“Chris, I want you to make this your highest priority!”
My boss was pretty excitable, so I was no stranger to being yelled at across the trading desk. Still, this struck me as a particular gem of absurdity.
“Sounds good, Dave. But… [out came the project management spreadsheet] what about all of these other projects that you’ve also told me are my highest priority?”
I didn’t want to disappoint my boss—but I also didn’t see how all of these “highest priorities,” including some projects I was particularly excited to move forward, came together.
It was frustrating to feel like I was always being pulled in a new direction, and I didn’t know how to work with my boss.
I didn’t have the secret question then.
It’s a question so powerful that many of my clients have used it to build trust with their bosses, work on what they’re most excited about, succeed with high-profile projects, and get promoted.
What are your objectives?
(Which is just a fancy way of asking “why?”)
Why does this question work?
It’s because our bosses are people too (something that we often forget!).
They have desires, they have beliefs.
They have mandates from their bosses and needs like ego, gratification, and promotion that they need to meet.
They have their own strengths and weaknesses, their own blind spots.
Bosses are just like us in many ways. 🙂
So, when you see a vexing problem, particularly one that stretches beyond your ambit—like poor collaboration with a remote team or tools that don’t work very well—take a moment before you start fantasizing about how you would engineer a solution.
I see folks get stuck and frustrated at this moment because their boss doesn’t support the change. That makes sense! You see a clear problem. “If only they got it! I could solve this problem.”
But your boss may not actually care about the problem.
Bosses like to solve their problems, not your problems.
The first thing you need to do is uncover what your boss cares about.
The good news is that we can take steps to make these shifts.
So how do you figure out what your boss wants?
You use curiosity and listening to find out what’s important to them, to explore their motivations and what they’re trying to do.
Ask questions!
- What’s the most important thing you’re working on right now?
- What are your top priorities this quarter?
- What are you hoping to get from this project/the projects that are on our plate as a team?
Start a conversation. Listen. Empathize. Reflect back.
You need to understand their perspective before you can move your ideas forward (even if your ideas are, and I say this objectively, obviously brilliant).
Move toward what negotiator Chris Voss calls the “That’s right” moment. You know that you’ve nailed it when your listening and reflecting creates an opening for your boss to affirm what you’ve said: “Yes, that’s right! That’s exactly why this is important.”
Let’s imagine that you’re an operations manager for an industrial plant; your boss, Sandy, is the plant manager. You’ve scheduled thirty minutes for a 1:1 with them and you want to talk about how you could solve some of the challenges you’ve been seeing with the purchasing group—which is a corporate function.
The typical approach would be to start the meeting by advocating for the solution you see. “We need to change how purchasing works. Here’s why.”
But that’s rooted in your perspective.
Instead, you want to get to Voss’s “That’s right” moment by creating common ground before you try to move things forward.
So how do you do this?
You can still start by bringing your own ideas—but marry them with curious questions.
You: Sandy, I’ve been thinking a lot about how we collaborate with the purchasing team and how it could be improved. But before I go into that, I was wondering: can you share the most important things you’re working on right now?
Sandy: Well, a lot of folks have been retiring or leaving for competitors and, in this climate, it’s hard to hire. We’re also not immune to “quiet quitting.”
Mirror and paraphrase, but stay curious:
You: I see that your most important focus right now is retention and hiring. Is that right?
Sandy: That’s right. I’m looking at training, our wages, our hiring process—our talent strategy across the board.
Deepen your understanding by asking why.
You: Got it. Why is that so important right now? What are your objectives with this effort?
Sandy: Sure. With the turnover and outages, we’re struggling to run at capacity because we don’t always have the people we need.
Restate the why and get confirmation.
You: Ah, so the underlying challenge that you’re trying to address is our ability to run at capacity. Is that right?
Sandy: That’s right!
(It doesn’t actually matter if you’re right. If you get a “That’s right,” you’ve gotten confirmation that you’re on the right track. If your boss corrects you—“Actually, that’s not the reason. What’s most important is…”—well, now you’re on the right track.)
Only then move on to your issue.
You: Ok, that makes sense. And that’s actually how I’ve been thinking about how we work with purchasing. There’s two challenges that I see that might be relevant here.
Purchasing is (quite rightly so) obsessed with controlling costs.
But, since they’re so focused on just-in-time, our people don’t always have the right tools or parts—which is demoralizing and disengaging. It makes us look kind of dumb—we’ve tasked someone with a job that we know they can’t complete. And, perhaps most importantly, it means that critical repairs are sometimes delayed and we lose capacity.
I’d like to see if I can craft a new way to work with purchasing. Is it OK if I write you a quick summary and run it by you for feedback before I get started?
They may still say no to your idea. But even if your project doesn’t move forward, you will understand your boss more. That’s a huge win.
This approach marries intentional listening with a set of specific skills (open-ended questions and mirroring). It is simple, but it’s not easy.
Listening is an intention, but it’s also a skill we can practice.
If you’re curious how I approach it, click here to be the first to get the details about the free Lead Curious Open House I’m running in December.
It’s an interactive workshop where you’ll get specific tools and practice with peers to make curiosity central to your approach to working with others — your boss included.
Click here and be the first to get the details when we firm everything up!
