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7 Questions Behind Successful Strategic Plans

Updated: Jul 6, 2022

If there's one thing I've learned from my clients over the past 20 years, it's that classic approaches to strategic planning are too rigid, burdensome, and ultimately ineffective. I decided to launch this blog series to distill and share state-of-the-art approaches used by renowned consulting firms to help organizations produce light-footprint, systems-oriented, and talent-centered strategies.

Unlike Deloitte, McKinsey, and Accenture however, the approach I use as an independent consultant at the Transformative Learning Institute is accelerated, comes at a fraction of the cost and time, enables close and consistent care, and produces internal capacities that eliminate (rather than reinforce) an organization's dependency on consultants.

Throughout this series, I'll provide links to short-form assessments, conversation starters, and a personally curated list of the best resources I've discovered!

In 1831, Katsushika Hokusai produced a breathtaking woodblock print titled The Great Wave off Kanagawa. Said to represent a sacred geometry, this highly recognizable work resembles the plight of modern organizations who are thrust about like paper boats. In the wake of a global pandemic, war, economic uncertainty, civil unrest, and a torrent of advanced technology, organizations must improve the way they develop and execute strategic plans.

7 Questions you Must Ask

If you wish to develop a successful strategic plan, there are seven questions you must ask yourself and your employees. The way you answer these questions tells a skillful consultant a lot about strengths you can leverage in the long-run, and pressure points you can address to immediately alleviate strategic burdens. While there are no quick-fixes, these short term successes inspires confidence, creativity, and commitment around the strategic planning process. To get started, let's frame this blog series through seven critical strategic questions we can all do something about!

  1. What measures have you taken to ensure that your strategy is aligned, agile, meaningful, desirable, feasible, and scalable?

  2. What types of organizational design elements have you customized to increase your chances of strategic success?

  3. What steps have you taken to develop a culture that inspires and rewards well-being, creativity, ethical-decision making, and continuous learning?

  4. What systems have you put in place to capture, share, and expedite innovation with regard to products, services, and management processes?

  5. What plans do you have in place to ensure that your leaders are clear, collaborative, and creative stewards of your strategy?

  6. How have you positioned yourself to identify characteristics, attract, retain and develop the type of talent that you'll need in the future?

  7. What approach are you taking to diagnose and lead dialogue around these first six questions in a collaborative fashion with your employee base?

Which of the "7 Strategic Questions" would be the most difficult for your organization to address?

Which question do you find most difficult to address in your organization?

  • Question 1: Strategy

  • Question 2: Design

  • Question 3: Culture

  • Question 4: Innovation

What do YOU think? Comment below and let me know if and how your organization specifically goes about answering these questions. If you're interested in learning more, I'd love to hear from you. You can reach out to me directly about my consulting, speaking, and workshop services at If you enjoyed this post, you might also find this workshop particularly helpful!

Don't forget to like, comment, share and subscribe!

Thank you! Bill


Strategy needs Creativity. An analytic framework alone won’t reinvent your business. Harvard Business Review. March–April 2019.

The Power of Vision: Statements that Resonate. Journal of Business Strategy. 2010.

Eliminate Strategic Overload. How to select fewer initiatives with greater impact. Harvard Business Review. May–June 2021. What’s your Digital Strategy? Harvard Business Review. May–June 2020. Why do so Many Strategies Fail? Leaders focus on the parts rather than the whole. Harvard Business Review. July-Aug 2021. Making Strategy Execution Work. MBR. 2021.

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