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.

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.

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 Inc.com.

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.


How transparent should you be as a leader?

Two things I’ve found helpful to consider when trying to decide what to be transparent about with my team – and what to keep to myself.

How transparent should you be as a leader?

This is a question many leaders struggle with — including myself. Do you share financials with the company? Or how about salary? How open should you be about why someone was fired?

From open-book management to making compensation public within the company, the concept of transparency in the workplace is more popular than ever.

Understandably (and rightfully) so. As a concept, transparency makes sense: If you want your team to behave the way that you would behave, they need access to the same information that you have. And, the more transparent you are, the more you’re likely to build trust within your team.

But what about the unintended consequences? Can transparency backfire? Do you inadvertently cause panic in a company when you reveal what the monthly burn rate is? Do you encourage resentment from more junior employees when you reveal how much senior employees in the company are making?

As a leader, how do you decide what to share with the rest of the team and what not to?

A few months ago, I spoke with the insightful Des Traynor, Co-founder of Intercom, on this topic. For Des, deciding how transparent he should be was one of the hardest lessons to learn as a leader. And as a CEO myself, I couldn’t agree more.

In our conversation, Des shared with me two things to consider when deciding how transparent you should be in your company:

Transparency requires context.

“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,” says Des. “It’s about transparency of context as well.” Many of the CEOs who are a part of our leadership community in Know Your Team, The Watercooler, echo this sentiment as well. One CEO remarked how he had shared revenue numbers once, and “things had gone sideways with individuals who just don’t understand or appreciate all that goes into starting and operating a business.”

In other words, the negative reaction came from the lack of context about the revenue numbers. What that CEO wished he would’ve done was share more context. If you share revenue numbers without context of monthly spend, people start wondering, “Where’s all that money going?” So for example, at my company, we share revenue numbers, within the context of also our profit margin and expenses — so it’s understood how revenue supports our business as a whole, and not just “here’s the pile of money we’re making.”

Transparency is a spectrum.

Transparency isn’t all or nothing — things don’t have to be either completely open or completely a secret. Des emphasizes this, saying, “I think it’s worth having a critical threshold to decide what’s actually good for everyone to know, what’s not a secret but needs context, and what actually genuinely might be a secret because you don’t want everyone panicking about something.” Transparency is a spectrum, and if you indiscriminately just make everything 100 percent public, you could be wasting people’s time, confusing them, or causing them strife. Everyone has a capacity of information, and overloading folks with every detail of what’s happening in marketing, support, design, engineering — it can be too much. As a leader it’s important to ask yourself: In what cases is transparency appropriate and helpful, and in what other cases is it distracting or a burden? Are you being transparent, just for the sake of being transparent, or are you truly trying to help people make better decisions, and feel a greater sense of trust?

At the end of the day, transparency is truly a positive force. When it does backfire or causes fallout, it’s often because a leader hasn’t often taken the time to consider these two things: Transparency requires context, and transparency is a spectrum.

As you think through what you should be transparent about in your company, keep in mind these two things. Hopefully, they’re things you won’t have to learn the hard way.


This article was originally published for Inc.com.

New! The Heartbeat Podcast about leadership and its 31 best management quotes

Listen to our leadership lessons now on iTunes, Spotify, and read the best management quotes from 31 leaders from each episode, so far.

I’ve got some fun news to share: The Heartbeat is now a podcast! You can listen to your favorite leadership lessons during your commute, daily walk, while you’re cleaning your kitchen… well, you get the picture. Anywhere you’d like 🙂

I’m lucky that a big part of my job as CEO of Know Your Team is talking to insightful leaders. So several years ago, I came up with the idea of filming those conversations, just via Skype, to share with everyone else. In each interview, I ask the question: “What’s one thing you wish you would’ve learned earlier as a leader?” The answers have been undoubtably fascinating.

Now, you can listen to all the answers in The Heartbeat with your favorite podcast app (Apple, Google Play, Spotify). Subscribe here.

In the meantime, below is a summary of my favorite quotes on management from each of the last 31 episodes I’ve done… lots of invaluable wisdom, here. Enjoy!

“Don’t worry about most things because most things don’t matter.”

– Jason Fried, CEO and Co-Founder of Basecamp, from Episode 1
Listen to the full episode here.

“Just execute.”

– John Maeda, Global Head of Design & Inclusion at Automattic, from Episode 2.
Listen to the full episode here.

“It’s reframing the question, not as, ‘How do you keep people happy,’ but, ‘How do you keep the right kind of people for your organization happy?’

– Patrick Collison, CEO of Stripe, from Episode 3
Listen to the full episode here.

“When your job is leading, you’re setting a precedent for acceptable and expected behavior. Which means, every single negative thing you do, every bad behavior you have, you’re admitting that you think that’s acceptable.”

– Des Traynor, Co-founder of Intercom, from Episode 4
Listen to the full episode here.

“Authentic leadership is a practice. You have to consistently exercise that muscle.”

– Halleemah Nash, Chief Partnerships Officer at The Academy Group, from Episode 5
Listen to the full episode here.

“You want to believe that everything can be, “We’ll all figure it out together as a team. It should be this really diplomatic thing.” It should be, but I have found that people need that person to look to, to act as a leader.”

– Joanna Wiebe, Founder of Copy Hackers, from Episode 6
Listen to the full episode here.

“Best intention is bullshit. What matters is outcomes, right, and whether you’re taking actually steps to anticipate those outcomes and mitigate those outcomes the best you can and just think through that whole thing.”

– David Heinemeier Hansson (DHH), CTO of Basecamp & Creator of Ruby on Rails, from Episode 7
Listen to the full episode here.

“Don’t be boring. It feels like companies hire people, but in fact people hire people.”

– Amanda Lannert, CEO of Jellyvision, from Episode 8
Listen to the full episode here.

“ I wish I would have hired every single executive a year to two years earlier. I was in my hustle mode, doing it myself, and doing a massive disservice to my team in the process.”

– Wil Reynolds, Founder of SEER Interactive, from Episode 9
Listen to the full episode here.

You don’t want to be the blind leader. You don’t ever want someone following you and not questioning.”

– Sara Sutton Fell, Founder and CEO of FlexJobs, from Episode 10
Listen to the full episode here.

If I ever am busy, I’m failing as a leader because I’m shouldn’t be busy. My job is to run the team well, and me being busy, it’s a fundamentally inefficient state.”

– Michael Lopp, VP Engineering at Slack, from Episode 11
Listen to the full episode here.

I think the number one important lesson to learn is just the importance of self-awareness.”

– Ben Congleton, CEO + Co-founder of Olark, from Episode 12
Listen to the full episode here.

“Disagreements are a central part of interacting with human beings and it’s a central part of doing good work. If you don’t have the skills and the courage to do that, you’re not doing your job, basically.”

– Amy Gallo, Contributing Editor at Harvard Business Review, from Episode 13
Listen to the full episode here.

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.” And that’s really absurd.”

– Laura Roeder, Founder + CEO of MeetEdgar, from Episode 14
Listen to the full episode here.

“The thing that I’m trying to put into practice now is the idea that the people with the most knowledge is where the authority should go.”

–  Dan Mall, Founder of SuperFriendly + CEO of SuperBooked, from Episode 15
Listen to the full episode here.

“If it is any percentage of your organization, of any size, whether you’re again a ten-person company or a thousand, you got to spend way more time than you think that you do with the team, helping them understand what’s going on.”

– Daniel Houghton, CEO of Lonely Planet, from Episode 16
Listen to the full episode here.

“When it’s about finding your own true north as a leader, it’s the idea that you are continuously learning and exposing yourself to all different kinds of styles. Even if you inherently know that, that’s not the right one for you, to the very least know that it exists.”

– Elena Valentine, CEO of Skill Scout, from Episode 17
Listen to the full episode here.

Everything stems from something. If you don’t know what your issue stems from, then you can never fully resolve it. It’s like psychology, but it’s really business.”

– Steve Larosiliere, President of STOKED, from Episode 18
Listen to the full episode here.

I kind of think about [leadership and management] as English gardening. If you want an English garden most of the work is actually the pruning and the taking care of. It’s not the planting, it’s not the plant selection. It’s this constant pruning. The day that you stop pruning is the day that the garden is full of weeds and overrun.”

– David Cancel, CEO of Drift, from Episode 19

“I wish that I had learned that I didn’t need all the answers. I don’t need all the answers as a leader, and that hiring people that are better than I am at something, and then when a problem comes up looking around the room and saying “I don’t know. What do you think?”

– Rob Walling, Founder of Drip + MicroConf, from Episode 20
Listen to the full episode here.

As you get drawn more and more out, you have to remember: How do you connect again?”

– Katrina Markoff, Founder + CEO of Vosges Haut-Chocolat, from Episode 21
Listen to the full episode here.

“I always say, “Don’t just be good on paper. Be good in real life.””

– Aynn Collins, Director of Talent Strategy at MailChimp, from Episode 22
Listen to the full episode here.

“Values, to me, mean how you conduct yourself and how you conduct your business– so the attributes and the method that you actually execute your vision to the world.”

–  Jordan Buckner, Founder and CEO of TeaSquares, from Episode 23
Listen to the full episode here.

“Am I just being nice? Or am I actually being honest?”

– Hiten Shah, Founder of KISSmetrics, CrazyEgg, FYI and Product Habits, from Episode 24
Listen to the full episode here.

“We have made a huge mistake in the tech industry identifying role models with God complexes, type-A behavior to have all the answers. We have made a huge, human, fundamental, cultural mistake in the tech industry, ’cause that’s not how we are as humans. That’s not actually how we do business. That’s not actually how we succeed in life.”

– Wayne Sutton, Co-founder + CTO of Change Catalyst, from Episode 25
Listen to the full episode here.

“I don’t actually expect you to trust me just because I’m your boss. I need to earn it.”

– Ryan Carson, Founder + CEO of Treehouse. from Episode 26
Listen to the full episode here.

“What I realized is that I should stop myself from doing things I’m good at — which is so counterintuitive — and instead, focus on delegating training and making sure that everybody gets good at doing those things.”

– Peldi Guilizzoni, Founder + CEO of Balsamiq, from Episode 27
Listen to the full episode here.

People talk a lot about building culture, but changing culture is very hard. I think understanding where decision falls and how irreversible it is is a really important tactic for deciding whether and how to delegate or when you need to just make and own that decision.

– Kathryn Minshew, Founder and CEO of The Muse, from Episode 28
Listen to the full episode here.

“Don’t beat yourself up too much when things go wrong, but also don’t take too much credit when things are going right. Because a lot of times there are things that are happening as a leader and as a company that are out of your control.”

– Desiree Vargas Wrigley, Founder + CEO of Pearachute, from Episode 29
Listen to the full episode here.

“I think the most important part, at least for me, is having a mission and then being driven by this mission. It forces you just to learn and adapt and want to improve.”

– Amir Salihefendić, CEO + Founder of Doist, from Episode 30
Listen to the full episode here.

“It’s great to have conflicting advice, because then you have to make your own decision. Then then you have to look within yourself and decide what is the right thing for this company, for the culture, personally for yourself, as well.”

– Joel Gascoigne, CEO + Co-founder of Buffer, from Episode 31
Listen to the full episode here.

What makes a good leader? Leadership is your product, not your identity.

The minute you stop tying your leadership so closely to your identity, you become a better manager.

Your leadership style is not your identity.

You are not your leadership style. In order to be a good leader, you must internalize this. As much as you might self-identify with being an “empathetic leader” or a “decisive leader”, you’ve got to let these notions go.

This is not an obvious truth because leadership feels inherently personal. The adjectives we use to describe our own leadership style might be the same adjectives we use to describe our own personality or disposition: Calm, patient, deliberate, compassionate, rational…

But the minute we fuse our identity to our leadership, we cling to it – and it blinds us.

I was recently reminded of this when I interviewed Desiree Vargas Wrigley, CEO and founder of Pearachute. She emphasized to me:

“The more you can remove your sense of self-worth from the performance of your business, the better your business and your leadership will be.”

Desiree admitted how, as a leader, it’s easy to cement yourself as “a certain kind of leader” – and you fail to see problems for what they are, because of this.

For example, if you see yourself as a “motivating leader” but an employee isn’t performing up to par, it’s tempting to feel frustrated. You might think to yourself, “I’m doing everything I can over here to be supportive… How can this person be flailing?”

Or, if you consider yourself a “fair leader” yet a team member implies you’re playing favorites, their critique feels like a personal attack. “Wow, I’m a fair leader, and they really think they’re not getting their chunk of the pie?”

In both situations, you view your own leadership as static – it’s the other person who needs to change. You shut the door on collecting more information, evaluating the situation objectively, and the possibility that there’s something better you could be doing.

The closer we tie our sense of self to how we lead, the harder it is to improve.

Instead, can you view your leadership as a product – not an extension of your identity?

With a product, you welcome feedback, you experiment with what works, you see it as a work-in-progress. With a product, you take a step back every now and then to reflect if it is indeed working.

You’re not incredulous if it’s not working for some folks. You’re not personally offended if some people don’t seem to like it. You adjust, test, readjust.

If anything, when leadership is your product, you’re excited for your leadership to evolve, and get better.

Otherwise, your leadership is self-righteous. “This is just the way I am” or “This is just how I’m wired” become the default mode of thinking.

The most important thing your leadership should be doing is serving your team – not your sense of self. Is the way you communicate, make decisions, handle conflict, set direction helping my team get closer to what they all want to make happen?

Leadership is a tool to help your team achieve the outcome it wants. It’s not a precious thing, in itself, that needs to be held on high.

Our leadership isn’t an outward expression of some grand inner personal philosophy, gilded in gold. Our leadership isn’t a foundational core of who we are, set in stone.

The more you relish in self-identifying as a “certain kind of leader,” the less responsive you become to the needs of your team and how you can become better over time.

The more you separate your personal identity from your leadership, the better leader you’ll be.

Building trust in teams: What and why?

How do you build trust in a team? First, let’s understand what trust really is and why it matters.

Who do you trust?

The first people who likely came to mind were your partner, your family, and your friends (hopefully). 

How about your boss? Your coworker? It’s harder to say. 

A 2016 study conducted by Edelman surveyed 33,000 people in 28 countries. From it, they discovered: One in three people don’t trust their employer. And only 24% of employees in this study believe their CEO exhibited highly ethical behavior.

In our own Know Your Team survey this past year of 597 managers and employees, we found that folks were slightly more trustful of one another: About 8% of employees said they rarely or never trust their manager. That’s almost 1 in 10 employees not trusting their manager. 

Why defining trust matters

Whether 1 in 3 employees or 1 in 10 employees don’t trust their managers – both are significant occurrences. Especially given the amount of time we interact with our coworkers, and the projects and outcomes that are on the line, it’s startling.

Are we really spending all this time with people we don’t trust? Should we be doing anything about this?

To answer those questions, we first have to define “trust” clearly. Misconstrue what trust actually is, and you spend time on the wrong things. Get it right, and building trust gets easier.

What trust is NOT:  Likability

We often equate trust with likability. We think, “This is a nice person” or “This is the kind of person I’d want to hang out with on weekends”… So we trust them. 

However, that’s only part of the equation. 

Consider someone in your company you don’t trust. You might like her. She’s affable, genuine and definitely tries her best. But trusting her with a high-profile project? You hesitate – she hasn’t shown the track record you need to feel confident. You don’t give her the big project because, honestly, you just don’t trust her enough.

So you if you want someone to trust you, it’s not enough that they like you. It’s not enough that they think you have good intentions. They’ve got to think you’re capable. They’ve got to think you have what it takes to prove something through. 

You might think someone is a good person – but you don’t trust them to actually get the work done. You need both.

This is an important distinction because many leaders accidentally optimize for likability as a means to build trust. They try to “be friends” with their direct reports, thinking it’ll mean their team will trust them more.

If we can internalize that trust is not likability, it causes us to not fall into the trap of trying to please everyone around us. If we want to build trust, there’s something deeper we have to access.

So then, if trust isn’t likability, what is it?

What trust IS: Intentions + Behavior

In a 1998 paper, Denise M. Rousseau suggested this definition of trust:  “A psychological state comprising the intention to accept vulnerability based upon positive expectations of the intentions or behavior of another.”

In short, trust is two things:  Intentions and Behavior. It’s people’s perception of who you are, and their expectation of what you can do. 

The 4 Cores

Stephen M.R. Covey defines trust in his popular book, “Speed of Trust,” similarly to Rousseau. To Covey, trust is the belief in who the person is, and a belief in their abilities – a person’s “Character” and their “Capabilities.” Covey then further breaks down trust into what he calls “Four Cores”:

  • Integrity – This means being honest, walking the talk, and being congruent with what you believe. You can’t trust someone unless you believe they have integrity. When someone is assessing your integrity, they’re wondering, “Do you have values I align with? Are you a good person?” 
  • Intent – This is your agenda or mission. Your team must trust your intent before they can trust you. A person sizing up your intent will wonder, “Are you thinking about yourself, or others, in this situation? Do you have the short-term, or the long-term in mind?”
  • Capabilities  – This is your talents, attitudes, skills, and knowledge. When someone is determining whether or not to trust you, they’ll consider, “Does this person have the expertise to do this job as well as they say they can?” Based on our survey, we found that both managers and employees most question their each others’ capabilities (26% of employees said this, and 36% of managers said this).
  • Results – This is your track record, your performance. You can’t be trusted unless you’ve shown results in some way that you can be trusted to follow-through. When you ponder about a coworker, “What has this person done that proves I can trust her?” you’re seeking results.

Warmth + Competence

Another related lens for understanding trust is described by organizational experts Amy J.C. Cuddy, Matthew Kohut, and John Neffinger. They revealed the two elements needed for a leader to be trusted were “Warmth” and “Competence” – with warmth needing to come first. 

According to their research, when you project strength too quickly, people have a harder time trusting you. They explain in Harvard Business Review, “Before people decide what they think of your message, they decide what they think of you.”

These perceptions of warmth and competence are powerful: “Insights from the field of psychology show that these two dimensions account for more than 90% of the variance in our positive or negative impressions we form of the people around us.”

How do you show warmth and competence? Cuddy and her research partners detail how warmth can mean positive body language, affirming words, generous actions, and even a smile. Competence can be projected similarly through body language (such as standing up straight), your past track record, and the actions you take going forward.

Like Covey, Cuddy’s research and explanation of the requirements for trust echo Rousseau’s definition of intention + behavior. Trust is all about who people think you are (warmth), and what they think you can do (competence).

Getting this distinction straight helps lay the groundwork for you to build trust in your team. You can now understand why someone might distrust you. Perhaps you haven’t defined your intent clearly enough. Perhaps it’s because of your past behavior. As a result, most importantly, you now can start to think how you can build trust in your team.

The clearer understanding we have of trust and what it really is, the clearer path we have to our teams trusting us more.

The Mindset Shift: How to become a good new manager

Are you a first-time manager? Of all the management advice for new managers, embrace this one, first.

Image for the mindset needed to become a good new manager

Don’t be fooled: Becoming a new manager is deceptively difficult.

No matter how many leadership books you’ve read or conversations you’ve had with mentors – the transition to becoming a manager is precarious.

Talk to any leader, and they’ll affirm this. “I was a terrible manager when I first started,” most will say. Myself included!

This is because the change required to be a good boss isn’t apparent from the outside looking in. You’re not truly aware of the change that’s needed in the role, until you’re actually in the role.

So what change do you need to make as a new manager? From 15,000+ people we’ve surveyed through Know Your Team and thousands of conversations with managers in our online community, the #1 consistent insight folks have shared is this:

Becoming a new manager isn’t merely a change in what you do – it’s a change in how you think.

When you become a manager, your responsibilities change and your daily schedule changes. But it’s your mindset that changes the most.

The biggest change in thinking, as a new manager, is that your best work is not you doing your best work. Your best work is creating an environment for others to do their best work.

You don’t think about, “Am I moving fast enough?” Instead, you now contemplate, “Am I removing obstacles so my team can move fast enough?”

You don’t consider, “Do I know the answer to this?” Instead, you ask yourself, “What am I doing to help my team become experts and find the answer?”

Becoming a good manager starts with how you think, not what you do. Shift your mindset, and the actions follow.

This shift in mindset, while seemingly obvious, is both substantial and hard to internalize. What previously indicated “success” for you as an individual contributor doesn’t indicates success anymore.

No longer do you pat yourself on the back when someone says, “Great work” or “I love what you did here”. As a manager, the small bump of validation happens when someone says: “Now I understand,” “Thank you for listening,” or “I’m excited to work on this.” The small wins change when you’re a manager.

This shift doesn’t happen overnight. We have to disregard the prior experiences of we were rewarded for as an individual contributor. We have to reconfigure our default settings of behavior that got us to where we are now.

But if you can embrace this mindset shift as quickly as possible, your ability to become a good manager exponentially increases.

You don’t have to wait til you’re in the thick of everything, as a manager, to know what you must change.

Now you know: You must change your thinking, first.

The most counterintuitive leadership tip? Leaders, stop doing what you’re good at.

Playing to your strengths as a leader doesn’t make you a good boss – in fact, it can make you a bad boss. Here’s why.

Of all the leadership tips to be a good manager, “leaning into your strengths” has got to be one of the most frequently cited.

“Do what you’re good at. Focus on your strengths.” That’s the conventional advice we all receive. There’s no shortage of StrengthsFinders assessments and personality tests urging us to triangulate which strengths we should zoom in on.

However, I recently had a conversation with Peldi Guilizzoni, CEO of Balsamiq. His insight on this topic turned my head sideways… in a good way. Peldi asserted:

“Doing what you’re good at hurts the team.”

Huh? Let me explain.

Peldi admitted to me that he’s good at getting stuff done. He makes things happen. He thinks he’s killing it. But as a CEO, 10 years in, should he really the one doing all the doing?

After a decade running his business, Peldi noticed he’d created an environment where his coworkers were depending on him to get things done. If he takes a vacation – he leaves them hanging. If he has to be out for a week – they’re stuck.

Peldi conceded:

“What I realized is that I should stop myself from doing things I’m good at  —  which is so counterintuitive  —  and instead, focus on delegating training and making sure that everybody gets good at doing those things.”

Doing what he was good at was hurting his team, not helping.

I could relate.

I’m good at communicating. So I do it internally. A lot. I write-up about what we’re doing, why we’re doing it, a new approach I’m thinking about, a new concept we should try… But, when I take a step back, it’s a bit too much. We’re a tiny, two-person company. For our size, all that communicating is overkill. I could easily spend some of that same time somewhere else in the business and have it be more meaningful.

For both Peldi and I, our predisposition became a preoccupation. We’re good at it, so we automatically assumed it was good for our team.

Whenever you’re good at something, you don’t objectively assess its effectiveness as you should. You apply less of a discerning eye. You know you’re good at it, so you figure the more you do of it, the better.

But as with anything, repeated actions without rigorous judgment become lazy and reckless. And naturally, they have unintended consequences.

Now avoiding this pitfall, and actually internalizing this counterintuitive leadership tip, is hard.

No one is going to stop you. Rarely do others have the temerity to stay, “What you’re good at is bad for the team.” Plus, doing what you’re good at is fun. It’s inherently satisfying to flex your strengths. Who wants to not feel that way?

So, you have to ask yourself: Are your actions feeding your team, or your ego?

Focus on what you’re good at, and the team never becomes good at it themselves. Focus on what you’re good at, and you never see things for what they really are.

Resist viewing your strengths as the only way to make the team strong. Resist falling in love with the short-term results of doing what feels good to be doing.

Pause. Don’t be so busy. Take stock. Why are you doing those things? Because you like doing them? Because you’re good at them? Or because it’s the best way to move the team forward?

Find someone who will tell you the truth. Your co-founder, your coworkers. Ask them if what you’re doing that you’re good at is really helping move the team forward.

This truth-seeking takes 10 minutes to do. Start today. And stop doing what you’re good at, all the time.