Strategic Leadership: PREPARE For Organizational Learning

John Cousins
March 4, 2023
5 min read

Strategic Leadership

Strategic Leadership is the ability to influence others to engage their own decision-making abilities and agency in navigating wiser outcomes that reduce risk and enhance the prospects for an organization’s success, while maintaining financial sustainability.

What is required of you in this role

Adaptive strategic leaders are who will thrive in uncertain environments. The ability of an organization and its leaders to adapt is the key survival skill.

Learn to be adaptable

Strategic Leaders

Strategic leaders are the focal point for organizational learning. They promote a culture of inquiry, and they search for the lessons in both successful and unsuccessful outcomes. They study failures — their own and their teams’ — in an open, constructive way to find the hidden lessons.

What you need

PREPARE is an acronym for an iterative 7 step process for framing organizational learning and providing a strategic framework for leaders.









Let’s dig into the details of each step in the process.


Take time to plan and anticipate what you expect to happen in any given situation. This doesn’t mean over analyzing and worrying about what might go wrong and getting into arguments in your head about events that probably won’t happen, but having a sober assessment of expected outcomes.

Write these down so as to review in an after-action post mortem and see how your expectations aligned with reality. This is a very helpful exercise. When we don’t write down what we anticipate we tend to bend our thinking to quickly to what actually went down and that cuts us off from some creative thinking and options.

Most companies focus what’s directly ahead and react or develop tactics to deal. The leaders lack peripheral vision and a sense of the adjacent possible. This leaves an organization vulnerable to competitors who sense and respond to tentative actions. If the sharks smell blood, your Blue Ocean is going to get Red in a hurry.

In order to predict and anticipate effectively:

Look for game-changing convergences on the periphery of you market segments.

Search beyond the current boundaries of your business seeking disruptive developments.

Develop broad external networks to assist scanning the horizon effectively.


Think Critically.

Question everything. Question the prevailing assumptions.

The manager asks how and when; the leader asks what and why.

Reframe problems to get to root causes.

Challenge current beliefs and mindsets, especially your own.

Root out contradictions, sycophancy, and bias in the organizational decision process.

Avoid Groupthink

Gather a diversity of opinions. Create a team of rivals. Use Red Team and devil’s advocates to challenge conventional wisdom and undisputed decisions.

Employ the dialectic method of thesis, antithesis and synthesis.

You cannot passively allow lemming behavior, herd-like belief, and safe opinion if you want your company to maintain or gain competitive advantage.

Critical Thinking Skills

The ability to think critically is a set of skills that help one determine shit from Shinola. It is each of our individual responsibility to cultivate these interactive capabilities that act as a filter set. Cultivate these:



Problem Solving

Decision Making



This is your ability to recognize and accurately interpret signals from the competitive marketplace. You have to get good at picking signals out of noise.

Ambiguity is uncomfortable and our innate tendency is to resolve it quickly. The challenge is to get comfortable with ambiguity while gathering more information from a diversity of viewpoints.

Hold fast and synthesize information from as many sources as you can gather and let your viewpoint develop. You’re looking for patterns and trends. Incorporate multiple sources of data. Encourage others in your organization to do the same.

Employ the scientific method and test multiple hypotheses. Iterate and pivot towards good decisions.

You need to be action oriented but not hurried. Make hast slowly.

Fastina Lente


There needs to be a pace and cadence to your decision making process that is action oriented. Don’t fall prey to analysis paralysis. Remember you will always be working with partial and incomplete information. Develop a culture and processes that arrive at a good enough position that balances speed and rigor. Perfection is the enemy of good enough. Time to take a stand.

It is important to explain and communicate the rational behind decisions and how they align with strategy. Articulate the decision in a manner that gets to the crux of the matter.

I have written more on choice and decision making in these posts:

Buridan’s Ass

Behavioral Economics


Build support. Try to bring diverse viewpoints into alignment by understanding what drives other people’s agendas including what remains hidden.

Discuss tough issues especially when it’s uncomfortable. Address the elephants in the room and don’t allow things to fester.


You won’t build complete consensus. If you do, go back and review the steps above as it is probably a signal of groupthink or lack of diversity. Foster open dialogue and build trust. Engage key stakeholders and address divergent viewpoints.


Honest feedback is harder and harder to come by as an organization scales. Cultivate it. This is crucial. Failure is a valuable source of organizational learning. Run a post mortem on all successes and failures. You learn more from failure than success. Be nimble and agile and course correct rapidly in the face of new information. Acknowledge and encourage failures that provide insight and were pursued in the manner of this framework.

Leadership and Management

Tactical thinking is “doing things right,” while Strategic thinking is “doing the right things.” Strategic thinking is typically leadership: creating the vision. Whereas Tactical thinking is management: implementing the vision.

Here is a follow up post on strategic management.

Prepare: the 7 Ps

The 7 Ps is a British Army adage for Proper Planning and Preparation Prevents Piss Poor Performance.

You have what it takes

No one is born excelling in all these different skills. The good news is that they are learnable and you can cultivate them with self-awareness and an open mind. Now get to it.

Share this post
John Cousins
Author, Entrepreneur, & Teacher

Receive my 7 day email course

Take your finance skills to the next level with my 7-day corporate finance email course. You'll learn all the essential topics from financial analysis to risk management in a fun, engaging format. Each day, you'll receive an email with practical examples, exercises and resources. Perfect for aspiring finance pros or anyone looking to expand their knowledge. Get ready to transform your finance game!

By clicking Sign Up you're confirming that you agree with our Terms and Conditions.
Thank you! Your submission has been received!
Oops! Something went wrong while submitting the form.

If you like this article. Here are some more articles I think you might like.


The Road to Becoming a Unicorn: A Quick Guide to Startup Funding Rounds

The whole process of funding and developing startups has become more widespread because the cost of getting a product to market has dropped so precipitously in the past couple of decades from millions of dollars to typically anywhere from under $20,000 to $500,000.
John Cousins
December 18, 2023
7 min read

Oh Behave! Behavioral Economics: Why we do what we do.

Behavioral Economics is a method of economic analysis that applies psychological insights into human behavior to explain economic decision making.
John Cousins
December 18, 2023
4 min read
Personal Growth

Professional Development: 3 Types of Skill Sets

To perform effectively in a job and advance to greater responsibilities requires developing a well rounded set of skills. Every job and every industry has its specifics but these skill sets are general and apply across all jobs. Skills are fundamental for turning a job into a career trajectory and this trajectory is part of our personal fulfillment in life.
John Cousins
December 18, 2023
5 min read