Do I truly want to become a manager?

We don’t ask ourselves this enough. Here are 6 critical questions to reflect on when considering if you should become a manager or not.

Two paths to becoming a manager or not.

When we’re asked, “Do you want to become a manager?” we often assume there is only one answer.

“Oh, of course I want to be a manager.”

Right? Who doesn’t? Especially when becoming a manager is seen as the primary path of upward progression in a person’s career.

But do you truly want to become a manager? Management is not some sacred club reserved for the hallowed few. Rather, deciding to become a manager should be viewed as one might decide to become a garbage disposal collector or a parking meter attendant: If you’re doing it, you’re doing it for a reason. It’s not for everyone.

In this sense, management is like any other job: There are pros and cons, specific skills, proclivities, and a mindset called for. And as a result, not everyone should feel compelled to aspire toward it. If you don’t love food, you shouldn’t be a chef. If you’re not into buildings, you shouldn’t be an architect. And if you’re not excited about certain things managers do (which I’ll share in a moment), you likely shouldn’t want to become a manager.

Many of us learn this the hard way. Just the other week, I talked to a Vice President of Engineering who had promoted someone who’d expressed a strong desire to become a manager. A year into the role, this person he’d promoted was miserable. He realized he didn’t like his day-to-day tasks a manager, and he wasn’t very good at it. Now he’s happily back to being a senior-level individual contributor.

This VP of Engineering is not alone. In their research, Gallup has found that companies choose the wrong manager 82% of the time. Often times, folks are promoted as managers because of their strengths as an individual contributor – but those strengths don’t necessarily translate to their role as a manager.

A manager in on our online community The Watercooler in Know Your Team had experienced this firsthand. He frankly shared with the other 1,000+ members:

“I had a tough time as a first time manager because I quickly and painfully realized that the skillset that got me noticed and moved me up to manager were not the same that would get the job done or help me keep it.”

Consequently, the question, “Do I really want become a manager?” becomes paramount. We can’t rely on others’ suggestion or affirmation that “Yes” to that question is the right answer. We have to dig deeper.

As you ponder “Do I truly want to become a manager?” for yourself, here are 6 critical questions to reflect on….

How much do you enjoy being in “flow” at work?

Positive psychologist ‎Mihaly Csikszentmihalyi famously described “flow” as an optimal state of consciousness where you are “completely involved in an activity for its own sake. The ego falls away. Time flies.” Pursuits like painting or rock climbing are often associated with flow – but perhaps you’ve felt it at work as a designer or a writer or programmer.

As a manager, this state of flow is less common, if not non-existent. You aren’t diving deep on a task during an uninterrupted block of time, as required in flow – you’re the one helping others dive deep on a task. You’re also not receiving immediate feedback about your progress in the same way you would as an individual contributor, which is another critical element of flow. As a manager, you might not find out until months later if a decision you made or a conversation you had positively or adversely affected your team.

If you relish being in flow, weigh how important the frequency of that experience is for you. As a manager, you’ll have to accept that you’re not going to be in it as often as you were when you were an individual contributor. Or, understand that you may have to find ways to reprogram what your original requirements for flow were.

Does repeating yourself drive you crazy?

You may be thinking to yourself, “Well, Claire, who doesn’t get at least a little annoyed when they have to repeat themselves?!” Surely, it’s not the most fun thing to do. However, as a manager, you’ll find yourself doing it all the time, no matter how adept you are at communicating. It’s your primary job as a manager, in many ways: To share, explain, reinforce, ask questions, share more, explain more, and ask more questions, over and over again, all the time.

As Ryan Carson, CEO of Treehouse has expressed this on our podcast:

“You have to over-communicate. […] And it feels really painful to be a leader like, ‘Oh my God, I have to say this again? Why are we doing this thing?’ And it turns out, yeah, you do, because people can’t read your mind.”

Yes, people can’t read your mind – and they shouldn’t have to. The best managers bear the burden of making what’s implicit explicit, so their team can function well. But if the idea of doing that – communicating constantly, all the time, over and over – sounds exhausting, you don’t want to become a manager.

How big of a control freak are you?

One of the hardest things to reconcile as a leader is how much you have to let go. Most new managers tacitly know this going into the job – they’ll have to delegate, not work on too many project details, support people on projects, etc.

But in reality, how tight is your grip? Do you have a tendency to be a bit of a control freak (be honest ;-))? Do you see yourself often as “the only person who can do X?”

I remember interviewing Laura Roeder, CEO of MeetEdgar, on this topic, and how she’d gained a ton of clarity on the degree to which good leaders must relinquish control. She said:

“You realize that what you’re really saying is ‘I’m the only person in the world who can do this and I’m the best. I am the greatest at reconciling PayPal downloads that this world has ever seen.’ And that’s really absurd.”

If you find joy in the meddling of details in projects, if you’re aghast at the idea of giving control away, if being the “the only person who can do X” gives you a sense of purpose in your work – that’s fantastic! However, it also mean being manager might not be for you.

Do you like to play detective?

The best managers understand that they’re not managing people – they’re managing an environment with interacting elements of dynamics, past experiences, relationships, cultural influences, and more. So as a manager, it’s up to you to figure out: What is really going on here? What is motivating this team member? Why might she be frustrated with this team member? What is the true underlying cause of why this other team member is struggling? You have to ask questions, be relentlessly curious, and uncover the truth of a situation. You have to play detective.

For some, trying to discover the nuances of people, personality, temperaments, and relationships, and then trying to piece them together is absurdly draining. For others, it’s fascinating, stimulating work. Consider which of the to two it is for you, before deciding to become a manager.

What is your default reaction to conflict?

You will never be able to make everyone happy as a manager. Nor should that be your goal. When you try to please others, you do your team a disservice. You start making compromises and decisions that are in the best interest of you looking good, instead of what is best for your team as a whole. In The CEO Next Door, the authors cite how the best leaders must keep their stakeholders “constructively dissatisfied” in order to move the team productively forward. Getting people to like you is not your purpose as a leader. Should your natural disposition be to avoid conflict, to want everyone to always be happy and like you, you may want to reconsider becoming a manager.

How disciplined are you with your time (really)?

As Peter Drucker, the seminal scholar on management of the 20th century has espoused, an effective executive is one who knows how exactly to spend her time. If you can’t manage your own time, schedule, and priorities, you can’t expect to help your team to manage theirs. This sentiment was reinforced by a Watercooler member who shared with us in online community managers from all over the world, “Shocking news, being a manager is not about managing other people, it’s about effectively and efficiently managing yourself as a resource (your time, productivity, logic aka brain power etc) which then transcends how you manage other people.”

You might find yourself discouraged reading this far – you thought you wanted to become a manager, but now maybe you’re not so sure? That’s a good thing! It means you’re being rigorous about what might be a good fit for you personally, instead of assuming the pre-laid path. You’re never going to be a good manager if you do it because you’re “supposed to.”

Here’s the other thing: You can develop a propensity for the skills, habits, and outlook that a good manager requires. For instance, while maybe you’re not as disciplined with your time as you’d like, you can focus on setting clearer priorities and following through on them. Or, perhaps if you know you tend to avoid conflict, you can practice how you respond and react to conflict in your current role at work.

Regardless, being honest with yourself is what matters. You can now ask yourself, “Do I really want to become a manager?” and know there is more than one answer.

Don’t solve problems if you want to be a great manager.

What makes a great manager isn’t the problems they solve, but the questions they ask. Start with these 16 questions here.

An employee comes to you and says, “I have a problem.” If you’re trying to be a great manager, what do you do?

Your initial instinct might be to roll up your sleeves. “Time to be the boss,” you think to yourself. You’re ready to step in, solve the problem and save the day.

Or something like that. You just want to be helpful.

In reality, your instinct is the opposite of helpful. Startlingly, when you jump in to solve a problem as a manager, it’s one of the biggest leadership mistakes you can make.

I was reminded of this counterintuitive concept when chatting with Wade Foster, CEO of Zapier, on our Heartbeat podcast. Though his company today is thriving with over 200 employees and over 2 million users, Wade admitted how he struggled in the early days as a CEO when an employee would come to him with a problem:

“When you [jump in and try to solve the problem yourself] you’re actually mistaking your roles. You’ve hired this person to solve problems. And if they’re unable to solve the problem, you’ve probably hired the wrong person.”

In other words, your role as a manager is not to solve problems. It’s to help others solve problems, themselves. Leadership is stewardship. It’s navigating your team through treacherous waters, around jagged rocks, to the desired destination, and making sure folks feel nourished and rested along the way. But you can’t be a good steward if you’re scampering around trying to paddle all the oars faster, yourself. To take the boat analogy one step further, a great manager is a coxswain, not a rower.

This confusion of roles leads to a highly undesired outcome: You prevent your team from learning how to solve the problem. A dangerous reliance develops that hinges on your expertise, your “final word.” Your team never gets to fuss, flail, and figure out how to crack a nut with their own hands. When you’re the one thinking through all the problems, you’re teaching your team members to not think for themselves.

You also inadvertently slow your team down. Every problem – especially the “hard ones” – are re-routed to you. So what happens if you’re out of the office that week? Or, what if your plate is full? Well, that problem will just have to wait. And wait it does. You become a bottleneck, the inhibitor of your team. You funnel your team into single mode of dependency that’s difficult to undo.

The best leaders know this, and are keen to avoid this pitfall – so they do something else. They become the team’s accelerator. They help team members think for themselves.

How? By asking questions. Wade of Zapier adopted this practice as a CEO, describing it as a “more Socratic way” to helping his team solve problems. Ultimately, it leads to better results.

Ask questions and a team member can come to the answer themselves. Ask questions and the problem they’re facing becomes more lucid, less daunting. Ask questions and your team member might even come up with a better answer than you would have.

To be a great manager, here are 16 questions you can start with instead of jumping in to solve the problem yourself:

  • What do you see as the underlying root cause of the problem?
  • What are the options, potential solutions, and courses of action you’re considering?
  • What are the advantages and disadvantages to each course of action?
  • How would you define success in this scenario?
  • How do you know you will have been successful?
  • What would the worst possible case outcome be?
  • What’s the most likely outcome?
  • Which part of the issue or scenario seems most uncertain, befuddling, and difficult to predict?
  • What have you already tried?
  • What is your initial inclination for the path you should take?
  • Is there another solution that isn’t immediately apparent?
  • What’s at stake here, in this decision?
  • Is there an easier way to do what you suggested?
  • What would happen if you didn’t do anything at all?
  • Is this an either/or choice, or is there something you’re missing?
  • Is there anything you might be explaining away too quickly?

What you’ll notice when you ask these questions is that most employees already have an answer (or several answers!) to a given problem. But they were uncomfortable with it, or they were worried about getting it “wrong.”

Part of asking the questions isn’t just to help them think through the problem more clearly, but also to help them realize they know more than they think, they’re more capable than they think, and that they’ve mitigated the risks better than anticipated.

Your job as a leader isn’t to just help clarify thought process – but to give confidence in their thinking.

As Wade says, “You’re trying to just help them get to that realization that, ‘You know what to do.'”

After all, a great manager is centered on building the capabilities of their team, not their own capabilities

Don’t solve the problem, yourself.

Announcing: Our Manager Workshop

Attend our in-person leadership training and manager workshop to get better as a leader, faster.

Want more hands-on, immersive learning to be a better leader? We offer in-person leadership trainings and a manager workshop based on data from 15,000+ people and years of research, personally run by none other than myself, Claire, CEO of Know Your Team. We’ve never fully publicized our manager workshops, but have found our clients benefitting from them so much, that we decided we ought to share a bit more 🙂

“Most attendees said it was the best training they’ve ever attended in their professional career and all felt it was super actionable.”

Emily Allen – Director of People Operations at SEER Interative

Our workshops are the perfect complement to using our software – or are excellent on their own, for a leadership retreat. We’ve delivered them to employees, managers, executives, and CEOs across the world, from New Zealand to Arkansas, for small tech companies to international corporations to national non-profits.

Results are accelerated when you practice – and our manager workshop is designed to give you practice as a leader, so you can improve and see outcomes more quickly.

“This was the most concrete and useful workshop I have ever attended.”

Bekki Freeman – Team Lead at Eggplant

Our most popular manager workshop: The Feedback Loop

We customize our training based on your needs – but here’s an example of our most popular manager workshop, “The Feedback Loop”:

Giving, receiving, asking for, and acting on feedback well are some of the most-valued – yet difficult to master – skills for any manager. After years of research across hundreds of companies in 25+ countries, I’ll share the playbook for how the most effective managers create a culture of feedback within their teams.

Here’s what you’ll learn:

  • Why leaders are constantly the last to know things in their company
  • The top leadership blindspots are and how you can avoid them
  • How to uncover your own leadership blindspots
  • How to get honest feedback, especially from your most introverted employees
  • The best questions to be asking every single employee in your company
  • How to hold an effective one-on-one with an employee
  • How to receive feedback without getting defensive
  • What to do with feedback you disagree with
  • How to tell what feedback to act on
  • What to do with feedback once you receive it
  • How to break bad news to your team
  • How to give employee feedback without damaging morale
  • The components of building an open, honest company culture

You’ll walk away with techniques, best practices, and a toolset you can put into practice immediately.

But don’t just take my word for it. Here’s what past participants have said about our manager workshops and in-person leadership trainings…

“Managers! This workshop was one of the best things I’ve ever done for my professional development. You should sign up.”

Caro Griffin – Director of Operations at Skillcrush

“As a co-founder, I found this workshop to be so useful that I asked Claire to do one just for our management team. It was a big success.”

Ujjwal Gupta – Co-Founder/COO at BenchPrep

“The workshop was valuable and fun. 100% worth every penny, including the trip out to Chicago.”

Sarah Park – President at MeetEdgar

“Claire did an incredible job — I feel super fortunate to have been able to attend.”

Samantha Lueders – Product Owner at Onpoint Promos

Interested in bringing our manager workshop to your company?

✨ You can learn more here (or reach out to us directly here).

Look forward to hopefully hearing from you!

The 9 leadership mistakes you don’t know you’re making as a new manager

Don’t accidentally become a bad boss by overlooking these often imperceptible leadership mistakes.

9 mistakes to avoid

I’ve never met you, but I’m going to make a guess about you:  You’re making leadership mistakes you don’t even know about. 

I don’t mean to sound presumptuous (or crass!). I’m in part reflecting on personal experience – I’ve made a boatload of leadership mistakes, myself.

More objectively, I’m citing probability: Gallup’s research on millions of managers over the past 7 years revealed that companies choose the wrong manager 82% of the time. And if that’s not disconcerting enough, they found only 1 in 10 managers possess what they describe “the natural talent to manage”. 

In short, the likelihood that you, as a new manager coming out of the gate, are inherently endowed with the perfect blend of traits, experience and skills to be a great manager… Let’s get real. It’s unbelievably low.  

Such is the “curse” of a new manager. Leadership is not as intuitive as we’re eager to believe. What we’d like to think work don’t actually work. And the only way to find out things don’t work is to mess them up pretty badly. 

Or, is that the only way?

Based on the research we’ve done over the past 5 years with 15,000+ people, and interviewing hundreds of CEOs, executives and managers, I’ve pulled together the mistakes most leaders tend to overlook. These are the most dangerous kinds of leadership mistakes – the mistakes that unintentionally hurt our team, without us ever knowing.

My hope is to spare you some of the self-inflicted suffering I and many other leaders have kicked themselves about, after-the-fact. So, without further ado, here are the 9 most common, imperceptible leadership mistakes to avoid:

Mistake #1:  You think building trust is about team-building.

When we want to build trust as a leader, we often resort to team-building activities:  Company retreats, informal lunches, recognizing employees publicly for a job well done, etc. However, in our survey of almost 600 people, we found that team-building activities were in fact rated as the least effective way to build trust. What was rated as most effective? Being vulnerable as a leader, sharing your intention, and following through on your commitment. In other words, trust isn’t about building rapport – it’s about you making clear why you’re doing something, and then acting on it. 

Mistake #2: You think your team members generally know what’s going on.

You’re in Slack, you’re on calls, you’re in team meetings… You do a ton of communicating and sharing of info as a leader with your team. What’s not to know? Well, a lot apparently. When we asked 3,197 people across 701 companies through Know Your Team, “Are there things you don’t know about the company that you feel you should know? 55% people said, “Yes, there are things I don’t know about the company that I feel like I should know.” Furthermore, in a separate survey we ran with 355 people in the fall of 2018, we found that 91% of employees said their manager could improve how they share information. Specifically, 42% of employees wanted their managers to communicate more regularly with them and 38% said they wish their managers shared more of their decisions and the reasons behind why they make them. While you might feel you’re communicating enough as a leader, your team feels otherwise.

Mistake #3:  You believe being busy as a leader is good.

You’re getting things done. You’re making things happen. When you’re busy as a leader, you can be tempted to believe you’re doing a good job. However, in leadership, that’s not the case.  I interviewed Michael Lopp, VP of Engineering of Slack, who underscored this for me: “If you’re too busy doing the actual work, as a manager, that’s a huge mistake.” The best leaders help employees navigate what’s fuzzy, provide structure around about what needs to happen, and reveal why the work matters. But you can’t do that as a leader if your nose is in your email inbox all day, or you’re out traveling to visit clients every week.

Mistake #4:  You sort-of prepare for your one-on-one meetings (when you have the time).

Did you prepare for the last one-on-one meeting you had with a direct report? Be honest 🙂  In a recent survey we conducted of 1,182 managers and 838 employees, we found that only 24% of employees believed their manager was well prepared for their one-on-one. The other 76% percent were managers who were seen as only “somewhat prepared”, “not prepared” or “not prepared at all.” Ouch. When you show up to a one-on-one meeting without a clear agenda or set of questions, it shows. You waste everyone’s time and squander a valuable opportunity to support your direct report. Here are some recommendations for how to prepare for a one-on-one meeting as a manager.

Mistake #5:  You try to solve the problem yourself, because you’re the domain expert.

Someone comes to you with a problem. As a leader, you roll up your sleeves and dive in head first to resolve it. After all, you’re the one with the most experience in this particular domain. It makes sense to do what you’re good at… Right? Wrong. Peldi Guilizzoni, CEO of Balsamiq shared this counterintuitive insight:  When you focus doing always on what you’re good at, the team never learns to get good at it themselves. “Instead,” shared Peldi, “focus on delegating training and making sure that everybody gets good at doing those things.”

Mistake #6:  You think transparency all the time is good.

From making salaries public within the company to open-book management, the concept of transparency in the workplace is more popular than ever. Understandably (and rightfully) so. However, transparency can backfire if you don’t hold two concepts in view:  Transparency requires context, and transparency is on a spectrum. Des Traynor, co-founder of Intercom, dispelled critical wisdom on this topic, explaining:  “The key thing people forget in transparency is it’s not about opening up the Google Drive and making sure that everyone can read everything – it’s about transparency of context as well.”

Mistake #7:  You think you communicate the vision in your team well.

Vision is crucial. But do you know how crucial?  According to our survey of 355 managers and employees, respondents said vision is #1 piece of information a manager should be sharing (45% of people said this). And yet, when we asked 2,932 people across 618 companies through Know Your Team, “If someone asked you to describe the vision of the company, would a clear answer immediately come to mind?” almost a third of employees (29%) squarely said, “No.” As a leader, we must thoughtfully reconsider how to help more folks answer “Yes” to that crucial question.

Mistake #8: You think you’re giving enough feedback. 

The barrage of feedback seems endless. You’re doing one-on-one meetings, employee surveys, annual performance reviews. Yet, despite this, in our data collected through Know Your Team, we found that 80% of employees want more feedback about their performance (1,468 employees were asked about this across 138 companies). And yes, these are folks who are already using Know Your Team as a tool to get feedback! What it illustrates is a strong desire from your team to receive even more critiques, suggestions, and ideas – the bad along with the good – about what they can be doing better. You might think you’re giving enough of it, but you could be giving even more.

Mistake #9: You’re nice. 

Don’t be an asshole, by all means. But don’t overcompensate by focusing solely on being nice. When we’re preoccupied with seeming likable instead of fair, when we optimize for feel-good conversations instead of honest ones — we damage our teams. Hiten Shah, founder of Kissmetrics, Crazy Egg and FYI, was emphatic about this point to me, describing how when you overly prioritize being nice, “there’s a level of toxic culture that develops that’s hard to see, especially on a remote team.” Instead of seeking to be nice, we should seek to be honest, rigorous, and consistent.

Was my guess not far off?  Have you found yourself making one (or a few) of these leadership mistakes, unknowingly? 

If you tensed your mouth and nodded a “Yes”, don’t be discouraged. Leadership isn’t about avoiding every mistake in the book – that’s impossible. Rather, the best leaders are unendingly curious to know what their mistakes could be, and deeply rigorous about trying to spot them in advance the next time around.

This is how you get better. It doesn’t always feel pleasant, but that’s the perilous process of gaining new knowledge: It’s bumpy, it’s uncomfortable, it’s frustrating, and, at times, humiliating. Rarely do you learn how to ride a bike and not get a scuffed up knee or two along the way.

Seeing your leadership mistakes for what they are – these nine in particular – is part of that learning. If you want to be a better leader, here is where you start.

Want to be a better manager? Work as a restaurant hostess.

The 6 indispensable leadership lessons I learned working as a restaurant hostess.

The most salient lessons on how to be a better manager can be found in the most unexpected places. For me? I learned how to be a better leader, in part, by working as a restaurant hostess.

Before I was CEO of Know Your Team, I picked up a job as a hostess, working nights and weekends at a local restaurant in Chicago. This was seven or so years ago when I was building my consulting practice and software prototype to help CEOs get honest feedback. I needed some cash coming in on the side, while I was pitching clients and coding during the week.

I’d never worked in a restaurant before. And aside from a few summers in high school as a tennis instructor and a sales associate at a clothing store, I didn’t have much experience in the service industry to begin with.

I had no idea what to expect with this job. All I knew was I was going to learn a lot. This proved to be exceedingly true.

What surprised me most was the amount of knowledge I gained. And it wasn’t about the service industry or restaurants. I didn’t expect to learn so much about well-functioning organizations and effective management in what some might see as the most “boring” job of my career.

In this “boring” job of mine, I learned so much that I wrote down my observations back then, and tucked them away in my private personal blog. Today, seven years later, I’d like to dust those lessons off on how to be a better manager, and share them with you….

#1: Everything is a system.

When something goes wrong at a restaurant, it’s easy to want to blame someone.

One evening at the restaurant, a table of guests had waited a long time for their food to come out. As I passed them, they gave me an earful (understandably so). In my head, I wanted to fault the kitchen – they didn’t fire the orders fast enough. But the kitchen likely would want to fault us, the hostesses, and say we’d sat too many guests, and the kitchen couldn’t keep up. Well, we’d sat the number we did because the managers had pushed us to seat parties faster – the tables were turning quickly that night.

But then, all of the sudden, the tables stopped turning. So, hmm, I guess it wasn’t the managers’ fault. Wouldn’t it be the servers? If the servers had turned tables quicker… Oh, but the servers would probably say that they tried to turn tables, but people were lingering longer during dinner that evening…

You get the picture. Rarely is it one person’s fault. The blame game does not work. A problem originates from an interrelated chain of events, with several obscure forces at play. Despite this, we swiftly declare what went wrong, why it went wrong, and whose fault it was. We focus on the symptoms of a disease, not the virus itself. We don’t always see the system.

In leadership, this couldn’t be more true. Our natural inclination urges us figure out what the problem is fast – so we often misidentify the problem. No wonder the solutions don’t work. The best leaders understand this: They never access a problem at face value.

For example, as a manager, you might wonder, “Why does my team move more slowly on a project?” It might be tempting to assume they’re just not motivated enough. But is that really the case? Perhaps they’re unclear what the true priorities are, so they’re not making progress on the right things. Perhaps unbeknownst to you, another department keeps requesting things from them, so they’ve been tied up more than usual.

Your consideration of the entire system, rather than an isolated part, will determine how well you’re able to solve problems as a leader.

#2: Confidence is why you execute well.

I remember the first night my manager asked me to “run the door.” The usual head hostess was out that night, and so I was going to be the one assigning tables and dictating who sat where and when. If you’ve never done it before, “running the door” can be a terrifying task. People stream in: Reservations, walk-ins, different size parties, some late, some early, special requests, VIPs…and you’re the calm, collected, friendly air-traffic controller amidst it all.

My face must have given away how petrified I was because my manager turned to say to me: “It’s fine, just shake it out. Be confident. You got this.”

It’s funny how a simple self-affirmation of “you got this” can make a difference in your performance. I recall how when I would seat people smoothly that evening, it’s because I’d gathered my confidence in my interactions with the guests. And when I stumbled – frantically poking around on the OpenTable floor plan – it’s because, in that moment, I doubted my own ability to find the right table. My execution came down to confidence.

As a leader, our insecurity causes us to overcompensate and perform poorly, as well. When we’re worried about being seen as “weak,” we rush to give answers, even when the answers aren’t always well thought-out. When we’re sensitive about being seen as “likable,” we avoid giving our team honest feedback, even when they need to hear it.

If instead, we can believe in our capabilities and intentions as a leader, we can support our team in a more steady way. Wondering, “Am I good enough?” or “Am I sucking at this?” can be debilitating, otherwise.

#3: Our assumptions are often negative.

I had a friend say to me once: “I would never work at a restaurant because I never want someone to think less of me.” Unfortunately, I don’t think my friend is the only person who has ever thought that.

I’d encounter negative assumptions like this almost every time I was at the restaurant. You receive some snootiness from a few guests as you take their coat. And as a hostess, you find yourself inadvertently price-checking in your head how much a guest’s Hermes belt might have cost.

These assumptions don’t just circulate between guests and the restaurant staff, but within the staff as well. Chefs ask you to call them “Chef” instead of by their first name. There are specific “codes of conduct” that vary between line cooks, servers, server assistants, and dishwashers – and you can bet there are a lot of assumptions are made based on which role you fill. I even recall a moment where I mentioned I’d attended Northwestern University for college, and the reaction of a fellow hostess both shocked and saddened me: “Oh my gosh, you shouldn’t be here! You totally are, like, better than me.”

While our negative assumptions as leaders may not be rooted around social class or organizational role per se, we have a strong tendency to make negative assumptions about our team when things aren’t going well. When someone is always late to meetings or gives overly harsh feedback to you, our mind jumps to the negative: “That employee seems lazy” or “That person is out to get me.” Good leaders recognize this temptation – and resist. They seek out greater understanding. They ask questions to learn the other person’s position. They acknowledge there is more they need to be doing as a leader. Never do they assume the negative.

#4: People notice details.

“Details matter” – I’ve always tried to heed that notion. But I’ve never quite seen it so consistently put into practice as I have at a restaurant.

One weekend, I was setting up tables before guests were sat and was wiping down one of the table. I’d noticed my rag had left a slight sheen of moisture on the table’s surface. You could barely see it. It would dry by the time the guests would sit down… right? I placed the rest of the table settings down.

As I walked back to the host stand, I then saw something out of the corner of my eye. One of the servers had walked by that exact same table – she was drying off the ever-so-slightly damp surface with her rag.

I took note: To her, that detail mattered. And it should have mattered to me too.

The best managers care about details to this magnitude. When you have an eye for details, you can pick up on problems before they become problems: “James’ chat seemed very abrupt, I wonder if he’s stressed. I should talk to him about workload.” Or, “Katie’s body language appeared dejected, I should ask her if she’s stuck on any decisions with the project.” For good leaders, the “small things” aren’t small things. They know they add up, so they put in the extra effort to notice them.

#6: Err on the side of over-communication.

One Friday evening, we were particularly busy at the restaurant and the lead hostess had to leave our post for a few minutes. “I’ll be right back,” she told to me, “but, make sure you keep tabs on everything.”

While she was gone, a woman in a red sweater approached me. “I think we already checked in,” she remarked. “But we’re just going to stand over there while we wait for the rest of our friends to show up.” I let her know that wasn’t a problem. A minute later, a party of three came through the door. Then, a young couple. Cool, nothing crazy, I thought to myself.

The lead hostess returned, and I promptly told her about the party of three and the couple that had checked in. I purposefully left out mentioning the woman in the red sweater – she said she’d already checked in. So we were good there. No need to share that.

Oh, was I wrong. About 15 minutes later, the woman in the red sweater approached us. “So we’ve been waiting for like 20 minutes already for our table, and I just wondering why we haven’t been sat yet.”

Shit. I should have said something.

I thought I was communicating “just enough” – but “just enough” isn’t good enough if you want to run an effective organization.

We assume that “people don’t need to know things,” and we’re doing them a favor and saving time. But in fact, we’re delaying what needs to be communicated eventually. Not doing so immediately only causes an eventual flare-up.

After all, people only know what we tell them. And we usually don’t tell them enough.

This isn’t unique to a restaurant. Our tendency to communicate “just enough” causes breakdowns for us as leaders all the time. Whether it’s hiring plans or explaining a decision or sharing the company vision, the best leaders are rigorous about communicating the same thing over and over. As leaders, we should err on the side of over-communication, not “just enough” communication.

#6: The incentive is the impact you create.

One of the bartenders I worked with had been promoted to a managerial position at the restaurant. I remember asking him how he’d been liking his new gig so far.

“It’s less hours,” he joked.

But then he replied seriously. “I like it more because now I have something to show for my work.”

“Something to show for my work.” That’s the core of what motivates us humans: We want what we do to leave an impact at the end of the day. Whether we’re in the restaurant industry, working at law firm, or running a software company, we want our work to matter.

Perhaps it’s an obvious, overplayed epiphany – but for me, it’s an foundational reminder of why we do our work in the first place, and how managers can think about leading their teams well.

Job perks, bonding events, employee recognition… surely, all those things boost morale on the surface. But what gives a team fuel to overcome tough challenges is if they can visibly see the impact they’re having.

Does your team have “something to show for their work”? It’s our job as leaders to answer that question for our team clearly, and in meaningful way.

Seven years later, those lessons from my hostessing gig have still stuck with me. As a CEO, I have a penchant for viewing problems systemically, caring about the details, and over-communicating. I remember what happens if you don’t.

It’s a funny thing to reflect on. When we want to learn how to become a better manager, we seek out roles that appear to have the most rigor or perceived clout associated with them. The manager role at X fancy company, or the Y job with the impressive title. But it’s potentially more sensible to reexamine what we gain from the most conventional or “boring” job experiences.

Have you encountered similar lessons from the “boring” jobs you’ve had? To a become better leader, we should zoom in on those experiences more.

7 things to consider when using a performance improvement plan (PIP)

Coaching an underperforming employee? Here are 7 things to consider if, when, and how to use a performance improvement plan.

It’s always easier to be a good manager when things are going well. But when an employee is struggling – especially someone who shows a lot of promise – what do you do?

The first step is to figure out if the employee knows they’re underperforming (I discuss this at length here.) Then, it’s time to coach an underperforming employee (hopefully) to success. You need a plan of action.

One way to help an employee improve their performance is through what’s classically known as a performance improvement plan – or PIP, for short. Some companies have a formal PIP process in place, with templates and predefined steps, while other companies and managers forgo having any type of PIP at all.

What works best depends on the employee’s particular situation and the company’s cultural environment. For instance: Has this poor performance been chronic, or something more recent? Does your company generally view process as a means to reduce complexity, or are they process-averse?

To get a better sense of if a formal performance improvement plan would work for you and your team, we asked our 1,000+ managers in our online community, The Watercooler, in Know Your Team about their experiences.

Based on their responses, here’s what you should consider when coaching an underperforming employee and using PIPs:

Is it a lever, or a crutch?

Netflix vocally eschews all performance improvement plans. They’ve observed how other companies use it as a crutch to flag poor performance, rather than as a lever to improve performance. Managers will put an employee on a PIP as “proof” to HR that they tried to help someone. Or in more nefarious situations, a manager will use a PIP to usher someone out of the company. Like any process in an organization, performance plans only work if the intention matches the outcome (whether that outcome is intentional or not.) If the ultimate outcome of PIPs are that they’re a convenient “out” for managers – rather than a genuine path for employees to improve – performance plans will be toxic for your company. Empty relics serve no one.

Never make the PIP a surprise.

Any low performance should have been discussed in a previous one-on-one meeting already. Your direct report should not be caught off guard that you’re suggesting a performance plan to them. In larger companies, this is also something that should have surfaced in feedback to HR (be it ad hoc or via your monthly feedback cycle, depending on what your cadence is.)

Let the employee know a PIP is a possibility.

Folks can turn the ship around, before needing a performance improvement plan. Knowing that a PIP might be on the horizon can be a powerful motivator for some. However, given this, be conscious to not frame the possibility as an ultimatum. Instilling fear is not productive in the long-run. Rather, be transparent as possible about the person’s level of performance is and what the potential next steps might be. For instance, during a one-on-one meeting, you could say, “We need your performance to be at [X tangible level], and I want to work with you to improve. I don’t think we’re at the point where we both need a performance improvement plan in place yet. But, I do want to share that could be a potential next step down the line if we don’t improve, together. Right now, I do want to support you to figure out how to make things better. Would you be open to discussing that?”

Consider having others in addition to the employee present for the conversation.

Watercooler members who are part of larger companies recommended the meeting about the PIP involve the employee, the manager, and HR. This is to make sure all relevant parties are on the same page. If you do choose to involve HR, be wary that some find it distracting (if not a bit ominous) to have HR in the room when the PIP is being discussed. At the same time, others prefer to have HR present from the beginning because it helps establish continuity of information. You’ll want to weigh these trade-offs, for your own team, when evaluating whether or not others should be a part of the PIP conversation.

Have an overall consistent flow for the PIP.

Based on what Watercooler members shared, here’s a general outline for how you could set up a PIP in your company:

  1. Meet with the employee to discuss the performance plan. Make it clear ahead of time that this is the purpose of the meeting, so the employee can plan accordingly in advance, themselves.
  2. Clearly define, together, what “success” tangibly looks like, and when it should be achieved by (typically 4 – 6 weeks out). Discuss why this marker of success is important to the team, and how it helps move the team forward. Get on the same page for how a successful outcome will be measured. Agree on the method of measurement.
  3. Develop a plan during the meeting for how to reach success. What might daily or weekly activities look like? Do either of you have suggestions for what should be done different so success is attainable?
  4. Set up 4 – 6 weekly checkpoints. Talk about what “success” for each weekly checkpoint might look like. What will the measurable output be?
  5. During each weekly checkpoint, discuss the progress made to date, based on the metrics you previously agreed to. What’s been going well and not well? How can either of you do things different to make better progress? How well is the employee tracking toward “success,” as was previously defined?
  6. During the last weekly checkpoint, declare success – or decide it is time to part ways. Obviously, one of these conversations is much harder to have than the other. If the employee has fallen short of meeting the successful outcome, have this discussion as directly and respectfully as possible. Here are some tips on letting someone go with grace and dignity.

Draft the plan always with the employee’s input.

This is paramount. An effective performance improvement plan is “we can improve together” and not just “I’m telling you what to change.” Every step of the way, from having the initial discussion about poor performance to defining the weekly check-points, you should be co-creating the PIP, and working together to figure out how to get to the outcome you both want to achieve.

Understand the cultural implications of a PIP.

For some Watercooler members, PIPs work incredibly well for their team because their team thrives on having clear processes and structures in place. However, another Watercooler shared how, because 80% – 90% of employees who were put on a PIP left the company during the PIP period, it culturally made the PIP “a herald of doom.”

Regardless of whether you decide to move forward with a formal performance improvement plan or something more informal – the important piece is that you’re purely focused on helping your employee improve. That’s your purpose as a manager, after all: To create an environment for your team to do their best work. It doesn’t matter if you call it by a three letter acronym (“PIP”) or not. The outcomes are what matter.

Is a CEO is worth working for? 4 questions to ask a prospective boss

If you’re looking to leave your company to work for another, you’ll want to consider this.

Recently, someone asked me for advice about getting a new prospective boss, and potentially leaving one company to go work for another. He was curious what factors he should consider before making the decision.

He’d already vetted the role, the company, and the offer itself — all important aspects to consider. But I told him, in my opinion, the most crucial thing to vet is the CEO.

If you’re about to join a new company, you must figure out:

“Do I believe in the CEO?”

No company is successful with a CEO who can’t communicate, who can’t get everyone on the same page, who can’t hire well, and who can’t chart out a vision.

Personally, I remember interviewing at one of my first job out of college, and I remember it being really hard to tell if a CEO is “good” or not.

Plenty of CEOs sound like they’d be a good CEO. They’re charismatic, they’re articulate — but does sounding like a good CEO really make it true?

After almost four years of researching and observing hundreds of CEOs, I’ve learned to ask these four questions to discern whether or not a CEO is a good CEO:

#1: “When have you had to sugar-coat the truth — or avoid telling the truth — to your team?”

How a CEO answers this question reveals her barometer for integrity. Your CEO might laugh and say, “Oh, all the time,” a little too flippantly — signaling that she intentionally misguides employees habitually. On the other hand, if a CEO is too hesitant to admit anything substantial, that’s a red flag as well. It’s likely she’s holding something back. Ideally you’re looking for a CEO to level with you and admit in a nuanced, considerate way when she’s chosen to not be transparent with the team, and why.

#2: “What do you think is your own greatest leadership blindspot?”

This is a take on the classic, “What do you think your greatest weakness is” question — but with a twist. The word “blindspot” implies that the CEO has a weakness she might often overlook. So her answer to this will reveal her self-awareness. Does she have a hard time giving you a straight answer? Or is it clear that this is something that she’s thought a lot about, self-reflected upon, and perhaps even talked about with peers or an executive coach. If it’s the latter, it signifies that this leader has the humility and self-perceptiveness you’re looking for.

#3: “What does ‘success’ for the company look like to you?”

This may seem like an unassuming question to ask — perhaps it’s one you’ve asked the CEO already. However, we often don’t listen closely enough to the answer. If all the CEO is focused on is “winning” and “making money” and “dominating the competition” in her answer, I can guarantee that’s 100% what the work environment is going to revolve around. On the contrary, if she also talks about creating a sustainable, healthy culture, and making sure people feel fulfilled, challenged and supported in their jobs — you can bet that the work environment is going to reflect that. The answer to this question makes is crystal clear what a CEO’s priorities are.

#4: “What would an employee who’s left the company say it’s like to work for you?”

This may feel like a tough question to ask you prospective CEO — especially if they haven’t hired you yet. But it potentially is the most important question. The answer to it demonstrates how cognizant the CEO is of how they’ve treated employees in the past, and how willing they are to admit if they’d haven’t been the ideal leader. Be wary of CEOs who say only positive things, as it shows their refusal to recognize their shortcomings, or failure to understand how their own leadership behavior may have driven the other person away.

If you’re worried that asking these questions — particularly the last one — might offend your prospective CEO, that in itself is a sign that the CEO might not be who you’d hope for. The best leaders welcome tough questions, and will be impressed by your desire to better understand how they lead.

If anything, asking these questions will make you look better in their eyes. And, it gives you all the information you need to decide if they’re a CEO worth working for.

This article was originally published for

Newsletter Issue 32

Every week or so, we send you our most recent blog posts on leadership, a new Heartbeat podcast episode, and recommended readings on management.

Subscribe to our Newsletter here.

From The Heartbeat Podcast: Interview with Natalie Nagele, CEO + Co-Founder of Wildbit

Natalie Nagele is the CEO and Co-Founder of Wildbit, a software development company that has built multi-million dollar products used by over 100,000 people all over the world. In our conversation, we chatted about her biggest leadership lesson learned in running Wildbit over the past 18 years. Watch the video interview below – or scroll down to listen to the podcast (yes, The Heartbeat is now a podcast too, yay!)

Listen to the podcast here.

Transcript of the interview is here.

What I’ve been writing lately

Leadership is your product, not your identity.
“The minute we fuse our identity to our leadership, we cling to it – and it blinds us.”

How to discuss poor performance with an employee
“Figure out if you have Problem A or Problem B.”

The 5 bottom-line benefits of building trust in the workplace
“85% of managers say they spend a moderate to large amount of time and energy on building trust. Yet, how many of us could specifically say what the specific outputs of trust are?”

31 best management quotes from The Heartbeat
“‘Don’t worry about most things because most things don’t matter.’ – Jason Fried, CEO and Co-Founder of Basecamp, from Episode 1”

What I’ve been reading lately

How to Tell Leaders They’re Not as Great as They Think They Are
“Although leadership talent is normally distributed, 80% of people think they are better-than-average leaders.”Written by Tomas Chamorro-Premuzic, Harvard Business Review

The Surprising Value of Obvious Insights
“When leaders there started training and evaluating managers on what sounds like Management 101 — setting and communicating a vision, caring about your team, staying results oriented — the company was able to improve performance for 75% of its worst managers.”Written by Adam Grant, MIT Sloan Review

When Collaboration Takes a Toll on Productivity
“Being busy may increase interruptions. At the end of the day, being busy may not equal being productive.”Written by Emily Stone, Kellogg Insights

Do You Offer as Much Flexibility as You Say You Do?
“Employees are 43% less likely to experience high levels of burnout when they have a choice in what tasks to do, when to do them and how much time to spend on them.”Written by Nate Dvorak and Rachel Breck, Gallup

A handy leadership tip

From our online leadership community of 1,000+ managers, in Know Your Team

What’s the best use of a leader’s time?

  1. Recruiting + Hiring
  2. Long-term strategy
  3. Communicating the direction to the team all the time

Read more here.

Just for fun

In Conversation: M. Night Shyamalan. The director on his failures, his successes, and Glass.
“Oftentimes, the reason we get into a cycle of success and failure is because we get blurry about what we can control. “

The Anti-Mentor: How a bad boss influences our leadership style

Having a bad boss shapes our leadership style more than we realize – for better and for worse.

Who’s the worst boss you ever had? Your answer to this question matters. It influences your leadership style in more ways than you think.

For myself, I can answer that question, “Who’s the worst boss you ever had?” almost immediately.

He’s someone I’d worked for coming out of college, after I’d started my first company. You’ve likely met a variant of him before: One of those leaders who looks you steadily in the eye, and with complete conviction and charisma, articulates a beautiful vision of the future the two of you could create together.

Back then, I nodded my head, convinced.

He then turned around… and he didn’t follow through on what he’d promised. He played favorites. His mood temperamental, at best. Ask a question, make a suggestion, offer a new idea – and he appeared irritated that you dared to speak up.

He wasn’t a bad person (he was a lovely person, in fact.) But having him as a boss showed me exactly the kind of boss I didn’t want to become. I took his template of leadership and whittled my own – a relief carving in opposition to his.

This worst boss of mine is what some would call an “anti-mentor.” Far from the person who you aspire to be like, they are who you avoid emulating, at all costs.

To this day, my “anti-mentor” influences my actions as a leader. For instance, I go to great lengths to be immaculate with my word. I’ve witnessed firsthand how destructive it is to say one thing and do another, as a leader. I strive to be unabashedly fair and consistent, because I’ve noticed how much instability and low motivation an unpredictable leader injects in a team. And, to this day, I’m highly conscious of creating an environment that encourages people to share divergent opinions. I’d seen what happens when the leader expects honest feedback to come to him – he never hears it.

When I reflect on my own leadership style, I realize that the bad bosses I’ve had influenced me more than any good boss I’ve had. Seeing what you don’t want to be like is more powerful than what you do want to be. The push is greater than the pull.

Psychologist Frank Oser calls this “negative morality” – learning from mistakes is markedly more powerful than learning from successes. However, you don’t necessarily need to experience the mistakes yourself to feel its impact. In the book The Moral Advantage, William Damon explains how the people he interviewed often cited the “anti-mentor” for shaping their values more than any other positive example or role model.

In this sense, an “anti-mentor” is a gift. My experience with my worst boss was a clarifying force. It helped me understand what I valued as a leader and as a person. Resistance shapes you. When know what you’re against, you more firmly know what you’re for.

At the same time, “anti-mentors” have unintended, adverse consequences when you model your leadership style in reaction to them. You can easily – and unknowingly – overcompensate. For example, my worst boss was never sensitive about extenuating life situations of his employees. If someone’s kid was sick, if something tough was going on in life, it was, “Well, that’s too bad. Can you get this done ASAP?” As a result, with my own team, I’m exceptionally generous about the time someone can take off. Sure, that’s good in the right doses… But I think in the past, I’ve been too liberal with it. There are people I’ve worked with who’ve taken advantage of my overly generous tendencies, and left our team worse off.

Most commonly, I talk to many leaders who have a problem being too nice because of their “anti-mentor.” Their former boss was as asshole and they are scarred by that experience. But inadvertently, now as a leader themselves, they lean the other way too far. They can’t bring up hard conversations with their staff. They have difficulty firing people who needed to have been let go months ago.

Whether or not you’re positively or negatively influenced by your “anti-mentor,” the critical thing is to realize that you are influenced by this person, to begin with.

Ask yourself: Who is the worst boss I’ve ever had? Then reflect. In what ways are you consciously or unconsciously reacting to your experience with this person? Are those reactions to this person – your “anti-mentor” – helping your team? Or, are they hurting?

Your worst boss is with you in more ways than you think.

The 3 most effective ways to build trust as a leader

Based on data from 597 people, the best ways to build trust as a leader aren’t what you think they are.

How do you build trust as a leader? The answer seems intuitive enough.

For many of us, we hold company off-sites and run team-building activities. Informal lunches, monthly social get-togethers, and one-on-one meetings are part of how we build trust at work.

We also thank our team publicly and give employee recognition for a job well done. And, we strive to be transparent with company information during all-team meetings.

These are among the most popular ways to build trust because they work… Right?


To my surprise, in our survey we ran this past fall with 597 managers and employees, these three ways to build trust were in fact viewed as the least effective by employees.

Specifically, these were the 3 least effective ways to build trust as a leader:

Company retreats + team-building activities.

Only 1% of managers and employees who responded to the survey said that this was the most effective way to build trust. This is fascinating, given the amount of money and energy many companies spend planning company off-sites and team-building activities.

Thanking your team and giving recognition.

Only 4% of people said that this was the most effective to build trust in a team. While this shouldn’t imply you should never thank your team, it goes to show there’s more to building trust than doling out compliments.

Being transparent with company info.

Only 10% of managers and employees stated that this was the most effective way to build trust in a team. No doubt that transparency is important in a company – if you want your team to be able to make the same decisions as you, they need access to the same information as you. But when it comes to building trust, perhaps it’s not as effective as we’d imagined it to be.

Now, just because these methods are not viewed as “most effective” for building trust at work doesn’t mean you should stop doing these things, all together. Rather, they may accomplish other worthy goals in the organization. (For example, being transparent with company info is helpful for alignment in a team.)

So what is most effective when it comes to building trust?

From our survey, here’s what 597 managers and employees said were the most effective ways to build trust:

#1: Show vulnerability as a leader.

Twenty-eight percent of people said that being vulnerable and admitting your shortcomings as a leader was the most effective way to build trust. For both employees and managers in the survey, they remarked how being vulnerable with your weaknesses and mistakes demonstrated empathy: The more empathetic someone was, the more likely they were to trust them. One person in the survey in particular remarked how their manager “needs to show more empathy,” and that “morally he is probably a good person but there are some times when it’s unclear if he actually has empathy due to challenges expressing it.”

#2: Communicate the intent behind your actions.

Twenty-six percent of people said making your intentions behind your actions clear was the most effective way to build trust. This makes sense, given that intent is such a primary part of the definition of trust, to begin with. Communicating the intent behind your actions means being open about why you’re saying something, and why decisions are made – including your decisions to not act on something. Be opaque about why you’re changing your mind, or fail to express why you’re giving feedback to someone and it can wreck havoc on your work relationship.

#3: Follow through on commitments.

Eighteen percent of employees expressed that simply following through on commitments was the most effective ways to build trust. This seems to be especially powerful given that we found that 48% of employees believed that the company has been all talk and no action on something lately – and 28% of employees said their manager has been all talk and no action. Similarly, 61% of managers believed that their direct reports had been all talk and no action on something lately.

In short, trust is not rapport. Trust is not team-building. It’s not about getting people to like you. And it’s not about getting people to just “feel good” about you or the company.

Trust is your intentions and your behavior. It’s making it clear why you’re doing something, being honest about it, and then following through with it.

You can hold as many company retreats as you’d like… But if you’re not vulnerable during those moments, your team won’t trust you.

You can be congratulatory with your team every week… But if you don’t follow through on your commitments, your words ring hollow.

You can share company financials far and wide… But if you don’t reveal your intentions about what you’ll do with that information, your team will be skeptical of you.

Align what you do with what you say. Your word and your action builds trust. Nothing else does.

PS: If you’re looking for a helpful system to build trust more authentically, you may want to check out Know Your Team – our software to help you become a better leader. In Know Your Team, we give you tools and resources specifically around building trust so you can put much of what I shared here directly into practice. Check it out here.