The worst year of my life was my first year of management.

It was like someone had turned on a firehose, and I saw no end in sight for when it would turn off. I took piles of notes, folders, and my laptop home every night and on weekends. The emails never stopped, so I began a bad habit of staying glued to my phone to keep the peace. I saw sides of colleagues no one else did: fastidious and disorganized, indecisive and impulsive. Some people emailed me about everything, from trouble with their spouses to the 16 paths their career might take. Others never uttered a peep. I supervised people older than me, and all seemed to be colluding to haze me. One walked out as we scrambled to meet an urgent deadline, saying she desperately needed a cigarette. I cried.

It’s been nearly two decades since then, and neither hindsight nor nostalgia has changed how I feel about that first year of management. It truly sucked. My reaction is apparently common: One survey of first-time managers found nearly two-thirds to be uncertain or anxious about their new role.

What might have helped? Perhaps some honesty about how hard the transition is, sure. What I really wish I’d had, though, was a sense of how I fit into the company, this team, and these lives.

Too often, people get promoted into management and we focus on their singular and upward trajectory: “Do this job for a year or two and you’ll soon be running the department.” The first management job is presented as a necessary stop to bigger things, and honestly, a lot of entrants treat it that way. What we don’t talk about enough is what it means to be in charge of other humans and play a role in their destiny. This is the hardest part of management, but also the most enduring and rewarding.

Some companies are now trying to go beyond the usual for first-time managers, which maybe used to go a little something like, “Congrats on the promotion. Good luck to you.” Amazon recently launched Leadership Liftoff, created for the company’s area managers who typically join the company directly out of school. Cohorts of 50-250 managers takes part in the seven-week course that straddles the theoretical, situational, and practical sides of management.

I asked Sandy Gordon, Amazon’s vice president for people, experience and technology, what new managers need to know, and she didn’t miss a beat. “I want them to know we have their backs,” she says. “Management can be lonely, and it’s nice to have other managers experiencing it in real time with you and have that additional support to make decisions.”

Indeed, the entry to management is a significant life transition, and we’d be better served if more of us shared honestly about its pitfalls and pleasures.

Having people’s backs

The trickle-around effect of someone having your back (and telling you so) in an organization is so powerful. What Gordon outlines—of an employer assuring first-time managers they are supported—then gets passed onto a new manager’s teams and colleagues. The scrutiny on our work, internal from colleagues, external from customers, can sometimes feel unbearable, and knowing a boss supports you helps create a culture of affirmation versus fear.

During that first year that I struggled, I clung to what my supervisor told me: that “99% of the decisions you make will be the right ones.” This steadfast clarity allowed me to stay the course, to learn to balance and prioritize the needs of myself, the team and the organization. As I channeled efforts into direct reports and their improvement, as I advocated for their work to be recognized and celebrated, I could palpably feel them loosen up and begin to trust me more. Our team meetings turned into raucous discussions, and I knew we’d all turned a corner when I stopped dreading them and awkward pauses were replaced with laughter. Another milestone came as more people were added to my group—and the veterans offered to “translate” my style and tone to the others. So much of management magic lies in our ability to decipher one another.

Being there

“Do I need to check in with you every day?” This question truly haunts me as a time-pressed CEO, even one with years of management experience. I never feel like I have enough time to talk to direct reports in between meetings with clients, funders, partners, and others. And so I asked Petrina Thompson, the head of human resources and client services at Brightside, an employee-benefit financial-care company. She told me that it’s the wrong thing to be asking.

Instead, the question should be: “How often do your direct reports need to talk to you?” she says, then goes on to explain the difference from the perspective of the manager versus the report: “Every person is different and we all have different needs. Notice I said ‘need’ and not ‘want’ here, which makes it tricky.”

For example, if someone only wants to meet weekly but is on a critical project and struggles with juggling, then it’s time to increase the cadence. “Having the ability as a leader to assess what your people need from you based on the tasks that they have and the lives that they are navigating outside of work,” says Thompson, “helps you to get the most from your team and helps them get the best value out of you.”

Others might need a weekly check-in filled with big-picture items to discuss, and can manage daily communications via email, text, or Slack.

Another leader I know employs the tactic of being a very hands-on manager for the first two to three weeks to establish workflow and relationship. In a column I wrote on onboarding, Nettie Nitzberg, co-founder and chief learning officer of the consulting company Saterman Connect, told me a big mistake managers make is not checking in every day for the new hire’s first two weeks, especially in remote or hybrid environments. “Being at home when you start a new job is lonely enough,” she said. “When your manager doesn’t care how you are doing or feeling, it sends the wrong message.”


There’s nothing like hands-on experience and making mistakes to understand the art and science of management. One curiosity about the Amazon program is that it targets those who typically join the company directly from universities. Don’t you need work experience to be a manager?

Both Gordon and Thompson shifted my thinking on this. “We have a very involved selection process,” says Gordon, that looks for “leaders who can think about leadership in its truest form.”

“Different management roles also have different expectations. Taking a personal approach to understanding a potential leader’s skills and desires for a role is key,” says Thompson. “And if you can give them some experience in parts of the manager role to help them grow before they become a leader, it only better prepares them for success as a newer leader.”

This commitment—to being a leader versus a manager—seems critical to success. It also corrects for the bias that pervades decision-making around who gets to be in charge. A so-called “assessment culture” sees talent as a fixed trait versus a developed one, and it’s applied unevenly: White men are hired for potential, whereas women and people of color are given opportunities once they’ve proven mastery.

Become a student of leadership

Most of what you need to manage effectively won’t be in a book or manual or podcast—but seek out those resources anyway. Thompson’s book recommendations: Seat of the Soul by Gary Zukav, to help you learn about yourself so you can be better each day, and The Art of Possibility by Ben Zander, to help you see what is possible within yourself and find it in others too.

I recently stopped reading business and management books to make more time to read for pleasure, but I still find leadership lessons in almost everything I do: plays, events, literature, even music. Listening to this podcast last night on a new album by a trio of South Asian artists inspired me to think about the vulnerability of improvisation, the power of collaborations, and the joy of community, for example.

Rookie mistakes will happen

First-time managers too often are guided by the desire to assert their newfound power. One of my greatest pet peeves is the use of the possessive “my” to refer to talent. As in: “My designer can work on that for you” or “Meet my account executive.” Another variation is to present yourself as the boss of everybody. “I’m Maria’s boss” seems like a horribly insecure way to introduce yourself.

There’s no need. Humility and humanity triumph over your recitation of the org chart.

Another struggle is the resetting of personal and professional boundaries with coworkers. Over the years, I’ve developed cues to let colleagues-cum-friends know I am firmly in the supervisor zone. Most are explicit like: “I am giving you some tough feedback…” or “I am switching into manager mode to make sure you understand what’s needed here…” or “I won’t sugarcoat this difficult conversation…” But I confess that in year one, I was a bit of a mess. I don’t know that any more coaching would have solved this; I learned a lot from those painful conversations. Go ahead and muddle through them. It gets easier.

If you think you might one day want to manage people, it helps to enter the management role with strong professional relationships already established. Especially when your peers become your reports, “having solid working relationships built on trust and a proven track record of delivering collectively to the end goal is critical,” says Thompson. “Although it may be awkward at first, you can move forward together with candid dialogue and action when they become a member of your team.”

This takes care and effort. One thing that surprises people, whether I am in a meeting or a panel discussion, is that I bring prepared notes. I used to hide them, but now I am more upfront. Rehearse, write a script, jot down bullet points. There’s absolutely no shame in preparing to be a boss.

Belief is a powerful motivator

I’ve spent my career toggling between being an individual contributor and manager of teams, and at this point have spent more of my time entrenched in the latter. When grooming folks to join these ranks, I am guilty of focusing on their skills and superpowers that make me think they are right for the job.

Really, the reason to become a manager is because management is the ultimate expression of belief in other people. This belief sometimes lets us down, sure, but it also propels forward momentum in our teams, companies, ourselves. If you don’t believe that the people around you can grow and rise to meet challenges, then your efforts won’t matter. You are basically running in place.

I often say talent is rarely innate and everything can be learned. To hear this (early, often, always) is actually liberating for your colleagues; how can we ask people to have confidence in themselves without extending the same courtesy? The greatest gift of my time as a manager has been watching the ascension of those I once supervised, the creation of a diaspora of dozens that believes in possibility. Their desire to reconnect humbles me and, more importantly, continues to teach me.

Management has been a form of future-proofing myself, because it’s a guaranteed way to continuously glean lessons from others, from trends in our industry to the stuff of life. And thus emerge the types of people I want to always work with and learn alongside.

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