For the last decade or so, I’ve been on a number of boards, consulted with a number of entrepreneurs, and have been both formally and informally involved in helping a number of young companies find their way.
Many young companies I’ve seen have one thing in common: They can’t wait to grow up. They desperately want to be taken seriously by others. They want to be perceived as sophisticated, as having it all figured out.
This is where they begin to get into trouble. As they technically begin to be able to do more things, it’s the things they can no longer do that turn out to be the big losses.
Take company size, for example. One way to be taken seriously is to hire more people. As a whole, bigger companies are taken more seriously than small companies. Thing is, small has major practical advantages over large. Small companies can do both small and big things. Big companies can not do small things. Once you get to a certain size, you can no longer do the small things. When you’re big, every initiative turns big, like it or not. Except the small things are often all that’s necessary.
Take “systems”, for example. I’ve seen a number of small companies jump into big sophisticated content management, inventory management, e-commerce management platforms. Buying into something the big guys use helps a small company feel like they’ve arrived. Now they’re ready to scale! But now all the sudden they can no longer do the things they need to do. Trying a quick idea they used to be able to just whip up becomes a wrestling match with the new system that prefers you do things the more complicated way. Now “let’s just try that” becomes “when can we schedule a time to figure out how we can try that?”
The other thing that’s lost in transition from small to big are instincts. I’ve seen companies paralyzed by ideas they can’t seem to implement anymore. They could still do things they same way they used to, but they can’t think that way anymore. For example, a small company that would have just spent a couple hours sending out 50 hand-written emails to test a personalized selling campaign, is stuck for days or weeks trying to figure out how to get their new e-commerce platform to automate the same thing. They could still just pick the customers and write the emails by hand, but they’re forgotten how to think about doing it that way. Once you have something in place that’s supposed to be able to do that work for you, you lose flexibility, your mind and muscles atrophy. You cease to be able to be scrappy.
Scrappy is a mindset, and the skills are lossy — once they’re gone, you can never recreate them the same way again. Being scrappy is easier the smaller you are, the younger you are, and the fewer options you have. Hang on to it for as long as possible! Don’t be in a rush to abandon such critical survival instincts.
It happens to all growing companies. We’ve certainly lost our fair share of scrappiness as well. My suggestion: Resist the allure of large — there’s very little payback, especially if you artificially get there before you’re really ready. Be aware — and beware — of the things you give up too early and never get back.
It’s time for another mailbag episode where Jason Fried and David Heinemeier Hansson answer your questions! In this one, they discuss how to apply calm company principles to client work and classrooms, and talk about healthy ways for business partners to disagree.
…Each [short chapter is] packed with a punch that seems both profound and practical — profound for how clear and different they tend to be from most accepted business wisdom, and practical because almost everything they describe is immediately applicable.
And the ⭐️⭐️⭐️⭐️⭐️ Amazon reviews are flowing in as well. And, BTW, if you’ve read the book, please do leave a review. Thanks much.
If you’ve read and enjoyed REWORK, you’re going to especially love “It Doesn’t Have to be Crazy at Work”. It’s really the spiritual follow-up to REWORK. Irreverent, direct, fluff-free, short-essays, and straight to the point. And because we hate long business books we can never seem to finish, we wrote “It Doesn’t Have to be Crazy at Work” to be read in just about 3 hours.
What’s the book about?
We put it all right on the cover.
The lessons and stories in the book are based on nearly 20 years of experimenting with how to build a calm company. Inside we push back hard against unhealthy work practices, the obsession with growth at all costs, and treating people as if they’re simply limitless resources rather than human beings. We also share the things we’ve tried, and how we came to figure out what works and what doesn’t.
If you’ve got a few minutes, here’s the full intro below to fire you up…
“It’s crazy at work.” How often have you heard that? Or said it yourself? Probably too often.
For many, “it’s crazy at work” has become their normal. But why’s that?
At the root is an onslaught of physical and virtual real-time distractions slicing work days into a series of fleeting work moments.
Tie that together with a trend of over-collaboration, plus an unhealthy obsession with growth at any cost, and you’ve got the building blocks for an anxious, crazy mess.
It’s no wonder people are working longer, earlier, later, on weekends, and whenever they have a spare moment. People can’t get work done at work anymore.
Work claws away at life. Life has become work’s leftovers. The doggy bag. The remnants. The scraps.
That’s just not OK. It’s unacceptable.
What’s worse is that long hours, excessive busyness, and lack of sleep have become a badge of honor for many people these days. Sustained exhaustion is not a badge of honor, it’s a mark of stupidity. Companies that force their crew into this bargain are cooking up dumb at their employees’ expense.
And it’s not just about organizations — individuals, contractors, and solopreneurs are burning themselves out the very same way.
You’d think with all the hours people are putting in, and all the promises of tech’s flavor of the month, the load would be lessening. It’s not. It’s getting heavier.
But the thing is, there’s not more work to be done all of the sudden. The problem is there’s hardly any uninterrupted, dedicated time to do it.
Working more but getting less done? It doesn’t add up. But it does — it adds up to a majority of time wasted on things that don’t matter.
Many modern companies seem to be great at one thing: wasting. Wasting time, attention, money, energy.
Out of the 60, 70, 80 hours a week many are expected to pour into work, how many of those hours are really spent on the work itself? And how many are tossed away in meetings, lost to distraction, and withered away by inefficient business practices? The bulk.
The answer isn’t more hours, it’s less bullshit. Less waste, not more production. And far fewer things that induce distraction, always-on anxiety, and stress.
Stress is an infection passed down from organization to employee, from employee to employee, and then from employee to customer. And it’s becoming resistant to traditional treatments. The same old medicine is only making it worse.
And remember, stress can not be contained. It never stops at the edge of work. It always bleeds into life. It infects your relationships with your friends, your family, your kids.
The promises keep coming. More time management hacks. More ways to communicate. More information spread across separate platforms and disparate places. New demands to pay attention to more and more real-time conversations happening all the time at work. Faster and faster, for what? Panaceas left and right. Snake oil.
On-demand is for movies, TV shows, and podcasts, not for you. Your time isn’t an episode recalled when someone wants it at 10pm on a Saturday night, or every few minutes in the collection of conveyor belt chat room conversations you’re supposed to be following all day long.
If it’s constantly crazy at work, we have two words for you: Fuck that. And two more: Enough already.
At the heart of it all is an unhealthy obsession with rapid growth. Towering, unrealistic expectations drag people down.
It’s time for companies to stop asking their employees to breathlessly chase ever-higher, ever-more artificial targets set by ego, not need. It’s time to stop celebrating this way of working.
Over the last 18 years we’ve been working at making Basecamp a calm company. One that isn’t fueled by stress, or ASAP, or rushing, or late nights, or all-nighter crunches, or impossible promises, or high turnover, or over-collaboration, or consistently missed deadlines, or projects that never seem to end, or manufactured busywork, or incorrect assumptions that lead to systemic institutional anxiety.
No growth-at-all-costs. No constant, churning false busyness. No ego-driven decisions. No keeping up with the Joneses Corporation. No hair on fire.
And yet we’ve been profitable every year since the beginning. We’ve kept our company intentionally small — we believe small is a key to calm.
As a tech company we’re supposed to be playing the hustle game in Silicon Valley, but we’re blissfully far away in Chicago with employees working remotely in 30 different towns around the world.
We each put in about 40 hours a week most of the year, and just 32-hour four-day weeks in the summer. We send people on month-long sabbaticals every three years. We not only pay for people’s vacation time, but we pay for the actual vacation too.
No, not 9pm Wednesday night. It can wait until 9am Thursday morning. No, not Sunday. Monday.
Walk into our office and it feels more like a library and less like a chaotic kitchen. Noise and movement are not indicator of activity and progress — they’re just indicators of noise and movement.
We’re in one of the most competitive industries in the world. An industry dominated by giants and frequent upstarts backed by hundreds of millions of dollars in VC money. We’ve taken zero. Where does our money come from? Our customers. They buy what we’re selling and we treat them exceptionally well. Call us old fashioned.
Our benefits are focused on getting people out of the office, not enticing them to stay longer. Fresh fruits and veggies are delivered to people’s houses, not the kitchen at work. Want to learn to play the guitar in your own time? We’ll gladly support you and pay for that too.
We’ll pay for you to get a massage, but we won’t bring the masseuse to the office. Loosening up for 60 minutes only to tense back up hunched over your desk is faux relaxation. No “stay here” signals. Everything’s about wrapping up your reasonable day, going home, and living your life.
Are there occasionally stressful moments? Sure — such is life. Is every day peachy? Of course not — we’d be lying if we said it was. But we do our best to make sure those are the exceptions. On balance we’re calm — by choice, by practice. We’re intentional about it. We’ve made different decisions than the rest.
We’ve designed our company differently. We’re here to tell you about it, and show you how you can do it. There’s a path. You’ve got to want it, but if you do you’ll realize it’s much nicer over here. You can have a calm company too.
This book points out the diseases plaguing modern workplace and work methods. It calls out false cures, and pushes back against ritualistic time-sucks that have infected the way people work these days. We have a prescription to make it better.
Chaos should not be the natural state at work. Anxiety isn’t a prerequisite for progress. Sitting in meetings all day isn’t required for success. These are all perversions of work — side effects of broken models and follow-the-lemming-off-the-cliff worst practices. Step aside and let the suckers jump.
Calm is profitability. Calm is protecting people’s time and attention. Calm is reasonable expectations. Calm is about 40 hours of work a week. Calm is ample time off. Calm is smaller. Calm is a visible horizon. Calm is meetings as a last resort. Calm is contextual communication. Calm is asynchronous first, real-time second. Calm is more independence, less interdependence. Calm is about sustainable practices that can run for the long-term.
By the end of the book you’ll understand it all.
It would mean a lot to us if you’d pick up a copy, absorb the ideas, consider the suggestions, and try to make the work world a better place for a lot more people. We hope you ❤️ it. Got questions? Post ’em below and we’ll do our best to answer everything we can. Thanks in advance for reading!
“Being nice” can be a crutch to avoid hard choices and uncomfortable conversations. Don’t fall into this trap.
Leaders, stop being so nice all the time.
I don’t mean to sound like an asshole. But when it comes to leadership, it’s true: Prioritizing “being nice” keeps us from being good leaders.
Now I’m not advocating for us to be mean. Disrespectful or dismissive leaders help no one. Rather, I’m calling for us as leaders to loosen our grip on “being nice.” To stop wanting our team to like us all the time. To let go of the expectation that every single interaction with our team should feel good.
Truth is, our team isn’t going to like us all the time. Our team isn’t going to feel good all the time. And trying to be nice to everyone all the time isn’t going to change that. Nor is it actually helpful for your team.
When we’re preoccupied with seeming popular instead of fair, when we optimize for pleasant conversations instead of honest ones — we hurt our teams.
I was reminded of this most recently while I was reading The Watercooler, our online community with almost 1,000 leaders. One manager revealed he was facing this exact dilemma. He was seen as “The Nice Guy” in his company, always complementary, never critical. As a result, he was struggling how to start giving his team difficult feedback — and his team was floundering.
He’s not the only one.
Have you ever found yourself in one of these situations?
You avoided giving tough feedback to a coworker… and now the person has made even bigger mistakes than you previously imagined.
You didn’t tell someone that you disagreed with them… and now you have to figure out how to course-correct without blindsiding the person.
You postponed firing someone… and now have to do damage control for the low morale they infused throughout the team.
You said something was “great!” even though it actually wasn’t… and now you have to fix the level of quality for what was produced.
Many of us focus on “being nice” as a leader more than we should. And we pay a price for it.
Hiten Shah, founder of Kissmetrics and Crazy Egg, emphasized this point to me, in a recent interview. He warned that when you’re concerned with being nice all the time, “there’s a level of toxic culture that develops that’s hard to see, especially on a remote team.”
Prioritizing “nice” as a leader is an easy trap to fall into. Being nice fits into our desire for belonging and companionship as humans. We’re social creatures. We want to be liked. Inherently, there is nothing wrong with that.
But “being nice” becomes problematic when it becomes your rudder as a leader. It leads you astray. You lose sight of your purpose as a leader: To help your team accomplish a specific mission. Your barometer for success as a leader morphs from “Are we accomplishing our mission?” into “What does the team thinks of me?”
Over time, “being nice” becomes your crutch. It’s a convenient rationalization to avoid hard decisions, uncomfortable conversations, and controversial actions. It’s easier to “be nice” than it is to have tell someone to their face that they’re rubbing a client or colleague the wrong way.
Ultimately, being nice as a leader is selfish. It doesn’t serve the team. It serves your ego. The team is looking to you to help them achieve a goal. And instead, you’re looking to have your decisions, actions, and yourself perceived as positive by them.
A leader is the only person’s whose sole job is help a team achieve the outcome they want to achieve. When you care about “being nice,” you’re essentially saying, “The needs of my team as a whole don’t matter as much as their perception of me as an individual.”
Instead of seeking to be nice, we should seek to be honest, rigorous, and consistent.
Or even better, we can seek to be nice and honest, nice and rigorous, nice and consistent. One of my favorite books, Crucial Conversations, discusses how being nice and being honest are not mutually exclusive. You can be both. The best leaders embrace this duality.
Let’s just stop being so damn focused on being only nice.
Claire is the CEO of Know Your Team – software that helps you become a better manager. Her company was spun-out of Basecamp back in 2014. If you were interested, you can read more of Claire’s writing on leadership on the Know Your Team blog.
Four steps to take when you’ve got a one-on-one meeting coming up.
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 125 managers and 45 employees, we found 35% of employees believe their manager is only “somewhat prepared” — and 15% 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. Sixteen 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 ten 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?”
“When have you felt bored in the past quarter?”
“Is anything holding you back from doing the best work you can do right now?”
“Is there any red tape you’d like to cut at the company?”
Questions that elicit feedback about work performance…
“Would you like more or less feedback on your work? Why/why not?”
“Would you like more or less direction from me? Why/why not?”
“What aspect of your job you would like more help or coaching?”
“What’s a recent situation you wish you handled differently? What would you change?”
Questions that help provide career direction…
“What have you been wanting to learn more of, get better at, and improve on?”
“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?”
“If you could design your ideal role in a company, what would it look like?”
Questions that foster a sense of personal connection…
“What have you been reading lately?”
“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.
#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.
Claire is the CEO of Know Your Team – software that helps you become a better manager. Her company was spun-out of Basecamp back in 2014. If you were interested, you can read more of Claire’s writing on leadership on the Know Your Team blog.
Smell ya later! We here at the Rework podcast are taking off the month of August. Before we left, we interviewed three business owners about sabbaticals. In this episode: Adeline Koh of Sabbatical Beauty shares the story of how she ended up starting a business while on leave from a different job; Jason Fried explains why Basecamp offers paid sabbaticals as an employee benefit; and Rachel Winard of Soapwalla talks about what it’s like to go on sabbatical when you’re the boss.
We’ll be back in September with all-new episodes of Rework! In the meantime, you can catch up on episodes you missed at rework.fm or peruse the archives of our previous podcast, The Distance.
They’re mostly terrible, but there’s room for smart choices.
Last week, DHH skewered the open office floor plan. He was right. But wait, we have an open office floor plan. And we’ve done a respectable job figuring out how to make it work. Maybe I should share something about that.
First off, an open office is appealing from a few perspectives:
It makes economic sense. Building out separate private spaces for everyone is costly. Yes, you could argue people being unable to work out in the open is even more costly, and I wouldn’t fight you on that, but that’s an abstract economic impact. Paying construction bills has a very direct economic impact.
It’s more flexible to remain open. Companies like to imagine growth. If you have 20 employees today, but may have 40, 60, or 80 a year or two from now, it’s very difficult to forecast what you’re going to physically need. If you don’t build enough private offices for everyone, then some people are going to get pissed. If you build too many, you’ve wasted a bunch of space. Open is flexible and flexible is comforting — especially if you’re signing a 5+ year lease.
You need less space. You can pack a lot of people into 5000sqft of open space. You can nudge desks together, you can squish people in a few feet, etc. I’m not suggesting these are good ideas, but they’re practical and workable. But if everyone needs private offices, you’re going to need a lot more space, which means a lot more rent. That’s expensive.
So it’s not hard to see why open offices make sense from a purely practical, economic perspective. They’re also easier to clean and maintain, too. But like DHH, I don’t buy the collaborative benefits. Not for a second. That’s a mask used to obscure the real reason — cost savings. Open plans are cheaper to execute, period. And the people who make the decisions about how the office is designed are usually the ones that make the financial decisions.
Ok, so given all that, if you do go open, how do you make open work?
Walk into any library in the world and you’ll notice a few things. One, they’re generally open spaces with a number of desks and surfaces scattered throughout — similar to an open floor plan office. And two, they’re quiet. There are few things as culturally consistent as library design and library behavior. At Basecamp we call these Library Rules.
Libraries are full of people working, reading, thinking, studying, writing, contemplating, designing, etc. Yet they’re silent. People are heads down doing independent work. In our opinion, this is the model business, the model office. We pattern our way of working around Library Rules.
So this is the first lesson: Embrace Library Rules. Open offices work all around the world every day. They’re called libraries! And the more you treat your office as a library of work — rather than a chaotic kitchen of work — the better an open floor plan is going to work. Making an open floor plan work is a cultural decision.
Library Rules means keeping to yourself, keeping your voice down in hushed tones, not distracting one another. If you do need to talk to someone at normal volumes, grab a room. A key to making open floor plans work is also having private rooms scattered throughout the space. A place where a few people who need to discuss something in real time can jump in, talk it up and work it out without bothering anyone on the outside.
At our office, we call these private spaces Team Rooms. Here’s what they look like:
BTW, eliminating distractions doesn’t just mean physical distractions. It increasingly means virtual distractions. Real-time chat rooms/channels are basically open offices — and worse in many ways. So even if you’re fortunate enough to work remotely, or in an office with private rooms for everyone, if you’re forced to follow multiple real-time conversations all day long, you’re effectively working in open plan office too. Sorry!
What’s worse than an open floor plan? An open floor plan loaded with hard surfaces! And given that many open plans are housed in old warehouse/loft-like spaces, you’re materially at a disadvantage. All that wood and brick and glass looks great, but it sounds awful.
Our office space started as a 10,000sqft concrete and glass box. It was a former furniture factory, and a present day echo factory.
A big part of our office design was acoustic design. For example, we built a huge volume in the middle of the office that’s wrapped in stacked felt. The felt serves as a sound absorbing material, and the irregular stacking helps deflect sound. The material and application looks like this:
We also lined one long wall with an acoustic material used in recording studios to help absorb and deflect sound.
Carpet tiles lines the floor of the open work area to further reduce echo and sound transmission when people are speaking openly:
And even the team rooms themselves — rooms designed for collaboration and normal volume communication — have been designed with acoustics in mind. From the acoustic ceiling tiles, to the stacked and slotted cork walls to deflect sound and kill echo, each decision was deliberately made to keep sound from traveling where it shouldn’t.
And because we can’t help ourselves, we even installed neoprene grommets between any team rooms that shared the same glass wall. It’s hard to see this in the photo, but there’s a slight gap between rooms where the glass passes across an inner wall. The neoprene expands to fill that space and kill sound transmission between rooms.
We also built a separate sound proof (room inside a room) recording studio for recording our podcasts. It’s also lined with the same material we had on that long back wall.
Desk dividers out in the open office are made of another acoustic material made from recycled plastic:
And finally, anyone who needs to make a private phone call (personal or business), can duck into one of three phone rooms. The rooms are sound proof and lined with the same material we use for the desk dividers. There’s also an IN USE sign that lights up whenever someone’s inside — reminding everyone that someone’s in there.
Density and desks
Aside from acoustics, there’s another consideration which plays a large role in keeping an office quiet a calm — density. Packing people on top of each other is a form of induced stress. Desks face each other (but dividers keep people from seeing one another), and there’s about 10 feet of space behind each person’s desk. You never have to worry about rolling your chair back and hitting someone.
Further, our desk layout is arranged so no one is looking at anyone else’s screen. Knowing people are looking over your back — even unintentionally — is a really uncomfortable feeling. We’ve eliminated that with our layout.
Last, the desks are lined up along huge windows to make natural light a full part of everyone’s day. Natural light is especially calming, and independently operated shades help with the rare glare based on the season.
Open’s a choice
Yes, an open floor plan is a choice, but it requires a cultural commitment to respect and quiet. Luckily everyone already knows how to do that since everyone knows how to behave in a library. Beyond that, it also requires a capital investment and deliberate office design choices. Even if everyone’s quiet, tossing a bunch of desks in an echo chamber isn’t going to get the job done. If you want to keep things quiet, you have to think about what you’re designing. Every decision has an impact one way or another.
And it’s all optional!
We did the best job we could designing an open office (and a culture) that allows everyone to work in focused peace and quiet every day. But even that’s not good enough, which is why no one is ever required to come into our office. Basecamp is a fully remote company of 54 people, and even the 14 people who work in Chicago work remotely from home most of the time. Walk into the office on any given day and you’ll see 3–5, if you’re lucky. Yes, it’s a tremendous waste of space most of the time, but that’s a concession we’re comfortable making.
You’re probably already asking at least one of them – but it’s never too late to stop.
Looking at the clock. Staring into the distance. Short, nondescript answers.
A CEO recently told me how he’d frequently see this body language from an employee during their one-on-one meetings. Flat. Disinterested. Preoccupied. It felt lousy to witness, but it’d always been this way. He’d silently concluded that he was wasting both of their time.
“I want to know what’s on his mind and how I can help, but these one-on-one meetings just aren’t working,” this CEO admitted to me. “I’m not really sure what to do except to stop having them.”
To see if I could help, I asked him what questions he was asking. He shared them with me… and then it clicked.
The once hazy picture zoomed into focus: This CEO was asking the wrong questions. All of his questions were common questions, no doubt. But therein lay the problem. Stock questions might be effective once or twice. But ask them during every one-on-one, every week, and over time, and the effectiveness of the question erodes. The person grows sick of answering the question. Or she doesn’t think you really care to know the answer anymore. Before too long, she starts looking at the clock, staring into the distance, and giving you those short, nondescript answers.
To avoid this, you’ll want to avoid the routine questions you lean on. Below are the four most common questions I’ve found used during one-on-one meetings that elicit dead-end, unhelpful responses. Take a look and see which ones you might be asking:
#1: “How’s it going?”
Ah, the perennial one-on-one meeting opener. It seems like a solid way to break the ice and initiate the one-on-one meeting. Yet it’s unusual that you ever get an answer other than “Fine” or “Good” in response. While someone might truly be fine and good in reality (which is great!)… the conversation usually stops there. Anything personal you wanted to learn, any sense of rapport you wanted to create dies with the question, “How’s it going?” This is because, as a society, the question “How’s it going?” has become our automatic greeting to each other, so our answer to it has become just as automatic.
What should you ask instead?
If you’re looking for a casual, open-ended way to kick off a one-on-one, ask “How’s life?” instead. It may not seem like a big difference, but it makes a big difference. “How’s life?” gives permission for someone to talk more personally about life — about what they did that weekend, how their family is doing, how their personal side project is coming along, how they’re managing their workload. “How’s life?” invites the other person to elaborate. Though, quite frankly, almost any other opening question than “How’s it going?” to going to help you learn more about how someone is doing in their life.
#2: “What’s the latest on __?”
It can be tempting to use your one-on-one session as time to get caught up on what’s going on. However, keep in mind that this completely squanders the purpose of your one-on-one meeting, to begin with. A one-on-one meeting isn’t a reporting session. It’s not an accountability tool. A one-on-one meeting is your radar. It’s your metal detector. It’s one of the only ways you have to unearth what’s actually going on in your team, and what an employee is thinking and feeling. You can get a list of deliverables in Slack any ol’ time. Client problems, unforeseen issues with the product, messy team dynamics, unspoken personal frustration — this is only time you’ll get to hear that stuff.
Some of you may be thinking, “Well, Claire, asking this question has helped me get good insights into the team’s problems.” Yes, I’m with you. This question “What’s the latest on X?” can be great if you’re using it to segue into asking deeper questions. For example, perhaps you follow it up with, “What’s most frustrating about how X has been going so far?” Or, “Where do you feel you need more support in working on X?” Merely asking “What’s the latest on X?” falls flat if you use it singularly.
What should you ask instead?
Ask something specific about the project, instead of asking for a general project update. Possibly my favorite question to ask to instead of “What’s the latest on X?” is “Can you tell me about what’s been most surprising about working on X so far?” If an employee has found something surprising, good chances that you’ll find it surprising too. A surprising insight is always useful for you to form an accurate picture of potential issues bubbling up within your team.
#3: “How can I help you?”
The intention behind this question is fantastic. You want to help, you want to get out of their way, you want to figure what you can be doing better. However, this question is the worst way to signal that. Why? It’s lazy. It makes the person receiving the question do all the hard work of having to come up with the answer. It’s also a very hard question to answer, especially on-the-spot and given that you’re a person in a position of power. You’re asking a person to critique you, “The Boss,” across all spectrums and come up with something actionable for you to do. If you do ask this question, answers tend to be, “Nothing I can think of right now,” something vague, or an answer that involves something that you’re already doing. Rarely do you get a precise, thoughtful to-do that you’ll then go implement the next day.
What should you ask instead?
Suggest something you think you can be doing to help. Then ask, “What do you think?” For example: “I was thinking I’m being too hands-on on this project. Should I back off and check-in with you only bi-weekly? What do you think?” By being targeted in what you suggest — and suggesting it yourself — you make it easier for that person to share the exact ways in which you can support them. You help your employees by suggesting what you think you can do to help, first.
#4: “How can we improve?”
This is the vaguest of questions. The problem with vague questions is they invite vague answers. You prompt the person to offer broad suppositions and knee-jerk assumptions, instead of exact details and practical examples. Ask an employee “How can we improve?” and they think, “Hmm, from a business development perspective? Marketing perspective? Leadership perspective? Where to even begin?” Now, some employees you work with will be able to craft a distinct, rich answer from this question. But it’s infrequent. And it’s probable they spent a good chunk of time thinking about the answer ahead of time. For most employees who you ask this question to without any warning, you’ll receive a variant of “I think things are pretty good right now” about 90% of the time.
What should you ask instead?
Focus your efforts on asking specific questions, instead of defaulting to general ones. For instance: “What do you think is the most overlooked area of the business?” or “Where do you think we’re behind in, that other companies are excelling at?” Notice how specific each of these questions are. The more specific the question, the more effective they are.
You may have cringed while reading this list. Many of you (including myself!) have found yourself asking all four questions, at one time or another.
No need to panic or be hard on yourself. You haven’t inflicted irreparable harm to your team. Your sins are not unforgivable. Rather, I hope sharing the unintended consequences of these four questions nudge you to evaluate the questions you ask during your one-on-one meetings a little more closely.
The questions do the heavy lifting. The questions determine the path to which your one-on-one meetings will take. Ask thoughtful, sincere questions, and there’s a higher likelihood your answers returned back to you will be thoughtful and sincere too.
I think I’ve cracked the obsession amongst much of the Silicon Valley set with compressing work life, sacrificing everything until the big exit, and running fast while breaking all the things: If you don’t plan to stick around, who cares how you leave the things behind?
This loot’n’leave strategy can justify much of what’s wrong with startup culture in the broad, below-the-titans cut (where reaching emperorhood brings its own justifications). Employees, customers, regulations, and, hell, even society at large, is much easier to screw over without regret if you don’t have to stick around for all that long. A few years of being the villain or the asshole is probably something a lot more people can imagine tolerating than if it was the condemnation of a whole career.
I can think of how the opposite dilemma frequently guides my decisions and opinions at Basecamp. If I’m going to be here for the next 10–20–30 years, what’s the right move that I won’t regret over the coming decades? How can we find ways to do right by more people, more of the time? How can we get to the root of what’s going wrong at our company or with our offering or with our technology? How can we fix them in such a way that we won’t have to worry about them all the time for the decades to come?
That perspective of permanence gives you a completely different outlook on your actions and your overall strategy. It’s like how most people end up treating a neighborhood they live in with a different kind of respect than one they’re just visiting. It’d be nice if everyone were just the best human they could be all the time, but it seems that most need some intrinsic incentive. Having to stick around is one such incentive.
How would things be different for you if you couldn’t just loot’n’leave?
Who needs a fancy office when you can work out of a dingy food court? Who needs fancy equipment when you can buy what you need at Walmart? Who needs to hire an SEO specialist? What does an SEO specialist do, anyway? (A question for another episode, or maybe another podcast altogether.) On this episode of Rework, three very different companies — a fashion brand, a company that sells fresh salads from vending machines, and an auto detailing shop — discuss their humble beginnings and offer practical advice about being resourceful and staying lean.