Designing Strategy in High-Volatility Environments

A conversation with Dan Canham, Founder & CEO at Tomorrow Strategy Co. In an age of constant disruption — economic, environmental, geopolitical — strategic planning can start to feel like an exercise in futility. But for Dan Canham, Founder and CEO of Tomorrow Strategy Co., volatility isn’t something to avoid — it’s something to design for.

In this Exec Edge Q&A, Dan shares a pragmatic framework for strategy in uncertain times: stay bold, stay structured, and above all, stay adaptive.

Below is our full conversation, lightly edited for clarity and flow.

When volatility is the norm, what does "good strategy" actually look like? Good strategy isn’t about predicting the unpredictable — it’s about preparing for it.

Uncertainty is now part of the operating environment, and strong strategies must reflect that. In this context, the best strategy is both clear and adaptive. It should define a bold ambition, provide a decision-making framework, and be robust enough to handle shocks without requiring constant reinvention.

That means regular reviews, testing key assumptions, and making evidence-based refinements. Leaders should prioritise clarity of intent and commit to openly communicating adjustments to keep the strategy relevant and resilient.

How do you build plans that stay flexible without becoming vague or reactive? It starts with a clearly defined ambition, supported by deliberate priorities and a shared path to progress.

From there, flexibility comes through scenario planning, running multiple initiatives, and maintaining a strong internal communication rhythm. Over communication is key — leaders should reinforce the strategy via presentations, voice memos, town halls, emails, and even social platforms.

Execution then requires structure: we use OKRs or KPIs to keep accountability intact, even as tactics evolve.

Can you share an example where high uncertainty forced a major shift in approach — and what you learned from it? We were helping a client expand into Queensland and Victoria via a market penetration strategy. Part of that involved acquiring an established business in Queensland. After three months of negotiations and a signed deal, the seller walked away — last minute.

Rather than abandon the strategy, we reframed the execution: we pivoted toward joint ventures and launched a satellite office. It was fast, unplanned, and ultimately smarter and more sustainable than the original plan.

The lesson? Strategy should be anchored but agile.

What tools, processes, or habits help your team stay strategic when everything feels urgent? Once strategy is set, we distil it into a "Strategy on a Page" — a single-pager outlining our ambition and categorising priorities into NOW, NEXT, and LATER.

It’s a shared language for sequencing and focus.

We reinforce it with monthly pulse meetings to track progress and surface blockers. Teams are coached to separate “must-do” from “nice-to-do,” ensuring that urgency doesn’t override intent. Quarterly reviews create space for reflection and recalibration.

How do you balance the need for fast moves with the risk of overcorrecting? Speed is essential, but context matters.

Overcorrecting in volatility is a real risk, which is why we use structured decision frameworks. We lean on test-and-learn principles — small-scale pilots, rapid prototypes, and sprints that validate assumptions before full rollout.

If it works, scale. If not, adjust quickly. This approach encourages speed with evidence — not just speed for its own sake — and keeps teams aligned with long-term ambition.

What’s the role of the strategy team in helping others stay focused when priorities are constantly shifting? The strategy team’s role is to drive clarity and cohesion.

When priorities shift, we help connect the dots — ensuring teams understand how their work contributes to evolving goals. We keep the strategy alive through engagement: alignment sessions, storytelling, updated artifacts, feedback loops, and listening deeply.

Above all, we help people focus not just on what they’re doing — but why it matters.