How do I become a better leader?” I couldn’t find one. So we decided to build our own.

The result is Know Your Team.

Introducing Know Your Team: The new product.

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

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

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

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

You can read more about our methodology here.

The best way to learn anything is to go do it. The second best way is to practice doing it. So with Know Your Team, we combined theory with practice. You can’t become a better manager by just reading books, or just by using software tools, alone. We built Know Your Team to include 3 complementary resources, to be used together:

  • Guides — Written guides on leadership, based on data, with 50+ chapters on topics such as one-on-one meetings, giving honest feedback, building trust, and more.
  • Toolbox — Dead simple software tools to help you run effective one-on-one meetings, ask for feedback, get high-level team updates, foster rapport, and more.
  • Community — Online support from 1,000 other managers from all over the world, where you can discuss tough situations like firing, hiring, and more.

You can read more about our resources here.

And, we’re not done! We’ve got loads of ideas for more guides, more tools, and more resources that we’ve already started working on creating. There’s so much to be done to help people become the leaders they’ve always wanted to work for.

Changing our business model.

For new customers who sign up for Know Your Team, we chose a new business model. Know Your Team costs $65/month per manager to purchase. As a monthly subscription, this makes it easier for managers to swipe their credit card without having to ask for permission from their boss.

Previously, our one-time pricing model had been useful to get us to profitability quickly. For example if you had 19 employees, we charged $1,900 one-time. We were essentially collecting the lifetime value of the product upfront.

But over time, we noticed our one-time pricing model becoming a big barrier to sales. A business owner had to justify a $2,000 or more expense to their finance department, to their investors, and to their leadership team.

Now that we’re selling to managers, there was no way a $2,000 product was going to feel accessible to them, even if the cost was only one-time. We wanted Know Your Team to feel like a “no-brainer” purchase for folks who might not have access to the company’s budget. So we moved to a monthly subscription model.

Building Know Your Team with two people.

We spent six months building Know Your Team. This meant designing and coding new features, writing 50+ chapters on leadership for our guides, and constructing a new billing system, new onboarding system, and new marketing site… All with just two people.

Every piece of copy, code, and illustration you see is something our CTO Daniel Lopes or myself created. (We did this while maintaining our current product, doing customer support, writing blog posts and pursuing other marketing projects.)

This is a big move for us. As a bootstrapped company, we don’t have piles of cash stacked up, in case it doesn’t work. We don’t have investors to run to if we get stuck in a bind. (In fact, we have $140,000 in the bank, to be precise.)

But, the change feels right. Since I’ve been running the company in 2014, this launch, today, is the most energized I’ve felt.

Why the weirdness?

Admittedly, our approach is weird.

You might be wondering, “Why are you making things so hard on yourself, Claire? Why not raise some money to make this change? Take out a bank loan or open a line of credit? Hire more people? Buy yourself more time?”

Those are not bad ideas. We considered them. And who knows, maybe we’ll pursue them in the future.

But for right now, the short answer is: I don’t want to.

When you run your own business, you have to remember why you wanted to run it in the first place. What you want. Not what others want.

In business (and in life), we’re addicted to pattern-matching. We snuggle into where the grooves are carved, where the tracks have been laid — not necessarily because we want to — but because they’re just there.

For me, I got into this whole starting-a-business thing because I wanted to do it on my own terms: Small in headcount, big in impact, independent, profitable. Life is short. Why build a business any different from your vision for it?

Of course, you shouldn’t mindlessly listen to your own din, in isolation. You should carefully choose who to listen to. The only people I want to listen to are our customers, current and prospective: Employees, managers, leaders, CEOs.

The minute you take on investors, accept money from a bank, put people on your board — you change the people who you’re listening to.

I don’t even want to listen to Jason and David, the founders of Basecamp (and Know Your Team board members) 🙂 We’re lucky that Jason and David want us to do things our way, too. We disagreed on some of the strategy of the roll-out of Know Your Team, but they were very supportive of us choosing to ignore their advice. (I’ll write more on this perhaps another time…)

If you have the luxury to choose who to listen to, choose intentionally.

Is Know Your Team for you?

You might be one of those people I want to listen to.

If you’ve spent late nights googling things like, “how to be a good manager” or “how to run a team meeting” or “how to delegate well”…

If you’ve bought carts of leadership books on Amazon, desperate to avoid beginner manager mistakes…

If you’ve ever thought to yourself, “I have no idea what I’m doing as a manager”….

Know Your Team is for you.

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

If there is anything else — truly anything — I can do to help you become the leader you always wished you worked for, I’m here. Feel free to email me at claire@knowyourteam.com or ping me on Twitter at @clairejlew.

I look forward to hearing what you think. I’ll be listening to you.

On the journey with you,
-Claire


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

You have a micromanaging boss. What can you do?

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

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

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

Here’s what I recommended to him…

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

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

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

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

Reason #1: Worry

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

Reason #2: Fear

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

Reason #3: It’s All They Know

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

Reason #4: Past Experience

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

Reason #5: You 🙂

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

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

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

Second, defuse the reason.

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

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

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

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

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

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

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

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

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

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

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

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


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

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

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

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


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

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

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

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

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

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

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

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

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

Peel back the layers of “why”

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

Emphasize the common destination, not the divergent paths.

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

Show, don’t just tell.

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

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

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

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

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

Look for an outside advisor or mentor.

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


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

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

Feeling “off”? How to be a good manager when you just don’t feel like being one

If you’re struggling to stay engaged as a leader lately, here are some leadership tips to pull you out of the slump.

Some days, being a good manager is more difficult than others.

You can’t focus. The day drags. You feel “off.”

The company isn’t doing as well as it used to. Or you received a scathing email from a client. Or you’re questioning the latest shift in the company’s direction.

Whatever the reason may be, there’s no shame in it. I’ve had these “off” days, myself — and so many other leaders have too. As companies go through highs and lows, and our mind and emotions ride the highs and lows along with it. In our online Watercooler community with almost 1,000 managers in Know Your Team, many folks shared this sentiment: We all “occasionally fall into slumps where being a good manager becomes more difficult.”

The question is: How do you handle “off” days, so you don’t stay discouraged as leader?

Here’s the advice that our Watercooler members gave to overcome the work doldrums:

Take a day or two off.

Perhaps this sounds like conventional advice when you’re feeling “off” — but it’s because it works. Go somewhere quiet and get away from anything that could remind you of work. No phone, no emails, no talk about work. Studies have shown how beneficial “unplugging” from technology is in particular to clear your head. Use this time to re-evaluate your priorities, the things that motivate you, and the sort of contributions you can make to your company and team.

Focus on the impact you have on the people you work with directly .

Even when you’re not particularly motivated by your company, think of the impact you can have on people’s lives and their careers. As a manager, your attitude and actions shape the everyday lives of your direct reports.

Revisit your team’s vision and purpose.

This should be the “why” behind your work, and re-evaluating it and can invigorate you. One member of The Watercooler did this by meeting with each member of his team to get their perspectives on the company’s direction. He listened to their feedback, looked at the market and their competitors, and reshaped the company’s vision accordingly. The adjustment in the team’s purpose gave him greater purpose to show up for work each day.

Dig into the work itself.

Sometimes you feel in “funk” at work is because you haven’t been able to be in a state of “flow.” Choose to get back to more hands-on work to make progress on something you love to work on. Before you were a manager, were you a programmer by trade? Roll-up your sleeves and write some code. Do you work at a public relations company and used to be the one interfacing with journalists all the time? Put together some traditional media pitches and pick up the phone. Reconnect with what you love to do most.

Switch up your role in the company.

You might be feeling “off” because you’re not in the right position in the company. One Watercooler member mentioned how he changed his role in to a “visionary” one (think CEO) rather than an “integrator” one (think COO). He then realized he was better suited — and qualified — for big-picture thinking than operating the business.

Consider going on a “work retreat.”

You could be missing some of the unstructured creative time you had prior to being a leadership position. To combat this, one Watercooler member will take little work retreats a few times a year where he can recharge his batteries. He normally spends about a week in an AirBnB in some random city all by himself. It’s like a vacation in the sense that he completely unplugs from his normal responsibilities, but instead he just works on design/programming.


Now, of course, these are not solutions to remedy serious core company issues. You may be feeling “off” for important reasons that you need to resolve: Your team culture is toxic or your work habits are unsustainable. Pay attention to the underlying reasons causing the “off” feeling.

Rather, these suggestions work well as a short-term boost, when you know it’s merely an “off” feeling, and you’d like to steady yourself.

If you’re stuck in a slump as a manager, you don’t have to stay in it.


 

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

The surest sign of a bad boss? You don’t listen.

You’re likely making these 4 leadership mistakes as a leader. Here’s what to do instead to become a better listener.

You’re not listening, as leader. You think you might be — but it’s highly likely that you’re not.

Think back to your last one-on-one meeting. Be honest: What percent of the time did you accidentally zone out during your direct report’s answers? Were you distracted by an impending meeting with an unhappy client? Were you trying to guess your direct report’s motives, and running through past one-on-ones with them in your head?

I don’t blame you, quite frankly. As leaders, we’re trained — and rewarded — to multi-task, rapidly context-switch, and think in parallel. We’ve got a firehouse of tasks, team dynamics, goals, customer requests that we’re juggling… How else are we supposed to weather the storm?

However, listening requires an opposite motion. Listening lives in silence. In stillness. You need to focus purely on the person you’re listening to. Not analyzing the response as they speak, not anticipating the next sentence, nor brainstorming ourselves what we’ll say next. Not thinking about the next meeting, the next phone call, or, hey, lunch is in 40 minutes.

The only way we’ll truly understand what the other person is trying to say is if we’re zoomed in on listening, in that moment.

When we do, listening becomes a powerful lever. A great listener gains knowledge that’s overlooked. They hear the tone of disappointment in an employee’s voice and discover that person is not happy on the team. They recognize that an employee has been having revealing conversations with a customer, and they finally understand why a customer isn’t satisfied with a particular part of the product. It’s knowledge only found in the nooks and crannies — you have to pay attention closely in order to spot it.

Not to mention, when you listen well, you show empathy and build trust in a way that’s more genuine than any office perk or team social event.

So how do you know if you’re a good listener — or a terrible one? Here are the 4 most common mistakes leaders make that reveal they’re not a good listener. Read on to see if you’ve been unintentionally committing any of them…

Mistake #1: You keep your phone on “just in case.”

Yes, emergencies do happen. But keeping your phone on during a meeting and having it buzz is enormously distracting for the other person. Countless of employees I’ve spoken to have mentioned how disrespectful it feels for their manager to have their phone go off — or worse, to be texting during the meeting. A recent study revealed that smartphones are distracting, even when we aren’t looking at them. So, what’s the solution? Just put it away for the meeting to be present as much as possible. If you do have to take a call or are expecting an important message, simply let the other person know so they’re aware, or reschedule the meeting.

Mistake #2: You assume people want your two cents — so you give it immediately.

As a leader, you’re often looked to as the expert. And, well, you are the expert most of the time. So it’s common to want to jump right in and help your team by providing the answers, or share how you’d attack a challenge. However, that eagerness to lend a hand can backfire. Rushing in with your opinion can crowd out any room for your team to share their opinion. I’ll always remember my interview with Laura Roeder, founder and CEO of MeetEdgar. One phrase Laura rigorously used with her team was: “Make this decision without me.” This gave her team the space to figure things out on their own, share their honest opinions with her — and helped her listen, not just tell.

Mistake #3: You only ask one question, before moving on to the next topic.

How many questions do you typically ask a direct report? Just one, then on to the next item? Or do you try to follow-up each topic with at least two, three, or more questions? Whether it’s during a one-on-one meeting, a Zoom video conference, or in a Slack message, the best managers frequently ask follow-up, clarifying questions — both about themselves, and their colleague. They ask, “What isn’t clear?” or “What am I not explaining enough?” Additionally, when their team members speak, they ask questions such as, “What do you need to make X happen?“ or “What can I take off your plate to help you do X?” The more clarifying questions you ask, the more listening you’ll do.

Mistake #4: You rarely ask yourself, “What’s my mood right now?”

We all have bad days. It’s inevitable. To make sure you can listen to someone well, it’s important to be aware of your current emotional state and to optimize for it. Not a morning person? Schedule your meetings in the afternoon. Just got out of some crazy traffic, or rushing to get all your tasks done before the weekend? Consider rescheduling — not avoiding — a tough conversation. The other person will be relieved that you asked if they don’t mind chatting with you once you’ve had time to take a breath.


If you’ve found yourself thinking, “Oh man, I’ve definitely done a few of those recently” — no need to get down on yourself. We all have been guilty of them, myself included. My hope is that in pointing them out, they no longer float under the radar. With awareness comes a small change in actions. We can all lift the veil that we’re all not as good listeners as we’d like to be. If we want to be better leaders, it starts with knowing what work we have to do 🙂


 

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.)

To be a good manager: 8 ways to avoid your opinion swaying your team too much

A good manager knows their opinion can influence their team sometimes TOO much. Here’s how to compensate for that.

When you’re a manager, something interesting happens: You mention an idea off-hand, and all of sudden, it becomes a priority. You casually ask a question out of curiosity, and all of sudden, everyone scrambles ASAP to get you an answer.

As a leader, your opinion matters. But sometimes, it can matter too much. You can unintentionally sway team members by stating your opinion prematurely. Or, you can accidentally quell perspectives that are critical for you to hear.

How do you keep this from happening? One of the managers in The Watercooler, our online community with almost 1,000 leaders, kicked off this conversation recently. Below is a summary of the insightful, practical replies.

Here are 8 ways for you to compensate for your opinion weighing too much, as “The Boss”…

Assign others the task of disagreeing with you.

Force the hand, and create a safe space for someone to disagree. For example, in a meeting with ~5 people, a good leader might pick someone and say, “The four of us seem to be saying the same thing, and I’m making it your job to disagree with us regardless of how you actually feel. So if you’re forced to play the role of the disagreer, what’s your argument?

Give someone less experienced a chance to speak first.

This helps prevent folks from just shutting down and saying, “Yep sure, what that person said.” Even if the person is way off the mark in their opinion, it either signals you should spend more time working with them, or it causes the team pivot on the original idea after hearing others. One Watercooler member mentioned how he was recently listening to Great at Work and a high performing example company followed this practice: Most junior employees shared their thoughts first, most senior shared their thoughts last.

Have the person with the strongest opinion speak last.

A strongly-held viewpoint can drown out any potential for diversity of thought to emerge. So have the person who has already thought about an issue and formed a strong opinion speak last. This is also helpful because they’re the least likely to be biased by what everyone else says.

Ask others what they think before jumping in with your own thoughts.

One Watercooler member shared that he’ll often send people a link to a story, article, idea, etc. and ask people, “Thoughts?” to see what he gets back. This helps provoke thoughts from other people, in an unfiltered way, before you insert your own.

Ask everyone to explain their thought-process, not tell you their opinion.

This keeps the people with opinions — but perhaps more trivial reasoning behind them — from dominating the conversation (and wasting everyone’s time). In addition, understanding how someone is coming to a conclusion is sometimes just as valuable, if not more, than the conclusion itself.

Use phrases like “you’re the expert.”

When talking to people about areas that they’re a specialist in, affirm that they are the person who has the required knowledge and expertise. This helps make it clear that your view isn’t any more correct than theirs.

Ask for advice.

When you say to someone, “I need your advice,” you can open the door wide to getting useful feedback from your direct reports. The statement both indicates openness to fresh ideas, as well as a clear request for that person’s personal viewpoint.

Admit what you’re unsure about or struggling with.

Try saying something like, “I’m pretty sure I know the direction I want to go, but I want to be sure I haven’t overlooked something important. Will you review this with me, and poke holes in my idea?” Or “I’m having a tough time figuring this out…” Good managers understand this leads to a very different dynamic. Even if you end up sticking to your original plan, people are more likely to feel respected for being asked to help vet the idea. You’ll get valuable input, regardless.

If you want your team to be making the best decisions, making sure your opinion isn’t driving all the decisions is important. You want people to be honest, to bring up what they think could be better, and to point out what they think is wrong. Try one of these 8 ways to help foster that openness in opinions. Your viewpoint may unintentionally sway others, as a leader — but it doesn’t have to.


 

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

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

Here are a few of my favorite leadership tips from CEOs, founders and executives featured recently in our Heartbeat interviews.

Every two weeks, I ask one question on a leadership lesson to a founder, CEO, or business owner I respect and share it on The Heartbeat ❤️, our bi-weekly newsletter on how to become a better leader. The question I always ask is, “What’s one thing you wish you’d learned earlier as a leader?” Here’s what some of our recent interviewees had to say…

Leaders don’t need to know it all.

Rob Walling is the co-founder of Drip, an email marketing automation software company that we in fact use a Know Your Company. What does Rob wish he’d learned sooner? That it’s okay for leaders to ask questions. He says:

“I wish that I had learned that I didn’t need all the answers as a leader. [I hire] people that are better than I am at something, and then when a problem comes up I can look around the room and say, ‘I don’t know. What do you think?’” — Rob Walling, co-founder of Drip

Embrace failure.

Aynn Collins is the Director of Talent Strategy at MailChimp, the world’s largest marketing automation platform with more than 900 employees. Aynn’s advice to her younger self is to understand that failure is part of growing as a leader.

“Embracing failure and understanding how you learn and grow from those failures is what I would tell people to learn early in their career. They can own failures, talk about them, debrief with your team on…and not try to just make everything shiny and pretty. Because we know business and leadership is not always perfect, and shiny and pretty.” — Aynn Collins, Director of Talent Strategy at Mailchimp

Forget the org chart.

Dan Mall is the founder of SuperFriendly (a design collaborative that’s worked with clients such as Apple, Time Magazine and ESPN) and CEO of SuperBooked (a software application that helps people find creative work). For Dan, he wishes he’d known that an organizational chart isn’t the end-all, be-all of business.

“The leaders aren’t the ones at the top. They should be the ones at the bottom. They should be the one supporting everyone else…They need to be able to see everything. They need to be able to support people. So, I wish I would have learned the idea of servant leadership, which is becoming more and more popular now.” — Dan Mall, founder of SuperFriendly and CEO of SuperBooked

 


 

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

11 must-read books for new managers

New to the whole “manager” thing? Get your feet wet by checking out these 11 most-recommended leadership books.

Congratulations on your role as a new manager! You’re likely feeling 80% excited… and 20% terrified. That’s completely normal 🙂 Becoming a first-time manager is intimidating. You’re about to start flexing skills you might never have had to use before.

Folks who were once your peers are now reporting to you. You’re now included in more high-level leadership meetings. Your entire focus in what you do has shifted, too: Your ultimate responsibility is no longer to just get your own work done. It’s to ensure the success of your team’s work.

So, how do you start getting into the mindset of a good manager?

I asked almost 1,000 leaders in The Watercooler, our online community in Know Your Team for managers, what helped them transition into their first managerial role and the majority of them said reading has helped guide them into the leader they are today. Here are the top 11 must-read books that have helped them become better managers and leaders for their teams:

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

Big caveat here, though: Becoming a good leader requires much more than just reading books. Much of what you’ll learn is through experience: Trial and error, talking to your own team, and talking to other leaders who’ve been in your shoes before. Books are merely a primer to give you a foundation for what it takes to be a good manager. These 11 books are a good start.


Do you have any books missing from this list that helped you transition into a managerial role? I would love to add it to our must-read list. Let me know in the comments or on Twitter at @clairejlew.


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

4 non-cringeworthy team-bonding events that people actually enjoy

Here’s what 1,000 managers in The Watercooler said their employees enjoyed most as a team-building activity.

Team bonding — known to some as “forced fun” — can bring feelings of dread and resentment to many employees. And who can blame them? When thinking of team bonding, many people picture awkward trust falls or hours spent with a facilitator asking corny questions.

However, a team does need to feel connected in some way. You can’t work well together if you don’t trust each other — let alone, know each other. And getting to know each other, while that can happen organically over time, only gets harder the bigger the team gets or the more spread out your office is.

Particularly for new employees, an effective team-building activity can go a long way. It’s rare, dedicated time for folks to not talk about work, relax, and just have fun.

I asked members of The Watercooler, our online community of almost 1,000 managers in Know Your Team, what their most successful team bonding events were. Below were the top four mentioned. Feel free to tailor these ideas to fit your own team dynamics and preferences.

Work ‘n Travel

Few experiences are as memorable and unique as traveling somewhere novel. For the past couple of years, one Watercooler member’s company spends a week together as a team, working remotely and traveling. So far, they’ve been to Lisbon, Portugal, and Poland. (And they already have their destination picked out for next year!) For them, it’s been a perfect way to spend high-quality time getting to know each other, while also getting to have a common shared experience of traveling.

Team Volunteering

Contributing to the community around you, together with your team, is a fantastic, non-cliché way for everyone to feel more connected. One Watercooler member’s company volunteered at a local food bank when everyone was in town for a company meeting. They spent the day providing thousands of meals to people in need while also bonding as a company.

3+ Lunch Fridays

Possibly the most common team-bonding event that teams seem to do is to sponsor lunch outside the office on Fridays. Several managers in the Watercooler mentioned how their company will cover the cost of lunch for groups of three or more employees if they go out to eat on Fridays. This in fact incentivizes folks to get out of the office and socialize a bit with one another.

Cereal Day

It sounds odd, I know. But a Know Your Company customer and Watercooler member shared how surprised she was that a seemingly insignificant team-bonding event had such a big effect on her team’s morale. Every month, she brings in a box of everyone’s favorite cereal to one of their most intense days of the month: The strategic planning meeting. It was a small, quirky move — not any big grand gesture – and it was a big hit with her team.

 


 

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

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

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

You’re not prepared. Or at least that’s what employees think when it comes to one-on-one meetings. In a recent survey we conducted of 1,182 managers and 838 employees, we found 36% of employees believe their manager is only “somewhat prepared” – and 40% of employees think their manager is “not prepared” or “not prepared at all.”

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

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

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

#1: Get up-to-speed.

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

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

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

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

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

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

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

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

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

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

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

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

Questions that uncover concerns / issues…

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

Questions that elicit feedback about work performance…

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

Questions that help provide career direction…

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

Questions that foster a sense of personal connection…

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

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

For more ideas for questions to ask during a one-on-one meeting, you can visit here. (We also give you hundreds of question ideas and four meeting templates to use in Know Your Team.)

#4: Calibrate your mindset.

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

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


 

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