Strategies Are Hard, But Worth It

Strategies are notoriously difficult to design, build, and even harder to bring to life. Without a coherent strategy, energy and attention often get diverted in the wrong directions, and tactical efforts can become misaligned within a company.

Strategy is essential—it provides a clear direction, ensures decisions are aligned, and creates a framework for meaningful action.

I’m old school. I like to understand the precise meaning of words. I often dive into etymology to uncover the roots of ideas as you'll see in many other posts.

Strategy derives from Greek, meaning something like “office or command of a general.”

Over time, it evolved into the sense of:

“that which spreads out, to lead.”

That’s a compelling definition for business: strategy spreads out and allows people to lead. It’s why strategies typically originate with leaders—they provide a guiding direction and an organising structure that everyone can work toward.


Principles of a Good Strategy

Over the years, I’ve crafted large and small strategies, refined existing ones, challenged many, and seen my fair share of poor strategies. Through these experiences, three core principles consistently emerge that I check all strategies against:

  1. A clear Painted Picture of a bright, compelling future (True North or Vision): An exciting, motivating, captivating, compelling and vivid depiction of the future you want to achieve, accompanied by measurable goals.
  2. The current reality - an evidence-backed assessment of obstacles: The problems preventing progress must be clearly identified and prioritised. In other words ask this question: "If the bright future is so compelling and interesting, what's stopping us achieving it next month, or next year?"
  3. A plan to address the obstacles: Concrete waypoints, assigned responsibilities, initiatives and timelines that bridge the gap between your current reality and your future – addressing the problems that are stopping you from achieving it.

Without all three, what you have is not a strategy—it is aspirational, incomplete, or ineffective.


Why Strategies Fail

In my experience, most strategies fail for a few recurring reasons:

  • Templates over thinking: Downloading a strategy template and filling in boxes rarely produces a meaningful strategy.
  • Dreams without grounding: Aspirations without evidence or planning are fantasies, not strategies. It's good to dream, but these need grounding high-level plans at least.
  • Personality-driven visions: Strategies that reflect a leader’s personal style and personality, rather than an organisational reality – these are rarely actionable. I.e. "destroy the competition", "dominate".
  • Buzzwords without substance: Plausible-sounding words may energise, but they do not guide action. "win", "compete".
  • Lack of evidence: Opinions are insufficient; decisions must be informed by data, insights, and research.
  • No Painted Picture: Facts alone rarely inspire; people connect with stories and visions.
  • Ignoring obstacles: A strategy must acknowledge reality. Without identifying barriers, teams cannot plan effectively – and moving forward they will face obstacles that should have been identified and mitigated.
  • Poor communication: A strategy only works when understood. Circulating documents is not enough — consistent, clear, and ongoing communication is essential.

Painted Picture and Goals

The first step is painting a vivid picture of the future. This is about being, not just doing.

The “painted picture” describes the kind of company you want to create — safe, innovative, customer-focused, enriching for employees, and valuable to society.

👉 Here's a deeper dive on letting go of how – and focusing on creating a compelling vision of the future through a painted picture.

This future painted picture is awesome, but we must create long term goals that lead us to this. Goals act as waypoints — mountains between today and the future.

They are measurable, time-bound, and concrete steps that move the organisation toward the vision. Standing in front of your Painted Picture, you can see these goals as points on a map; achieving them brings you closer to the bright future.

Note: Most painted pictures are rarely achieved in full – but that's fine, the point of the painted picture is to give people something compelling to aim at.


Leaning Into Reality

Once the painted picture is defined, leaders must confront the current reality. Understanding obstacles requires humility and factual assessment:

  • What is stopping progress?
  • Where are bottlenecks, slow processes, and low performance?
  • What structural or cultural problems prevent the organisation from reaching its goals?
  • What preventing us from achieving this future next month, or next year?

Mapping these as a “current reality tree”, or any other method, helps distinguish symptoms from root causes. Only by addressing root causes can meaningful progress be made.


Addressing Obstacles and Planning

With reality mapped, you need a plan:

This ensures your strategy is actionable, not just aspirational. Tactics should always address obstacles and contribute to measurable progress toward the painted picture.


Strategy in Motion: Tactics Inform Strategy

Here is where strategy meets action. The most effective strategies are not static—they live through tactics. In fact, tactics (action) is the most valuable part of a strategy – it's where you start moving towards your bright future and you learn.

Tactics are the day-to-day experiments, actions, and initiatives that implement the strategy. They are where learning happens. Teams test ideas, observe results, and adapt. Insights gained from tactical work feed back into the strategy, refining it and making it stronger. This creates a feedback loop: strategy guides tactics, tactics inform strategy.

At the end of the day the strategy is usually in the form of a document. Whilst it gathers dust in a folder somewhere, people are in the work and implementing the tactics learning what works, what doesn't and understanding how to pivot towards the bright future.

That's why the bright future is so important - it helps people see waypoints and horizons to move towards, all the time implementing, working and taking action in the right direction.

Aligning processes, removing friction, and empowering teams ensures tactical work contributes meaningfully. When executed well, tactical implementation creates momentum, engagement, and yes—even joy and spirit and hope—because people can see the impact of their work on the larger picture.


Communication is Key

A strategy is only as effective as its communication. Presentations, emails, intranet posts, town halls, and ripple communication from managers all reinforce understanding. People must know:

  • What the strategy is.
  • How their work contributes.
  • Why obstacles matter and how their actions help overcome them.

Feedback loops, stories, visuals, and consistent messaging reinforce clarity and alignment. Over time, clarity enables teams to operate with autonomy, align and keep moving, while remaining connected to the strategic vision.

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Fun and Engagement

When strategy, tactics, and communication align, work becomes engaging. Teams experience momentum, clarity, and purpose. The side effect is joy — not mandated fun, but the natural result of seeing work contribute to a larger vision.

Fun, engagement, and alignment act as signals, they are early warning systems: if people aren’t enjoying the work, clarity or alignment may be missing, the painted picture may not be compelling, confusion may be setting in and the work may lack meaning.

Constant attention to strategy in motion (tactics and action) ensures everyone contributes toward the shared vision and everyone learns how to get better, how to move forward and how to overcome the problems that stand between where you are now, and your compelling bright future.


Closing Thoughts

Strategy is hard. Painting a compelling picture, assessing reality, building a plan, communicating effectively, aligning processes, and fostering engagement — all while iterating based on tactical feedback — is no easy task.

But it is worth it. A well-executed strategy releases value, enables learning, and builds a culture of alignment and purpose. Tactics and strategy together create a living, organic feedback system: one where each informs the other, and the organisation grows smarter and stronger with each step.

Test: If printing your strategy consumes all the paper in your office, it’s too detailed. A few concise pages, clearly articulating vision, obstacles, plans, and communication, are all that’s needed.


Bibliography

  1. Hawken, P., 1987. Growing a Business. Simon & Schuster, New York.
  2. Rumelt, R., 2011. Good Strategy/Bad Strategy: The difference and why it matters, Main edition. ed. Profile Books.
  3. The 4 Levels Of Strategy: The Difference & How To Apply Them [WWW Document], n.d. URL - https://www.cascade.app/blog/strategy-levels (accessed 7.16.24).
  4. Making the Future Visible: Psychology, Scenarios, and Strategy - Hardin Tibbs, 2021 [WWW Document], n.d. URL https://journals.sagepub.com/doi/full/10.1177/19467567211014557 (accessed 7.16.24).
  5. What is Current Reality Tree? [WWW Document], n.d. URL https://online.visual-paradigm.com/knowledge/problem-solving/what-is-current-reality-tree/ (accessed 7.16.24).

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