Most of us are very good at answering the question in front of us. Reply to this email. Fix that bug. Get the slides done by Thursday.
Strategic thinking asks something harder. Where is this going? What am I assuming? What happens after the thing I’m planning actually works, or doesn’t? It’s the habit of zooming out before you zoom in, and it’s a skill plenty of capable people never get trained in.
They know it, too. In DDI’s Global Leadership Forecast 2025, which surveyed 10,796 leaders across 50 countries, leaders named setting strategy as one of their two biggest skill gaps, alongside managing change. If people whose job is to lead feel shaky on the long view, the rest of us shouldn’t feel too bad. Add the constant pull of small choices that drains your energy (we’ve written about decision fatigue before) and it’s no wonder the big picture gets squeezed out.
The good news is that strategic thinking isn’t a personality trait you either have or don’t. It’s closer to a set of mental moves, and moves can be practised. Below are 12 of them, each backed by research, data or people who have spent careers studying how good decisions get made. You don’t need a corner office to use any of them. A notebook and a bit of protected time will do.
1. Put thinking time on your calendar
You can’t think strategically in two-minute slices. And for a lot of people, two minutes is about all they get.
Microsoft’s Work Trend Index special report “Breaking down the infinite workday” (June 2025) looked at anonymised Microsoft 365 activity and found that, among the most heavily contacted workers (the top 20% by volume of pings received), people were interrupted by a meeting, email or chat roughly every two minutes during core hours. Over a full 24-hour day, that added up to about 275 interruptions. In Microsoft’s accompanying survey, 48% of employees and 52% of leaders said their work feels chaotic and fragmented. Those figures describe the busiest users rather than the average worker, but if you recognise yourself in them, you’re not imagining it.
Why does this matter for strategy specifically? Because strategic thinking means holding several moving parts in your head at once: the goal, the obstacles, the options, the knock-on effects. Every interruption knocks some of those parts off the table, and you have to rebuild them before you can carry on. Do that over and over through a morning and you never get past the setup.
So treat thinking like a meeting with your most important client. Put it in the diary. Close the inbox. Turn off notifications, and if you’re worried about missing something urgent, tell people when you’ll be back. If deep focus is hard for you in general, these ways to get into a flow state faster pair well with this habit.
Test it this week: block two 45-minute slots, write one big question at the top of a blank page (say, “What should my team stop doing next quarter?”), and stay with that question until the time is up.
2. Ask “what would have to be true?”
Most strategy arguments are really arguments about the present. Is the market growing? Do customers want this? Are we good enough? People dig in, and whoever talks loudest wins.
Roger Martin, former dean of the Rotman School of Management and co-author of Playing to Win, has spent years pushing a different question. Instead of debating what is true, ask what would have to be true for a given option to be a great choice. In a January 2025 essay on risk and strategy, he goes a step further and defines a strategic risk as exactly that: an assumption your plan depends on that might turn out to be false. He suggests looking for those assumptions in four places: your industry, your customers, your own capabilities, and your competitors.
The shift sounds small. It isn’t. Once the conditions are written down, the conversation moves from “you’re wrong” to “how would we check?” That also makes it easier to stay calm with people who always think they’re right, because you’re no longer arguing positions.
Picture this, as a hypothetical. Say you’re weighing whether to turn your free newsletter into a paid one. Rather than asking “will people pay?”, you list what would have to be true: enough readers open it every week, a meaningful slice of them value it more than a coffee a month, and you can keep the quality up without burning out. Now you have three things to test instead of one big guess.
Your move: take a decision you’re stuck on, write each option at the top of a page, and list three to five conditions under each. Then circle the condition you’re least sure about. That’s where your next bit of research goes.
3. Take the outside view before you trust your plan
When we plan, we look at our own project from the inside: our team, our timeline, our clever idea. We rarely ask how similar projects usually turn out. That’s a costly blind spot.
Bent Flyvbjerg, a professor at Oxford and the IT University of Copenhagen, has built a database of more than 16,000 projects across many sectors and countries. The figures he and Dan Gardner report in How Big Things Get Done (2023) are sobering:
| Outcome across 16,000+ projects | Share |
|---|---|
| Over budget, over schedule, or both | 91.5% |
| On time and on budget | 8.5% |
| On time, on budget and delivering the promised benefits | 0.5% |
Source: Flyvbjerg & Gardner, How Big Things Get Done, 2023. These are large projects, mostly infrastructure, IT and similar; small personal plans aren’t in the data.
Flyvbjerg’s fix is reference class forecasting. You find a group of past projects that resemble yours, look at how they actually went, and use that as your starting estimate before you adjust for anything special about your case. He argues that much of the damage comes from what he calls uniqueness bias, the belief that your project is so different the usual numbers don’t apply.
Picture a kitchen renovation (again, hypothetical). Your builder says six weeks. Your neighbours’ renovations, though, took ten, twelve and nine weeks. The outside view says plan for about ten and be pleasantly surprised if it’s six. The same logic applies to launching a product, changing careers or starting over in your 30s.
Here’s a simple way in: before your next estimate, find three to five comparable cases (your own past projects count), note how long and how much they really took, and start from their average.
4. Run a pre-mortem before you commit
A post-mortem tells you why something died. Useful, but late.
Psychologist Gary Klein proposed the reverse in a September 2007 Harvard Business Review article. Before a project starts, the team imagines it’s a year later and the project has failed. Badly. Then everyone writes down, independently, why it failed. Klein’s argument is that projects often go wrong because people with doubts don’t voice them during planning, and the exercise makes it safe, even expected, to say the uncomfortable thing.
There’s some research behind the framing. In a 1989 study published in the Journal of Behavioral Decision Making, Deborah Mitchell, Jay Russo and Nancy Pennington found that imagining an event as if it had already happened led people to generate about 30% more explanations for it than imagining it as merely possible. Worth noting the limit: that study counted reasons; it didn’t measure whether they were the right ones. The pre-mortem is a way to surface more risks, not a guarantee you’ll find the fatal one.
It also works solo. If you tend to sabotage your own plans by ignoring early warning signs, a pre-mortem gives those warnings a voice before they cost you. (If that pattern sounds familiar, our piece on signs of self-sabotage is worth a read.)
Next time, do this: give yourself (or your team) ten minutes, start with the sentence “It’s six months from now and this has completely failed,” and list every reason you can think of. Then fix or watch the top three.
5. Put numbers on your hunches
“This will probably work” is not a forecast. It’s a mood.
Strategic thinkers get comfortable saying “I’d put this at about 65%.” It feels odd at first, but numbers force precision, and precision makes you accountable to yourself. The strongest evidence that this can be learned comes from the Good Judgment Project, which competed in forecasting tournaments run by the US intelligence research agency IARPA. Welton Chang, Eva Chen, Barbara Mellers and Philip Tetlock reported in Judgment and Decision Making (September 2016) that a training module lasting less than an hour, covering ideas like base rates, reference classes and common biases, improved forecasters’ accuracy by 6 to 11% compared with untrained controls across four years of tournaments.
That’s a modest gain from a tiny intervention, and the authors suggest it’s likely a lower bound. The caveat: the participants were volunteers forecasting geopolitical and economic questions, so we’re extrapolating when we apply it to, say, a hiring decision. Still, the principle travels well. When you assign a number, you have to ask what would move it up or down, and that’s strategic thinking in miniature.
Start writing a probability next to your predictions at work (“70% the client signs by March”) and keep a simple list. After a few months you’ll see whether your 70s come true about 70% of the time, or whether you’re consistently too sure of yourself.
6. Follow the chain past the first consequence
Most decisions are judged by their first effect. Strategic thinking keeps going: and then what?
The mechanism is simple, which is exactly why it’s easy to skip. Every action changes someone else’s situation. They respond. Their response changes your situation again. Let’s walk through a hypothetical. You cut your prices to win customers (first-order effect: more sales). A competitor matches the cut (second-order: your advantage disappears). Now you’re both selling more cheaply, margins shrink, and there’s less money left for the product improvements that would actually set you apart (third-order). Nothing here is guaranteed, which matters: it’s a chain of plausible reactions, not a proven law. But each link is something you could have anticipated.
Employers have noticed. The World Economic Forum’s Future of Jobs Report 2025 lists systems thinking among the skills growing in importance over the next five years. It’s not a mystical talent. Mostly it’s the discipline of writing the chain out instead of stopping at link one, because the reactions of customers, rivals and colleagues are where plans usually go sideways.
A quick experiment: for one decision this week, draw three columns headed “then”, “then” and “then”. Fill each with who reacts and how. If column three surprises you, you’ve just done more strategic thinking than most meetings manage.
7. Use AI to stress-test your thinking, not to replace it
Generative AI is brilliant at producing a plausible answer fast. That’s also the risk.
Researchers from Microsoft Research and Carnegie Mellon University surveyed 319 knowledge workers who use generative AI at work, collecting 936 real examples of how they used it. In their paper, presented at the CHI 2025 conference, Lee and colleagues found that higher confidence in the AI was associated with less critical thinking, while higher confidence in one’s own ability on the task was associated with more of it. They also noticed that critical thinking didn’t disappear; it shifted toward checking information, integrating the AI’s output and overseeing the work.
Two limits worth knowing. The data is self-reported, and it’s correlational, so it doesn’t prove that AI use causes weaker thinking. It does suggest a trap, though: the moment you start trusting the tool more than your own judgment, you stop doing the part that makes your thinking strategic. There’s a parallel with memory, too. Offload everything and you lose the practice, which is one reason memory training habits still matter in a world of search engines.
Start small: write your own answer to a strategic question first, even a rough one. Then ask the AI to argue against it, find the weakest assumption, or give you the strongest counter-case. Use it as a sparring partner, not a ghostwriter.
8. Sketch three or four possible futures
You can’t predict the future. You can prepare for several versions of it.
Finland does this at the level of an entire country. In September 2025 the Finnish government submitted Part I of its Government Report on the Future to parliament. Built through cooperation between all the ministries, it identifies 26 drivers of change, picks out 14 critical uncertainties, and lays out four scenarios for 2045 with names like “World of Tech Giants” and “Crumbling World”. Crucially, the report doesn’t stop at describing them. Ministries mapped the risks and opportunities in each scenario and listed actions that would help Finland regardless of which future arrives. The government also held 40 public dialogues on the country’s future as part of the process.
The useful part for you isn’t the scale. It’s the structure: identify the two or three uncertainties that matter most, imagine how they could combine, and then look for moves that make sense across most of the combinations. Those “no-regret” moves are often the best place to start, whether you’re planning a business or thinking about how to invest in yourself over the next decade.
Give it a go: pick two big uncertainties in your work or life (for example, “Will my industry adopt automation fast or slowly?” and “Will I stay in this city or move?”). Combine them into four short scenarios on a 2×2 grid, then write down one action that helps in at least three of the four.
9. Break big problems into smaller questions
“Grow the business” is not a problem you can work on. “Which of our three customer groups is most likely to buy more if we improve onboarding?” is.
Employers are paying attention to this skill. In the World Economic Forum’s Future of Jobs Report 2025, which draws on a survey of more than 1,000 large employers, analytical thinking remains the top core skill, with seven out of 10 companies considering it essential. The same report says employers expect 39% of workers’ core skills to change by 2030, and that 50% of them now treat curiosity and lifelong learning as a core skill. Put plainly: the ability to pick apart a messy problem is the one skill employers keep ranking first, even as everything around it shifts.
Here’s why decomposition helps strategy so much. A vague problem triggers vague thinking, because your brain has nothing concrete to grab. Split it into sub-questions and each one suggests its own data, its own owner and its own next step. It’s the same trick that makes beating procrastination easier when a task feels too big to start. You also start to see which pieces matter most, which is the heart of prioritising.
Take one fuzzy goal, write it in the middle of a page, and keep asking “what would that depend on?” until every branch ends in a question you could actually answer this month.
10. Don’t make big calls on a short night
You already know sleep matters. What’s easy to forget is how specifically it affects the kind of judgment strategy depends on.
A scoping review by Felix Agyapong-Opoku and colleagues, published in Behavioral Sciences in June 2025, mapped 25 studies from 2014 onwards with 2,276 participants in total. Many of those studies found that partial or total sleep deprivation impaired decision-making, often by pushing people toward riskier choices. The picture isn’t uniform. Effects depended on the type of task and how long people went without sleep, and a few studies, particularly on economic decisions, found no significant effect. So it’s a strong pattern, not a simple rule.
The mechanism makes sense. The review points to the prefrontal cortex and hippocampus as the brain regions most involved in decision-making, and those systems need sleep to work well. Short on sleep, you’re more likely to grab the option that feels good now and less likely to weigh what comes later, which is the opposite of strategic thinking. If your mind races at bedtime because of a big decision, try these ways to stop overthinking at night, and build an evening wind-down routine that protects the hours before an important day.
Here’s a simple way in: if a decision is big and not truly urgent, write down your current leaning, sleep on it, and reread it in the morning before you commit.
11. Build a red team mindset
Groups drift toward agreement. It’s comfortable, it’s polite, and it’s one of the fastest ways to walk into a predictable mistake.
The UK Ministry of Defence’s Development, Concepts and Doctrine Centre takes this seriously enough to publish a Red Teaming Handbook. The third edition, released in June 2021, made an interesting shift: rather than focusing mainly on formal red teams (separate groups paid to attack a plan), it promotes a “red team mindset”, where individuals and teams use challenge techniques as part of their everyday routine. The handbook explicitly says it applies to civilian audiences as well as military ones. The idea is simple: build the habit of challenging your own assumptions before reality does it for you.
What does that look like outside the army? Imagine a hypothetical: your team is about to approve a new product feature. Before the vote, one person is formally assigned to argue the case against it for five minutes, and everyone knows it’s a role, not a personal attack. Suddenly, objections that would have stayed silent get aired. Leaders who invite this kind of challenge tend to get better information, which is one of the qualities of a great boss that’s easy to underestimate.
Your move: in your next important discussion, ask someone to play devil’s advocate on purpose, and rotate the role so it never becomes one person’s reputation.
12. Review your decisions after the fact
Experience doesn’t automatically make you wiser. Reflecting on experience does.
The military-born “after-action review” (also called a debrief) is one of the better-tested tools here. A meta-analysis by Nathanael Keiser and Winfred Arthur, published in the Journal of Applied Psychology in 2021, pooled results from 61 studies and found that after-action reviews produced a large improvement in training outcomes (an effect size of d = 0.79). An earlier meta-analysis by Scott Tannenbaum and Christopher Cerasoli in Human Factors (2013), covering 46 samples, estimated that debriefs improve effectiveness by roughly 20 to 25%. Most of that research comes from training settings such as the military and healthcare, so treat the exact numbers with care when you apply them to your own job. The direction, though, is consistent.
The questions are simple. What did we expect to happen? What actually happened? Why the difference? What will we do differently next time? Separate the quality of the decision from the quality of the outcome, too. A good decision can turn out badly because of luck, and a bad one can get away with it.
A quick experiment: after any significant decision, spend 15 minutes answering those four questions in writing. Keep the notes in one place. Over a year, they become your personal strategy textbook, and turning the review into one of your good habits is how the lessons actually stick.
What to do when you slip
You’ll skip the thinking time. You’ll make a big call after a terrible night’s sleep. You’ll fall in love with a plan and forget to pre-mortem it. Everyone does.
What matters is how you talk to yourself afterwards. In a series of experiments published in Personality and Social Psychology Bulletin in 2012, Juliana Breines and Serena Chen at UC Berkeley found that people encouraged to respond to a failure with self-compassion were more motivated to improve than those who focused on boosting their self-esteem or received no instruction. In one study, students who were prompted to be kind to themselves after doing badly on a test spent longer studying for the next one. More recently, Marios Biskas, Fuschia Sirois and Thomas Webb (2023, Journal of Psychoeducational Assessment) found that simply prompting people to respond to a goal lapse with self-compassion raised their self-compassion in the moment, while reading information about self-compassion beforehand didn’t add a measurable boost. Knowing the idea isn’t enough; the useful part is actually doing it when you slip.
So when it happens, skip the lecture. Name what went wrong, treat it as information rather than a verdict, and restart with the smallest version of the habit: one 20-minute thinking block, one question asked before one decision. If you’re prone to beating yourself up, our guides on how to stop hating yourself and radical acceptance can help you get back on track faster.
Conclusion
Strategic thinking isn’t reserved for CEOs with whiteboards. It’s a handful of habits: making room to think, questioning your assumptions, borrowing the experience of others, imagining failure and alternative futures, putting numbers on your hunches, protecting your sleep, inviting challenge and learning from what happened.
If you want more evidence-based ways to plan, decide and get the important things done on the job, head over to our Work section next.
