When we talk about leadership, we usually talk about leading teams, managing people, making decisions, and building culture. But there's another form of leadership that doesn't get nearly enough attention.
Leading UP.
I'm talking about learning how to gain alignment with your direct boss, understanding what matters most to them, and making sure the work you're doing is moving in the same direction.
Sounds simple, right? Well, not necessarily.
For many people, the idea of initiating a conversation with their boss about goals, strategy, and expectations can feel intimidating. What if I ask a stupid question? What if they think I should already know this? What if I'm stepping outside my lane?
Here's what I've learned over more than 25 years of leadership across banking, economic development, and professional sports. Some of the biggest opportunities in your career come from conversations you're initially uncomfortable having.
And leading up is one of them.
The best part? This applies to EVERYONE. Full-time, part-time, entry-level, middle management, seasoned executives. It doesn't matter what industry you're in or where you sit on the organizational chart. You can lead up.
Before You Can Lead Up, You Have to Understand Where You're Going
Let's start with something that might seem painfully obvious. Do you know your organization's vision, mission, and values?
You might be thinking, "No shit, Toni."
But you'd be surprised how many employees can't actually answer that question. Even more surprising? How many organizations haven't clearly defined them in the first place.
Your organization's mission explains why it exists. The vision describes where it's going. The values establish how people are expected to operate along the way.
These aren't just fancy words to hang on a wall or put on a website. At least they shouldn't be. They're supposed to guide decisions, priorities, and behavior.
Start with a simple search of your organization's website. Can you find them? Do they make sense? Can you explain how your role contributes to them?
If the answer is no, congratulations. You may have just uncovered an opportunity.
Put it on the agenda for your next meeting with your boss. Ask about the organization's mission, vision, and values. If they haven't been established, perhaps this is a project you can help tackle.
Imagine being the employee who identifies that gap and volunteers to help solve it. That's leading up.
Your Boss Has Goals, Too. LOL.
Here's another question I encourage you to ask yourself. Do you know what your boss is trying to accomplish this year?
Not what you THINK they're trying to accomplish. Not what you've picked up from random conversations or company announcements. Do you actually know their annual goals?
This is where things can get a little uncomfortable. Asking your boss to share their goals might feel intrusive, especially if you've never had that kind of conversation before.
Ask anyway.
You might be surprised how receptive they are. Leaders spend so much time asking other people about their goals, performance, and priorities that we aren't always asked about our own.
Yes, bosses have goals, too! LOL. And those goals matter to YOU.
How can you possibly know where to focus your energy if you don't understand what success looks like for the person you're reporting to? Once you understand their priorities, you can start evaluating your own.
Are your goals supporting theirs? Are you spending time on projects that contribute to the bigger picture? Or are you working incredibly hard on things that aren't necessarily moving the organization forward?
I've seen plenty of talented, hardworking people get frustrated because they're putting in the effort but aren't gaining traction. Sometimes the issue isn't their work ethic or ability. It's alignment.
When your goals support your boss's goals, things begin to feel different. Instead of swimming against the current, you're swimming WITH it.
That doesn't mean blindly agreeing with every decision your boss makes. It means understanding the direction, contributing your perspective, and finding ways to move forward together. That can be a game changer.
Don't Forget the Strategic Plan
Let's take this one step further. Does your organization have a strategic plan for the year?
A strategic plan should connect the organization's bigger vision to actual priorities, initiatives, and measurable outcomes. In other words, it helps turn good intentions into action.
If your organization has one, ask to see it. Take the time to understand it. Look for the areas where your role, department, or individual contributions fit.
If there isn't one, you've potentially uncovered another opportunity. Could you help develop one? Before you immediately decide that's above your pay grade or outside your expertise, hear me out.
You don't have to know how to do everything before raising your hand.
We live in a time when information is literally at our fingertips. AI, Google, YouTube, books, online courses, and countless other resources can help you learn how to tackle something you've never done before.
Despite what some people would have you believe, AI isn't evil. LOL. It's a tool. Learn how to use it responsibly, ask better questions, verify what it gives you, and put it to work.
You might not be the person ultimately responsible for creating the organization's strategic plan, but you could certainly offer to research best practices, develop a starting framework, or help coordinate the process.
That's initiative. That's curiosity. That's leadership.
How to Start Leading Up
Now, before you schedule a meeting with your boss and attempt to tackle all of this in 30 minutes, a little advice.
Don't.
These conversations will likely happen over multiple meetings. You're building understanding, alignment, and trust, not conducting an interrogation.
Here's where I'd start:
Understand the mission, vision, and values. Research what already exists and ask questions about anything that's unclear. If something is missing, explore how you might help.
Ask about your boss's annual goals. Understand what they're accountable for and what success looks like in their role.
Align your goals with theirs. Identify where your work can directly contribute to their priorities and the organization's success.
Review the strategic plan. Understand the organization's priorities for the year. If a plan doesn't exist, ask whether developing one would be valuable.
Take ownership of the conversation. YOU schedule the meeting. YOU create the agenda. YOU come prepared with thoughtful questions and ideas.
Follow through. After the conversation, take action on what you've learned. Alignment means very little if your behavior and priorities don't change.
One more thing. Don't expect your boss to have every answer immediately.
They may need to gather information, clarify their own priorities, or involve other people. That's okay. The purpose is to open the conversation and begin working more intentionally together.
Stop Waiting for Someone to Invite You to Lead
One of the biggest misconceptions about leadership is that you have to wait until someone gives you permission.
Permission to contribute. Permission to ask questions. Permission to think strategically. Permission to take initiative.
You don't.
Leading up isn't about trying to do your boss's job or positioning yourself as the smartest person in the room. It's about showing that you care enough about your work, your boss's success, and the organization's future to understand how everything fits together.
It's also about taking responsibility for your own professional growth.
Your boss may be fantastic, but they aren't a mind reader. They don't automatically know what you want to learn, where you'd like to grow, or what you're capable of contributing beyond your current responsibilities.
Sometimes you have to raise your own hand. Yes, that can feel scary. Do it anyway.
Here's My Challenge to You
Within the next two weeks, schedule a meeting with your direct boss. Not a meeting they schedule for you. One YOU initiate.
Create a simple agenda. Start with the organization's vision, mission, and values. Ask about their annual goals. Begin exploring how your priorities can better support theirs.
You don't need to solve everything in one conversation. You just need to start.
Here's what I predict will happen. Your boss will be impressed.
Not because you showed up with all the answers, but because you showed initiative, curiosity, and a genuine interest in the bigger picture.
You'll gain clarity about where to focus your time and energy. You'll begin building a stronger relationship with your boss. And you may uncover opportunities to contribute in ways you hadn't previously considered.
Perhaps most importantly, you'll start being seen as someone who thinks beyond their own job description. That's how you begin unlocking the next level of your leadership journey. It starts with one meeting.
Go schedule it.
