Rupert Picardo

What He Builds

Leadership programmes and facilitation. Rupert runs sessions built around live decision-making and structured reflection. No slide decks performing at people. The point is to create the conditions where real insight happens — which usually means designing the right amount of pressure, the right kind of constraint, and a debrief that doesn't let anyone off the hook.

Business simulations. Scenario-based learning experiences that put participants into realistic, pressured situations — stakeholder management stand-offs, strategy calls with incomplete data, team dynamics under time pressure. The learning comes from what people discover about their own instincts when consequences are on the line.

Competency assessments. Through Tryitowl, he built the assessment suite he always wished existed: one that tells a manager exactly which behaviours are present, which aren't, and what the gap looks like in practice. Not a type. Not a colour. Specific, actionable, indicator-level feedback.

Gamified onboarding platforms. Enterprise-grade onboarding built to feel like something other than a compliance exercise. Clients include Thomson Reuters, Virtusa (50,000+ employees across 50+ countries), and BMA — one of the largest retail chains in the Middle East, with 173 stores across the region and Africa. Internal referrals up 115%. Retention up 30%+. The numbers matter because the design decisions behind them matter.

How He Thinks About Learning

There is a version of "experiential learning" that is just rebranded PowerPoint with a group activity bolted on at the end. It produces good feedback scores. It changes nothing.

The question Rupert starts every design process with is not: what should people learn? It is: what should people experience?

That shift sounds small. It isn't. It changes every decision — what scenarios you build, what decisions you force, where you create friction, when you pull back. It's the difference between a programme that people talk about for a week and one they reference two years later when something hard happens at work.

His perspective on onboarding reflects the same logic: create the employee journey as an experience. Focus on what the new hire will feel, not just what they will know. The information will be forgotten. The experience won't.

Speaking

Rupert spoke at TEDxLavelleRoad in 2019 — a session on the gap between how leaders think they show up and how they actually land on the people around them.

He facilitates regularly for L&D conferences, HR forums, and leadership programme cohorts. His sessions are not keynotes with a Q&A tacked on. They are structured experiences: participants make decisions, see consequences, and reflect on what that reveals. The format adapts to the audience. The principle doesn't.

He also designed the world's largest body percussion ensemble — which exceeded the previous world record by 160%. This has nothing to do with leadership development and everything to do with how he thinks about group dynamics, engagement design, and what happens when you give 1,000 people a shared beat and very clear instructions.

Watch the TEDx Talk →

Speaking topics: Leadership under pressure — how people actually decide; decision-making in ambiguity; stakeholder management — the political skill nobody admits is a skill; gamification in L&D — what works, and what's just a leaderboard; designing employee experiences — onboarding as a signal, not a process.

Tryitowl

Tryitowl is where everything he has learned about learning design lives in product form.

Gamified onboarding for enterprises who want new hires to arrive engaged rather than overwhelmed. Leadership assessments that go eight competencies deep and come out the other end with a development plan worth reading. And Guild — the platform for OD consultants and L&D teams who want to build, run, and report on assessments without the enterprise price tag or the three-month implementation timeline.

Same design logic across all three. Experience first. Output that's actually useful. No binders.

Also

Teamification.in handles the in-person side: leadership workshops, team-building experiences, and conference formats designed to do something other than fill a slot in an agenda. teamification.in