You likely waste your money on training sessions that go nowhere. Employees sit in front of a PowerPoint slide. Employees attend a workshop. Employees then come back to work and make the same decisions they’ve always made. It’s not that they don’t want to think strategically; it’s that your training methods aren’t effective.
You can’t train someone to think strategically through lecture alone. You must give them the experience, the consequence, even if the consequence is simulated, to know what strategic thinking means. A failure to encourage strategic thinking results in a team that becomes reactive, creating a business that’s always fighting fires rather than preventing them.
Understanding What Strategic Thinking Actually Is
Before we dive into training methods, it’s best to assess what strategic thinking is. Strategic thinking is not big-picture decision-making or vision-casting. It’s about understanding cause and effect and how business components interact and interconnected to drive decisions over time for various contingencies.
It’s important to note: Most people are more than capable of making tactical decisions. They can solve the immediate problem at hand. But that’s the easy part; strategic thinking requires stepping back from the issue at hand and asking if resolving this one problem creates three more further down the road, or at least, in the foreseeable future. Strategic thinking requires thinking about trade-offs, anticipating competitors and their moves, and recognizing patterns before they develop into something so obvious no one can miss them.
Therein lies the chasm between strategic and tactical. Teams get bogged down, focusing on day-to-day operations without seeing the bigger picture.
Why Traditional Training Methods Fail Us
Traditional business training relies on case studies and theory. Employee sees what another company did in another situation, assumes different actions could have led to success, discusses it with their peers, and…. that’s it. There’s no accountability built through muscle memory, actual decision-making under stress – just hypothetical “what-ifs.”
The same is true of workshops and seminars, where one person lectures at your team for a few hours about models of strategic planning or decision-making frameworks, maybe includes a group exercise or two, where everyone leaves motivated but unable to apply those experiences to day-to-day work when conflicts arise because there’s no muscle memory; the learning occurs through passive observation or abstract engagement.
The reality is that strategic thinking is a doing skill, not a knowing skill. You can know how to play chess strategically without being capable of playing chess well. The same goes for business strategy; one can read about it and discuss it theoretically but comes nowhere close to prepared for the messy realities of real strategic decisions.
The Value of Repetition Over Time
The most productive means of creating strategic thinkers is through practice over time in repeated scenarios where they play in decision-making roles, see consequences, and can adjust approaches accordingly for future tasks. Organizations that prioritize experiential learning through business simulations tend to produce new strategic thinkers faster because participants can engage in intricate decision-making without incurring real losses or undermining actual business progress.
The reason this works is because it’s how we learn other complex skills that require extensive exploration over time with dedicated practice. Pilots learn in a flight simulator before ever sitting in a cockpit with passengers; surgeons practice on models before wielding knives on human flesh. The same goes for business strategy; people need a safe place where an explored failure doesn’t cost them their job but educates them how to do better next time.
But these simulations must be real enough for people to feel compelled to take them seriously (as if they’re real decisions) instead of as a game without stakes. When entrepreneurs create constraints, other priorities that compete for attention on an imagined basis, and uncertain outcomes linked to equity for those making decisions – which end up being hundreds of thousands for everyone – only then will people start thinking differently.
Making Strategic Thinking a Reality
Training programs won’t resolve how teams think; instead, daily expectations must cultivate strategic thinking every day. Shifting your culture starts with how meetings are run, how decisions are made, and what behaviors are rewarded constantly.
First, ensure that discussions with teams implement time for strategic questions. When someone suggests a solution, challenge that conclusion with second-order effects – what happens when we do this? What resources do we allocate to this long-term? This cannot be an afterthought; instead, these must become automatic.
Leadership also plays a critical role; if management focuses on quarterly metrics or next month’s goals instead of what they mean in twelve months or five years or assessing how this decision impacts everything over time – they will limited strategizing themselves as well as their teams. When leaders exemplify connections based on strategic thinking, weighing contingencies and acknowledging equity needed over time for other decisions – those behaviors spread.
What Actually Works
There are excellent exercises that develop skilled thinkers aside from formal training, ones you can implement while working together regularly that help strengthen strategic thinking muscles easily.
One of the most valuable is scenario development – taking an upcoming decision and mapping out three different ways it could play out – contributing factors that get there and how a team might respond in each situation. Another fantastic exercise occurs through competitive analysis – but in depth longer than most companies do it; before assuming the next move ahead of one’s competitors, they’ll have to think deeply about what others are doing now – and why – and what they might do next.
The same goes for post-mortem assessments after significant decisions – whether they’ve worked or they haven’t – as long as the group believed they would work; however, it’s important to note there’s no blame – only independent lessons that can create transformed future thinking (what did we assume would happen? Did we get it right? What could have gone better?).
How to Measure Progress
Unlike tactical execution, successful strategic thinking is less measurable – but it’s not impossible. Pay attention to framing once the training takes place – or lack thereof – for how problems become framed when solutions come forward. Are they doing so by looking at relative time spans? A system-wide impact instead of an isolated solution?
Track question quality; strategic thinkers ask different questions than tactical thinkers; they want to know about anti-deductive reasons – elements that haven’t been considered yet – and how they’re interconnected like a domino effect. When more people automatically ask those questions – the team has succeeded.
Furthermore, assess how unexpected challenges arise per decisions. Strategic thinkers are those who have taken the time to consider multiple outcomes ahead of time, so nothing should catch them off guard too much because they’ve weighed their options early on.
Reinforcing Training
Where companies go wrong is attempting strategic thinking training only once; someone goes off-site to attend a workshop and returns with lackluster implementation – but effectiveness is not an immediate exercise – but over the development of skills.
In order for transformative trained thinking to occur – it needs reinforcement over time. Whether it’s practice sessions every few months or continually ingraining transformation into daily thought processes – the specific style does not matter as consistency is the key; team members need repeated exposure and implemented practices daily so new ways of thinking become habit.
It also helps if during this reinforcement session learning brings real-time opportunity as new development paths are opened from currently worked-on projects rather than hypothetical lessons that produce vague ideas. Use what needs learning now as an opportunity instead of checking something off the list.
When trained thinkers emerge from transformation, you’ll find better strategic thinkers who create big-picture ideas quickly through well-reasoned decisions before they become risks prematurely. The return on investment occurs everywhere – even if it feels too good to be true – but until you switch up your training methods for champions who gain nothing other than pride in success – which is sometimes even greater than financial security – you’ll wind up paying for programs that don’t put money where their mouths are. Properly entrenched hands-on learning through realistic scenarios from leaders who cultivate change creates teams who actually can think strategically when they need it most.
