Top 19 Leadership Lessons from AMA with David Heinemeier Hansson (DHH), CTO of Basecamp

How do you structure your day as a leader? Favorite leadership books? CTO of Basecamp and Creator of Ruby on Rails, David, shares his answer to these questions and more.

What kind of leader is David Heinemeier Hansson? We were lucky enough to find out his management style, leadership lessons learned, and more during our most recent Watercooler AMA with him.

For many of us, David needs little introduction. Not only has David bootstrapped Basecamp into a company with million dollar annual profits with only 50 people located remotely all over the world, he invented a wildly popular web framework that Airbnb, Twitter, Shopify, Square and hundreds of thousands of companies are built on (including ours at Know Your Team). Oh, and he’s a NY Times best-selling author and Le Mans class-winning racing driver, to boot.

Wondering how David does it all? Or if he might have a perspective on an issue you’re facing in your company? Well, we’ve got some of those insights in this AMA he did for The Watercooler, our online leadership community.

We’re honored to have David as a member of The Watercooler, along with 400 other business owners, executives, and managers.

Read the entire AMA below on his leadership lessons learned (and join him over at The Watercooler to participate in our next AMA)…

Question #1

What systems has Basecamp used successfully to ensure employee accountability while maintaining equity and sustainability? Is it all about hiring, or are there systems you’ve put in place to ensure everyone is performing at their peak?

DHH: Good question. I think it’s something a lot of business owners and managers worry about, especially when it comes to remote work.

At Basecamp, our approach starts with the culture. We assume that people are here to do the best work they know how. If that’s not happening, it’s unlikely that’s because they’re lazy or dumb or ill-willed.

It’s more likely that it’s either because they don’t have the skills and maybe are afraid to ask. We can help fix that with mentorship and encouragement. It may also because there’s something else going on temporarily in their personal life. If so, we give the space and understanding that we would like if it was our situation.

On top of that culture, we have a number of processes that help bring evaluation of the work itself on a regular basis. We use Basecamp to ask everyone on a daily basis: “What did you work on today?”. That question has a way of ferreting out issues pretty quick. Either because someone might stop answering it for a while or because the answers are anemic. That’s a trend you can pick up on after observing answers over a few weeks.

The other element is that we work in short 6-week cycles and it’s pretty clear what a reasonable pace looks like. So if things aren’t getting done. If projects aren’t wrapping within the cycle, well, then we investigate.

We also have small teams. If you work on a team with 1 designer and 2 programmers, well, there’s nowhere to hide! If someone isn’t doing work at the level we’ve assessed them at, well, that’ll stand out pretty clearly to the other team members.

Finally, we now have a clear seniority structure that spells out expectations and scope for, say, a “junior programmer” or a “senior programmer” or a “lead programmer”. We’ve codified the responsibilities that each such level warrants. If someone is a “senior programmer”, but constantly needs someone else to drive their progress or continues to exhibit low levels of understanding, then again, there’s something to look into.

Hope these techniques are helpful!

Question #2

What’s the single most important factor in Basecamp’s success? Why did you pick that one out of a myriad of likely candidates? Why was it important?

DHH: I totally get the sentiment behind “what’s the one thing…” type of questions, but I don’t actually think it’s that helpful of a lens. The success of Basecamp comes from doing dozens, if not hundreds, of interconnected things right. Take any one principle or practice from that collection, and there’s a good chance it won’t have any discernible impact on your situation.

The fact is that different organizations and people need different things at different times to unlock their potential. That’s why our books, like REWORK and REMOTE and Getting Real and soon The Calm Company, provide a buffet of lessons and observations. Out of the, what, 80 essays in REWORK, there might just be 5 that really can change how you do things, but it’ll be a different 5 from what will help someone else.

So I try to put everything that I’ve learned and know out there. Then someone can dive through that and find the blocks that fit into the open spaces in their mind.

Question #3

You state that you have no expense policy and that you “trust employees to spend money wisely”. What experience have you had with this, have people behaved in the way you expected, or have there been some unexpected dynamics (positive or negative)?

DHH: The expense policy at Basecamp flows from the same overall culture of trust that underpins the rest of the company. We believe the people we hire are fundamentally good and want to do the right thing. We believe that if we show them trust, they will reward trust. They’ll live up to our expectations rather than down to our fears.

We’ve had this expense policy, the “spend it wisely” moniker, for over a decade. In that time I think I’ve been involved with 2 or 3 cases where I disagreed with how corporate funds were spent. And it wasn’t out of malice or deceit. It was out of a misalignment of “what’s reasonable”, and it was quickly corrected.

Imagine all the time we’ve saved in over a decade through this policy. Letting the little things slide. Taking a larger view of it. Only addressing issues if they seem like they’re representations of a larger misalignment. It’s immense.

So the overall conclusion from our end has been that this has been a monumental success. People have spent it wisely. We have shown them trust, they’ve rewarded trust. And we’ve cut out of a ton of “things that some companies do that we just don’t”.

Question #4

I’d love to learn more about your how you interview candidates. Do you have a list of questions you frequently ask? And/or do you have a list of characteristics (curious, grit, etc) that you look for in a candidate?

DHH: We’ve changed how we interview a lot of the years, but some things still carry through. For technical work, we don’t do fake gotcha work on a whiteboard or present candidates with puzzles to solve. We ask for representative work samples up front (portfolio from designers, code from programmers, writing samples from support, etc), and we use that as the basis of a human discussion about work, approach, principles, experiences, and challenges.

I do think we could stand to improve at the earlier stages in our interview process of a bit more standardization. For the last programmer position we listed, we had 400 applicants. That’s a lot to sort through, and you simply need a structure and a method to make that tolerable.

But looking back at all the hires we’ve made, I’ll sum it up as looking for “sparkle and promise”. Is there a human hook in the cover letter, or is it just a dry resume that looks like just every other resume? Is there an eagerness to learn? Is there a sparkle of future potential?

We’ve had really good success hiring junior people who’ve shown just that “sparkle and promise”. Better success than hiring senior people with a mile-long resume.

Question #5

What books/courses have had the most impact in your leadership style at Basecamp?

DHH: Some of my favorite books for leadership:

  • Maverick by Ricardo Semler. This was the book that really served to give us “permission” to do a lot of things differently at Basecamp. Here’s this guy running a major industrial company with 8,000 employees, and he’s doing all sorts of unconventional stuff, and it’s working. Surely we can do it too!
  • Turn The Ship Around by David Marquet. Wonderful illustration of having people live up to your high expectations rather than down to your fears. Assuming that competence is all around you, just waiting to be giving the trust to flourish.
  • The Meditations by Marcus Aurelius. He was the most powerful man in Rome. Emperor of the Republic, wealthy beyond imagination. Yet his days were filled dealing with people. Subordinates, enemies, friends, politicians, warriors. The Stoic principles gave him the calm to do that job perhaps better than any emperor before or since.
  • Punished By Rewards by Alfie Kohn. Management lore is full of tips and tricks on how to use incentives and other rewards to drive performance. It’s all bullshit. It does not work, at least not in the long term. Kohn deconstructs this dangerous idea with impeccable scientific rigor in domains of both employees and kids. Intrinsic motivation is really the power plant that we need to run this high level of impact that we’re all looking for.
  • Drive by Daniel Pink runs along the same lines as Kohn, but wraps it in more of a business’y framework. Motivation comes from Autonomy, Mastery, Purpose. A bit repetitive and a bit stylized, but probably easier for most people to swallow than Kohn’s work.
  • The Undoing Project by Michael Lewis. Half biography of two researchers, half summary of their work on human fallacies and predictable cognitive deficiencies. Kills the idea of “the rational human” and replaces it with a much more nuanced picture of a faulty human that makes mistakes in similar ways, which you can learn to identify and counter.
  • An Introduction to General Systems Theory by Gerald M Weinberg. To understand organizations and systems alike, you need to be able to analyze them, examine them, study them. Gerald is a master teacher in just that.
  • The Effective Executive by Peter Drucker. Full of all sorts of good tidbits, but nothing stuck more than examining how we as managers actually spend our time vs how we think we do, and what the gap between the two tells us.
  • The Halo Effect by Phil Rosenzweig. We have a tendency to idolize people and companies who show success in one area and think that everything they do must be wonderful because they’re successful. Not so. The Halo effect clouds our judgment and makes us cargo cult terrible practices and traits of successful people.
Maverick, one of David’s favorite leadership reads.

Question #6

I would love to hear how you at Basecamp approach releases, communication around them. How do you release a new product within Basecamp, make sure it gets used etc?

DHH: At Basecamp our release process isn’t overly structured. We mostly decide what to build based on gut instincts, developed over two decades of making products like Basecamp. But there are a couple of pointers.

We try to use what we’re building as quickly as possible internally. That means running things on beta servers against real data, so people can use the new features in their actual workflow. Not just dummy clicking around.

Some times we will look at usage data before making a decision, but it’s not a major component for us deciding either way. We do a lot of things that has no a priori support in a data conclusion.

When we do release it, we usually write up a tale about the why, the how, and finally the what on Signal v Noise. Introducing features isn’t just about telling people about what they can do now, it’s just as much inspiring them to use it, explaining why this was important. Setting the stage.

Then after something has launched, we now do a retrospective immediately after, and then another 3–6 months later. Talk about how the project went, look for lessons in the customer reactions.

Question #7

What are the things you DON’T do, to ensure high personal growth? How do you grow and achieve in more than one area? Is it the same method for each area?

DHH: I love thinking about all the things I and we at Basecamp don’t do 😄. There’s perhaps more to learn in the negative space than there is in the positive.

One of the things I don’t do is engage with any sort of physical community of developers or business people on a regular basis. Maybe part of that is just being an introvert, but I often find myself dreadfully bored at social events in technology, and I rarely find myself learning much. So that’s out.

Same goes for networking in general. I very rarely if ever agree to meet people for lunch or a drink or even get on the phone. It punctures the day and takes energy away from moving forward on the things I really care about. Again, that’s partly a luxury of our small-business focus. We don’t need to schmooze, so we don’t.

I don’t do things out of obligation, as a general rule. “We probably should” is in my book code for “we probably SHOULD NOT”.

Rather than engage with most people directly, I prefer to engage with people from the present and past via their writing and actions. I have better relationships with many ancient philosophers and writers than I do with contemporary business leaders or managers 😂.

I constantly think about how I can cut things out from my life. If I do ever less, there’ll be ever more time to focus on the very few things that truly matter to me.

Question #8

Based upon the Jim Collins’ mantra about it is more important to determine what you don’t do as opposed to what you will do, how hard was it to get all of the 37 signals team on board to say, we are dropping everything else and focusing on Basecamp?

DHH: Rodney, it’s always good to have a look at your vision and values, but I find it’s often much easier to sit down in some brainstorm session and bullshit about it rather than actually living it. The hard part isn’t deciding, it’s doing.

At Basecamp, we don’t do 3-year plans. Or much of any planning at all. We think at MOST about what “themes” we want to cover within a year. And then we make decisions about what to work on every 6 weeks.

As for deciding to focus on Basecamp, it came at a time where we were just ready for that. The existing structure was straining. There were too many products doing too well for us to continue as we were as a small business. We decided that staying small was more important to us than growing many businesses, and that was actually pretty uncontroversial within the company.

At the end of the day, Jason and I run the show in terms of making the major business decisions. Of course we want people on board, but even if there had been more opposition, we would probably have pushed ahead regardless.

Question #9

Since Basecamp is a geographically dispersed organization how do you structure and staff (and their locations e.g. overlapping timezones) within project teams to facilitate expedient development with asynchronous communications?

DHH: Dave, we wrote a whole book on the topic of remote work called REMOTE: Office Not Required. That’ll be the best and most comprehensive take on how we’ve solved those challenges over the last two decades of working.

But my fundamental belief is that remote doesn’t actually make things any harder, but it does expose the hardship quicker. So it seems like there’s more challenges but they’re just visible. It’s like turning on the light on your process and culture.

David’s book, Remote.

Question #10

Do you think your strategy of paying everyone at the same level equally, and then automatically upping it every year contributes to any social loafing? Are employees engaged when it doesn’t feel like they have to give 110% or “earn it” in some way?

DHH: Aubrey, we’ve spent a lot of time thinking about pay at Basecamp in the last few years. We used to not really have any structure, individuals negotiated their own packages, we’d occasionally give bonuses, and I became sick of the whole process.

We have great people because we hire good humans and give them the room and trust to excel. Why should some of them be paid more than others because they’ve taken a negotiation class or are just more bullish by nature? Doesn’t feel fair at all.

But beyond that, I just don’t think that raises or the prospect of raises, and other monetary rewards like bonuses, are long-term effective as motivators. I cited a couple of books that cover the research on this topic, Punished by Rewards and Drive, in the book answer, but I’d highly recommend diving into the science. Dangling carrots have a few short-term benefits and many long-term ills.

So now we pay everyone in the same role at the same level the same. Regardless of where they live. And we track the industry to ensure that we’re staying near the top. We used to track top 5% of Chicago rates and just switched to top 10% of San Francisco rates. We want and can run with the top, so we do.

That’s a privileged position to be in after two decades of running a profitable company. I wouldn’t advice most companies to set such high targets. But I would encourage them to look at pay in a more equitable fair way that doesn’t require arm-twisting or begging for raises.

Question #11

What is your take on OKR’s? Did you guys at Basecamp implemented such a process or do you just track the success on some basic KPI’s?

DHH: Peter, it’s funny, I had to look up what OKR’s mean. I’m not current on corporate lingo. But no. We don’t track OKRs or the like. We boil things down to a bigger level of “do the best work of your career while you’re here”. I don’t believe in chasing metrics.

Are we generally growing? Are our A/B experiments working? Are we still profitable? It doesn’t have to be that fancy. Maybe that’s because we don’t have a sales department or a suite of executives that get rewarded in that way, but that’s how we roll.

Peter Drucker has written a lot about the toxicity of explicit targets and metrics. I find that compelling too.

Question #12

If growth isn’t the goal anymore, what is? How do you think about this personally, and how do you communicate different goals to your team to keep them motivated and challenged?

DHH: The goal at Basecamp is to be able to keep doing what it is that we’ve been doing: Make a great product that customers are happy to pay for, and take exceptionally good care of our employees.

We hit success on that scale a very long time ago.

These days it’s more about not fucking that up. It’s so easy to fuck up a good thing. Much easier than it is to make a good thing.

We’d fuck up Basecamp, as I know and love it, by growing the headcount by 2–3x. So we work hard to stay small. We’re just over 50 people. That’s enough to do the things we want to do. So we cut out things rather than hire more to stay in that zone.

I don’t think most employees are that motivated by goals, in the sense of metrics and financials. At least not the kind that we generally want to attract and hire. They’re motivated by doing great work. By becoming better at their craft. By making decisions that have a real impact for customers.

Question #13

How do you know when/if it’s time to focus on the product and stop being a consulting company?

DHH: At Basecamp, we switched from a consulting to a product business when the product business could pay our salaries and expenses and still be profitable. But we were also motivated to get out of consulting, so maybe that’s a too low bar for you. If you like doing consulting, that’s great, and you could wait longer.

For us, it took just over a year from the launch of Basecamp until we could focus on that exclusively.

Question #14

From what I understand about you, you personally you live a life that allows you to contribute in your company but also lead a life by design (travel, location, hobbies, work schedule, etc). How do you maintain this balance and what are some ways that you have over the years moved towards the balance you lead today to contribute to Basecamp while maintaining the lifestyle you want?

DHH: Adam, Basecamp was founded on habits that allowed Jason and I to have lives outside of work from the get-go. We never did the crazy 80–120 hour/week thing. Never appealed to us, never found it necessary, never saw it as productive.

So in that regard things have hardly changed since the beginning. We put in about 40 hours per week, and then we spend the rest of the time indulging in hobbies and family and travel and reading and whatever else makes life interesting. That balance is pretty much the same today.

40 hours is enough. And beyond that, taking multiple vacations every year is a good thing too.

Question #15

How do you structure your days?

DHH: Anders, I don’t believe in starting out with mad hours. And we didn’t. I didn’t. We built Basecamp on the technical side with me putting in 10-hours per week! Not per day. I was going in school at the time and I also wanted a life outside of work.

I think 40 hours is more than plenty whether you’re junior or senior. It’s all about how you spend the time and on what. Yes, if you waste it in meetings or in days punctured by interruption, that time doesn’t go very far. But if you get long stretches of uninterrupted time to yourself, it’s more than plenty.

So I don’t recommend that people starting out put in the mad hours because they generally won’t be able to stop. You are what you do and habits are very hard to break.

Focus on getting quality lessons out of your time, not quantity. You’re not going to learn more by doing the same things over and over again.

Jason and I are friends. Not hang-out-every-week-at-each-others-house friends, but friends. We have lots of overlapping hobbies as well. We split the burden of running the company pretty evenly. And then his area of expertise is design, mine is programming.

Question #16

Do you have any specific thoughts about how you can agree-to-disagree without breaking bonds?

DHH: Oana, it’s tough to align fundamental differences like that. Not impossible, but hard. One way that can help is to read the same literature and be inspired by the same voices. Maybe one way to start is to do a bookclub of sorts. All the books I recommended in my answer on leadership books could serve this purpose.

That doesn’t mean you need everyone to be clones, far from it. But there needs to be a fundamental set of shared principles.

All the best!

Question #17

Could you elaborate a little on how you involve existing customer and users in new product features and roadmap? Do you run separate beta/preview features for selected customers? Can all users opt-in to trying out new features? Finally, how do you bring the feedback from the actual users to your product team?

DHH: Anders, we’ve done a lot of Jobs To Be Done research to understand the pressures and motivations of our customer base. So that serves as a backdrop always. But fundamentally, we make Basecamp like we want to have it.

We try to build software on behalf of our customers, not by their request. So that generally means you can’t just ask them “what would you like”, because they’ll like a faster horse. You have to aggregate all the inputs and then formulate a product vision that encapsulates that.

So we don’t do any beta/preview/opt-in stuff with customers. We use it ourselves and then we push it live. If there’s a ton of pushback on certain things, we reconsider, and sometimes we change what we do.

The feedback flows up from customer support and the product group watching the channels (announcements on Medium with comments, twitter, etc).

Question #18

I’m curious to ask you to compare your experience as a leader in a large, open-source project/community (Rails) to your experience as a leader in a corporation (Basecamp)? What lessons from one have influenced your behavior in the other?

DHH: Jason, I think most leadership lessons are pretty universal. I don’t have one persona for Basecamp and another for Rails. I believe that people are generally motivated by the same factors. So whether I’m working with an employee or a peer, it’s the same factors that help unite us and drive us forward.

So I’d say that all the leadership books I mentioned in the other answer applies equally to both domains.


Question #19 (a long one!)

We have tried many development processes over the years but none of them felt quite right. Last summer we switched to something mimicking basecamps workflow (pitches, 6 week cycles with off weeks, etc). Best version of ourselves yet!

Couple things we still struggle with:

Pitches. Can’t seem to get people to write them, or if they do very weak on details. Salesmen baulk at the idea of writing them, so developers usually do it for them. Our two week off cycle weeks seems to be very intensely focused and stressful taking pitch paragraphs (or worse sentences) and converting them to well formed ideas. Wondering was this difficult to implement in the beginning? Is there a wide variety of people that actually write the pitches, or does it generally come from the same sources? Any tips?

Customer Support Balancing. Our customer support can fix some bugs and help confused customers out, but semi-frequently issues ends up needing higher level support, in our case a developer to take a look. Is your support capable of fixing anything? Can they make patch releases if necessary? If not do bugs get fixed right away or pushed to the small batch list? This might fall in the “it depends” bucket.

Versioning. We have multiple versions of our app that we support. Do you ever have requests for a new feature to get backported to an older version? Is that just a flat no? Do you worry that in 10 years it might be hard to support all the versions? Do bugs for basecamp 1 and 2 come up often?

DHH: On pitches, we don’t see it as the main way to drive the product development selection. It’s a source of input, but you need someone in charge of the product who have their own vision and does their own research into what you should be building to make it work. Pitches are more an outlet than anything, really. A way for people who DO have good ideas and do the work to present them well to be heard. I wouldn’t try to force pitches out of anyone.

On support, we used to just have front line support send tickets they couldn’t handle straight to developers. That became very disruptive pretty quick. Then we went to a rotation style where all developers would rotate in to do a week of “on-call”, where all they’d do would be working with these tickets. Now we have both front line, or tier 1, and a tier 2 consisting of more senior support people with some technical chops to do backend data manipulation. And then, if it really is a bug, we log it in the system for later fixing. Very rarely these days is something so critical that it must go straight from a customer ticket to a developer immediately fixing it.

I love our versioning. I did a whole talk on the topic here:

Remote work: I’d recommend our book on the topic. REMOTE: Office Not Required. It gives you both the ammunition to convince management and it gives you patterns for how to do it well.

Pay: Answered that in another question. We do top 10% of San Francisco rates for everyone according to role and seniority. There are companies like Radford and PayScale that can help you understand the rates in your industry and area. But fuck having to arm-twist for market rates.

Roadmaps: We don’t do them. Ugh. Planning Is Guessing is a chapter in our book REWORK that covers this.

If you keep cutting against the grain and not making progress, then it’s time to think about getting out. Either by starting your own thing or finding like-minded people to work with instead.

7 ways to prepare for an effective one-on-one meeting with your manager

Got an upcoming one-on-one meeting with your manager? Consider a few of these tips in preparation for it.

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

Yikes, really?

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

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

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

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

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

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

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

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

Share what’s been most motivating to you.

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

Reveal what’s been draining and demotivating to you.

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

Explain how you want to stretch and grow.

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

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

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

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

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

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

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

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

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

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

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

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

The power of assuming positive intent

My greatest leadership weakness, and how I’m learning to overcome it…

My parents were in town last week. During one conversation we had, my mom shared an opinion that I strongly disagreed with. And as I responded to her, she said this to me:

“You’re getting defensive.”

Throughout my life, I’ve heard this quite often. Getting defensive is my greatest personal weakness. It’s a terrible habit of mine that I’ve been aggressively working to counteract, especially in the last few years.

When I hear something I don’t want to hear, I jump to conclusions about why that person is saying that thing. Instead of trying to genuinely hear out the other person, I’ve already decided in my head that they’re misinformed, or have an ulterior motive, or don’t have my best interest in mind.

This tendency of becoming defensive doesn’t just show up in my personal life…

As the CEO of Know Your Team, I’ve felt moments of my own defensiveness creep up when our programmer Matt has made a suggestion about how to respond to a customer support request, or when he’s critiqued a layout of a design I’ve mocked up.

This defensiveness is dangerous. Because when you’re defensive, you stop listening. And when you stop listening, you shut out critical information that could benefit you. Whether it’s from your mom or from your co-worker, you have an opportunity to learn something meaningful… such as, how you need to be more generous with your time to others, or an idea that leads to increased sales in your business.

But when you become defensive, none of that information reaches you. Defensiveness cuts you off from learning.

Over the years, I’ve noticed the root cause of my defensiveness: I misread the intention behind what someone is saying.

For example, when I react defensively to my mom’s critique, it’s because I think she’s just being negative. Or when I react defensively to a suggestion Matt has about a design, it’s because I assume he’s trying to advocate for something else that he created.

When you accuse another person of bad intentions, you create defensiveness. Instead, assume good intentions, and your defensiveness goes away. That is the best way to combat defensiveness.

In fact, Indra Nooyi, the CEO of PepsiCo, describes learning to assume positive intent as the best advice she’s ever received:

My father was an absolutely wonderful human being. From him I learned to always assume positive intent. Whatever anybody says or does, assume positive intent. You will be amazed at how your whole approach to a person or problem becomes very different. When you assume negative intent, you’re angry. If you take away that anger and assume positive intent, you will be amazed. Your emotional quotient goes up because you are no longer almost random in your response. You don’t get defensive. You don’t scream. You are trying to understand and listen because at your basic core you are saying, “Maybe they are saying something to me that I’m not hearing.” So “assume positive intent” has been a huge piece of advice for me.

Now when I feel myself starting to get defensive, I remind myself to take a step back and assume that the other person has good intentions.

With Matt, if you know him, you know one thing is clear: he’s vocalizing a suggestion because he truly cares about Know Your Team.

And if you know my mom… Well, I don’t think there’s another person on the planet who has more of my best interest at heart!

Recognizing this doesn’t mean I’ll submit to whatever Matt’s suggestion is when he offers it. And it doesn’t mean I’ll always end up agreeing with my mom when she shares her opinion.

But it does mean I’ll widen my mind. I gain a greater understanding and perspective of a situation. By truly listening to the other person’s viewpoint, I can make a more informed decision.

So when your employees raise a concern, don’t assume that it’s because they’re just miffed about their current job titles or how long the last client meeting was. That might very well be their underlying motivation — but you shouldn’t rush to that conclusion right off the bat before even hearing them out.

Assume positive intent. Thank them for their feedback. And then listen. Don’t interrupt. Ask questions. Clarify where they’re coming from. And then form your own opinion about the content of what they’re saying and what their true intentions might be.

Is it a bit more work to navigate the friction that comes from assuming positive intent, and not merely brush off someone’s idea?

Absolutely. But that friction is productive energy — it pokes holes in my own thinking and strengthens the actions I do take.

When I choose to assume the best intentions in others, I become a better leader, co-worker, family member and person. I don’t practice it as often as I should, but I’m vigilantly committed to working on it until I do.

Don’t let worry become a leadership weakness

Worry is a natural byproduct and characteristic of a leader. Here are five ways to cope with worrying as a leader.

The other week, I interviewed Jason Fried, CEO and co-founder of Basecamp. I asked him what he wish he would’ve learned earlier as a leader.

His response? Worry less.

I smiled when he said this. Oh, how I could relate!

Over the past few years, I’ve noticed how many CEOs (myself included) are stressed out and worried about something. They’re worried about employees leaving, internal team conflict, growing fast enough, their product failing, the market changing, the competition beating them, running out of money, hiring great people…

The list of worries seemingly has no end.

But how do we put an end to it? Personally, I know I’d like to worry less. I think more clearly, act more intentionally, and enjoy life a hell of a lot more when I’m less worried.

In an effort to worry less as a leader, I decided to write out what works for me. Here are five things I try to keep in mind to worry less:

Ask yourself: “What’s the most I can do with what I have right now?”

Most of my worry stems from feeling a lack of control over a situation. I want something to turn out a certain way. So I start to feel overwhelmed and worried when I don’t believe I have the agency to influence that outcome. Here’s the funny thing, though: We have more control than we think. We can control ourselves — our actions, reactions, decisions, and beliefs. What we can’t control are other people and external events. And if that’s the case, well, why bother worrying about them?

Let’s choose to focus on the former: The things we can control.

To do this, a helpful question I like to ask myself is, What’s the most I can do with what I have right now?This question re-focuses my energy on what I am in control of right now. Instead of idling in indecision and mulling over every possible path and course of action, the question “What’s the most I can do with what I have right now?” forces your hand. You must deal with the cards in front of you. And once you do, you’ll clear a path to move forward within the constraints you have. Now you can focus on what you can control.

Remind yourself that the present is real — the future isn’t.

My worry also comes from my mind operating too much in the future. I think, “What if…” or “That could happen…” and brace myself for a future scenario, trying to strategize two steps ahead of it. While in some ways that can be beneficial for thinking through certain complex decisions, it is enormously distracting, for the most-part. The only thing that’s real is what is happening now. The present is real. The future isn’t real yet. It hasn’t happened. Remembering that always lightens the load of my worries.

Realize how good you have it.

When I stop for a minute and look at my life, I realize how goddamn lucky I am. Lucky that I was born in this country, to have the parents that I have, to go to the schools that I did, to meet the people I have across my career… I hope I’m not the only person who feels this way. So many of us, even in our worst, most pained, stressed, and worried work moments, live lives that 99% of the world would trade places with in an instant.

Of course, it’s tough to remember when we fall victim to our own worry-ridden train of thought. To combat this, at the end of every day, I try to think of three specific moments earlier that day when I felt joy or gratitude. (Studies have shown that in fact writing down daily what you’re grateful for significantly reduces stress in people.) I realize that I’ve got it good — and so many of us do.

Share your worries.

Tell other people what your worries are. It does no good to suffer in silence. Often times, when I say my worries aloud to another person, it becomes immediately apparent how stupid that worry is, how pointless it is… and the worry evaporates. If it doesn’t, at the very least, you now have a confidant, a pal, who you can think things through with and discuss a plan of action around. Don’t keep worries to yourself. Share ‘em.

Step away, move your body, get some sleep.

My worries become exacerbated when I don’t take care of my mind and my body. When I’m in a particularly stressful or worrisome situation, usually the best thing is to take a step back, get my body moving, and go do something different. Go for a walk. Get on a bike. Breathe some fresh air. Go surround yourself with greenery, or good music. Talk to a sibling, parent, friend, boyfriend, or spouse about something completely non-work related. And get some sleep. Rest the mind, rest the body. The break is needed. I always return feeling clearer and fresher on what matters.

I hope these tactics may be as helpful to you as they’ve been for me.

If anything, as I shared with Jason during our interview, do keep in mind what a friend once told me:

“Worry is the most useless emotion.”

Fresh eyes: The most important thing a new hire brings

When welcoming a new coworker, keep this in mind.

On the first day of one of the first jobs I ever had coming out of college, a mentor of mine pulled me aside, and said to me…

“Claire, take a look around the company. Take in everything you see and hear, what you think could be better, and write it all down. Don’t forget that stuff. Since you’re new here, you’re going to see things that we’re not going to see. You’re going to turn over rocks and go, “What’s that? That’s stupid.” You’ll question stuff that we’ve just been assuming. You’ve got fresh eyes — and we need that.”

Years later, that concept still sticks with me. As a business owner, I’ve experienced firsthand the importance of seeing things with “fresh eyes.” Especially, as I’ve begun to hire new folks. I’ll explain my business process to them, and catch myself justifying “the way we do things” because it’s “the way we do things” — not because it’s the right way. What good is that?

The longer we do something, the more “used to” it we become. And the more “used to” it we become, the more details and nuances we stop seeing. Changing circumstances, changing market, changing competition, changing problems…we develop blind spots when we get too “used to” running our own business.

So we need fresh eyes. We need to seek out new perspectives on our business, particularly from the newest employees in the company.

This is a tricky thing to do because new employees are often the ones who are least likely to speak up. The longer you are at a company, the more comfortable you feel in providing a dissenting opinion. But if you’ve just joined the company last week, you don’t want to rock the boat.

To get this information from new folks, you’ve got to actively seek it out. Ask yourself…Who are the people in your company who have fresh eyes? What can you learn from them? What questions are you asking them?

As a CEO, owner, or manager, if you want fresh eyes, you’ve got to ask for it. Sit someone down. Tell them that they can bring something to the team that no one else can.

Tell them you need their fresh eyes.

How to not take negative feedback personally at work

Three things to remember when you handle criticism in the workplace.

I often look like this when I take feedback personally.

I recently finished reading a book called, The Four Agreements. The title is a bit hokey. But the content is spot-on.

The book talks about the importance of creating personal freedom. One of these four agreements to create personal freedom is: “Don’t take things personally.”

This really hit home for me. I realized how often I take things personally — especially when it comes to giving and receiving feedback in the workplace.

Our tendency is to interpret the feedback we hear as a personal attack. It’s the biggest reason for why we don’t ask others for feedback.

When someone gives us feedback on our performance at work or about how our company is doing, we get an icky feeling in the pit of our stomach. “What?! How could this person think that?!”

We’re scared to hear something that we might not want to hear. So we avoid asking for feedback.

That’s a problem.

Not wanting to hear feedback means we shut ourselves off from information that will almost certainly be useful in some way.

In any piece of feedback, there is a nugget of helpful information. You’re guaranteed to learn something about a person or your company. Maybe it’s about how your actions are perceived by your employees, or the sentiment about a recent change you made to the company — that information is useful.

You don’t have to agree with the feedback, but you will learn something in listening to it.

The key is to not take feedback personally. Here’s how…

First, remind yourself: “It’s not all about me.”

There are other external forces shaping why a person may be giving you this feedback.

Maybe something happened earlier that day that caused them to be in a sour mood. Or, maybe something happened with their old boss that’s caused them to believe “this work environment sucks.” It has nothing to do with you.

Second, remind yourself: “I don’t need to be liked.”

You don’t need your employees to like you. You do need them to like their jobs and feel fulfilled and excited and motivated to work. But you don’t need them to like you as a person.

The minute you let go of the notion that you don’t need to be liked, by your employees, your leadership team, etc., your focus begins to shift toward what’s best for the company overall. Doing so allows you to open up and hear things that you might’ve previously taken personally.

Third, remind yourself of what you care about.

You do care about your company being successful. You do care about creating the best environment for your employees to thrive.

So if that’s the case, focus on hearing that feedback through the filter of:

“How can I listen for information that will help move my company forward?”

After all, that’s what you want. You want your company to do well. Listen for things that will help you meet that goal — everything else is secondary or irrelevant.

Granted, it’s incredibly hard to not take something personally.

But in reminding yourself of these three things — it’s not about you, you don’t need to be liked, and you care deeply about your company as a whole — you can begin to escape the trap of taking things personally.

By committing to not taking feedback personally, you open your mind to suggestions that could help your company. Employees will appreciate your willingness to ask for feedback — I promise.

You and your company will be so much better for it.