The Art of Managing Up: Making Your Boss's Job Easier (And Your Career Better)

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Hello team,

Early in my career, I watched a talented director torpedo their own project. They'd done brilliant work—solved a complex technical problem, delivered ahead of schedule, and energized their team. But when they presented to leadership, they buried the headline in technical details, failed to connect it to business priorities, and left execs confused about what they were being asked to decide.

The work was exceptional. The managing up was non-existent. And the project got stuck in limbo for months.

This week, let's talk about a skill that's rarely taught but absolutely critical: managing up.

Let's clear up a misconception right away: managing up is not manipulation, brownnosing, or playing politics. It's recognizing that your relationship with your leader is a two-way partnership that requires active management from both sides.

Your boss has their own pressures, blind spots, communication preferences, and constraints you may not see. When you manage up effectively, you're making their job easier by giving them what they need to support you, advocate for your team, and make good decisions.

Here's what many mid-level leaders miss: your success is directly tied to your leader's ability to champion your work. If they don't understand what you're doing, why it matters, or how to talk about it with their peers and superiors, you're creating an artificial ceiling for yourself and your team.

The leaders who advance aren't always the most talented—they're the ones who help their bosses succeed.

It's peak season, so volume's about to spike. Most teams either hire temps (expensive) or burn out their people (worse). See what smarter teams do: let AI handle predictable volume so your humans stay great.

Check your options

Not all leaders consume information the same way. I've found most fall into three categories:

The Strategist wants context and implications. They care less about how you got there and more about where it fits in the bigger picture. Lead with outcomes, connect to business goals, and save the details for when asked.

The Operator wants to understand the mechanics. They need to know the plan is sound before they can support it. Give them enough detail to build confidence, anticipate their questions, and show you've thought through the risks.

The Relator wants to know about people and dynamics. They're thinking about stakeholder reactions, team morale, and organizational impact. Proactively address the human elements and don't just focus on deliverables.

Most leaders are a blend, but they typically lean one direction. Your job is to figure out which and adapt accordingly. The update that works for one will frustrate another.

1. No surprises. This is the golden rule. Bad news doesn't get better with age, and leaders hate being blindsided—especially in front of their peers or superiors. If something's going sideways, flag it early with context and options. You don't need to have all the answers, but you do need to give them visibility.

2. Come with solutions, not just problems. When you bring an issue to your leader, bring your recommendation too. Even if you're not sure, showing you've thought through options demonstrates ownership and makes their job easier. Frame it as "Here's what I'm thinking—what am I missing?" not "What should we do?"

3. Understand their priorities, not just yours. Your project may be your top priority, but it's one of twenty things your boss is juggling. Before you ask for time, resources, or decisions, understand where your work fits in their world. If you can connect your needs to their goals, you'll get better support.

4. Make them look good. This isn't about ego—it's about creating a virtuous cycle. When you help your leader succeed, they have more capital to invest in you and your team. Share credit upward, communicate wins in ways they can relay, and give them ammunition to advocate for your work.

Managing up isn't just about big moments—it's about consistent, structured communication. Here's the rhythm I recommend:

Weekly touchbases should be sacred. Come prepared with a tight agenda: progress on key initiatives, decisions you need, risks on the horizon, and anything they should know. Keep it focused and respect their time.

Monthly written updates create a paper trail and help leaders who process information better in writing. Use these for broader context, strategic thinking, and connecting dots across multiple workstreams.

Quarterly alignment conversations are where you step back and ensure you're still pointed in the right direction. Discuss priorities, resource needs, development goals, and recalibrate expectations.

The leaders who do this well don't wait for their boss to ask. They create the structure and own the relationship.

Until next week, Your Leadership Partner

In the premium section below, I share the exact templates and frameworks that have helped me build trust with every leader I've worked for:

These aren't theory—they're battle-tested templates you can use Monday morning.