Managing up, managing up, managing up
5 practical ways to improve the way you collaborate with your manager.
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When I first started working post college, the only type of working relationship that I understood was: Managers manage people. They move parts. Managers punish people when they don’t work well, and reward them when they do. If you want to accelerate in your career, do everything your boss tells you to.
But the more I work, the more strongly I feel that the surest way to accelerate your career is to do the opposite.
The first time I had this realization was when I became a manager for the first time. I thought that I’d enjoy telling people what to do and have them do exactly what I say, but turns out, what I subconsciously expect is for them to have the self-maturity to set their own goals and to raise the important issues I need to be aware of.
On the opposite side, I’ve also learned how true this is when I reported to my manager. The moment I decided to bring the discussions to my manager instead of the other way around, I started to notice other things that otherwise would not happen if I didn’t take the initiative.
Managers appreciate people that takes the initiative. Self-starter folks are more reliable, and they are worth to advocate for.
Below I’ll share some practical tips that you can do to improve the way you collaborate with your manager. Everyone will have different situation, but I found these to be the most effective in my experience.
1. Deliver 🚛
There’s a reason why I put this as #1. Managing up is a cycle of telling your managers what you will do and actually do it. Among all the practical ways about managing up, the most important factor is to deliver.
If you deliver and do great work, your manager will trust you. If they trust you, they will micromanage less. If they micromanage less, you will be given more freedom to explore more and do great work.
Before all else, make sure you deliver.
2. Regular + effective report 📑
The #2 fundamental of managing up is regular communication. But making it regular is not enough. It has to be effective. Otherwise, you will end up spamming your manager with non-important details that add little value for both of you.
Few ways to build this habit:
Send a regular report to your manager — The cadence is up to you. It can be every weekly, bi-weekly, or monthly. Three ways to determine the right cadence for your report: The urgency of your projects, the pace of your projects, and personal preference (you and your manager).
Figure out the right format — There are many templates for a regular update. Some used the regular “highlights, lowlights, ask for help”, while others use a more personalized formats. If this is the first time you're doing this, I suggest to make it simple enough for you to do regularly, yet still enough to give context to your manager about what has been happening.
Be regular, but be concise — Your manager has a very limited time and energy to absorb what you write. While they will appreciate that you keep them in the loop, giving them unnecessary details might be counterproductive.
Click here to use my personal weekly report template that I currently use.
3. Be comfortable with communicating failure 📉
Many people feel uncomfortable to communicate when some projects don’t work well. I’ve been in both ends (as a manager and as a team member). Ironically, as a manager, few things are more relieving than finding out about an issue or a failure sooner rather than later.
That being said, it makes sense why communicating failure can be uncomfortable despite of how beneficial it can be.
Few things to remember when communicating failure:
You are not the project you work on — Startup are all about doing something that has never been done before, and it must be done quickly. There’s no playbook for it. By definition, most projects WILL fail. So really, it’s not about you.
Share what you learned — The project might fail, but that shouldn’t stop you from learning. Build upon the learnings you got to determine what to do next.
Don’t be defensive, focus on what’s next — Building on the previous point, it’s important for you to share with your manager on what you think should happen next. It sounds obvious, but most people don’t do it.
Managers appreciate it when you don’t feel discouraged by a failure. They like it when you acknowledge a failure and waste no time to learn from the failure. What worked, and what didn’t? Did it fail because the idea didn’t work? Did it fail due to poor execution? Should we shut it down? Do we want another try?
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4. Think one step ahead 🧠
Managers are obsessed to know what happened in the past, but they are even more obsessed with what you will do next. One of the most memorable things my manager said was to be a domain expert. He said that a domain expert doesn’t only mean knowing what’s happening, but also means knowing what to do next (and all the possible scenarios).
Few ways to build this habit:
Carve out a dedicated time for thinking — Whenever I have an important project, I would carve out 1 - 2 hours just to think about all the possible outcomes and brainstorm on the next action items for each.
Understand what your manager cares about — Different managers might have a different definition of “ think one step ahead”. Try to ask yourself (or even better, your manager) about what other topics they might expect you to cover on your project update.
Communicate this to your manager — After doing the thinking, it’s time for you to share your decision-making framework. Let them know your approach, and ask for their inputs.
5. Ruthlessly prioritize 🗡
The reason I’m putting this last is because this is the last thing that I recently learned about managing up, and I also believe this is super underrated. Sometimes, you’re given a new project from your manager, and this project is labeled as “urgent”. But now you have 4 projects in your to-do list that’s labeled as “urgent” and “important. You only have so much resource, but you don’t know which one to prioritize.
Few tips to ruthlessly prioritize:
Share your updated priorities with your manager — Given the recent addition and other projects that were there already, how might your priority change? Does the recent addition make other projects suffer? What are you working on right now? What’s your constraint?
Work with them to update your priorities — If you’re too confused to update the priority yourself, ask them to work with you on updating your priority.
Your manager is just a human being. It’s possible that they give you a new project while knowing your bandwidth, but it’s also possible that they don’t. Give them a chance to make things easier for you.
How to tell if you’re doing it right ✅
Being great in managing up is super valuable. While it might not always guarantee a promotion, a gradual improvement in your career is almost certain. Short-term wise, effective managing up should allow you to:
Be trusted to make important decisions, given that your manager knows you have all the context needed to make a sound judgement
Be micromanaged less due to your manager trusting your capability to deliver and communicate regularly
Take ownership of your work since you mostly dictate the project you work on, not relying on your manager to give you instruction
Be more productive due to better prioritization and the fact that your manager is well aware of all the potential blockers that might slow down your progress
Be involved in strategical discussions with leaders from other departments — you have shown that you are capable of strategical thinking and you can be self-sufficient.
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