At least 16 questions to help you think about your strategy

“It’s either about out thinking the competition, or even better, about finding new, even greater opportunities” so says Max McKeown in “The Strategy Book”.


“Opportunities the competition hasn’t found yet or opportunities the competition doesn’t understand because it hasn’t done the kind of thinking that you have. There are always better ways of doing anything. There are always shorter routes for getting from where you are to where you want to be. There are always new markets that are growing faster than your market. There are forever methods, relationships and ideas just waiting to be discovered, and these can only be discovered by creating room – slack – for thinking.”


Max McKeown like Cynthia Montgomery in her book “The Strategist” asks the questions that get the juices flowing, and boy are there a lot of questions. If it’s your first time looking at the subject or you have felt a bit overwhelmed by the topic or you’re looking for a more hands on look this is not a bad place to start. Thinking is key for McKeown, “There are lots of reasons why organisations don’t think before they plan. The most important given is probably the lack of time. People say they are so busy planning, organising, doing and coping with problems that they don’t have time for thinking. Thinking is a luxury they wish they had time for, but don’t.”


McKeown goes on to say “Strategy is about out thinking your competition. It’s about vision first and planning second. That’s why it’s so important that you think before you plan. And that the thinking part of what you do is given priority. Strategists who don’t take time to think are just planners”. McKeown encourages you to become “a strategic thinker – a strategist – is about getting better at shaping events. In the business world, you need to understand how strategy is usually done. You need to know how to create a strategy that convinces others to support you (including your boss or shareholders). And you need to know how to make strategy deliver success in the real world.”

No guarantees

For a strategy that works, he says you must realise, “There is no guarantee that the future will turn out the way you want. Just writing a plan does not mean that the plan will happen. The world is more complex than our ability to plan, but that’s part of what an effective strategist learns to accept. You learn that reacting and responding to events is just as important as planning”

Shape your future

He goes further by saying that, “The real heart of strategy is the strategist. It’s what you know, how you think, and how you get people to care enough about what you are doing to achieve your goals. It’s also about setting in motion the sequence of events that will shape the future in a way that you like. The more you understand the people who make events happen and the connections between what they do and those events, the smarter you will be. You have already used strategy to get a lot of what you have. You got a job. Or you got an education to get a job.” He backs up his consulting experiences with a dip into the four schools of strategy:

  • Classical, which seeks to maximise profit with deliberate processes;
  • Evolutionary, which seeks to maximise profit with emergent processes;
  • Systematic, which seeks plural objectives with deliberate processes; and
  • Processual, which have plural objectives with emergent processes.

Understanding the basics of strategy

As a Strategists your measure of success according to McKeown will be on the foundation of,  your understanding the basic origins of modern corporate strategy, the difference between creative and analytical strategy, how creative and analytical tools and principles are used together. How stable and dynamic markets are treated differently. You know there is more to strategy than beating or copying your competitors. A strategist asks what balance of these approaches is most helpful in any particular situation.


And then there is always time for more questions,

  1. What are you doing at the moment?
  2. How does that compare to your competitors?
  3. What do you want to achieve?
  4. How can you create something people want?
  5. Does your organisation have enough constructive conflict

Every part and everyone

According to McKeown, shaping the future of an organisation involves every part and everyone. Strategy considers things inside and outside the organisation that will make a difference to its success. The strategist also looks for opportunities and threats to the future of the organisation. Ideally, these are explored with imagination, ambition and a creative understanding of customers, products and resources. He says that ,“ One of the valuable roles creative strategy can play is to overcome the sources of conflict.

Look for disagreement

First, you identify areas of disagreement (which is easier if people are being open about it) then look for contradictions in the way you run your business and the strategy you are meant to be following. Look for clever ways of overcoming those conflicts and contradictions. This process is never perfect, and it’s often messy, but it is the only way of figuring out what to do next and engaging people with the problem-solving process and the solution implementation activities.” As a strategist, “you have to observe the level of conflict. Look at whether it is open, transparent and constructive. Or is it closed, hidden with smart people biting their tongues and keeping their best ideas quiet?”

More questions

McKeown argues that because shaping  the future requires a combination of thinking, planning and reacting to events that emerge along the way that they provide further key strategy questions:

  1. What do we want to do?
  2. What do we think is possible?
  3. What do we need to do to achieve our goals?
  4. When should we react to new opportunities and adapt plans?


McKeown always comes back to your thinking “Look for more varied, eclectic, diverse inputs into your thinking process.”

  1. How does your industry (or sector) work?
  2. What does success look like for your organisation?
  3. What would it take to do it ten times better?
  4. What is the most important (root) issue you face?
  5. What would you do with no limitations?
  6. How many of those limitations are real?
  7. What are older, younger, richer, or poorer people doing?”

The strategist

Like Montgomery in The Strategist he is always asking the tough questions:

  1. “How much time have you invested in thinking about strategy?
  2. How many options have you considered before the plan was written?
  3. How have you ensured that the thinking behind the plan is challenged?
  4. How much time do you spend exploring trends, possibilities and cool stuff?
  5. How much time is spent playing with ideas, hopes and dreams?”

 The review on Newstalk


sensemaking cover


Sense making; morality, humanity, leadership and slow flow. A book about the 14 books about the impact and implications of technology on business and humanity.

Ron Immink

I help companies by developing an inspiring and clear future perspective, which creates better business models, higher productivity, more profit and a higher valuation. Best-selling author, speaker, writer.

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