Oblique Strategies Development Lab

Unblock ideas fast. Generate fresh angles.

When a project stalls, the instinct is to push harder — more meetings, more analysis, more “perfecting”. But after ten years working with creative and technical teams at the Apple Developer Academies, I’ve learned the opposite is usually true: the fastest way to get unstuck is a well-designed constraint.

Inspired by Brian Eno and Peter Schmidt’s Oblique Strategies, this half-day development lab uses prompts, constraints and structured exercises to help teams break patterns, unlock original thinking, and leave with real next steps — not just inspiration.

Format: Half-day (3–3.5 hours) Delivery: In person or online Group size: 6–25 (larger groups possible with adaptation)

WHEN TO USE IT

Run this lab when your team is:

  • Stuck in circular thinking, or repeating the same solutions
  • Over-analysing and under-creating
  • Struggling to generate options
  • Needing fresh concepts fast — product, content, strategy, brand, or learning design

It also works brilliantly as a kick-off for innovation days, product discovery, brand or campaign ideation, team off-sites, and new project launches.

HOW IT WORKS

Constraints to force originality. Prompts to change direction quickly. Rapid iterations for volume and variety. Light facilitation so the group stays moving. Then edit and share: make decisions, sharpen thinking, and articulate what matters.

It’s hands-on and fast.

It’s hands-on and fast.

THE HALF-DAY AGENDA

1) Set the challenge (15–20 mins) — Define the problem clearly and choose a target: “What are we trying to create, solve, or decide by the end of today?”

2) Tame the inner critic (10 mins) — A quick reset: separating ideation from evaluation so people stop self-editing mid-thought.

3) Oblique rounds (60–90 mins) — Fast cycles using prompts and constraints to generate options: solo → pairs → small groups; build, remix, combine; “wrong ideas welcome” rounds; forced perspective shifts; quick share-outs to keep momentum.

4) Patterns + shortlisting (30–40 mins) — Identify what’s emerging, cluster ideas, and select the strongest directions.

5) Make it actionable (30–45 mins) — Turn the best ideas into next steps: what to explore, prototype, test or develop — and who owns what next.

OUTCOMES

By the end, your team will have a burst of new ideas (quantity first, quality second), fresh angles on a current challenge, a shortlist of directions worth developing, and clear next steps with owners. They’ll also take away a simple method for breaking creative blocks on demand — and the experience of presenting new ideas quickly and clearly.

Most importantly: people leave feeling unstuck and energised, with momentum, not just inspiration.

A WORKSHOP THAT STAYED WITH SOMEONE

Hi Oscar I wanted to thank you for the Oblique Strategies workshop at Apple Developer Academy – UFPE in 2024. It stayed with me, and eventually led me to build an iOS app around that experience. I tried to approach it with real care for elegance, rhythm, and simplicity. Just wanted to share my gratitude and let you know that the workshop had a lasting impact. Caio Silva App Developer. 

Download Caio’s App Oblique Strategies Ritual Here

WHO IT’S FOR

Product, design, engineering and marketing teams. Founders and startups. Educators, facilitators and creative professionals. Anyone who needs to generate ideas quickly and move forward.

No “creative background” needed — the lab is designed to make creativity practical and repeatable, and it’s built especially for teams who’d say they’re not creative.

WHAT’S INCLUDED

A pre-workshop call (15–30 mins) to shape the challenge and outcomes. Half-day facilitation, in person or online. A simple takeaway pack: prompts, frameworks, and the repeatable process.

FAQs

Is this the official Oblique Strategies deck? The lab is inspired by Oblique Strategies and works in the same spirit — prompts and constraints to shift perspective. I facilitate a structured process around that approach to generate usable outcomes.

What if our team isn’t “creative”? Perfect. This is built for teams who think they’re not creative, because it removes the pressure to be brilliant and replaces it with a repeatable method.

Can this link to pitching and presentations? Yes. Many teams pair this lab with a follow-up session — Storytelling for Pitching or The High-Stakes Presentation Intensive — turning the best ideas into a clear story.

THE ORIGINS

Brian Eno developed Oblique Strategies with artist Peter Schmidt as a practical recording-studio tool: when a session hit a deadlock, he’d pull a card at random and treat its cryptic instruction as a creative constraint — a way to disrupt habits, shift perspective, and get the work moving again. First published in 1975, the deck became closely associated with Eno’s approach as a producer — chance, prompts and “productive accidents” — including his celebrated Berlin-era studio work with David Bowie.

Brian Eno Talking About Oblique Strategies with Bloomberg.

 

BOOK THE LAB

Tell me:

  1. Your challenge or topic (one sentence)
  2. Team size, and online or in person
  3. Your preferred month or date range
  4. Any context — deadline, audience, constraints

Contact Oscar here to discuss workshops for you or your team.