Dear manager of the employee with Imposter Syndrome

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Dear manager of the employee with Imposter Syndrome

Thoughts and suggestions about management from the trenches


I dedicate this article to every manager with a direct report suffering from Imposter Syndrome. It's a silent killer that suppresses and humbles. Like myself, many engineers have felt the crippling sting without the mental or emotional awareness required to label it. The corollary is that balance eludes us while paralysis erodes the progress that could have been. Through the scars, I've reflected on what I thought would help me with the hopes that I can help someone else navigate this maze. My message today is to the managers because I think you're uniquely postured to make an indelible impact on the trajectory of your employees... if you're careful.

My story

Hi. I'm a Jamaican-born software engineer. I spent my formative years in a small company in Jamaica. I started as the lone engineer until I built a team of about five developers. Being in a small company meant I wore many hats. I was the chief technical officer, chief architect, product manager, occasional designer, customer support hero, engineering manager, and individual contributor. I spent 8 years building many solutions from the ground up.

Of all the products we built, I'm most proud of two particular ones. First, we built an Incident Management and Reporting system for our government. It had forms to collect information on major crimes and fatal accidents and an interactive map that clustered the data points once you were beyond a certain resolution. Blah. The part that excited me was the reporting engine that we built. It did some fancy introspection of the database schema and exposed a really powerful interface that permitted the generation of tabular reports and charts along with filters to refine the output. The expressive power was unusually satisfying. We built a poor man's version of SPSS. Using the interface we built they could visualize and capture so many perspectives on the data collected.

The other project I hold dear is an Insurance platform we built from the ground up. Never mind that you could get a quote, purchase motor vehicle insurance and submit claims - the technical underpinnings were much more compelling. Using thoughtful component design, we built a premium calculation engine, notification system, and a bevy of other features on top of a small set of modular components. The emphasis being on the "small set" of components with high reusability. Reflecting on those days always brings me pride and joy.

The unfortunate truth, however, is when I started working in Canada, you would never have known I was remotely capable of building anything sizeable. Unless you saw my resume, you would never have thought I could be trusted with the autonomy to build a small component, much less, design an entire system. You would never have known I've conducted numerous trainings, addressed countless execs with confidence, written numerous technical specifications, and obsessed about customer experience.

When I migrated to Canada, it appeared my confidence and much of my self-esteem missed the flight. Whatever was left of my years of experience was likely surrendered at immigration. Somehow I convinced myself that all my experience was third-world, and by extension, subpar. All of the previous years I concluded were irrelevant for the years ahead of me. I had zero leverage, I'm here to learn from all the mighty folks who've worked with systems at a greater scale than I've ever imagined.

When I landed my first job, I joined a team that was pretty happy to have me. Never mind the warm welcome, deliberate inclusion attempts, or my manager's attempt to convince me that tangible contributions weren't expected yet, I was determined to hit the ground running flying. I probably deployed in the first week. I deprecated some unused code, and then quickly moved to more substantive changes. "He totally skipped onboarding" was a common rhetoric my teammates used to caption how quickly I integrated myself into the team.

The struggle to be relevant quite likely explained what was left of my voice and dominated my motivation. I managed to express my opinions, and I did in many team discussions. In retrospect, I wasn't remotely as confident as I was previously. I made several suggestions and hinted at improvements I never followed through on. I bowed out of several discussions where I swallowed my passion and conviction on the topic. From the early days, I saw opportunities where I could make an impact, but I convinced myself, my thoughts would be deemed primitive. I didn't want to risk exposing my third-world experience, or identity in a grown-up world. So, understandably, 1-on-1 most conversations about opportunities stayed right between my manager and me, where they'd be best kept safe. In the early years, there was very little kinetic that exposed the potential within.

There were a few other factors that compounded the problem. First, on starting this new job I was overwhelmed by all the unfamiliar tools they used on the job. The bevy of tools reinforced the message that I wasn't doing real engineering and that my learning had just begun. I didn't use GitHub or do code reviews, I wasn't accustomed to defending my position or articulating my design choices. We never shipped logs to a third-party tool or used a dedicated tool to capture errors, or used metrics to evaluate and monitor systems.

Secondly, an overdose of personnel changes paralyzed me or undid much of the progress I made. In the first couple of weeks, our designer was fired. He seemed pretty competent and I liked his work. I was eventually told that there were unresolved, long-standing issues that aggravated the team and negatively impacted progress. Not before I cross-examined myself trying to determine how I could be next. After that incident, my manager left some weeks after. In the second year, our company was acquired. This change inspired quite a bit of uncertainty across the company. Ultimately, many of the original teammates, and manager at the time left. The teammates who created the welcoming atmosphere left, along with the manager who I first had conversations about seniority with.

Thirdly, two persons eventually joined our team which made me particularly self-conscious about my competence. Two exceptionally competent engineers with really strong opinions joined my team. One was an IC, and the other was my manager. The former ran his own startup at one point, and the latter had names like Google and Amazon on his LinkedIn. This helped me to deepen my bond with my insecurities. In those days I learned to specialize in overthinking and moving just enough to escape the definition of immobility. I learned a lot from them both, but my concerns about appearing incompetent repeatedly crowded out opportunities to acknowledge the progress made to a shared outcome. I would focus much more on the debates I lost, and how I could avoid such ignorance in the future.

It took several years to build the perspectives that helped me retrospect on my pre-Canada years in a way that enabled me to see my own leverage. I learned to caption my previous experience, not as insufficient, but rather, as different. Everyone has different competencies, and we're all imbalanced in some respect. I realized the tools I never used before were all accelerants for my current capabilities. I discovered that articulation of technical design choices was a simple, practicable skill. I read and got a lot better at articulating the gut feelings that predated coming to Canada. I started adding more structure to 1-on-1's and deliberately sought feedback that helped calm my limbic system. I grew to love the input from teammates with stronger opinions and used them as a deliberate vehicle for critically evaluating my designs. I looked forward to and sought out code reviews from them. I started focusing on outcomes, rather than on individual positions (actual quote from the ex-lots-of-big-name-companies manager I had).

Most importantly, I discovered that leveraging some of the disregarded foundations of my formative years made an incredible platform for career growth. I've long been pretty passionate about education and sharing and building bridges between teammates. Seniority requires impact outside your team, forging bonds that deliver value. By reviving my passion for sharing and education, I've been able to use that talent as a vehicle for leading cross-team initiatives. Last year, for instance, I delivered training to some folks in Engineering challenging us to level up on how we monitor and observe our production systems. I'm currently training trainers to spread the learnings to the rest of the Engineering org, chipping away at the bigger vision of changing the culture to build more debuggable systems. There are also plans to consult with another team as they rebuild certain areas of their system with a renewed focus on Observability. It's thrilling... and a little terrifying!

Five years later, I'm a Senior Engineer II at my company, and proud of my progress thus far. I'm incredibly grateful to all the folks I've encountered along the journey. There are so many people who played a key role in getting me to this point. I haven't fully relinquished my citizenship as an imposter just yet, but I'm working on it. All in all, I believe I could have compressed a few years, but you don't get to keep the lessons and the impact, so I'm still trying to embrace the journey.

My advice

Know your employee

I think one critical point is the importance of knowing your employees. For starters, take their resume and have a conversation with them about their past work experiences and what they've worked on. Most folks can speak positively of past accomplishments. This will help to provide a baseline that provides perspectives that aren't always discovered in organic day-to-day interactions. Conversations about past work can help to uncover latent or otherwise undervalued skills. This also provides an invaluable reference that can be relied on later to determine how to best grow that employee. This is also a great opportunity to validate some of those experiences and explore ideas for growth. Having these conversations early before the team dynamic and other environmental factors crowd out the motivation can be pretty powerful and help accelerate or combat irrational fears.

Help them to practice objectivity

Recall when I moved to Canada, I convinced myself I had zero leverage. I downloaded my accomplishments and disregarded my past foundations. This proclivity only increased as the years passed by. I continued to view my achievements in a lesser light. Rather, actually, I never identified or gave them any spotlight. My new focus was a yardstick that shifted aggressively as I received feedback or insights from someone else.

What would have helped was external perspective unblinded by the irrationality that dominated my personal evaluation. I wanted someone to question the downplayment of my work. I needed someone to challenge the utility and impact I had.

By far, it's not a panacea, but challenging your employee helps them peel back the layers of irrationality that cripple their ambition and attenuates their progress.

Strongly encourage self-reviews

A powerful tool for building objectivity is self-reviews. You should really encourage your reports to do it. There's a guide here that was particularly helpful for my last promotion cycle and I wished I had been using it all along. In this article, the author shares her very thorough process for doing self-reviews. In short, you're cataloging all the work you've done over whatever period you're reflecting on. You start with your memory, then you check all the tools (JIRA, GitHub, Google Calendar for meetings, Notion, Slack) to catch things you've missed.

You end up with a compelling list that details your progress - a real dent to the irrationality that typically reigns. It subdues the voice that shouts imposter, replacing it with fine details of what you've actually accomplished. When I did the exercise I was particularly shocked at the countless initiatives my mind glossed over when quantifying my impact. If you have employees you're proud of, self-reviews will help them better see your perspective. As a bonus, if your employee does a self review this makes your job much simpler come promotion time. You'll be able to pick from the catalogue your report has already drafted.

Talk about energy levels and expectations

As a growing imposter, I would constantly keep my pace in check. I would keep trying to maintain an unreasonable pace where I could convince myself that I wasn't doing horribly. There were periods where I felt somewhat accomplished -- but those periods weren't void of the self-inflicted pressure to maintain that pace. It was a vicious and unforgiving cycle. I'd beat myself up for not doing enough to feel accomplished, and then I'd eventually feel accomplished, but then I'd burn out and start beating myself up again. What a cycle!

As a manager, help your employee understand that energy levels ebb and flow. There are times when we'll feel energetic and ready to conquer the world. However, as sweet as victory is, the battle that took us there is also quite draining. It's fine to relish in the sweetness of victory, while we rest and lick our wounds. Rephrased less poetically, it's okay to grab some mindless, smaller tickets after you've just landed a huge PR. Or, after finishing a round of technical design where you refined your approach with feedback from your colleagues, it's okay to take something less intimidating.

Level with your employee! Help them understand that you experience these struggles too. We all do! I appreciated my manager responding to some of my questions about feeling unproductive. He was transparent enough to share that he felt very unproductive at points and shared some perspectives that helped. Often it's just our minds deemphasizing the impact and focusing on impostership. You can help by being transparent about productivity and energy levels.

Understand the power of feedback

I close with a petition to give your employee thoughtful and thorough feedback. Your feedback is often the only compass in the conversation that has the potential for accuracy. The internal compass of a budding imposter is deeply skewed. I don't know that compasses are repaired, but loaning your compass can create the environment for our compasses to heal.

Give feedback regularly, and strategically. Look out for the peaks and troughs for your employee and give feedback targeted around those points. When they've shipped a massive new feature, be prepared to engage and offer critical feedback. Find out how they felt about it. That's a unique opportunity to provide perspective about the impact their compass has crowded out, or that they aren't privy to. Also a great time to preempt conversations about rest.

On the flip side... when your employee is going through a low phase, that's also a great opportunity to connect and understand what's going on. Having open conversations can lead to a formalization of a plan that facilitates their rest, or whatever else they're going through. For example, let's work on smaller tickets for the rest of this month and then we can check on your energy levels. A formal plan with the manager really helps to silence the inner irrationality flogging you to keep going.

Your feedback, if you're careful, can really being the transformative process that results in less aspirations for impostership.


In conclusion, if you wear the coveted title of "Manager of the employee with Imposter Syndrome", remember to whom much is given, much is expected. You've got to really understand and nurture your employees. By initiating conversations about past experiences, managers can unearth hidden skills and provide a platform for growth. Encouraging self-reviews and objectivity is essential to combat the pervasive influence of irrational self-doubt. Recognizing the natural fluctuations in energy levels helps employees maintain a healthy and sustainable pace, fostering a more authentic and productive work environment. Crucially, regular and thoughtful feedback serves as a guiding compass, offering perspective and support during both triumphs and challenges. With these strategies, I'm hopeful that you can help your employees steer clear of the pitfalls of imposter syndrome.

Thanks for listening!