Managing Up for Leaders

"Luckily, there’s a template that helps avoid all these problems: 1. Hi manager, let me tell you about a challenge I ran into ______ 2. Here’s how I’m thinking of handling it (or did handle it) ______ 3. Any thoughts?"

"Start by telling your manager you want this, e.g. “Hey, manager, I just want to let you know that I’m really interested in product growth, and I want to get into a growth-focused role as soon as I can. What do I need to do to get there?”"

"How might you bring them along the same journey you went on that convinced you that this was the wrong direction? What were the key data points, experiences, and learnings for you? Share them as you experience them, with your takeaways, and always with a “here’s what we’re doing next to continue learning how to make it work.”"

"But once a CEO has made up their mind, the product leader needs to commit to the decision. Otherwise they’ll irreparably damage their trust with the CEO."

"Start exercising responsibility and control over the product slowly at first, and then more quickly over time as you build bonds with your CEO. Don’t expect full autonomy for the first months, until you’ve proven yourself. Your #1 goal in your first 90 days is to ensure that your CEO feels comfortable with you, and increasingly hands the product reins to you."

"I suggest sending a simple weekly “State of The Me” email to your boss with (1) your current priorities, (2) things on your mind, and (3) blockers you need help with. Try it for two weeks — it’ll work wonders."

"When asked to take on new work, particularly last-minute, prioritize it amongst your existing priorities and most importantly share your updated priorities with your manager. Don’t assume your manager knows what else you’ve got on your plate, or how you’re prioritizing your work."

"My advice to you for saying no effectively is to follow this three-step process: Step 1: Listen, ask questions; Step 2: Form your own point of view; Step 3: Respond constructively."

"What I find works best is to be as unbiased as I possibly can in my writeup. Let facts speak for themselves. Leave opinions off the table, especially at first."

"Your manager may have identified a big opportunity but may not have nailed the optimal way to tackle it. While marinating on the idea in step 2 of our process, look for a simpler, or even more impactful solution, to the opportunity your manager found."

"When you first hear your manager’s idea, avoid reacting with a quick yes or no. Especially if you think it’s a terrible idea. Instead, start by getting curious. Force yourself to ask at least three questions."

"A good way to ask is to wait until a relatively quiet time, when there is no crisis going on (or less of one than usual, for a chaotic workplace), and ask your manager if you can talk with them for a few minutes. Sit down (a non-threatening posture) and say something like, 'It’s been a while since I last checked in with you. I want to do a good job here and be helpful. I was wondering if you could tell me how you feel I am doing.'"

"When crafting an argument, first share the Situation, then the share the Complications, and then share your proposed Resolution. That’s the SCR framework! It’s a deceivingly simple-but-powerful way to structure your narrative, and can be applied to emails, strategy docs, presentations, etc."

"It’s critical that your manager, and other influential leaders, understand the situation that you are being put into. It’s likely for the next 6-12 months you’ll drive less business impact than you had previously, and that some team members will become upset with you (particularly if you implement difficult changes)."