Five-step design thinking framework for solving leadership problems

Executive overview

Most leaders jump to solutions without fully understanding the problem from the perspective of those affected. The design thinking framework — originating from Stanford d.school and embedded in agile product development — brings people into problem solving rather than solving for them.

Five steps: empathy, define, ideate, prototype, test. The cycle repeats; each pass yields better information and tighter solutions.

Starting with the people you're trying to affect — not your own assumptions — is the single biggest lever in solving the right problem.

Step 1: Empathy — listen before you act

• Talk directly to the people impacted; understand their feelings, context, and what they actually want.
• Resist the assumption that past experience in their shoes means you understand their current situation.
• Listening builds buy-in: people feel heard and invest in the solution.
• Example: A conversation with an Academy graduate surfaced a gap — no small-group coaching experience existed post-Academy — that hadn't been clearly named before.

Step 2: Define — clarify the real problem

• Data collection drives problem definition; don't rely on anecdote alone.
• A community survey (75% response rate) identified the top opportunity areas and helped rule out directions that felt obvious but weren't priorities.
• The goal is a clear problem statement: what outcome do you want to drive, and for whom?
• Initial direction may shift once data surfaces — that's the process working, not failing.

Step 3: Ideate — co-create testable hypotheses

• Generate ideas with the people affected, not just for them.
• Form hypotheses you can actually test; avoid over-investing in any single direction before validation.
• Example hypothesis: having a past Academy graduate co-facilitate sessions would improve the experience for current cohort members.
• Inspiration can come from adjacent contexts — a Dale Carnegie instructor model informed the idea of fellow-led facilitation.

Step 4: Prototype — start small, learn fast

• Run the smallest experiment that can produce useful signal.
• The first prototype (fellow co-facilitation) produced direct feedback through structured debriefs using Kujo Teshner's debrief model.
• That experiment revealed an under-utilised asset: fellows could lead conversations independently, not just support the host.
• The second prototype — peer momentum groups, fellow-led small cohorts for Pro community members — addressed the original gap identified in step 1.
• Minimum viable product thinking is required; building while learning creates some ambiguity for participants, but is preferable to over-engineering upfront.

Step 5: Test, learn, adapt — make iteration a habit

• Treat every version as a draft; build feedback loops in from the start.
• Post-launch survey on peer momentum groups surfaced two issues: participants wanted a clearer session framework, and monthly cadence was too infrequent.
• Both were fixed in the next version.
• Fellows debrief sessions together monthly — the loop continues even after launch.
• The framework is cyclical: version three is already being shaped by conversations happening now, returning to step 1 (empathy) with current members.

Applying the framework in leadership contexts

• Works for any decision that affects a group — team changes, program design, process improvement.
• The value compounds: repeated use builds the habit of checking assumptions against real user data.
• Being too close to a problem is normal; involving others (a fellow, a peer, a direct report) provides the outside perspective needed to break familiar patterns.
• "If you're not occasionally disappointing people, you're probably not pushing the envelope enough" — imperfect experiments are part of the process.
• The five steps in brief: empathy → define → ideate → prototype → test/iterate.