Photo by athree23 via Pixabay.
After I had my first baby, I took three months off from work before returning. I knew the transition back would be hard, but I was not prepared for a “Winter is Coming” kind of difficult. A few weeks in, I found myself overwhelmed by every little thing. My mind felt like the aftermath of a fourth-grade volcano project, all thick and sticky and slow. When I was at home, I thought about work, and when I was at work, I thought about home. My inability to focus became a source of debilitating stress.
Convinced that I had suddenly transformed into a weepier and less capable person, I asked my manager Chris if I could get an executive coach. That’s how I was first introduced to Stacy McCarthy.
The first thing I blurted out to Stacy after we introduced ourselves was that I needed to fix everything. In increasingly high-pitched tones, I began listing off one tangled issue after another: areas that were desperately understaffed, people who wanted a change in their roles, a product strategy I didn’t agree with, and so on. I imagined her helping me unravel each problem until they were simple, soft balls of yarn ready to be reknit with purpose.
Instead, Stacy listened calmly until I was done. Then she said, “We’ll get to all that later, but first, why don’t we take a step back? Tell me about you.”
I could only blink. Talk about me? But how would that help any one of the seven fires that needed putting out?
But Stacy persisted. She asked me about my past and the road I’d taken to get here. We talked about the future — the way, way future — where she asked me to picture myself at eighty, sitting on a beach and looking back on my life. What did I want to remember? Then she asked me if I would be okay with her interviewing several people who I worked closely with.
I said yes. Two weeks later at our next meeting, she showed up with a twenty-page report all about me. There was nothing about the specific problems at hand. Instead, this stack of papers asked deeper questions about how I worked — what were my perceived strengths and weaknesses? In what ways did I impress or annoy those around me? What was my management style like?
I remember the weight of the document as she handed it to me, tucked neatly into a manila folder. I shoved the package in my backpack, unwilling to deal with it. It was only later at night, when the baby was asleep and I was alone with the lights dimmed, that I felt ready to confront the truth. I took a deep breath and turned to the first page.
At that moment, feeling so ungrounded and unsure of myself, I struggled to read the report. I felt like a specimen dissected and laid bare. As much as you try to tell yourself that your inner turmoil lives inside your own head, the truth is that most of us aren’t very good actors. People know. They see the faults that you don’t want to admit, like how my anxiety was leading to wishy-washy decisions. But they’re also kinder to you than you might imagine. I remember tearing up reading comments about how I was kicking ass in ways that I wasn’t giving myself credit for.
Looking back, that twenty-page report was one of the best things that happened to my career. It helped me calibrate my own internal compass. It allowed me to understand where my fears were overblown — nobody actually thought I was a weepy and less capable person — and where I wasn’t paying enough attention — like setting clear expectations for myself and others. Once I knew where I stood, I could start moving forward.
Being a great manager is a highly personal journey, and if you don’t have a good handle on yourself, you won’t have a good handle on how to best support your team. That’s what Stacy was trying to tell me. No matter what obstacles you face, you first need to get deep with knowing you — your strengths, your values, your comfort zones, your blind spots, and your biases. When you fully understand yourself, you’ll know where your true north lies.
Everybody feels like an imposter sometimes
I first learned the term imposter syndrome during my junior year of college. A professor studying gender differences stood in front of a packed lecture hall, citing example after example that gave me shivers. Yes! This describes exactly how I feel! I don’t deserve to be here in this auditorium, at this dazzling institution, with so many brilliant students. I must have gotten here by error or luck or the grace of the stars. When are they going to figure out that I got good grades because I have a good memory, not because I’m actually smart?
As a new manager, I’ve felt this way countless times as well. Rebekah made a terrible mistake — I have no idea what I’m doing, my inner voice would whisper every time I fumbled an interaction or struggled to make a decision.
But over the years, I have learned a secret that bears repeating: Every manager feels like an imposter sometimes. Every manager was once new, stumbling through interviews and 1:1s and awkward conversations. It’s so common that instead of pretending like we are all ducks gliding effortlessly on the surface of the water, we should own up to the furious paddling that is happening beneath.
Imposter syndrome is what makes you feel as though you’re the only one with nothing worthwhile to say when you walk into a room full of people you admire. Imposter syndrome is what makes you double-, triple-, or quadruple-check your email before hitting Send so that nobody finds any mistakes and figures out you’re actually a fraud. Imposter syndrome is the sensation that you’re teetering along the edge of a sheer cliff with flailing arms, the whole world watching and waiting to see when you fall.
Here’s the thing to remember: feeling this way is totally normal. Linda Hill, a professor at Harvard Business School, has spent years studying the transition into management. “Ask any new manager about the early days of being a boss — indeed, ask any senior executive to recall how he or she felt as a new manager. If you get an honest answer, you’ll hear a tale of disorientation and, for some, overwhelming confusion. The new role didn’t feel anything like it was supposed to. It felt too big for any one person to handle.”
Why does imposter syndrome hit managers so hard? There are two reasons. The first is that you’re often looked to for answers. I’ve had reports tell me about difficult personal issues and ask for my advice. I’ve gotten requests for permission to do things that the company has never done before, like spend hundreds of thousands of dollars on a new initiative. I’ve received emotional inquiries from people about countless decisions that I didn’t make myself but that I still had to explain.
When the sailing gets rocky, the manager is often the first person others turn to, so it’s common to feel an intense pressure to know what to do or say. When you don’t, you naturally think: Am I cut out for this job?
The second reason is that you are constantly put in the position of doing things you haven’t done before. For example, say you have to fire someone. How do you prepare yourself for such a task? It’s not like improving your skills in drawing or writing, where you can invest time on nights and weekends to sketch or compose short stories. You can’t just snap your fingers and say, “I’m going to practice firing a lot of people this month.” You must actually go through the real thing in order to gain the experience you need.
Management isn’t an innate skill. There is no such thing as an “all-around great manager” who can transition effortlessly between different leadership roles. We must look at the specific context.
For example, I consider myself a seasoned manager, but if I were to lead a team that was triple the size or in a discipline I don’t know well, like sales, I’d probably fail to produce strong results immediately. I’d need to identify my growth areas in that environment — such as how to communicate effectively with a much larger group of people or how to set good sales goals — and spend time honing those skills.
No matter how often imposter syndrome rears its ugly head, it doesn’t have to derail you. In these next sections, we’ll look at techniques for how to deal with the inevitable doubts and discomfort that will arise.
Get to brutal honesty with yourself
Let me tell you a few facts about me: I’m more comfortable in small groups than big ones. I care deeply about understanding first principles. I am more articulate in writing than in person. I need time alone to reflect and process new facts before forming an opinion. I skew toward long-term thinking, which means that I sometimes make impractical short-term decisions. And at the end of the day, nothing gives me more satisfaction than learning and growing.
Why does any of this matter? Because these strengths and weaknesses directly affect how I manage.
Some of my colleagues have completely different superpowers. Among the people I work closest with, one has an ability to take incredibly complex topics and transform them into easy-to-remember frameworks that get at the heart of what really matters. One’s strategic prowess is so strong that I’m convinced he must have been a five-star general in a past life. And one amazes me with the way she manages to keep twenty threads moving full steam ahead at the same time. Yet these same folks have told me there are things I do that they admire as well.
The facets of our personality are like the ingredients that come together for a recipe. Could you make a tasty dinner if you peered into your fridge and saw some broccoli, eggs, and chicken? Sure. What if you had potatoes, beef, and spinach? Of course. The key is to understand what works best with what you have.
The world’s top leaders come from vastly different molds — some are extroverts (Winston Churchill) and some are introverts (Abraham Lincoln); some are demanding (Margaret Thatcher) and others remind you of a favorite relative (Mother Teresa); some leave a room breathless with their vision (Nelson Mandela) and others prefer to avoid the spotlight (Bill Gates).
The first part in understanding how you lead is to know your strengths — the things you’re talented at and love to do. This is crucial because great management typically comes from playing to your strengths rather than from fixing your weaknesses. There are some useful frameworks for understanding your strengths, like StrengthsFinder 2.0 by Tom Rath or StandOut by Marcus Buckingham. If you want to do a quick version, jot down the first thing that comes to mind when you ask yourself the following questions:
How would the people who know and like me best (family, significant other, close friends) describe me in three words? - My answer: thoughtful, enthusiastic, driven
What three qualities do I possess that I am the proudest of? - My answer: curious, reflective, optimistic
When I look back on something I did that was successful, what personal traits do I give credit to? - My answer: vision, determination, humility
What are the top three most common pieces of positive feedback that I've received from my manager or peers? - My answer: principled, fast learner, long-term thinker
Like mine, your responses will likely cluster around a few themes. Here, you can see that my strengths are dreaming big, learning quickly, and remaining upbeat. Whatever yours are, remember them and hold them dear. You’ll be relying on them time and time again.
The second part of getting to an honest reckoning with yourself is knowing your weaknesses and triggers. Right beneath your list of strengths, answer the following:
Whenever my worst inner critic sits on my shoulder, what does she yell at me for? - My answer: getting distracted, worrying too much about what others think, not voicing what I believe
If a magical fairy were to come and bestow on me three gifts I don't yet have, what would they be? - My answer: bottomless well of confidence, clarity of thought, incredible persuasion
What are three things that trigger me? (A trigger is a situation that gets me more worked up than it should). - My answer: sense of injustice, the idea that someone else thinks I'm incompetent, people with inflated egos
What are the top three most common pieces of feedback from my manager or peers on how I could be more effective? - My answer: be more direct, take more risks, explain things simply
Again, you may see some themes emerging. The biggest barriers that get in my way are self-doubt, a tendency to complexify, and not being clear and direct enough.
Okay, now that we’ve got our lists, the next part is calibration, which is making sure that the view we have of ourselves matches reality. This is harder than it sounds. Our self-perception is like a roller coaster. Some days, we struggle with self-compassion. We make a mistake and our inner critic chirps loudly about how we’re worthless. Other days, we think we’re the best thing since sliced bread. (There’s even a term to describe the cognitive bias where people who aren’t actually very skilled have a tendency to think they’re better than they are: the Dunning-Kruger effect.)
Calibration matters because it doesn’t do me any good to think that I’m one thing when the world views me as another. For example, if I believe I’m an amazing public speaker but everyone else thinks my talks are tedious, I might make a bad decision like choosing to present a bold new idea myself instead of asking someone who would sell it better. Even worse, people will start to discount what I say because they’ll conclude that I have a warped sense of reality.
To develop our self-awareness and to calibrate our strengths and weaknesses, we must confront the truth of what we’re really like by asking others for their unvarnished opinions. The goal isn’t to seek praise; the goal is to give our peers a safe opening where they can be honest — even brutally honest — so that we can get the most accurate information. In the same way that you gather feedback for your reports, you can learn about yourself through the following tactics.
Ask your manager to help you calibrate yourself through the following two questions:
- What opportunities do you see for me to do more of what I do well? What do you think are the biggest things holding me back from having greater impact?
- What skills do you think a hypothetical perfect person in my role would have? For each skill, how would you rate me against that ideal on a scale of one to five?
Pick three to seven people whom you work closely with and ask if they’d be willing to share some feedback to help you improve. Even if your company already has a process for 360-degree feedback, it helps to be specific about what you want to know and to provide reassurances that you’re looking for honesty, not just pats on the back. Take the example below.
Hey, I value your feedback and I’d like to be a more effective team member. Would you be willing to answer the questions below? Please be as honest as you can because that’s what will help me the most — I promise nothing you say will offend me. Feedback is a gift, and I’m grateful for your taking the time.
Examples of specific asks:
On our last project together, in what ways did you see me having impact? What do you think I could have done to have more impact?
With my team, what am I doing well that you’d like to see me do more of? What should I stop doing?
One of the things I’m working on is being more decisive. How do you think I’m doing on that? Any suggestions on how I can do better here?
Ask for task-specific feedback to calibrate yourself on specific skills. For example, if you’re not sure how good of a public speaker you are, follow up with a few people after you give a presentation and say, “I’m hoping to improve my speaking skills. What do you think went well with my presentation? What would have made it twice as good?”
I’ll pause here and acknowledge that asking for feedback is hard. You might have read the suggestions above and cringed when thinking about doing them.
It took me years before I got comfortable asking for feedback from others (outside of formal reviews where I had to). Why? It goes back to the imposter syndrome. Because I constantly worried that I wasn’t good enough, I shied away from doing anything that might confirm that view. I imagined someone I respected telling me that yes, indeed, I wasn’t doing X or Y very well. They’ve found me out! So I’d keep my mouth shut and soldier on, pretending that everything was fine.
It takes a certain amount of confidence to ask for critical feedback. For me, the breakthrough came when I realized I needed to change my mindset. If I saw every challenge as a test of my worthiness, then I’d constantly worry about where I stood rather than how I could improve. It’s like stressing out more about your exam grade than about whether you’re actually learning the concepts being taught.
On the other hand, if I approached challenges with the belief that I could get better at anything if I put in the effort, then the vicious cycle of anxious self-evaluation would be broken. No matter how good or bad I am at any particular skill, the notion that it’s within my power to improve has allowed me to approach learning with curiosity instead of apprehension. And the rewards have been tremendous . — I would never have known that my feedback was often vague and hand-wavy had I not invited that comment from a colleague. Once I heard it, I was able to work on making my points more precise and actionable, and now that’s praised as one of my strengths.