Over the past decade, I’ve worked with hundreds of leaders who were told they needed to be more strategic. I see this pattern over and over again, and honestly, hearing it makes me cringe.
One client, whom we’ll call Sue to protect her identity, was the perfect case study. Sue was an outstanding leader, and people loved her. She worked hard, demonstrated strong commitment, and lived for the mission. Everyone trusted her and relied on her for everything. But one day, her boss said something that hit her where it hurt. He told her that she was stuck in the weeds and needed to be more strategic.
Sue took it hard. She was working more hours than many of the other executives on the team, but the reward for all that effort was being told she wasn’t good enough.
So what did she do?
She did what almost every high-performing, type A, overachiever does. She decided to tackle the problem head-on.
She started reading everything she could about strategic thinking. She signed up for an executive development course at a prominent business school. She hired a coach to work with her and started planning a strategic offsite. She even blocked time on her calendar every week to focus on “strategy,” even though she didn’t really know what to do with that time.
And just like that, Sue made the critical error that plagues almost everyone who has been given the “You’re not strategic enough” feedback.
How to be more strategic
Sue failed to realize that the answer to how to be more strategic is less about addition and more about subtraction.
This is a very common mistake. Being told to be more strategic feels like being handed one more thing to do, so we do what we know how to do. We work harder at the edges of a day that is already full.
But almost nobody stops to ask the more obvious question. What if being strategic is not something you add? What if it is something you subtract?
“The essence of strategy is choosing what not to do.”
That line is Michael Porter, writing about companies, but it’s just as true for a calendar.
Sue wasn’t struggling with strategy because she lacked a skill. She was struggling because she had no room to maneuver. She was stuck in a cycle of doing rather than thinking.
Strategy happens in the space between tasks, and when we fill that space with too much noise, we rarely see anything strategic. Every issue becomes another thing to wrestle with or manage, and we end up forming a habit of doing things for the sake of doing them. It becomes impossible to see the big picture when your nose is pressed too closely against the canvas.
Here’s the uncomfortable truth about the weeds. They’re comfortable.
Down in the weeds, everything is clear. A problem shows up, you solve it, and you get that small hit of dopamine that makes you want to come back for more. Someone needs you, you deliver, and the gratitude keeps you coming back. Every meeting you attend and every decision you sign off on feels like proof that you matter, and eventually, being busy starts to feel the same as being valuable.
But those two things are not the same, and deep down most of us know it. Busy isn’t what stands between you and strategy. Busy is where you hide from it. Strategy asks a harder question than “what can I get done today?” It asks, “What are we actually trying to do, and is any of this it?” That question is slower, and it doesn’t come with the satisfaction of a cleared inbox.
I’ll be honest. I do this too. When I’m unsure about what is really important, I reach for the small thing I know I can finish. I’ve called plenty of days productive simply because they were full, then looked up a month later and realized I’d been sprinting in a direction I never actually chose. Motion is easy to confuse with progress, and I confuse it all the time.
But when I look back at the leaders who genuinely became more strategic, the change was never that they found more hours or a better framework. The change was that they got comfortable dropping things. They let a meeting run without them. They handed a decision to someone who might not make it as well as they would. They disappointed a few people on purpose.
That last part is the piece nobody talks about. Getting out of the weeds isn’t a productivity upgrade you bolt onto your week. It’s a series of small, uncomfortable subtractions, and almost every one of them feels, in the moment, like you’re letting someone down.
Sue’s turn didn’t come from the reading list or the offsite. It came from what she was finally willing to give away. She handed a handful of recurring approvals to her team. She stepped out of two standing meetings she had always attended out of habit. She let the polish on a few low-stakes things settle at good enough. For weeks, she felt like letting go was a failure. A couple of things slipped through the cracks. But as she learned to loosen her grip, something shifted.
For the first time in years, she had room to think about where her team was heading instead of just keeping it from falling over. She started bringing ideas to her boss rather than mere status updates. About six months later, she was handed the role he had been quietly wondering if she was ready for.
The subtle shift
Being more strategic didn’t mean thinking bigger, doing more, or working harder. It meant carrying less so you can lift your head above the weeds. That is the subtle shift worth making.
So if you’re wondering how to be more strategic, here’s a quick gut check you can run this week. Take your calendar and your to-do list, look at each item, and ask two questions:
- Am I the only person who can do this?
- Does this change where we’re going, or does it just keep today from falling apart?
If you’re honest and the answer to both is no, you’re looking at a weed. Not a failure, not a character flaw, just not strategy. Pick two or three of those items and give them away. The goal isn’t a lighter workload for its own sake. The goal is the open space on the other side of it, because that space is the only place strategy has ever come from.
So the real answer to how to be more strategic is almost backwards. Most leaders wait until they feel strategic before they’ll make room for it. It works the other way around. You clear the room first, and the thinking shows up to fill it.
