Let me guess—you started this week with every intention of carving out time to “think strategically.”
You blocked the calendar.
You closed your inbox.
You opened a blank document.
Then your phone buzzed. A team issue popped up. A fire that only you could put out. Two back-to-back meetings turned into five. Now it’s Thursday, and the time you set aside for strategic thinking has quietly vanished beneath the week’s chaos.
Sound familiar?
If you’re a senior leader, you’re not just managing a calendar—you’re managing chaos. And somewhere between all the urgency and endless decisions, the one thing you desperately need keeps slipping through your fingers: time to think.
But not just any thinking—strategic thinking. The kind that helps you lead, not just react.
My favorite story on this topic surfaced when I was coaching the President of a division. The leader told me he was totally overwhelmed and wanted me to help him find more time for “strategy.” We unpacked his calendar and quickly found that he had a lot more time for operational meetings than strategy set asides. He thought he was being “helpful and engaged,” by attending everything. And let’s be honest, when you run a big operations team that is scorecard driven you feel this tension to stay involved. When I interviewed one of his Vice Presidents for his 360 feedback report, they said, “we appreciate how engaged our President is in our business. However, we often wonder if he is back here with us, who is driving the bus?”
That is the million-dollar (or billion dollar) question. As senior leaders, our job is to drive the strategy bus for our team, so we arrive at our next destination.
So, if we all know that we should spend time on strategy, why is it one of the most common issues brought up in my classrooms and coaching sessions with executives? If you’re wondering why it keeps falling off your calendar, I’ve got a few ideas.
First, Let’s Get Honest About What Strategic Thinking Actually Is
Strategic thinking isn’t a luxury reserved for retreats or sabbaticals.
It’s not vague brainstorming or high-level vision-casting that happens once a year in a conference room with snacks and sticky notes.
It’s the disciplined, often uncomfortable act of stepping back from your day-to-day to ask:
- Are we doing the right things?
- What’s working—and what’s not?
- Where are we headed?
- What’s changing that we haven’t accounted for yet?
Strategic thinking is where you lead—not manage. And that’s exactly why it matters.
So Why Can’t You Seem to Make Time for Strategic Thinking?
Let’s break it down.
1. You’re Overbooked and Overextended
Your calendar isn’t just full—it’s overflowing. Meetings, reviews, decision-making, performance conversations, fire drills. Somewhere along the way, being a good leader became synonymous with being constantly available. I have even heard people say, “a servant leader is always available.” But is it really serving your team if they don’t have a clear road map of prioritized initiatives?
2. You’re Still Rewarded for Doing, Not Thinking
Many executives got where they are because they were exceptional at getting things done. Delivering. Solving. Executing. But at the senior level, the work shifts. You’re not supposed to do everything. You’re supposed to guide the people who do.
And yet—old habits die hard. So instead of thinking long-term, you’re staying in the weeds, fielding every ping, solving every issue, and running out of space to lead.
3. You Wait for the “Perfect Window” That Never Comes
You keep telling yourself that things will calm down next week. After the quarter ends. Once the org change goes through. Spoiler: it won’t. There’s always another wave of urgency coming.
Thinking time isn’t something you wait for. It’s something you protect.
What Happens When You Don’t Create Space to Think?
When strategy takes a back seat, a few predictable things happen:
- Your team stays busy but not necessarily aligned
- You react instead of anticipate
- Important initiatives stall—or never get off the ground
- Burnout creeps in because you’re always in motion, never in reflection
And perhaps the worst part? You start feeling like a manager again instead of a leader.
The Fix Isn’t Fancy. It’s Intentional.
I found that as a senior leader there is no such time as “organic strategy time.” Creating time for strategic thinking isn’t about a fancy system—it’s about making small, intentional shifts in how you protect your time and lead your team.
Here’s where to start:
Block It Like a Board Meeting
Would you cancel the meeting with your CEO? Didn’t think so. Treat your strategic time the same way. Make it a recurring appointment with yourself, and don’t move it unless the building is on fire.
Drop a Meeting You Don’t Belong In
We all have them. Meetings where we’re more ornament than asset. Let one go. Use that time to think. I promise the team will survive if you have fully empowered them with your direction and tradeoffs.
Get Out of Your Norm
Leave your office. Step away from desk. I have a client who is ultra marathoner and plans her strategy while on long runs. If you are like me and allergic to running you can take a page out of another client who regularly takes 30-minute walks around the lake behind their office during the day to give space to reflect, process, and lead. No one is above a glass of wine and a seat on the patio to free up space.
Coach Instead of Solve
The more you solve for your team, the less they grow—and the less space you create for strategic work. Next time someone comes to you with a problem, try coaching them through the decision instead of owning it yourself. Respond with a question vs. just an answer.
Ask Yourself Better Questions
Strategic thinking starts with strategic questions. What’s no longer serving us? What’s one assumption we haven’t challenged? What would I stop doing if I wasn’t afraid?
Keep one question in your back pocket every week. Use it to fuel your reflection. There was and still is something about curiosity being a game changer for me in leadership and asking better questions of others and myself!
And a Quick Note on Guilt…
Many leaders feel guilty about protecting thinking time. They think about all the work their team is doing and think they should be equally busy. It’s not about being lazy as a leader or dumping work, it’s about prioritizing the strategy work you are most uniquely qualified to do in your seat and doing it with excellence.
Here’s the truth: the more senior your role, the more your thinking drives value.
You’re not being paid to do more—you’re being paid to inspire/teach/anticipate/plan/advocate more. That requires space. And courage.
Final Thought: If You Don’t Think, You Can’t Lead
You can’t run at full speed and steer at the same time.
If strategic thinking keeps falling off your calendar, it’s not because you’re bad at time management—it’s because you haven’t made the shift from operator to organizational leader. The work has changed. The expectations have changed. And your habits need to catch up.
Your calendar tells the story of what you value. Make sure strategy is in the script.
