BELLWOODS STRATEGY PERSPECTIVES

Ideas, observations, and stories that shape how we think about strategy and clarity.

Leadership, Strategy, Brand Positioning, Strategic Planning Douglas Anweiler Leadership, Strategy, Brand Positioning, Strategic Planning Douglas Anweiler

The Strategy Paradox: Why Leaders Can't Wait for Perfect Conditions

The temptation to postpone strategic work until conditions improve has become one of the most dangerous defaults in business leadership. Overlapping crises aren't temporary obstacles anymore, they're the permanent backdrop. Organizations that wait for calm waters to define their strategy risk being caught unprepared when the next wave hits. The ones that thrive are learning to build clarity in the rain.

How do you build strategy when perfect conditions never arrive?

"The organizations that win this year won't be the ones that found calm waters. They'll be the ones that refused to let turbulence turn into drift."

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Leadership, Strategy, Community Douglas Anweiler Leadership, Strategy, Community Douglas Anweiler

The 3Rs of Engagement: A Framework for Focus and Clarity

Leaders face constant pressure to engage everywhere—on social media, in partnerships, at conferences, in every conversation. It can create a false binary: either participate or miss out. But strategic engagement requires a framework that shifts from reactive response to deliberate choice. The 3Rs of Engagement (Relevance, Return, Regret) help leaders decide when engagement advances their positioning and when it dilutes it.

What happens when you stop engaging everywhere and start engaging precisely where it counts?

"When you know what you stand for, it becomes easier to know where to stand."

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Leadership, Strategy, Community Douglas Anweiler Leadership, Strategy, Community Douglas Anweiler

Three Things Champions Do That Everyone Else Talks About

The 2025 World Series proved that completely different strategies can lead to the same destination when executed with discipline. Most organizations understand the fundamentals of strategic success, but understanding and doing are different games. Champions separate themselves not through revolutionary thinking but through relentless commitment to clarity, coherence, and consistency under pressure.

What's the difference between talking about strategy and actually executing it?

"Most organizations have strategy documents. Champions have strategic coherence."

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  • I have worked with Doug for over 40 years. His sharp strategic thinking and deep understanding of what makes people and organizations tick is legendary.

    He’s a trusted partner who knows how to find clarity and a path forward despite complex and seemingly insurmountable hurdles. He cuts to the chase and focuses the leadership on what truly matters and that has made all the difference.

    — Chris Macleod, Founding Partner, Cambridge LLP

  • Douglas Anweiler is one of the clearest thinkers in and for an increasingly complex business environment.

    We’re going to see good things come from Bellwoods Strategy.”

    — Marc Kealey, Chief Advocate, Kealey & Associates Inc.

  • Working with Bellwoods Strategy has been transformative for our organization.

    Doug brought a rare combination of strategic clarity, deep listening, and genuine care for our mission. He helped us see the bigger picture, make tough decisions with confidence, and tell our story in a way that truly connects.

    — Devi Arasanayagam, Co-founder and Chair, Fort York Food Bank

  • Doug is the strategist you want in the room when the path forward isn’t clear.

    He distills complex ideas into direction, aligns strong personalities around a shared vision, and helps brands find the through line that makes everything click. We’ve worked together on fast-moving fintech brands, and I’ve seen firsthand how Doug brings momentum, clarity, and purpose to every stage of growth.

    — Brianna Petz, Partner & Creative Director, Sherpa Creative