Open Sky Leadership Institute · Module 06
Divergent
Thinking
Before you decide what to do, you need a real choice to make. Most leaders don't give themselves one.
Section 1 · The Premature Convergence Problem
We decide before we've really thought
Most organizational decision processes have a structural flaw: they move from problem to solution too quickly. A challenge is framed, a small number of options are identified (often two or three), and the group converges on the best among them. This feels like good decision-making. It is actually premature closure.
The options evaluated were not chosen from a wide field. They were the first options that came to mind — shaped by organizational habit, existing mental models, and the cognitive biases of whoever framed the problem. The group converged on a choice from a set that was never properly explored.
A decision is only as good as the option space it was chosen from. Most leaders underinvest in generating that space.
Divergent thinking is the discipline of expanding the option space before evaluating it. It is not about being creative for its own sake. It is about ensuring that the decision you make is chosen from a genuine range of possibilities — not just the ones that were easiest to see first.
This is deeply connected to the Both/And framework. Either/Or thinking forecloses options by forcing choices too early. Both/And thinking keeps the option space open long enough to find solutions that might integrate, rather than simply choose between, competing possibilities.
Opening reflection
A decision made from a narrow option space
Recall a significant decision where you evaluated two or three options and chose one — but never seriously considered that the initial framing of the options might itself be the constraint. What might you have found if you had generated 10 options instead?
Section 2 · Diverge Before You Converge
The Double Diamond model
The Double Diamond — originally developed at the UK Design Council and now widely used across disciplines — is a simple, powerful framework for structuring creative problem-solving. Its core insight is that genuine innovation requires two cycles of divergence and convergence, not one.
Discover
◇Explore the problem broadly before defining it. Gather diverse perspectives. Question assumptions about what the challenge actually is.
→ DivergeDefine
◆Synthesize what you've discovered into a clear, well-framed problem statement. Resist the urge to jump to solutions here.
→ ConvergeDevelop
◇Generate a wide range of potential solutions. Defer judgment. Volume and variety matter more than quality at this stage.
→ DivergeDeliver
◆Evaluate, select, prototype, and implement. Now convergence is appropriate — because it follows real divergence.
→ ConvergeThe critical insight: most organizational problem-solving skips the first diamond entirely. Teams jump to "Develop" (generating solutions) without first "Discovering" (exploring the problem space). This means they are solving the wrong problem — efficiently.
Key principle
Never evaluate during divergence. The moment you begin assessing whether an idea is good, you have collapsed divergence into convergence. These are fundamentally different cognitive modes, and mixing them prematurely kills creativity. Keep them separate — not just in concept, but in time and in the explicit rules of the conversation.
Section 3 · Rules of Divergent Thinking
How to run a divergent session
Divergent thinking is a structured discipline, not just a freewheeling brainstorm. The rules matter because they protect the generative phase from the convergent instincts that naturally dominate organizational thinking.
Defer judgment. Every idea stays on the table during divergence, regardless of feasibility. "Yes, and..." is the only permitted response to another person's idea. "But..." and "We tried that..." are not allowed.
Go for quantity. The goal is volume — 15, 20, 30 ideas — not a handful of "realistic" ones. Quantity creates the raw material from which unexpected combinations emerge.
Welcome wild ideas. The most impractical ideas often contain seeds of breakthrough thinking. An absurd option can be reverse-engineered into a feasible innovation. Don't filter at the generation stage.
Build on each other's ideas. The richest options often emerge from combinations — taking two ideas that seem unrelated and asking "What if we put these together?" Divergence is more generative as a social process than as an individual one.
Make the convergence moment explicit. Divergence without convergence is chaos. Set a clear time when evaluation begins — and protect the generative phase by keeping these two modes visibly separate.
Section 4 · What Blocks Divergence
The forces that close the option space prematurely
Divergent thinking is not natural in most organizational contexts. Several structural and cultural forces work against it — and effective leaders name them explicitly rather than simply asking people to "think more creatively."
- Hierarchy. When the most senior person speaks first, most divergence ends. Status cues tell others what kinds of ideas are safe to offer. Effective divergence requires temporarily flattening the room — write before you speak, speak without attribution, give everyone equal airtime.
- Time pressure. Divergence requires slack. The faster a decision must be made, the narrower the option space will be. Leaders who consistently operate in urgency mode never develop the option-generation capacity that complex environments require.
- Fear of looking foolish. Without psychological safety, people self-censor. They offer the polished, defensible idea — not the strange, half-formed one that might actually be the seed of something new. Safety is the prerequisite of genuine divergence.
- Cognitive anchoring. The first idea stated in any conversation becomes the anchor around which all subsequent thinking organizes. Whoever speaks first shapes the option space for everyone who follows. This is why generating ideas individually before sharing them collectively produces more genuinely diverse options.
Reflection prompt
What is blocking divergence in your context?
Of the four blockers above, which is most active in your current leadership context? What would it take to address it directly — not just wish it were different?
Section 5 · Application
Generate 10 options
Pick a current challenge — a problem you are trying to solve, a decision you need to make, a tension you are navigating. Apply the rules: defer judgment, go for quantity, welcome wildness. Generate at least 10 options before you evaluate a single one.
The challenge
10 options (no evaluation yet)
Number them. Include at least one wild/impractical option. Don't cross any out.
Now evaluate: which 2-3 are most worth exploring?
After generating all 10, now evaluate. Which options or combinations seem most promising? Is there something surprising on the list?
Leadership Discourse Foundations
The scholars beneath this practice
Divergent Thinking combines organizational exploration, growth-oriented learning, psychological safety, and complexity-informed experimentation.
Follow the intellectual trail: open any Scholar Profile above, or study the full chronology, four theoretical streams, and seven Open Sky lineages in Module 00: Leadership Discourse →
Section 6 · Key Takeaways
What to carry forward
- Most organizational decision-making suffers from premature convergence: evaluating a small set of options that were never systematically generated. A decision is only as good as the option space it was chosen from.
- The Double Diamond model separates problem exploration from solution generation, each followed by a convergence phase. Most organizations skip the first diamond — exploring the problem before defining it — and pay the price in misdirected solutions.
- The rules of divergent thinking protect the generative phase: defer judgment, go for quantity, welcome wild ideas, build on each other, and make the convergence moment explicit. These are structural rules, not encouragements — enforce them.
- Four forces reliably block divergence in organizations: hierarchy, time pressure, fear of looking foolish, and cognitive anchoring. Naming them is the first step to countering them.
- Divergent thinking is a Both/And practice: it keeps multiple possibilities alive simultaneously, resisting either/or logic until the option space is genuinely rich. The goal is not a creative exercise. The goal is a better decision from a wider field of real choices.
Closing reflection
Where will you apply this first?
Name a meeting or decision process in the next two weeks where you will explicitly build in a divergent phase before any evaluation begins. What will you do differently to protect that phase?