Managing Up, Leading Forward: Real Talk on Work, Growth & Better Boss Relationships

From the Ground Up: Real Talk on Leadership, Growth & Work Culture

We wanted to kick off this issue with something close to our hearts: the power and practicality of “managing up.” If that phrase sounds a bit corporate or vague, hang tight—we promise this is not another dry workplace productivity manual. We’re featuring insights from Wes Kao, an operator and communicator we deeply admire for her no-fluff approach to leadership. In her article “15 Principles for Managing Up,” Wes unpacks something we’ve all struggled with at some point: how to work with your boss, not just for them.

Now, don’t get us wrong—we’re not career coaches, and we’re not pretending we’ve got it all figured out. But we do care about growing in our roles, building healthier work relationships, and helping each other find momentum (and meaning) in our careers. This issue isn’t about telling you what to do—it’s about sharing what we’ve learned, what we’re still figuring out, and how someone else’s experience like Wes’s can reflect something we’re all going through.

Why does “managing up” matter so much? Because—surprise—it’s not just for people trying to kiss up or fast-track a promotion. It’s about trust, clarity, influence, and ownership. And let’s be real: if you’ve ever had a boss who didn’t understand your work, gave you little feedback, or left you feeling stuck, you know how frustrating things can get. This topic touches everyone—whether you're an intern, a seasoned manager, or running your own team.

So, let’s dive in together. Wes’s essay isn’t just a collection of tips—it’s a wake-up call and a mirror. And here’s the thing: we’re not just sharing her principles. We’re reflecting on them, relating them to our own experiences, and offering what we believe you’ll find genuinely helpful.

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The Shift We All Need: Owning the Relationship

One of the strongest takeaways we had while reading Wes’s work was this: It’s not just your boss’s job to “manage” you. That might sound obvious in theory—but in practice, it changes everything.

We’ve definitely been in situations where we assumed, “Well, I’m doing my job. If something’s off, my manager will tell me.” But truthfully? That mindset is risky. Wes talks about how early in her career, she thought leadership only came with a title. Same here. We used to equate leadership with authority—but in reality, it's more about initiative, alignment, and communication.

Her first principle—“Embrace managing up”—set the tone. It reminded us that even if it doesn’t feel fair or fun, owning how we communicate upward makes a massive difference. When you make things easier for your boss, you're making things better for yourself. That’s not about manipulation. It’s about alignment.

Wes points out that your manager might only spend 10% of their time thinking about your work. Meanwhile, you’re in the weeds 100%. So, if you're not connecting the dots for them, who will? Honestly, when we reflected on how busy our past managers were—juggling multiple direct reports, planning for future quarters, navigating office politics—we realized how many blind spots they probably had... and how we could have filled them.

Tip from us: Try this simple reframe: Instead of asking “What does my manager want from me?” ask “What do they need to be successful?” That unlocks everything.

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It’s Not About Talking More. It’s About Saying the Right Thing First

Let’s talk communication—because this part hit us hard. If you’ve ever drafted a Slack message and then deleted it five times (we’ve been there), Wes’s thoughts on clarity and hierarchy are a goldmine.

Her principle about focusing on the punchline got us thinking: too often, we bury the lead. We give backstory, build up slowly, and by the time we reach the “ask,” our manager has either zoned out or gotten confused. Wes’s advice? Start with the conclusion. Lead with what matters, then offer context if needed.

This approach isn’t just useful for Slack messages—it’s a mindset. It forces us to ask ourselves: What’s actually important here? What do I need help with? What’s the action?

Another gem: use information hierarchy. Think of your communication like an article—headline first, details below. As Wes said, managers are often catching your message between meetings. Make it easy for them to help you.

And let’s not forget showing your thought process. We once feared sharing half-baked ideas would make us look unprepared. Wes flipped that on its head—saying it’s better to share your logic early. That’s what invites collaboration and helps your manager give better feedback.

A quick practical tip we’ve adopted: Try sending updates with this format:

• TL;DR: [One sentence summary]

• What I recommend: [Clear action or direction]

• Why it matters: [Brief rationale]

• Questions/Concerns: [Optional]

Simple, effective, and repeatable.

When Feedback Feels Like Micromanagement

Let’s be honest: being “micromanaged” sucks. At least… it feels like it sucks.

But Wes raised a point that really humbled us: maybe it’s not micromanagement. Maybe it’s a lack of communication. Maybe your boss is checking in constantly because you haven’t kept them informed.

We had to sit with that one. There were definitely times we bristled at repeated check-ins. “Why don’t they just trust me?” we’d think. But looking back, we realize we weren’t giving them enough reasons to. That doesn’t mean the manager is faultless—but it means we could have handled things better too.

And here’s the counterintuitive truth: over-communication is often the right amount. Especially early in a working relationship. Wes shares a powerful quote from Intel’s Andy Grove—basically, how much oversight you get should depend on how well you’ve handled that exact task in the past.

That was eye-opening. Trust isn’t personal—it’s contextual.

Wes also talks about the importance of proactively asserting what to do. Don’t wait to be told. When you make decisions (even just recommendations), you free your manager from doing all the thinking. They don’t need to agree with everything. But it creates momentum, not confusion.

Tip we’ve used with success: Whenever you’re unsure, say this:
"Here’s what I’m leaning toward. I’m about 70% confident—would love your take before I move forward."
This shows initiative and openness.

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Keep Going: Why Managing Up Never Really Stops

Wes’s final principle really stuck with us: “Expect to manage up forever.”

This might sound exhausting, but there’s comfort in it too. It’s not just a phase. It’s a practice. Even founders, CEOs, and board members are managing up—to investors, partners, peers. There’s no graduation day for clear communication, mutual respect, or aligned goals. We’re all in this loop, just at different stages.

For us, that realization has been freeing. We stopped expecting things to magically “click” once we reached a certain level. Now we approach each relationship—new boss, new teammate—with the mindset: How can we work better together? What do they need to hear from me to feel confident?

Wes isn’t preaching perfection. She’s sharing a playbook that we can revisit over and over. And we’re sharing it with you because we believe these ideas work. Not just in some abstract theory, but in the day-to-day tensions, missed signals, and small wins we all experience.

As you close this issue, we invite you to reflect:

• Where have you been waiting for someone else to “get it”?

• What’s one small thing you can do to communicate better upward?

• Are you ready to see your relationship with your boss as a two-way street?

We’ll leave you with that.

What’s your next spark? A new platform engineering skill? A bold pitch? A team ready to rise? Share your ideas or challenges at Tiny Big Spark. Let’s build your pyramid—together.

That’s it!

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