The Oblique Strategies Development Lab
Unblock ideas fast. Generate fresh angles. Make progress when you’re stuck.
When a project stalls, the instinct is to push harder, more meetings, more analysis, more “perfecting.” However my experience of working with creative teams in The Apple Developer Academies, is that constructive constants can have a huge impact on shifting individual and team perspectives.
Oblique Strategies is designed to: shift perspective quickly and get ideas flowing again, from fresh angles.
Inspired by Brian Eno and Peter Schmidt’s Oblique Strategies, this half-day development lab uses prompts, constraints, and structured exercises to help individuals and teams break patterns, unlock original thinking, and leave with real next steps.
Format: Half-day (3–3.5 hours)
Delivery: In-person or online
Ideal group size: 6–25 (larger groups possible with adaptation)
This helps with
Oblique Strategies is especially useful when your team is:
- stuck in circular thinking
- wants an out of the box thinking experience
- over-analysing and under-creating
- repeating the same solutions
- struggling to generate options
- needing fresh concepts fast (product, content, strategy, brand, learning design)
It also works brilliantly as a kick-off for:
- innovation days
- product discovery
- brand or campaign ideation
- team building offsites
- new project launches
Outcomes
By the end, participants will have:
- a burst of new ideas (quantity first, quality second)
- fresh angles on a current challenge
- a simple method to break creative blocks on demand
- a set of shortlisted ideas worth developing
- clear next steps and ownership (who does what next)
- expense of presenting new ideas quickly and clearly
Most importantly: people leave feeling unstuck and energised with momentum, not just inspiration.
Interested in running Oblique Strategies with your team?
Tell me what you’re stuck on, how many people are involved, and whether you want online or in-person delivery.
Get in touch with Oscar here
How it works
Oblique Strategies works because it interrupts default patterns.
Instead of “try harder,” we introduce:
- constraints (to force originality)
- prompts (to change direction quickly)
- rapid iterations (to get volume and variety)
- light facilitation (so the group stays moving)
- edit and share (make decisions, sharpen thinking, and articulate what matters)
This isn’t a theory session. It’s hands-on and fast.
Half-day agenda
A typical flow:
1) Set the challenge (15–20 mins)
Define the problem clearly and choose a target:
“What are we trying to create/solve/decide by the end of today?”
2) Tame the inner critic (10 mins)
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 quickly:
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solo → pairs → small groups
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build / remix / combine
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“wrong ideas welcome” rounds
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forced perspective shifts
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quick share-outs to keep momentum
4) Patterns + shortlisting (30–40 mins)
In small groups, 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.
Who it’s for
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Founders and startups
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Product, design, engineering, and marketing teams
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Educators, facilitators, and creative professionals
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Anyone who needs to generate ideas quickly and move forward
- No “creative background” needed. The workshop is designed to make creativity practical and repeatable.
- What’s included
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Pre-workshop call (15–30 mins) to shape the challenge and outcomes
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session facilitation (half day)
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A simple takeaway pack: prompts, frameworks, and a repeatable process
Book
If you’d like to run Oblique Strategies with your team, email:
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Your challenge/topic (one sentence)
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Team size + whether you want online or in-person
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Your preferred month/date range
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Any context (deadline, audience, constraints)
Contact Oscar here to discuss your requirements.
FAQs
Is this the official Oblique Strategies deck?
The workshop is inspired by Oblique Strategies and uses 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/presentations?
Yes. Many teams pair this workshop with a follow-up session turning the best ideas into a clear story and pitch.
The Origins of Oblique Strategies.
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. The deck (first published in 1975) was designed specifically to spark lateral thinking and break blocks, and it became closely associated with Eno’s approach as a producer: using chance, prompts, and “productive accidents” to unlock new directions in the room. It’s even been linked to his work in the recording studio with David Bowie during the Berlin-era recordings, where the idea was to change the process so the music could change too.