7 reasons your strategic planning sucks (and the simplest way to fix it)
A minimalist's guide to approaching strategy in a simple, clear and less-sucky way
Once upon a time in a bustling office, there was a team so dedicated to perfecting their strategic plan that they lost sight of its purpose. They mapped out every possibility, forecasting scenarios even a crystal ball would envy. Their plan ballooned into a colossal tome, with charts for their charts and Powerpoints for their Powerpoints!
Then, one day, a new team member, Straightforward Susan, asked innocently, "Hey, what the frack are we actually trying to achieve here?" This simple question cut through the complexity like a knife through butter (the kind that’s been at room temperature for a while). The team paused, looked at their mountain of data, and burst into laughter.
Realising they had been getting tangled in their web of overplanning, they quickly ditched the labyrinthine plan for a simpler, clearer strategy.
Nice story.
Now only if people were that open-minded and adaptable in real-life scenarios! In my experience, what happens more often is that senior voices dominate with a ton of conviction and little clarity, like trying to force a butter knife to cut through a block of butter straight out of the freezer. Sunk cost fallacy be damned!
The junior voices - often the more pragmatic ones - are too timid to speak up and ask the kind of questions that Straightorward Susan asked. And ultimately the entire strategic planning process feels exhausting, with lots of outputs, but very little actionable follow-through.
If you have anything to do with strategic planning in your career, chances are you can relate to this pain. But there is a better way, and I’m going to give it to you very soon in this article.
We just need to cover some basics first.
What is strategic planning?
Strategic planning is a systematic process of setting goals, allocating resources, and deciding the steps needed to guide an organisation, program or project towards its desired future vision and outcomes.
Originating from military strategies in ancient Greek and Roman times, strategic planning evolved significantly over the centuries. Key military figures like Sun Tzu and Julius Caesar highlighted the importance of planning in warfare.
In the 20th century, these military strategies began to influence corporate planning. Post World War II, the complexity of warfare led to the development of advanced planning techniques, which were soon adapted for business use. The 1950s and 1960s saw business leaders like Peter Drucker and Igor Ansoff shaping modern corporate strategy concepts.
By the 1970s and 1980s, strategic planning became commonplace in large corporations, introducing various models such as SWOT analysis, Porter's Five Forces, the BCG matrix, and PESTEL analysis. However, criticism for being too rigid led to the development of more flexible and adaptive strategies in the late 20th century, incorporating real-time planning and scenario analysis.
Today, strategic planning combines historical and modern approaches, focusing on agility and adaptability in a fast-changing business environment. It’s less about accurately predicting the future and more about preparing for various possibilities, ensuring organisations can respond effectively to new challenges. This is a fairly big part of what I do professionally.
Why does it get so messy and frustrating?
Strategic planning often gets convoluted, inefficient and downright annoying due to some apparent and less apparent reasons. The obvious issues include:
complexity of the business environment the planning is happening in,
unclear objectives to lay a solid foundation for the strategic planning, and
resistance from employees who feel excluded from the planning process, or simply cynical due to past strategic planning processes.
Personally, I find the not-so-obvious issues more interesting and more sinister, which can include factors like:
an over-reliance on data for decision-making leading to analysis paralysis; and
trying to build consensus across too many stakeholders, without having a clear tie-breaker when things get stuck in discussion whirlpools.
All of that though tends to happen when the strategic planning is already set up and underway. What I’m most interested in sharing with you is even more fundamental and critical to successful strategic planning. And it’s so much simpler.
Your strategic plan will always be useless
A few years ago, I used to champion Benjamin Franklin’s wisdom “if you fail to plan, you plan to fail.” These days, whilst I don’t discount the value of that wisdom, I’m a big fan of a different quote.
“Plans are worthless, but planning is everything.” - General Dwight Eisenhower
This paradoxical wisdom highlights that while specific plans can quickly become obsolete in the face of real-world chaos and unpredictability (hence 'worthless'), the process of planning is invaluable. Planning forces individuals and organisations to think critically, anticipate potential challenges, and consider various scenarios.
It involves not only strategising but also understanding the dynamics and interplay of different factors that could influence outcomes. And this is actually the discipline of strategic design.
Strategic design is an approach to problem-solving that combines design methodologies with systems thinking and business strategy to create innovative solutions, particularly for complex, 'big picture' challenges.
Whilst it seems like lofty, aspirational semantics, it’s not. Understanding the difference between strategic design and strategic planning allows a healthy focus on building adaptability into the whole strategising journey, and ensures that when unexpected changes occur, those involved are better equipped to make informed, agile decisions.
In essence, the act of “designing” and then “planning” cultivates a mindset and a set of skills that are crucial for navigating the ever-changing landscapes of both military and civilian business realms.
If all you do is focus on producing a strategic plan, without this thoughtful regard to designing and planning your strategy, your strategic plan will be at best useless, and at worst dangerous.
Let’s get back to first principles
“Strategy” itself is a pretty loaded word. If you ask a group of executives in a room to raise their hand if they’ve participated in strategy exercises before, they will almost always all raise their hands. If you ask them to keep their hand up if they feel they have a decent understanding of what strategy means, almost always all hands will remain up.
If you then ask the same people to individually write down, quickly, how they would define strategy, you’ll get varying answers. Some won’t know what to write.
I’ve done this. More than once. And the above is exactly what happened.
On top of this, strategic planning workshops and exercises are full of jargon and I’ve never met a group of people who all had a shared understanding of even most of it. Not to mention, if you Google definitions for things like “strategy”, “plan”, and “roadmap” you will find contradictory definitions and descriptions of what these things mean. This unfortunately adds to the confusion and consultants often take advantage of this not-at-all-plain language by running hard and fast with the jargon to peacock and posture expertise and command.
So here’s my take.
Forget the jargon. I will tell you exactly what you need to know to make “strategic planning” useful and approach it in a way that sets yourself and your team up for success. And it won’t cost you a cent, and it won’t make you feel dumb or ignorant. It’ll be an all-round pleasant - even if not easy - experience for everyone involved.
The 4 primary questions
The point of strategic planning - or any similar exercise - is to answer the following 4 questions:
What are we trying to achieve?
How do we know at any point in time that we’re heading in the right direction?
How do we know that we’re doing a good job?
How do I know that I’m doing a good job?
The “we” in the above refers to the business, program, project, product etc. team that is doing the strategising.
Question 2 prompts you to consider what kind of feedback loops are in place to test and iterate for optimising agility. I wrote about directional correctness in detail here.
Question 3 is about quality assurance and validation.
The “I” in question 4 refers to any individual in that team and is about individual expectations, feedback mechanisms, incentive structures, etc.
These 4 questions together give you a minimalist approach to think about your strategy and help set you up for useful planning.
But wait! There’s a little more before you dive in.
The 3 key artefacts
Business leaders, especially in large organisations, love their artefacts. Sometimes so much that everything becomes about the artefact and you’d think there’s some magic alchemy going on where the right PowerPoint presentation is going to create all the business results as soon as you hit that present button.
That said, there is some utility to having a set of shared artefacts that can represent the collective thinking, designing and answering of those primary questions for everyone involved. It’s just a shame that the definitions of typical business artefacts all get jumbled up and people forget the point of them.
Let me fix that for you.
There are just 3 key artefacts that you need, and the test of their usefulness is if they can clearly and confidently answer a specific question relevant to their purpose.
Strategy: What’s the overarching approach to accomplish our mission and what are the resources required?
Plan: What are the step-by-step actions that need to be taken, when and by whom, to accomplish the mission?
Roadmap: What does the big picture view look like of the trajectory towards “mission accomplished”?
If your strategy and plan are simple enough, you may not even need a roadmap. Or maybe a strategy and roadmap will sufficiently cover the level of detail you need. Depth will vary on a situational basis and that’s why having a good facilitator will still be very helpful.
To be clear, I do appreciate other artefacts may be needed and useful in various organisations for various reasons. Business case, pitch deck, organisational design, etc. I also appreciate there are different ideologies about what should go into a strategy, plan or roadmap document.
I’m not trying to be facetiously simplistic here. But when it comes down to the absolute first principles of strategic planning as we’ve defined, these are the 3 key artefacts that will get you moving together and keep you all moving in the same direction.
Don’t forget: People over process
One more thing. Prioritising people over the process of strategic planning is so important for so many reasons. If you read my ‘Choreographing change management’ article, you’ll have a good sense of this already.
Here’s how to do it.
Don’t just run into a planning workshop or create a strategy document. Run a “primer session” first. If you want the paint on a wall or a canvas to stick well and present itself in the best way, you apply a primer first. Same thing here. A primer session is where everyone who will be involved in the strategic designing and planning gets together and agrees on some terms of engagement.
Make one of those terms of engagement a commitment to psychological safety.
Psychological safety relates to a person’s perspective on how threatening or rewarding it is to take interpersonal risks at work. For instance, is this a place where new ideas are welcomed and built upon? Or picked apart and ridiculed? Will my colleagues embarrass or punish me for offering a different point of view, or for admitting I don’t understand something?
- scienceforwork.com
To make it even more practical, I like to explain to everyone that psychological safety requires conversational equality and deep listening. As a facilitator, it’s my job to ensure conversational equality across the group. It’s everyone’s job to ensure deep listening and generally looking out for one another.
Share with everyone “the prime directive” and get everyone to agree with it.
"Regardless of what we discover, we understand and truly believe that everyone did the best job they could, given what they knew at the time, their skills and abilities, the resources available, and the situation at hand."
- Norm Kerth, Project Retrospectives: A Handbook for Team ReviewWhilst Norm Kerth introduced the above prime directive in the context of retrospectives, I’ve found this to be incredibly useful for teams embarking on any exercise where several people need to open up and share their practice wisdom, opinions and perspectives in a potentially vulnerable setting. And no matter how well you think you know your team, it’s always safer to assume that there will be some level of vulnerability in such an exercise.
In our journey through the labyrinth of strategic planning, we've uncovered some profound truths. We've seen how strategic planning when misunderstood or misapplied, can transform from a tool of empowerment into a convoluted burden. However, we've also discovered the transformative power of strategic design—a beacon of hope in the often murky waters of corporate strategy.
The tale of Straightforward Susan in the opening parable isn't just a whimsical anecdote; it's a metaphor for the clarity and simplicity we should all strive for in strategic planning. It teaches us that sometimes, the most powerful question is the simplest one: "What are we trying to achieve?" This simple yet profound inquiry is the heart of effective strategy—it's the guiding star that keeps us aligned with our true purpose.
As you stand on the threshold of your next strategic venture, remember that the success of your plan hinges not just on the strategies you employ, but on the people who bring them to life. Foster a culture of psychological safety, where every voice is valued, and every idea is considered. Embrace the prime directive as your guiding principle, ensuring that your team operates with empathy, respect, and mutual support.
Finally, your journey in strategic planning doesn’t have to be just an annual corporate obligation, or even just about reaching a destination. It can be about growing, learning, and evolving along the way. So go forth with courage and conviction, knowing that the path to excellence is paved with clarity, simplicity, and the collective wisdom of your team.
I agree with everything in this article and found myself reacting deeply to one part.
“Psychological safety” whilst I personally like to work in a psychologically safe space I also can’t stand it when others take no responsibility for their “psychological fitness”
I think there’s an emergent opportunity to move from safe spaces to brave spaces.
In my opinion safety is a triggering word for me because I’ve observed snowflakes who haven’t done any psychological fitness use it to avoid taking 100% ownership.
Anywho this isn’t ti divert attention away from the great article, just me sharing my two cents on one aspect