Managing Up Effectively In A Complex Organization

How do you manage up—without losing yourself in the process? I talk to a lot of smart, capable leaders who are stuck in a difficult dynamic with their boss. Sometimes it’s a distracted executive who doesn’t give feedback. Sometimes it’s a reactive founder who changes direction constantly. Sometimes it’s someone who avoids conflict, micromanages, or just makes alignment feel impossible. These are often mid-level leaders—PMs, EMs, ICs, or directors—who care deeply about doing great work. But managing their boss has become a second job. One that drains their energy, clouds their confidence, and makes them wonder: is it me? If that’s you, here’s what I tell my clients: First, get clear on what you need to be effective. That includes role clarity, decision-making rights, and emotional safety. Then, look at your boss like a system—not a personality. What do they respond to? What times of day are best? What do they ignore? Make your communication easy to absorb. Lead with context. Connect your points to their priorities. Be crisp. Set boundaries without escalation. It’s possible to be assertive without being combative. And don’t try to figure it all out alone. A sounding board helps—especially when the situation is nuanced, messy, or political. I’ve helped a lot of people work through this—both as a coach and a fractional executive. It’s not about manipulating anyone or giving up your authenticity. It’s about building real influence in a difficult context. If managing your boss feels like your hardest job, it might be time for some new strategies. Let’s talk. #managingup #leadership #executivecoaching #orgdesign #careeradvice

Learning how to manage up is a key to success. Here's one template I wish I had earlier in my career to help people manage up (and down) better. Ideally you have an experienced manager who knows how to create clear goals, provide specific detailed feedback and helps you remove blockers. Unfortunately I chat with tons of operators who don't feel like they get clear enough direction. Instead of waiting for things to change, take things into your own hands and drive a clear 1:1 or regular communication with your manager. How? Fill out this document, update it weekly and go over it with your manager. The Keys: 1. Goals this quarter, your current results and projected results - this will help you get alignment on the goals and force your manager to be clear about what success looks like 2. Wins - What went particularly well this week. It's important for both of you to celebrate your successes and to reflect on why certain things worked (this make it a lot easier to get critical feedback when they need to give it) 3. Updates - Last week I completed X -This upcoming week will be successful if: (write out 2-3 priorities) - Throughout my career I've found people throwing more and more things at me. The reality is that we only have so much time and everything has an opportunity cost. Therefore, by writing out your 2-3 priorities, you are explicitly getting alignment on what other things you are putting on the back burner. If your manager doesn't agree with your priorities then at least you can discuss that and get aligned on what should be rearranged. 4. Roadblocks, concerns & items needing input - This is the section or the conversations throughout the week where your manager can help you problem solve based on their previous experiences or knowledge, they can help you think through different solutions to the problem and pressure test your thinking or they can just sign off on whatever it is that you are trying to get across the line. 5. Personal Development (PD) - This is the section where you're going to both reflect and push for specific and clear feedback from your manager. It'll force both of you to reflect regularly and figure out what to focus on to improve. -PD skill I am working on: -PD update from last week: -PD idea for next week:   -Feedback from this week: -What I think I did well: -What I think I could have done better: -What manager thinks I did well or could improve: (Ask!) -What I think my manager did well or could improve: 6. Stretch Question (Your manager will ask you a question. No need to fill anything in.) Now I understand that many companies are opting not to do 1:1s. Each company should do what they believe is right, but even if you don't have 1:1s I do believe you should be having each of these conversations regularly Huge thank you to my partner Rebecca Price for creating this template that has helped me as a manager immensely and put structure around many of the things I did naturally earlier in my career.

A 21-year-old asked for my best career advice. My answer: learn to manage up. Most people suck at managing up. They say too much or too little. 8 ways to manage up like a pro: 1️⃣ Set the stage. Executives are busy. Start every email or meeting with 60 seconds of context: ↳ "What are we talking about?" ↳ "Why is this important?" ↳ "Where did we leave off?" 2️⃣ Value their time 10x more than yours. This will make you disciplined about: ↳ Follow-ups ↳ Action items ↳ Clear, concise communication 3️⃣ Use FYI and NNTR. Not every message needs a response or action. ↳ Example: "FYI, the dashboard is updated as you requested. No need to reply." 4️⃣ Understand the hierarchy of communication. Some modes are better for urgency: ↳ Most Urgent: Phone ↳ Less Urgent: Text, Slack ↳ Async: Email (with "Request" in subject and a clear deadline) 5️⃣ You still own the monkey. If you ask your boss for something, it’s still your job to ensure it’s done. Escalate as needed until it’s complete. 6️⃣ Always follow up. After meetings, send a quick summary with action items. ↳ Specify: WHO will do WHAT by WHEN. 7️⃣ Regular reporting. Create a system for progress updates. Make them: ↳ Regular ↳ Quantitative ↳ Data-driven 8️⃣ Seek feedback. Ask: "Do my updates make it easy for you to see progress? What can I do to make it a 10/10?" With these principles, you'll become invaluable to any leader. ♻️ If you found this useful, follow me, Jesse Pujji, and share this to help others learn how to manage up effectively!