“It’s a manager’s job to make their team’s jobs enjoyable, challenging, and fulfilling. Most managers end up saving those aspects for themselves and throw endless grunt work at their folks. Give people things to achieve and own and you’ll see magic happen.”
I first put that on Twitter as a provocation, half wish, half mission statement. I was thrown into the absolute deep end a little over a year ago- I went from IC to head of an incredible team. The shift into management has been exhilarating and awkward. I’m now scrubbing my old habits, asking myself: What did my past bosses do right? What burned me?
When I started, I was neck-deep in a crash course called “Congratulations, you're now the boss.” No warning, no training wheels. Just me, a suddenly swelling team, and a calendar that looked like a losing game of Tetris. Overnight, I went from being the one doing the work to the one people looked to for direction. That shift been messy, mind-bending, and meaningful in ways I didn’t expect.
This post is my love letter, open diary, and battle plan for anyone finding themselves managing others before they feel fully ready.
Reverse-Engineering My Managers: What to Keep, What to Burn
I did what most first-time managers do: I panicked. Then, I reflected.
I mentally replayed every job I’ve ever had like a highlight reel and a horror show. I remembered the manager who gave me a problem, a whiteboard, and the freedom to think. I also remembered the one who double-checked every comma in my emails. I remembered the applause I got in one all-hands for leading a product launch, and the eerie silence in another when my hours of invisible labor simply...disappeared.
So I made a literal list:
Keep: Trust, big-picture goals, timely feedback, air cover, public celebration, private correction.
Burn: Micromanagement, spotlight-hogging, last-minute chaos, emotional unpredictability, and the dreaded “just get it done.”
This list became my compass. I pull it out often.
Your past managers are your user research. Study the data. Decide what to replicate and what to reject. You don’t need to reinvent the wheel, you just need to spin a better one.
What the “Move Fast and Break Things” Era Got Wrong
We’re all children of the “blitzscale” generation- the time when breaking things was seen as edgy, when burnout was a badge of honor, and when people management was treated as a necessary evil instead of a core craft. There’s a kind of mythos around early tech culture that I bought into hard. Blitzscale! Hypergrowth! Founders-as-gods! The chaos was romanticized, the burnout was normalized, and managers? Managers were just...bigger ICs with a meeting problem.
Here’s what that era missed:
Breaking things also breaks people. The myth of chaos breeding creativity rarely included HR budgets or mental health support.
Hero culture undermines teams. When founders are the rockstars, everyone else becomes a roadie. That doesn’t scale.
Speed without direction = waste. Rapid execution with unclear goals created bloated codebases, confused customers, and disillusioned teams.
Facebook might have survived that era. Your early-stage startup? Probably won’t.
Now, I want to build the opposite of that. A workplace where clarity is kindness. Where urgency doesn’t become a battering ram. Where people know what’s expected of them and are allowed to be proud of what they build.
Learning from Great Work Cultures: Who’s Doing It Right?
Let’s stop romanticizing “grind culture” and start learning from the companies that quietly figured out how to treat people like people. Not perks-as-bandaids. Not vague values on a mural. Real, living, breathing cultures that have cracked the code of sustainable performance.
I made this ‘living list’ when I started out and keep adding to it when I come across a cultural more I admire.
We’re not talking about free lunches and glossy team offsites. We’re talking about systems that build trust, autonomy, clarity, and care. And if you’re building your own team, leading one, or trying to make your current workplace less of a dumpster fire, I hope these help you too.
Shopify: Trust is the KPI
Shopify famously talks about the concept of a "trust battery", a metaphor for how much trust exists between two people on a team. Every interaction either charges or drains that battery. And they take it seriously. When trust dips below a certain level between a manager and their team, it gets flagged- not to punish, but to repair.
What this taught me: Trust is not a vibe. It’s a metric. It can be built, measured, and replenished. But only if you treat it as real. If your team doesn’t trust you, they won’t take risks, ask for help, or tell you when things are going wrong until it’s too late.
How to use this: In your one-on-ones, ask: “What’s something I did recently that built trust? What’s something that chipped away at it?” Normalize talking about it. And when someone gives you a hard truth—thank them. That’s a battery charge right there.
Netflix: Freedom with Brutal Clarity
Netflix’s culture is often misread as “total freedom,” but that’s a half-truth. The real secret is clarity. They pair high autonomy with radical candor and extreme context. Their internal deck says it plainly: “We’re a team, not a family.” They don’t pretend work is warm and fuzzy. They just make sure it’s functional, fast, and focused.
What this taught me: Autonomy without direction isn’t freedom. It’s confusion. You can give your team all the flexibility in the world, but if they don’t know what “great” looks like, they’ll flail.
How to use this: When assigning work, don’t just say what to do. Explain why it matters, how it connects, and what “great” looks like. Then step back. Clarity isn’t micromanagement. It’s oxygen.
Basecamp: Calm Work is Deep Work
Basecamp doesn’t buy into hustle culture. They cap workweeks at 40 hours. They run asynchronous meetings. Their leaders write detailed memos instead of calling panic Zooms. They even wrote a book called It Doesn’t Have to Be Crazy at Work.
What this taught me: Calm is not the enemy of growth. Chaos doesn’t mean creativity. And if your team is always on the verge of burnout, they’re not working harder, they’re just running scared.
How to use this: Audit your meetings. Can three of them become one memo? Respect weekends like they’re sacred. And if someone’s logging 14-hour days, don’t high-five them. Ask what system failure forced them into that mode. Then fix it.
Atlassian: Management ≠ Promotion
At Atlassian, people move into and out of management without shame. If an engineer becomes a manager and realizes they miss building, no one treats it as a demotion. They just… move back. Because management isn’t a prize. It’s a role. One of many ways to contribute.
What this taught me: Leadership is about fit, not ego. Not everyone needs to manage people to grow. And when we treat it as a status symbol, we force people into roles that drain them and damage others.
How to use this: Ask your team: “What kind of work gives you energy?” If they want to lead, great. Train them. But if they want to stay ICs and deepen their craft? Celebrate that just as much. Build ladders that don’t only go up, they go sideways too.
IDEO: Leadership is a Rotation, Not a Throne
At IDEO, leadership often rotates based on projects. Designers may lead one initiative, then go back to contributing on the next. No one wears the crown forever. This builds empathy, diffuses ego, and encourages mentorship across levels.
What this taught me: Power is fluid. Authority doesn’t have to calcify. When you let people lead in cycles, you create a culture where everyone learns to support and be supported.
How to use this: Rotate meeting leads. Let junior folks own small projects with senior backing. Use “shadowing” or “co-leading” as training tools. And most importantly, model what stepping back looks like. When you share power, you multiply it.
The Real Takeaway: These Cultures Work Because They Respect People
Not just their output. Their time, thinking, learning curves, communication styles, and aspirations. They don’t create perfect harmony, but they do offer intentional scaffolding for people to thrive.
So if you’re building a team, or trying to be a better manager, or simply deciding where you want to work next, ask:
Does this place respect my time, or does it treat urgency as default?
Does it value trust, or just track productivity?
Does it allow for different leadership styles, or glorify a specific mold?
Does it normalize feedback and clarity, or rely on guesswork and politeness?
Cultures don’t need to be trendy. They need to be consistent. When you get that right, people don’t just work better. They stick around, grow faster, and build cooler things.
Because they feel seen. And safety, real safety, is the ultimate productivity hack.
The Identity Shift: From Doer to Enabler
Let me be honest. I grieved a little. I missed being the go-to. The fixer. The one who pulled late nights and got high off solo wins. That dopamine is addictive.
But management is less about personal highs and more about designing the conditions for others to thrive. And when it clicks? It’s better than any solo win I’ve ever had.
Still, I give myself “IC time” every week. Not because I need control, but because I want to stay grounded. It’s where I reconnect with my craft and stay fluent in the language my team speaks. But I no longer measure my worth by output. I measure it by whether my team feels confident, safe, and seen.
So How Do You Actually Do It?
Let’s get real. Advice like “empower your team” sounds great until you’re staring at Slack threads, a missed deadline, and someone on your team crying in a conference room. So here are three stories, three realities, and three deeply human ways to navigate them, whether you’re a manager, being managed, or choosing who to work for.
If You’re a First-Time Manager: Welcome to the Deep End
Imagine you’ve just been promoted. Yesterday, you were the one building the deck. Today, you're reviewing three decks, troubleshooting a hiring issue, and trying not to cry during your fourth back-to-back meeting.
Welcome. This is where it gets real.
Start here: know that you’re allowed to feel disoriented. Management isn’t just a bigger job. It’s a completely different one. You’ve gone from doer to multiplier, and that shift requires you to rewire how you define success. It’s no longer about what you accomplish, it’s about what your team accomplishes because of you.
Now, what no one tells you: you’re not failing. You’re just transforming. This isn’t a job upgrade. It’s an identity shift. And like any shift, it comes with friction. That awkwardness you’re feeling? That constant question- “Am I doing this right?”- that’s the work. That’s the new skin forming.
Now here’s your starter kit:
Audit yourself: Ask yourself this: what habits from your IC days are you clinging to like a comfort blanket? Maybe it's obsessing over pixel-perfect output. Or double-checking your team’s every move because that’s how you would've done it. Those instincts, while once useful, might now be sabotaging you. Try this: make a list of everything you did last week. Mark what only you could have done, versus what someone else on your team could’ve done with some support. If you're doing everything yourself, you're not managing, you’re just multitasking with a title.
Start small: the next time you're tempted to rewrite someone’s doc, don’t. Instead, leave constructive comments. Ask them to revise it. See what happens. You're not losing control, you're building capacity.
Define success differently: Success is no longer about you being the star player. It's about being the coach that helped the team win. That’s a wildly uncomfortable transition if your self-worth is tied to output. But here’s a better metric: did your team meet their goals this week? Did someone do something they were scared of, and nail it? Did you create an environment where they felt confident and clear? That’s your scoreboard now.
Start a “Team Wins” doc. Every week, log something each person nailed, big or small. Share this during team meetings. Public celebration sets the tone. Private success is no longer the mainstay.
Don’t hoard the interesting work: This one’s hard. Especially if you like the work. If you were the IC who shipped cool features, wrote slick threads, closed major deals, it’s easy to want to keep a toe in that glory. But here’s the secret: great managers don’t gatekeep exciting work. They create pathways for others to step into it.
So when the next shiny, high-impact project rolls in, and your first instinct is “I’ll handle this,” pause. Instead, ask: “Who on my team would grow from owning this?” Then back them up with the resources, airtime, and support they need to shine. Yes, they might not do it your way. But if they do it their way and succeed? That’s leadership gold.
Also, let them be better than you. It’s not a threat. It’s your legacy.
Set expectations, not playbooks: It’s tempting to hand over a list. A play-by-play. But giving someone a GPS doesn't teach them to read a map. Your job now is to define the destination, not drive the car.
Start by clearly stating the outcome: “We need a stakeholder-ready report on X by Friday.” Then resist the urge to say how to do it unless asked. Be available. Offer support. But let them find their own best route.
Write down the what and why of a task before assigning it. Then, in your 1:1, give that context first. Let them design the how. You’ll be amazed by what emerges when people are given permission to think.
Ask more than you tell: Early managers talk too much. It’s usually fear- fear of losing control, of seeming unprepared, of being challenged. But one of the most powerful things you can say is: “What do you think?”
Start meetings with questions, not updates. Instead of “Here’s what we’ll do,” try “What’s our best next step here?” If someone’s stuck, ask “What’s blocking you?” instead of jumping to fix it. This builds problem-solving muscles. It shows trust.
And when someone pushes back? Listen. Really listen. Because your job is not to be right. Your job is to make the team better than you were yesterday.
Every one of these is hard. Especially in the beginning. But here’s what I’ve learned: it’s not about perfection, it’s about practice. About course-correcting fast, apologizing when you mess up, and constantly checking: Am I building something I would’ve loved being part of?
That’s the only North Star that matters.
If Your Manager Is Young, New, or Learning: Managing Up Without Losing Yourself
Imagine this: your manager is technically brilliant but constantly overwhelmed. Tasks fall through the cracks. Priorities change overnight. You’re working double-time to stay afloat, and you’re starting to wonder why no one’s steering the ship.
Let me say something clearly: you deserve good management. And also, many young or first-time managers simply haven’t been taught how to lead. They’re learning on the job, often in real time, with no guidance and enormous pressure. If you feel like you are holding things together, you're probably right. But here’s the truth: you can set boundaries and build support systems without becoming a silent martyr.
Start by offering clarity, not confrontation. Don’t just say “This isn’t working.” Say, “Here’s where I’m unclear on priorities. Can we agree on what’s most important this week?” Frame it as shared accountability, not criticism. Good managers (yes, even new ones) will take that cue and appreciate the honesty.
If they’re overwhelmed, offer structure. Suggest a weekly check-in. Share a simple update template you’ll send each Friday. Help them see your progress. When you take initiative like that, it lifts a burden they may not even know how to articulate.
But, and this is crucial, don’t start doing their job for them. That leads straight to resentment. Your job isn’t to protect your manager from their responsibilities. It’s to protect your own time, sanity, and development. If something truly major is falling apart, it’s okay to escalate. Go to HR, a skip-level leader, or someone you trust. Say, “I’m committed to this role, but I need more clarity and support.” That’s not disloyal. That’s professional.
And remember: feedback flows both ways. If your manager does something well- gives you autonomy, has your back, or celebrates your work- tell them. “Hey, I appreciated the way you handled that meeting. It made me feel supported.” That kind of positive reinforcement doesn’t just help them grow, it builds a culture where feedback feels safe and regular, not like a ticking time bomb.
A ‘How To’ Recap for Managing Up:
Translate chaos into structure. Suggest standups, progress check-ins, or written updates.
Push for clarity without hostility. Ask questions like: “What does success look like this week?” or “Can I help prioritize my own tasks based on bandwidth?”
Protect your bandwidth. Don't let vague leadership become your burnout.
Praise out loud. Positive feedback isn't flattery, it's team culture scaffolding.
Escalate with care, not drama. If you must, escalate in a way that’s honest, fact-based, and rooted in your desire to grow, not punish.
If You’re Interviewing: Choosing the Right Manager (and Spotting Red Flags)
Picture this: you’re in an interview. The role is exciting, the product is buzzy, and the startup vibes are immaculate. But something about the manager’s tone feels clipped. They dodge your question about failure. They talk a lot about themselves. Your gut twinges, but you tell yourself to ignore it.
Don’t.
One of the most career-defining choices you’ll make isn’t what company you join, it’s who you report to. A great manager opens doors, invests in your growth, and helps you fly. A bad one? They’ll slowly dim your spark until you start questioning your own instincts.
So what do you look for?
Ask real questions, not just polite ones. Try: “Tell me about a time someone on your team failed. How did you respond?” Watch their face. Is there empathy or deflection? Or try: “What’s the most common feedback your team gives you?” If they say “Nothing,” run. That means their team is either scared or checked out.
Another strong cue? Look at how they talk about their team. Do they say “we” or “I”? Do they highlight others’ contributions? Or position themselves as the only brain in the room?
You can also get sneaky. Ask: “What would someone who left the team say was hard about working here?” Their answer tells you how self-aware they are. And if you can, try to talk to a peer or someone already on the team. Ask, “What kind of manager are they on a hard day?”
Finally, listen to your body. If you walk out of the interview feeling heavy or unsure, trust that. The worst thing you can do is ignore discomfort because the role looks good “on paper.”
A ‘How To’ Recap for Assessing a Manager:
Ask questions that surface character, not just competence. “What’s a time you were wrong?” is more telling than “What’s your management style?”
Pay attention to language. Do they say “I built this team” or “My team built this product”?
Get behind the curtain. Try to speak to a peer or ex-team member. Ask, “What’s it like to work with them when things go wrong?”
Watch the non-verbal cues. Do they listen carefully? Ask you thoughtful follow-ups? Or are they just waiting to talk?
Don’t override your gut. That subtle sense of “Hmm…” is data. Respect it.
These two sections- managing up and assessing managers- are often the most overlooked in career advice. But they’re where the hidden power lies. Because no matter how good you are at your job, your growth will always be shaped by who has your back—and who lets you grow with grace.
Letting Go, Lifting Others
Walking this new path has been challenging, but also incredibly rewarding.
I’ve had to unlearn a lot. That ambition means hoarding, that urgency means micromanaging, that management is about being in control. None of that is true.
We’re breaking old cycles of toxic management one day at a time. As first-time managers, we have an opportunity (and responsibility) to build something better: teams that work hard and thrive. The next time I’m tempted to fall back into old habits, tempted to keep the best bits for myself or dump grunt work on others, I recall how it felt as an IC. That memory keeps me honest. After all, I wouldn’t want my past self to think less of me tomorrow.
What’s true is this:
Leadership is leverage.
Management is craft.
And joy at work is not a perk. It’s the damn point.
I want my team to be better than me. I want them to outgrow me. I want them to look back someday and say, “That was a good season. I felt seen. I did the best work of my life.”
If you’re a new manager, here’s your reminder: you are not alone, you are not behind, and you are not supposed to know everything yet.
But you are supposed to care. That’s the job.
And if you do it well- if you choose humility over ego, trust over control, growth over credit- one of your former teammates will step into your shoes, notebook in hand, reverse-engineering what you did. I hope they find something worthwhile to emulate.
This is so well collated!
I love these nuggets. They are crisp, clear, and compassionate. Keep sharing.