What is one strategy you use to foster a culture of strategic thinking within your team or organization? How do you encourage proactive planning?

Question

Strategic thinking is a critical skill for organizational success in today's rapidly evolving business landscape. This article explores innovative approaches to cultivating a strategic mindset across all levels of an organization. Drawing insights from industry experts, it presents practical techniques that can transform how teams approach planning, decision-making, and long-term visioning.

Steven Manifold · Answer

The challenge with traditional approaches to strategy is that it's an annual occurrence. Plans often end up in a slide deck that is quickly forgotten, not updated with actual results, and only reviewed after the fact, when the year has ended and the results are what they are.
As a CMO, switching to a dedicated live planning system changed that for our business. We captured our strategic goals, the programs of work and trade-offs we had agreed as a management team, and tracked real-time results against those strategies in one place. It helped align the day-to-day tasks with the overriding direction. Strategy became a thing we questioned almost daily (certainly weekly) as we asked both 'Are we on course?' and 'Is the course still correct?'
Planning became part of the natural working rhythm. As a management team, we consistently checked with each other that we were spending as much time working 'on the business' as we did working 'in the business'. Strategy was reviewed and revised frequently during working sessions (not just leadership reviews) and baked into the operational goals throughout the organization. Every marketing campaign, client proposal, and product roadmap feature could be explicitly linked to the strategy and a measurable business outcome.
At its heart, strategic thinking is about making choices. Having a living plan that permeated the business, with those choices and trade-offs well documented and shared, empowered team members to question 'Why are we doing this?' and 'How does this support our strategy?' It quickly became obvious if something didn't, and allowed colleagues to stop wasting time and effort, and switch to more strategically aligned work.

Kristin Marquet · Answer

I carve out a weekly "Strategy Hour" on Thursdays where everyone—regardless of role—brings one "what-if" scenario or emerging trend they've spotted. We use that time to map potential impacts, brainstorm responses, and assign a small "experiment" sprint for the week ahead. By giving the team permission (and space) to step out of task mode and think big-picture, they start anticipating challenges instead of just reacting. Over time, those collective mini-projects have sparked new service ideas, refined our PRISM Ascend™ framework, and turned proactive planning into an ingrained habit.

Vikrant Bhalodia · Answer

At our company, we prioritize integrating strategic thinking into everyday work, not just high-level planning. One effective method we employ is holding quarterly "what if" discussions. These provide our team leads and managers with an opportunity to step away from immediate deliverables and consider what's coming next: changes in client needs, shifts in the market, or potential areas of challenge.
We also encourage teams to ask, "What's the next problem our client might face?" rather than focusing solely on the next task. This approach helps them anticipate issues and suggest solutions early. For example, our developers recently identified a potential scalability problem for a client months before it became critical and proposed adjustments in advance.
Recognizing people for proactive ideas has been another driver. When team members see that forward-thinking is valued, it motivates others to think in the same way.
In leadership meetings, we avoid being the ones with all the answers. Instead, we ask, "If you were in the client's position, what would worry you six months from now?" That simple shift sparks deeper planning and makes long-term thinking second nature.

Stanley Anto · Answer

At our workplace, we implement "Horizon Sessions," two-part meetings separating creative ideation from practical planning.
This is a formula we've perfected to ensure bold ideas are explored without inhibitions or boundaries before putting them through a practical filter and grounding them in reality. While encouraging proactive planning, this approach also offers the added advantages of fostering initiative and facilitating real-time progress.
This entire exercise is carried out in two phases:
Phase 1 - The Expedition: This is where unrestrained brainstorming is encouraged in a judgment-free zone where the main goal is to generate ambitious ideas. "What if...?" prompts, such as "What if our competitor vanished?" or "What if we achieved our five-year goal in 18 months?", push teams beyond incremental thinking to envision transformative possibilities.
Phase 2 - The Blueprint: This phase can be compared to creating an imaginary tree of possibilities and then picking tangible fruits from it. After selecting one or two of the most compelling ideas from the Expedition, we use backcasting, starting from the desired future state and mapping milestones, obstacles, and a critical path backward. We conclude with a tangible first step for the following week.
Regular sessions enable us to balance present-day execution with proactive planning, making strategic thinking a continuous habit rather than a sporadic exercise.

Joe Spisak · Answer

I've found that one of the most effective strategies for fostering strategic thinking is creating what I call "strategy circles" - cross-functional teams that meet regularly to tackle specific business challenges. These aren't just leadership meetings; we intentionally include team members from various levels and departments.
In the 3PL space, where operations can easily become siloed, these diverse perspectives are invaluable. I've witnessed warehouse associates identify optimization opportunities that our executive team completely overlooked. Several of our current directors started in coordinator positions but distinguished themselves through their contributions in these strategy sessions.
To encourage proactive planning, we implement a simple but powerful practice: the pre-mortem exercise. Before launching any significant initiative - whether it's onboarding a new eCommerce client with complex fulfillment needs or expanding warehouse capacity - we gather key stakeholders to imagine the project has failed and work backwards to identify potential pitfalls.
This approach transforms planning from a theoretical exercise into practical risk mitigation. It's particularly effective in the fulfillment industry where variables like seasonal demand spikes, inventory management complexities, and carrier performance can derail even the most carefully planned operations.
The key is creating psychological safety where team members feel comfortable challenging assumptions without fear of repercussion. When our team identified potential integration issues with a major client's ERP system during a pre-mortem, we adjusted our implementation timeline accordingly, avoiding what would have been a costly disruption.
By embedding these strategic thinking practices into our regular workflows rather than treating them as separate activities, we've developed a culture where proactive planning happens naturally rather than being forced. The result is a more resilient organization capable of navigating the inevitable challenges of the dynamic eCommerce fulfillment landscape.

Derek Pankaew · Answer

One of the best things we did to encourage real strategic thinking wasn't some quarterly planning workshop or a mission-alignment document—it was way simpler and honestly kind of weird:
We started asking every team member, "What's the hill you're dying on this month?"
Let me explain.
Strategic thinking often dies because people don't feel ownership—they're just following the checklist, not making real decisions. So we flipped it: once a month, every person on the team picks one thing they're willing to fight for. Something they think would make a meaningful impact if we focused on it. It doesn't matter if it's product, process, marketing—just one strategic bet.
We track it. We check in on it. And most importantly, we let them actually drive it—even if it's not technically their department.
It does two things:
1. It trains people to think in terms of leverage, not just tasks.
2. It surfaces the quiet, buried insights that usually get lost in the noise.
Over time, it creates a culture where people expect to be decision-makers. Not just button-clickers. And it turns strategic thinking into a monthly habit, not a once-a-year offsite activity.
It's one of those deceptively simple rituals that changes how people show up—and we've gotten some of our best innovations out of it.

Rory Keel · Answer

Strategic thinking thrives when every team member feels as accountable for tomorrow's flavor as they do for today's output. In our roastery at Equipoise Coffee, we begin each week with a "future-flavor" cupping: we sample experimental roast curves alongside market trend data so baristas, green-bean buyers, and operations folks all taste where we're headed before we commit precious inventory. This physical ritual turns abstract projections into something sensory and shareable, sparking questions like, "If climate shifts nudge Kenyan harvest dates, how will that affect autumn blends?"—exactly the kind of proactive planning you want in any organization.
Because we roast in small batches to ensure each bag delivers the bold, nuanced flavors you crave, we can afford to iterate quickly, document the insights, and loop them back into quarterly roadmaps. Our name, "Equipoise," encapsulates that balance: pairing data discipline with hands-on experimentation keeps the team poised between creative possibility and operational rigor. By tying long-range goals to the tangible pleasure of a smoother, less bitter cup—no cream or sugar needed—we make strategy both delicious and non-negotiable.

Brian Fontanella · Answer

One strategy I've used that has worked really well is asking my team to think in terms of "next steps" during our project reviews. Instead of just reporting what has happened, I have them answer, "What's coming next, and how does it impact the client or the business?" This shifts the conversation from reactive to proactive without needing a whiteboard session every time. It's a small adjustment, but it starts training their mindset toward strategic planning.
I remember a time when one of our technicians flagged a client's aging firewall—not because it was failing, but because he had been thinking ahead about upcoming compliance changes. That mindset saved the client time, money, and potential risk. I use that story often because it demonstrates how strategic thinking isn't just for executives; it's about seeing what's around the corner and acting on it before it becomes urgent.

Martin Weidemann · Answer

We once turned a 20% vacancy rate into fully booked rentals for 6 months, simply by getting one strategic habit right.
As the owner of RentMexicoCity.com, if I have learned anything, it is that proactive planning is not about predicting the future, but creating systems that require you to plan strategically every week. One of the worthwhile strategies I use every week is a simple, but unavoidable habit: the Friday Forward Review. Every Friday (virtually or in person), we take the time to review not just what we did, but what we delivered, and the signals we are seeing, for the next 90 days. It's more than just a review. It is a lens for strategic thinking on a weekly basis.
Now for the best part. In Q1 last year, our team noticed a sudden increase in Google searches from "digital nomads" and U.S. traffic increasing on listings with private outdoor spaces. Because we had trained them to think in trends rather than tasks, we initiated a three-week sprint to photograph, catalogue, and share our best terraces and patios. As a result, our 20% vacancy disappeared, and we booked those listings for 6 straight months at 30% above the average nightly rate.
Getting your team to think strategically doesn't require a big org chart. It just requires a habit of democratizing insight. Everybody on the team, from our cleaning crew to our team of photographers, knows that they can bring forward a trend, and they can celebrate when they do. I also display the dashboards transparently, and every week I ask my team one question: "What might break if demand doubled tomorrow?"
This one question has triggered our biggest enhancements.
So no matter how small your team is - if you teach them to see around corners, you won't just be better prepared to react ... you will lead the market.

Wayne Lowry · Answer

I've found that strategic thinking flourishes when every team member can connect their daily tasks to a long-term vision. To facilitate this, we conduct a monthly "roadmap rewind" where developers, marketing, and clinical operations teams each present one initiative that has significantly improved patient experience. This conversation compels us to articulate not just what we built, but why—and it uncovers cross-department synergies more effectively than any formal memo.
At Best DPC, we're transforming healthcare with a patient-first approach. Our KPIs begin with member satisfaction and work backward. When an engineer sees how a new appointment widget reduced a patient's journey by ten clicks, they naturally start planning features with the next friction point in mind.
I also encourage proactive planning by limiting sprint capacity to 80 percent, reserving the final 20 percent for "future bets" that staff propose after listening to our podcast's success stories from thriving Direct Primary Care clinics. This buffer legitimizes forward-looking ideas, transforming them from wish-lists into prototypes we can rigorously evaluate.
Finding quality care is simple—search our site to instantly connect with trusted Direct Primary Care providers. We apply the same principles to our internal strategy: clear, accessible, and relentlessly focused on a healthier, more patient-centered future.

Anthony Sorrentino · Answer

I've found that the best way to encourage strategic thinking is by shifting our team's focus from just "getting through the list" to thinking a step ahead. It starts with how we talk about the work. Instead of only asking, "What's on your schedule today?" I ask, "What's coming up that we can prepare for now?" That small change in language helps everyone start thinking proactively, not reactively.
One moment that stands out was when one of our technicians noticed a trend of increased mouse activity earlier in the fall around some of our lakefront accounts. Instead of just noting it, he proposed we move up exclusion services by a few weeks and notify clients ahead of time. We tested it out, saw fewer follow-ups, and made it part of our fall preparation schedule going forward. It was a great example of proactive planning from the field, and it all started because he was encouraged to think ahead, not just follow the clipboard.

Ali Yilmaz · Answer

One strategy I use to foster a culture of strategic thinking is making "Why now?" part of every conversation.
Whether we're launching a feature or adjusting pricing, I ask the team to justify not just what we're doing, but why it matters now. That simple framing turns reactive decisions into intentional ones and forces us to think in terms of opportunity, timing, and trade-offs.
To encourage proactive planning, I also share a lightweight 3-month vision deck every quarter. It's not a rigid roadmap, but a narrative of what we're aiming to unlock and why. It gives context without micromanaging, and it invites the team to think ahead and shape the path with me.
Strategic thinking doesn't start in a boardroom; it starts with everyday decisions made with purpose.

Elisabeth Galperin · Answer

Strategic thinking isn't just for quarterly retreats — it should be part of our daily mindset. I regularly encourage teams to explore the "why" behind the "what," prompting thoughtful dialogue around decisions and actions. In meetings, I assign a rotating "devil's advocate" role to ensure we challenge assumptions, uncover blind spots, and stretch our thinking. This practice builds a habit of proactive planning and keeps strategic thinking alive in everyday conversations.

Belle Florendo · Answer

Strategic thinking flourishes when every staff member can trace today's tasks to the long-range safety and belonging we promise each child. Every quarter, I run a "Ten-Year Test": we pull one real case file, imagine the child at age 25, and brainstorm which decisions made this week will still matter to them—placement stability, therapy milestones, alumni mentoring. That future-back lens reveals gaps a standard KPI meeting would miss and sparks proactive planning; suddenly, the maintenance supervisor is pitching solar panels because lower utility bills mean more counseling hours down the road.
In operation since 1936, Sunny Glen has been a refuge of stability and love for children in need, and that legacy gives us rich data we share openly—showing how strategic bets like our Allen House Independent Living Center paid off with 78% college or career placement among former foster youth. I reward forward-thinking ideas with a "prototype budget" that lets any team test a small version within 30 days, turning vision into muscle memory.
By weaving long-view storytelling with rapid-fire pilots, we embed strategic curiosity into daily routines, ensuring our comprehensive programs—from residential services to foster care—continue evolving so every child finds a nurturing home.

Joe Reale · Answer

To promote a strategic thinking culture, one of the strategies available to me is to encourage the development of future-focused planning, rather than constantly focusing on day-to-day activities. I usually tell the team, "Imagine we have a time machine and we are fast-forwarding 12 months. What would we say in 12 months to indicate, 'We nailed it?'" This shifts the discussion from short-term difficulties to long-term impact, prompting everyone to think beyond the confines of short-term success.
I have also initiated quarterly strategic reviews, during which individual teams are expected to present their plans and objectives for the next three months, accompanied by a strong strategy. It is not a reporting session; it is an opportunity to communicate openly about the assumptions, possible roadblocks, and how each plan connects to the high-level strategic objectives of the firm. It makes everyone understand that their work is an integral part of a greater mission and makes them accountable, aligning them with the overall goals. The difference is to ensure that not only the top leadership thinks strategically, but the entire staff should be able to think strategically as well.

Corina Tham · Answer

Trading is a battleground of swift choices and narrow margins, and assembling a team that excels here requires more than just routine—it necessitates a mindset of tactical anticipation. One approach I've adopted with notable results is enabling my team to approach challenges like traders, rather than merely employees. It begins with fostering a culture where inquisitiveness aligns with calculated experimentation. I motivate my team to dive deep into market research, not just to gather information but to detect trends, foresee changes, and develop strategies rooted in data-backed intelligence.
For me, proactive preparation means consistently asking, "What comes next?"—not only for the market but also for our methods. For example, I frequently encourage the team to engage in simulations of theoretical trading scenarios, helping them predict possible market movements before they occur. This practice hones their tactical instincts and establishes a mental framework for confronting ambiguity with assurance—essential for anyone immersed in trading or the forex sector.
By promoting open teamwork and hands-on problem-solving, I ensure everyone feels confident to challenge, propose, and adjust adeptly. After all, in trading and business alike, reacting late is costly—but being tactically prepared? That's how success is achieved.

Fredo Tan · Answer

One thing that's made a real difference for us is sharing the "why" behind what we're doing. Not just the goals or KPIs, but the context. What problem are we solving? What feedback led us here? What trade-offs did we make? Once people understand the bigger picture, they naturally start thinking more strategically. They stop waiting for instructions and start contributing ideas.
The other thing we do is give people real ownership. If someone owns onboarding, they're not just ticking off tasks. They're expected to ask hard questions, run experiments, and tell us what's working and what's not. It shifts the mindset from "Do what I'm told" to "What's the best move for the customer and the company?"

How to Foster a Culture of Strategic Thinking in Your Organization

How to Foster a Culture of Strategic Thinking in Your Organization

Live Planning System Transforms Strategy

Weekly Strategy Hour Sparks Innovation

Integrate Strategic Thinking into Daily Work

Horizon Sessions Balance Creativity and Practicality

Cross-Functional Strategy Circles Drive Success

Monthly Hill to Die On Empowers Decision-Making

Future-Flavor Cupping Aligns Team Vision

Next Steps Mindset Cultivates Proactive Planning

Friday Forward Review Drives Strategic Habits

Roadmap Rewind Connects Tasks to Vision

Shift Focus from Tasks to Preparation

Why Now Approach Fosters Intentional Decisions

Devil's Advocate Role Challenges Assumptions

Ten-Year Test Reveals Long-Term Impact

Time Machine Exercise Promotes Future-Focused Planning

Tactical Anticipation Mindset Prepares for Success

Share the Why Behind Strategic Decisions