Strategic Thinking and Planning

In broad sense, strategic thinking is the process of coming up with ideas in order to reach goals. Still, there isn’t one ‘right’ way to describe strategic thinking. One view is that it is one part of larger strategy creation and execution:

  1. Strategic thinking (out-think competitors): what could be done and why?
    Problem analysis, stakeholder involvement, innovation, exploring possible futures, hypothesis, criticism, testing.
  2. Strategic planning (out-plan): how could it be done? Analysis and synthesis creating a strategy.
    1. Analysis: gather the dots
    2. Synthesis: connect the dots
  3. Operational planning: how to put the strategy into practice in daily operations?
  4. Monitoring and reacting (out-maneuver): Measuring that the strategy has a desired effect. Keeping an eye on new opportunities. Reacting by iterating or pivoting.

Attributes of good strategic thinking

What to do and which skills to have to be a good strategic thinking?

  • Perspective of the whole value creation system from one end to another, and one’s role in it.
  • Focused attention
  • Bridge the gap between current reality and future plans (Scenario planning)
  • Responsiveness to new opportunities and seeking them, even when they are not part of the current strategy. Be creative and open to new ideas.
  • Be critical:
    • question everything (including yourself), challenge current conventions and uncovers biases,
    • test assumptions
    • try to find the root of problems
  • Good decision-making process:
    • interpret information from multiple sources
    • make a balanced decision (on time, quality, rigor) on the crux of the matter
    • move on (avoid analysis paralysis)
  • Align conflicting views, even on tough issues
  • Learn by interpreting feedback, debriefing and reflecting, and use the lessons to improve or pivot

How to interpret and think better

Thinking revolves around gathering data and making new interpretations based on it. But how to test the reliability of the interpretations?

  1. Make a list of assumptions that have to be true for your interpretation to be correct. Organize from the easiest to resolve to the hardest.
  2. Look at the data: does it support the assumptions? Also look out for biases in the data, think broadly and challenge your perspective.
    1. Get information about the assumptions from (three) different viewpoints. Talk with people with different views and backgrounds. Use scenario planning.
    2. If an assumption is not supported, rethink your interpretation.



Learn Constantly to Achieve Success – The Five Hour Rule

Learning new things is the best investment you can use your time on. So, instead of obsessing on becoming productive with routine tasks today, focus on learning. Learning pays back in the long run by opening new possibilities and making yourself more valuable for employers and society. Most successful people have committed to lifelong learning, from Benjamin Franklin to Bill Gates and Elon Musk.

The “Five Hour Rule” says that you should set aside at least five hours a week for learning (one hour per weekday).

Ways to learn constantly:

  • Dedicate time for learning and thinking.
  • Set goals for learning and improving yourself, not just tasks and achievements.
  • Read. Concentrate on reading e.g. books, instead of skimming the latest blog posts.
  • Be curious. Diversify yourself. Be curious about what the world needs and wants.
  • Experiment. Test what is possible in your field. Learn from your experiments.
  • Treat every event as an opportunity to improve. Don’t settle on automation and doing “okay”, but figure out ways to learn, experiment and improve.
  • Practice deliberately. Do new things, challenge yourself and get feedback.
  • Solve problems as you face them, instead of leaving that for later. Learn from the problems.
  • Stepping away from your normal work and location might stimulate thinking. Go for a walk, do some gardening or work in a coffee shop.

Never stop learning. Commit to this.


Michael Simmons: Why Constant Learners All Embrace the 5-Hour Rule

Empact: Why the Smartest People Are Constant Learners

Elle Kaplan: How to Use the “5 Hour Rule” to Radically Improve Your Intelligence and Success

Negotiate by Listening and Aiming for “That’s right”

Leadership is negotiation and getting people to agree on a common goal.

Agreement comes when people feel that they have been listened and understood.

This emotional connection can be achieved by first listening carefully, and then summarizing what you were told. Ask whether there was something misunderstood or missing. The goal is to reach such an understanding that the other person can give his voluntary agreement by saying “that’s right”.

Listening opposing views carefully is difficult, but helps reaching agreement, especially if at least part of the view can be incorporated to the outcome.


Andy Raskin: To Be a Better Leader, Learn This FBI Hostage Negotiation Tactic