Challenging Your Strategic Plan — How Prepared Minds Drive Better Decisions

Published On - July 13, 2022

Ted Bonel 2. STRATEGY
Strategic Plan
“Strategy is about making choices, trade-offs; it’s about deliberately choosing to be different.” — Michael Porter

Most leadership teams believe they have a solid strategic plan.
But the truth is, most plans fail long before execution — not because the strategy is bad, but because it’s never truly challenged.

An unchallenged plan is a dangerous one.
Markets evolve. Competitors shift. Teams change.

That’s why effective strategy is not just about planning — it’s about thinking.

And that starts with building prepared minds across your leadership team.

 

Why “Prepared Minds” Matter

Strategic planning isn’t about producing slides and charts — it’s about engaging your team in strategic conversation.

Your leaders need the skills, information, and context to make strong decisions and challenge assumptions.

Before every strategy session, send a detailed discovery questionnaire to your leadership team.
This ensures you walk into the room informed, not reactive.

Then, during your session, create space for open dialogue, not “show-and-tell” presentations.
Encourage your team to push back on ideas, question assumptions, and test options.

Because strategic strength comes from debate — not consensus.

Three Ways to Challenge Your Strategic Plan

To create a truly robust strategy, leaders must rigorously examine three areas: Scope, Choices, and Process.

1. Challenge the Scope — What Business Are You Really In?

Most companies rely on their annual SWOT analysis to set direction, but few use it to test assumptions.

Ask yourself:

  • What is the real definition of our market?
  • Are current trends forcing us to adapt faster than we are?
  • What should we stop doing — or stop chasing?
  • If we needed to double our growth, where would we expand?
  • What products or services should we evolve, reinvent, or retire?

Your scope defines your playing field.
Challenge it before the market does.

2. Challenge the Choices — Are We Bold Enough?

Strategy is as much about what you say no to as what you pursue.

Use these prompts to test your strategic choices:

  • Are we pursuing growth aggressively enough?
  • What are we deliberately rejecting — and why?
  • How do our choices make us preferentially different from competitors?
  • Do we have the right people in the right roles to deliver this plan?
  • What’s our most high-risk, high-reward opportunity over the next three years?

As Kaihan Krippendorff’s Outthinker Process teaches, every great company explores a “fourth option” — the bold move competitors overlook.

3.Challenge the Process — How Are We Thinking, Not Just What We’re Doing?

Even the best strategies fail when the process behind them becomes stale.

Ask your team:

  • When did we last rethink our approach to strategy?
  • Do we have a system for capturing new ideas and dependencies?
  • Have we validated our assumptions with customers — not just internally?
  • How do we measure strategic effectiveness and learning?
  • Are our people truly committed to improving the plan?

Your strategy is a living system — it must evolve as your business and environment change.

 

Final Thought — Strategy as a Learning System

A great strategic plan doesn’t just align your company — it educates it.

The goal is not just to build a plan, but to build a team of prepared minds capable of seeing opportunities and challenges before they happen.

So before your next strategy day, pause and ask:

  • Are we truly challenging our assumptions — or just confirming them?

 

Need help facilitating your next strategic planning session?

Contact me at tedb@strategyandexecution.com.au to schedule a free 30-minute discovery meeting.

To Scale Up your business! Take our Scaling Up/Four Decisions Needs Assessment to discover how your business measures against other Scaled Up companies. We’ll contact you.

 

 

TED BONEL, SCALING UP PRACTITIONER – STRATEGY & EXECUTION BUSINESS ADVISORS

Are you looking to scale your business and execute strategy with clarity and impact? I help CEOs and founders turn big ideas into real-world results, guiding small to mid-market companies through tailored strategic insights that drive growth.

My expertise lies in simplifying complexity – bridging high-level strategic frameworks with the practical realities of running a business. Unlike many consultants who focus solely on theory or execution, I specialise in both—translating strategy into actionable, transformative steps that deliver lasting results.

 

Need help facilitating your next strategic planning session?

Contact me at tedb@strategyandexecution.com.au to schedule a free 30-minute discovery meeting.

 

ABOUT STRATEGY & EXECUTION

For over 20 years, Strategy & Execution has supported leaders and organisations in developing and executing winning strategies. We provide expert facilitation, executive education, and hands-on consulting to help businesses refine their strategic direction and implement it effectively.

Using proven methodologies like Scaling Up, E-Myth Mastery, Outthinker, and more, we challenge conventional thinking and equip organisations with the tools to accelerate growth. Our approach is dynamic—combining deep business experience with practical execution. We don’t just advise; we roll up our sleeves and work alongside you to make strategy happen.

If you’re preparing for a strategy development or execution challenge and are committed to creating real value, we’d love to hear from you. Learn more about our work or upcoming workshops