If I had a dollar for every time someone said, I need my leader to be more strategic this year, I could fund a fun vacation to Aruba. The requests keep coming, and they usually sound the same: a senior leader, slightly exasperated, saying some version of I need my managers to think strategically, make better strategic decisions, or my favorite just be more strategic.
They’re not wrong to ask. But “strategic” is doing an enormous amount of undefined work in that sentence. Until you define it, you can’t develop it, and you definitely can’t measure it.
So first, we’ll define it – and then I’ll give you the exact questions to ask next time ‘more strategic’ lands on your desk.
The Old Order Is Dead
For decades, strategy had a tidy org chart. Executives did the thinking, middle managers translated, and frontline leaders executed. Development budgets followed suit:
- strategy offsites at the top
- execution training for everyone below.
Two things broke that deal in 2025.
Speed of Cycles
The World Economic Forum reported this year that the five-year strategic plan has compressed into roughly a twelve-month view. When planning cycles turn that fast, a handful of executives can’t sense and redirect quickly enough on their own. They’re too far removed from execution. Strategic judgment has to live closer to the work.
Doing The Math
A McKinsey study found 97 percent of executives call strategic thinking the most critical leadership skill, while only 28 percent think their organization is any good at it. Rich Horwath’s research, with 400 talent executives, found that roughly three in ten managers actually think strategically.
Demand spread across the org chart, but supply didn’t.
And the payoff for closing that gap is enormous. A Management Research Group study of 60,000 managers across 140-plus countries found a strategic approach to leadership was, on average, ten times more important to perceived effectiveness than any other behavior they studied.
“Strategic” Varies
Most organizations stumble in the way they think about “strategic.” They treat strategic as one skill and buy one workshop to teach it. In reality, it’s one discipline practiced at three different altitudes.
Priorities & Frontline Leaders
The tactical frontline leader asks, “did we finish the list?” The strategic one asks, “Did the finished work move the outcome that matters?” One question keeps the team busy and the other keeps the team pointed at what matters.
And it matters more than you’d think: McChrystal Group research found frontline employees are three times more likely to hear about strategy from their supervisor than from any executive. For most of your workforce, the frontline leader is the strategy.
The Mid-level Translation
Mid-level management turns abstract direction into work a team can act on. Not “we’re doing a digital transformation,” but “this new system will fix the manual data entry you’ve been complaining about.” Just as important, they carry reality back up: flagging the implementation problems executives can’t see from thirty floors away, before those problems get expensive.
The trap at this level is becoming a pass-through: forwarding messages down and status reports up, adding judgment to neither.
Senior Leaders Trade-offs
At the top, strategic means knowing what to prioritize, what to pause, what to question, and what to advance, all while keeping today’s business and tomorrow’s bets funded at the same time. This is called dual-horizon planning: weighing near-term and long-term investments together so the future doesn’t lose out to the urgent now.
The trap is confusing “having a strategy document” with “being strategic”.
The Workshop Failure
If the skill differs by altitude, the development has to differ too. A one-day event won’t cut it at any level. The research on learning transfer is clear: single-event training rarely changes on-the-job behavior. Strategic thinking gets built through repeated practice in real work, with feedback from someone who can spot strategic reasoning when they see it.
What that looks like at each altitude:
- Frontline leaders
build daily habits: end the week asking what signal you noticed and whether the work moved the priority - Mid-level leaders
need translation practice plus actual latitude. You can’t develop strategic mid-level leaders while denying them authority to shape how strategy lands. The autonomy is part of the curriculum - Senior leaders
need coaching and scenario work: a structured space to rehearse trade-offs and shift from functional thinking to enterprise thinking
Plus, there’s one more major thing to note.
Managers default to tactical mode because the urgent work rewards it. If your metrics, incentives, and meeting culture all celebrate firefighting, no program on earth will overcome that pull. The reward system needs to change.
The good news, per Harvard’s Liz City, who has studied this for decades: strategic leadership is a learnable skill, not a personality trait. Learnable, yes. Trainable-in-a-day, no.
The Question Resource
This is the practical part you should definitely copy and paste out. The next time a senior leader says “I need my people to be more strategic,” resist the urge to start shopping for programs. Ask these first.
Find The Trigger
- What did you see, or not see, that prompted this request?
- Can you give me two or three recent, specific moments where a leader wasn’t strategic? What happened, and what should have happened instead?
- Is this about all your leaders, or honestly about three people?
Make “Strategic” Observable
- If these leaders were more strategic six months from now, what would you see them doing differently in meetings, in decisions, and in how they communicate?
- Who on the team already does this well? What specifically do they do?
That second question gives you an internal benchmark and cuts through the fog fast.
Examine The Environment
- Do these leaders actually know the strategy? How is it communicated to them, and how often?
- What are they measured and rewarded on today?
- Do they have the authority to make trade-offs and say no to work?
- What happened the last time someone pushed back on a plan? Was that welcomed or punished?
If the answers are “they’ve never seen the strategy, they’re rewarded for output, and pushback gets people in trouble,” you don’t have a training problem.
Agree On Measurement
- What business outcome is at stake if nothing changes?
- Which existing metrics should move: engagement, retention, initiative cycle time, fewer escalations landing on your desk?
- Will you personally assess whether you’re seeing the new behaviors at ninety days?
- Can we take a baseline now, so we have something to compare against?
There is one expectation to reset up front: behavior change shows up over three to six months, and business results take six to twelve. If someone expects proof in thirty days, have that conversation before you start, not after.
These questions will take you less than an hour to go through, and it’ll save you from the most expensive mistake in leadership development – buying a beautifully designed solution to an undefined problem.
Start With The Altitude Question
Before your organization spends a dollar making leaders “more strategic,” ask four things:
- Which altitude do you mean?
- What does the behavior look like there?
- What’s currently preventing it?
- How will you know it changed?
The organizations that answer those questions build strategic capability where it’s actually missing. The ones that don’t? They buy a workshop, then ask me the same question again next year.
If This Request Just Hit Your Desk
You don’t have to untangle it alone. If you’d like help defining what “strategic” looks like for your leaders, building development that fits each altitude, or setting up measurement your executives will trust, let’s talk. The first conversation looks a lot like the questions above, and it’s one we’d be glad to have with you.
