Hey there! Welcome to Level Up Weekly newsletter, where I leverage 18+ years in Stanford tech to help emerging leaders think strategically, build influence, and execute with confidence - so you’re seen, heard and valued.
“Be more strategic.”
Sound familiar? I hear this all the time from the leaders I coach.
They’re sharp. Dependable. They deliver. And still—when their manager says, “I need you to be more strategic,” it feels like a riddle with no clear answer.
Not because they aren’t capable of thinking strategically.
But because they’re buried.
Buried in meetings, decks, shifting priorities, Slack pings, and an endless to-do list.
And the irony? The very habits that earned them their reputation—being reliable, responsive, and detail-oriented—are now keeping them stuck in the weeds.
You’re Not the Problem. The System Is.
Legacy organizations are often built to reward execution, not reflection. So if you feel pressure to "keep the trains running" instead of stepping back to ask where the train is even headed, you're not imagining it.
You've been trained to prioritize output. Strategy? That’s what gets bumped for “when there’s time”—but there never is.
It’s not a skill issue. It’s a pattern issue. And shifting that pattern starts with how you think about strategy itself.
What Strategic Thinking Actually Looks Like
Strategic thinking isn’t reserved for offsites or senior titles. It’s a practice. And more often than not, it begins in small, consistent moments.
It starts when you pause—just long enough to zoom out and ask:
- Where are we now?
- Where do we need to go?
- And what’s actually going to get us there?
Every buried leader I’ve worked with already had valuable ideas. What they lacked wasn’t insight—it was oxygen. Once they made space to think, they moved from scattered to clear. From reactive to intentional. From overwhelmed to back in the driver’s seat.
Four Shifts to Reclaim Your Strategic Mindset
Let’s break it down into four tactical shifts that will help you start thinking like a visionary again—even when your calendar is full.
1. Anchor yourself with a bold vision
You can’t lead strategically without knowing the direction. JFK didn’t start with a checklist—he started with a bold goal: We’re going to the moon.
Try this:
- Ask yourself, “If I could fast forward three years, what do I want to have built? What impact will my team or work be known for?”
- Write one sentence that starts with, “We are going to…”
- Share it with someone. It doesn’t need to be perfect. Just real.
Then, invite your team to do the same. You’ll start to see where the energy and alignment already exist—and where a shared vision can take root.
Clarity isn’t a lightning bolt. It’s a decision you revisit again and again.
2. Protect your sharpest thinking time
You don’t get your best ideas at 9:30pm after three Zoom calls and 100 emails.
You get them in whitespace—in the early hours, on a walk, or in a quiet moment with a notebook. That’s when your brain finally has the space to connect the dots.
Try this:
- Block one 45-minute “thinking session” before 10am—once or twice a week.
- Use that time to write down one question: What’s the most important thing I haven’t made time to think about?
- Let yourself explore without needing to solve.
Thinking time isn’t a luxury. It’s part of your job as a leader
3. Stop trying to “earn” strategy time
One of the most common traps I see?
“I’ll think strategically—once I get through this list.”
But the list never ends. You don’t earn thinking time. You claim it.
Ask yourself:
- What’s one thing I can delegate, delay, or delete this week?
- Where am I spending 40 minutes perfecting something that doesn’t move the needle?
Start using the 80/20 rule: focus on the 20% of effort that drives 80% of the value. That’s where strategic leadership begins—not when the list is done, but when you decide what’s worth doing.
4. Create a weekly rhythm of reflection
If your calendar drives your priorities, strategy will always take a back seat. Flip the script.
Use this 3-question lens each week to stay grounded in your bigger goals:
- Where are we now?
- Where do we want to go?
- What will get us there—sustainably?
Try building this into your Monday mornings or Friday wrap-ups. Use it with your team, or reflect on your own. Over time, it becomes a leadership habit.
Strategy Doesn’t Always Feel Productive—And That’s Okay
If you’re someone who thrives on output, strategic thinking might feel uncomfortable at first. You might finish a 60-minute session with nothing more than a few notes.
But here’s the truth: that’s the work.
Strategic thinking is like building a mosaic. It might not look like much after one session, but each tile matters. And over time, the picture becomes clear.
If This Resonated… Let’s Keep the Conversation Going
With 18+ years in tech and higher ed, here’s what I know for sure:
When you create space to think, you lead differently.
You influence differently.
You show up not just as a doer—but as a driver of real change.
👉 Want help getting started? Download the free worksheet: “3 Daily Habits” to build simple, powerful routines in 30 days. It’s a simple 1-page PDF to help you protect time, clarify direction, and reconnect to the work that matters. 3 Simple Daily Habits for More Focus & Energy
You’ve already earned your seat at the table.
Now, it’s time to lead it.