Looking back on my career, I can absolutely claim that I was a really good project manager. It felt very easy for me to zoom into the details of a construction project: the specifications, the schedules, the contractor coordination—and also zoom out to see the bigger picture: the client's goals, the community impact. Quite honestly, I was comfortable in both spaces, and that made me effective in that role.
But then I started a tech company.
Suddenly, it was much more challenging for me to zoom into the details because the landscape shifted. I don't write code. I can't debug the program or optimize the architecture. And to be candid, that limitation has made me a better leader.
You see, when you’re not the most technically knowledgeable person in the room, you have an opportunity to lead differently:
✔️ Creating Vision
✔️ Asking Better Questions
✔️ Developing People
✔️ Trusting your Team (in ways you might not have before)
Here are some things I wish I'd understood earlier about the transition from managing projects to leading people and organizations.
Think One Step Beyond Your Role (But Know When to Zoom Back In)
I was talking recently with a project manager who had just stepped into a leadership position. I was interviewing him about how software tools could help him level up in his new role—what would help him oversee his team more effectively? His answers kept focusing on features that would help him manage individual projects better.
My mind kept repeating: Think bigger.
And I realized—I did the same thing throughout my entire consulting career. I was always thinking about how to be better at the role I was in, not how to prepare for the next role. I'd think about how to manage my one project more effectively, not how to oversee five project managers. When I was overseeing five people, I'd focus on that, not on how to improve the whole department or company.
Here's what I wish I'd done:
It's not about being dissatisfied with your current role—it's about building the perspective that will make you effective when you grow into more responsibility.
But here's the paradox: even as you're thinking bigger, you still need to be able to dive into the details when something is going wrong. Maybe one of your staff doesn't understand the goals. Maybe they're in the weeds and don't know how to tell you they're struggling. Even as an executive, you have to be able to stop, take a breath, and focus on the specifics.
The skill isn't staying in the details or staying in the vision—it's knowing when to zoom in and when to zoom out, and being able to move between them fluidly. That's one of the hardest things to learn as a leader.
Ask "Why" Five Levels Deep
Professor John Ullmen at UCLA did this exercise during my Executive MBA program, and it has changed the way I set vision and think bigger. (Sidenote: go take his LinkedIn Learning course on Executive Leadership too—it's worth every minute.)
You might be familiar with the "5 Whys" exercise for problem-solving—you ask "why" five times to get to the root cause of an issue. Ullmen uses the same technique but applies it to finding deeper motivations rather than just diagnosing problems.
This exercise helps you get really clear on what's actually important—for yourself, your vision, your goals, and your people.
Here's how I used this to move from initial product concept to company vision for BridgeDoc:
As a construction manager, I wanted to create a solution that helped me standardize paperwork across my consulting firm, while improving efficiency and maintaining quality.
Why? Because I want to improve the existing tools.
Why? Because I can make an impact on my capital projects with my clients.
Why? Because these projects matter to my community—they're parks our kids play in, roads we drive on, water we drink.
Why? Because I care about my community and want to leave an impact.
Why? Because I think we can do something bigger to transform the way these projects are delivered in our communities.
Can you see how that shifts from "I want better project management software" to "I want to transform how communities deliver infrastructure"? That's the power of asking why-5-levels-deep. I went from a product idea to our company's true vision.
Do this with your own goals. Do it with your company's vision. And do it with your people—understand what really motivates them, not just what they say they want in their role.
When you know the deeper "why" for yourself, your business, and your employees, you can make sure they all align to accomplish everyone's goals. That alignment can separate good organizations from great ones.
Know the Boulders and the Pebbles
For me, I know I thrive at getting tasks done under pressure . With that said, I sometimes have trouble moving the big-picture goals along.
You've probably seen the demonstration: a professor tries to fit large rocks, medium rocks, and sand into a jar. If you start with the sand and small rocks, the big rocks won't fit. But if you put the big rocks in first, then add the medium rocks, then the sand—everything fits.
As you move into leadership, those big rocks—the strategic goals, the long-term vision—become more and more important to move along every day, not just the small wins.
You still need to accomplish tasks. You still need those quick wins. But you can't let the pebbles and sand crowd out the boulders.
So how do you actually do this? Here's what works for me:
▶️Block Time for the big goals. I literally put them on my calendar so they don't get scheduled over. If I don't protect that time, meetings and urgent requests will fill every available slot, and the strategic work never happens.
▶️Find out where your brain flows best. Where are you “in the zone”? For me, it's hiking. Living in Santa Barbara helps, but I've learned that my best thinking happens when I'm walking. So I take my voice recorder with me and capture ideas when they hit. Maybe your brain works best in the morning before anyone else is awake, or in the quiet of late evening, or during a long drive. Figure out when and where your strategic thinking happens, and create space for it.
The tactical work will always demand your attention—it's urgent and visible. The strategic work requires you to be intentional about making it happen.
Final Thoughts
The transition from Project Manager to Company Leader isn't about striving for perfection (I mean, will we ever truly be perfect?). It's about recognizing the skills that made you successful as a project manager: attention to detail, task completion, technical expertise, must balance with new skills: vision-setting, people development, strategic thinking.
Yes, as a leader you're responsible for everything. But remember: your most important job isn't about solving every problem or making every decision, it’s to keep the vision in front of people. When your team knows where you're going and why it matters, they can make better decisions on their own. They'll have the potential to solve problems you never even hear about. Trust that they will be equipped to move the boulders forward while you're dealing with something else.
Here's he good news; You already have problem-solving skills (most especially if you are a construction manager! It’s what we do!). You already know how to figure things out.
Now you need to apply them at a different altitude.
Keep zooming out, ask why, and move the boulders. But most importantly, remember that it's your job to help your team see where you're going and why it matters.
And, of course, keep learning as you go. I certainly still am.