“My boss told me I need to be more of a strategic thinker,” Charles told me.
“What does that mean to you?” I asked.
“To be honest, I’m not sure. I didn’t want to ask her because it might make me look like I wasn’t up for the promotion I just got. But I don’t really know how being a strategic thinker would change what I do.”
Charles isn’t alone. Many leaders are told to “be more strategic” without anyone explaining what that looks like day to day. Does that sound familiar? If so, keep reading for a few simple ways to bring strategic thinking into your everyday responsibilities.
The Shift from Expert to Leader
Charles is a recently promoted mid-level leader who’s built his reputation on strong technical know-how. Now he’s being asked to lead in ways that go well beyond his expertise — but no one has spelled out what that actually looks like.
“Let’s look at this from a couple of angles,” I said. “Start with what your boss does that she might be inviting you to step into.”
“That’s easy,” he replied. “She’s always anticipating the future and what could change. She bases every decision on our organization’s vision, mission, values, and culture. She doesn’t wait to be told what to do and she’s willing to take some risks in exercising her judgment.”
“Okay, so it sounds like you understand what your boss thinks of as strategic thinking. How might you start doing more of that yourself?”
“Oh, boy… I’m risk averse! I have a hard time with uncertainty and like to have all the relevant information before deciding. Plus, I don’t always trust my judgment. What if something goes wrong and it was my decision?”
“Those are real concerns,” I acknowledged. “But what about the downside of waiting for all the information—or waiting until someone else decides for you?”
“I guess I wouldn’t be exercising leadership,” he said. “Plus, there’d be opportunity costs. We might lose the chance to act.”
“Exactly,” I said. “So what if you practiced in low-stakes situations? Sort of like building your strategic thinking muscles?”
He nodded. “We can give it a shot. What do you have in mind?”
Seeing the Bigger Picture
This kind of conversation comes up often with clients who’ve been promoted because of their subject matter expertise. There’s a common fallacy that leadership is simply an extension of what got you promoted — just more of the same, at a higher level.
In reality, leadership requires a new set of muscles. Strategic thinking is one of them — and it can be especially challenging for those who’ve excelled through precision and expertise.
To make it concrete, Charles and I decided to do a thought experiment. He chose one of his core responsibilities: ensuring that his team receives ongoing training in both technical skills and soft skills.
Recently, his boss had asked him to send his team to a training on the applications of artificial intelligence in their industry.
Turning a Task into a Strategic Opportunity
To help Charles think about this request more strategically, I drew on a tool from systems thinking called the Iceberg Model. It helps leaders move beyond reacting to surface events and consider the deeper patterns, structures, and assumptions that shape them.
“What would you like to accomplish with the training your boss asked you to arrange?” I asked.
“I’d like my team to learn some new tools for using AI in the work they do.”
“That’s a good starting point,” I said. “What else?”
“If they go to the same training, they’ll have a common language, knowledge base, and maybe they’ll strengthen their teamwork,” he added.
“That sounds like a great investment of time. Lots of payoff. What could you put in place to make sure there are long-term benefits from the experience? What’s been your experience with these kinds of trainings in the past?”
He laughed. “We go for the day, have a good time, get a fancy binder with lots of content, then go back to work the next day. I guess I need to think about how to break that pattern!”
“Exactly. And what you’re doing right now is strategic thinking—looking at both immediate benefits and long-term results. What could you build in before, during, and after the training to maximize the impact?”
He paused, then lit up.
“Lots of things. In a staff meeting before the training, we can brainstorm areas of our work that could benefit from more AI and designate team members to explore that during the training. During the training we could have lunch together and share what we’re learning. Afterward, we could meet to plan how to apply what we learned. We could even brief another team or host short in-house sessions on AI since it’s evolving so quickly.”
In that moment, Charles transformed a simple assignment into a strategic initiative with long-term value for his team and organization.
A Simple Strategic Thinking Checklist
You can do the same. The checklist below distills the questions we explored — use it whenever you’re deciding how to carry out an assignment or opportunity.
Strategic Thinking Checklist
What’s the bigger purpose?
How does this activity connect to our mission, vision, or long-term goals?What patterns do I notice?
Have we done something like this before? What worked—and what didn’t?What could make the impact last?
How can I set things up before, during, and after so the benefits continue beyond the event?What assumptions am I making?
What beliefs about “how we do things” might be limiting what’s possible?
Practice Makes Progress
Try using this checklist with one upcoming project, meeting, or decision. Notice how it shifts your perspective from execution to intention. Over time, asking these questions before taking action will strengthen your strategic thinking muscles—and your leadership impact.
Please take a minute to leave a comment below: Have you struggled with strategic thinking? What has worked for you?
I’m pleased to announce the development of a new leadership program that my colleague Shelley Pernot and I designed. Synthesis Leadership is a 6-month program aimed at creating coaching-oriented, self-aware, and compassionate leaders of the future. Its purpose is to provide a balanced approach to leadership in a way that embraces both care for others and accountability, recognizing the dynamic tensions leaders navigate so that people feel deeply engaged and motivated to bring their best to the work they do. Stay tuned for more information soon!