Strategic Planning Answers the Right Questions

Strategic Planning Answers the Right Questions

Strategy answers all the questions of “why, where, how, what, when, and who.” When you construct the answers to these questions from the top down, you create a coherent business strategy.

Planning that comes from this top-down approach is strategic planning. It leads to a program of initiatives that delivers your business positioning. Your employees and customers understand why you exist and how your actions support it. Planning that comes from less integrated approaches can lead to disjointed action. It's just planning.

Let's explore how to answer these questions in a top-down hierarchy through positioning, strategy, and plans to align efforts, track progress, and achieve vision with clarity and purpose.


People don’t buy WHAT you do, they buy WHY you do it. - Simon Sinek

Positioning: Answering “Why?”

Positioning is the foundation of any strategic plan. It answers “why the business exits” by defining:

  • Mission: The enduring purpose of the organization. It explains why the company exists and what it aims to achieve.
  • Vision: The aspirational goal of the organization. It paints a picture of what the company will become and how it will be viewed by the world when the mission is fully achieved.
  • Values: Principles and beliefs that guide the business' operations, actions, and decisions. They establish the company’s culture and ethical standards.

Together, these elements provide a clear sense of purpose and direction, ensuring that everyone in the business and their customers understand why it does what it does.

Strategy: Answering “Where and How?”

Next, strategy sits in the middle to answer the questions of “where to play” and “how to win.” This creates a coherent framework for moving the business toward its positioning. Strategy connects why you exist with what you do based on assumptions and answers to these questions.

You cannot fully control strategy. Strategy makes assumptions about customers and the context that influences your business. Who are your customers? What do they want? How will you reach them? How do your offerings differ from or complement competitors? Which competencies are needed? What trends are important? The answers create assumptions to be tested by a strategy that informs planning and allows for monitoring of results. Strategy creates coherent action that makes sense to employees and customers.

This involves defining:

  • Themes: The broad areas of focus that drive the business' efforts. They represent the strategic priorities that advance the mission and vision over the next about 3 years. At a minimum, themes answer what differentiators you offer, how you go to market, and how you make money.
  • Outcomes: These are the specific results that the organization aims to achieve within each theme. They describe success.
  • Measures: The metrics used to track progress towards the outcomes. They ensure that the organization can objectively assess the accuracy of its assumptions and make necessary adjustments.

By defining these, strategy informs a roadmap for achieving the organization’s vision, outlining where to focus efforts and how to achieve success. The answers ensure that everyone in the business and their customers understand 'where' and 'how' it does what it does.

Plans: Answering “What, When, and Who?”

Armed with your best answers to the 'strategy' questions, you next align plans and actions. Plans lay out the practical questions of “what, when, and who.” You can control planning, so it's tempting to start here. But, resist the urge since planning will not be aligned unless it has answers to the questions above it to create needed alignment. Planning questions should be answered annually by creating focused:

  • Initiatives: These are the specific projects that have defined scope and timeframe and actions that will be undertaken to achieve the strategic themes and deliver the desired outcomes.
  • Targets: These are the specific objectives that the organization aims to achieve through the initiatives usually set for about a year out. They should tie to Measure where possible and can also be more subjective.
  • Budgets: These outline the people, financial, and other scarce resources allocated to each initiative within the planning horizon (normally annually.)

And then at least quarterly by detailing:

  • Rocks: The major priorities or milestones that need to be accomplished by the end of each planning period (normally quarterly.)
  • Goals: The objectives that define success for the rocks.
  • Issues: The challenges and obstacles that need to be addressed to ensure successful execution of the plans. Defining and resolving issues allows teams to make steady progress.

Plans define and periodically refine these to provide a detailed blueprint for action, ensuring that the organization knows 'what' needs to be done, 'who' will do it, and 'when.'

Leaders can mistakenly use 'goals' as a replacement for strategy. Goals do not create strategy on their own. They are important at each layer to clarify and allow measurement of the essential strategic questions. Vision is a long-term goal that describes how you will be viewed if you achieve your mission. Outcomes, measures, targets and goals are all ways to describe success for their associated levels and timeframes.


StrategyOS is a framework to keep these questions current so that you maximize success. In previous newsletters, we covered implementing strategy transformation using iteration to validate and improve strategy and creating people practices needed for good strategic planning.

How does your business answer the basic questions of “why,” “where to play, and how to win,” and “what, when, and who?”

Let me know how I can help your business answer these questions as you set up for success in 2025. Jon Strickler |?720 323 0793 |?Schedule a Call | Strategy Workshops

Stay humble, adventurous, and bold!







Steven Smith

Vistage Chair | GCommerce CEO | M&A expert | Supply Chain | Cloud Commerce pioneer | SaaS | EDI | Automotive Aftermarket | Rancho Santa Fe Rotary

3 周

I like this John. Good leaders harness the brilliance of their organizations with a highly diverse and dynamic strategy team

Jim Ristuccia

Connecting CEO's to Build Power Peer Groups | Vistage Chair | Executive Coach and Mentor | Strategic Compassionate Leader

3 周

Great framework Jon Strickler. Nice clear and the the point. This would be a great exercise for most any company to go through.

Marc Emmer

President at Optimize | Keynote Speaker at Vistage Worldwide | Forbes & Inc.com Contributor | Expert Strategy Facilitator

3 周

Really like the visual distinction between a "plan" and a "strategy"

Mark Taylor

NYC Master Chair & CEO Coach @ Vistage NYC | Leadership Development

3 周

Jon Strickler, your emphasis on answering the fundamental questions of "why," "where," and "how" is crucial for any organization aiming for clarity and alignment. You've really put together a coherent and comprehensive guide to one of the essential skills of leadership.

Brian Thomas

Proven Chief Executive | Accomplished Leader | Executive Mentor & Coach | Vistage Chair ? Entrepreneur | Veteran

3 周

Great post Jon Strickler. Positioning is the goal, strategy creates the milestones, and plans (tactics) steer the bus.

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