De-Risk the Biggest Swings First
Run discovery and delivery in parallel — and put the top-right, riskiest bets into discovery first.
- Difficulty
- Advanced
- Time to result
- ~months to results
- Steps
- 5
- Confidence
- 91%
Hearst's favourite operating framework inverts how most teams use an impact/effort or risk/reward two-by-two. Everyone maps opportunities onto the grid; most teams then ship the safe, predictable, small swings and defer the top-right. Hearst's rule is the opposite: send the biggest, riskiest swings into product discovery first, run discovery continuously alongside delivery (dual-track agile), and treat the leader's job as absorbing the accountability so the team has permission to fail. Ideas graduate from the discovery track to the delivery track only once their risky assumptions have been de-risked into predictable ones.
Origin
Hearst learned dual-track agile from a manager at Hailo who introduced her to Marty Cagan's work (SVPG); she has since befriended Cagan. Dual-track agile itself originates with Desiree Sy and Lynn Miller's agile UX work and was popularised by Cagan and Jeff Patton. The 'prioritise the top-right first' inversion and the leader-absorbs-accountability rule are Hearst's own emphasis, and she links it to the folk-wisdom of 'eat the frog' (do the hardest thing first).
Core principles
- 01Discovery and delivery run simultaneously and continuously, not sequentially — never lob designs over the wall to engineering.
- 02Discovery is a de-risking engine: it converts high-uncertainty assumptions into known ones fast enough to keep innovating.
- 03If you always favour the low-risk, predictable, smaller swings, you will never truly innovate.
- 04The top-right of the grid — biggest impact, biggest risk — is where discovery belongs, not where things go to be deferred.
- 05It's a less safe choice, so the leader sits in the hot seat: accountability for failed bets belongs to the leader, not the team.
- 06Permission to fail is what makes de-risking possible — teams that can't fail can only ship safe work.
- 07An idea only moves to the delivery column once it's been de-risked into a low-risk, predictable bet.
- 08Full de-risking is not always available — sometimes you draw the owl: start with the circles and just figure it out.
How to run it
- 1
Map opportunities on the two-by-two
Plot every opportunity on an impact/effort or risk/reward two-by-two. This part is standard; the framework departs from convention at the next step.
- 2
Send the top-right into discovery first
Take the biggest swings — the high-reward, high-risk items in the top right — and prioritise them first for product discovery. Do not defer them behind a queue of safer work.
Pro tip This is the product equivalent of eat-the-frog: do the hardest thing first and everything after it is easier.
Watch out Constantly deferring the top-right in favour of lower-risk, more predictable smaller swings is exactly how a team stops innovating without noticing.
- 3
Run discovery and delivery as two live tracks
Keep a continuous cycle where discovery de-risks assumptions while delivery ships already-de-risked work. Do not let designers tinker in isolation for a month and then hand off to engineering.
Pro tip Speed of the discovery loop is the whole point — it's how you chart new paths to innovation by finding your thinking errors early.
Watch out Waterfall in disguise — a long design phase followed by a build phase — kills the loop and re-introduces all the risk at build time.
- 4
Take the accountability yourself and give the team permission to fail
As the leader, publicly own the downside of the risky bets. Explicitly grant the team permission to try things and have them not pan out, so they will actually test the risky assumptions rather than quietly steering to safe work.
Watch out Without this, teams read 'de-risk the biggest swing' as 'be blamed for the biggest failure' and will not engage honestly.
- 5
Graduate de-risked ideas into delivery
When discovery has reduced an idea's risky assumptions to the point where it is low-risk and predictable, move it into the delivery column and execute it.
Pro tip Accept that some things never fully de-risk. At some point you draw the owl — start with the circles, then just go do it.
In the wild
A manager at Hailo introduced Hearst to Marty Cagan's work, and the team emphasised dual-track agile — running discovery and delivery simultaneously, with a continuous cycle of de-risking assumptions rather than a waterfall hand-off from designers to coders.
→ It became the framework Hearst still returns to and shares, and she has since befriended Cagan directly.
Hearst cites Twilio's company value 'draw the (effing) owl' — the meme where the instructions are 'draw some circles, then draw the owl'. It names the case the de-risking framework can't cover: sometimes you can't know the exact path, and you simply have to go for it.
→ A paired heuristic: de-risk what you can, and when you've run out of de-risking, start with the circles and get it done anyway.
Common mistakes
Deferring the top-right forever
Consistently choosing the lower-risk, more predictable, smaller swings feels responsible quarter to quarter, but it means the team never innovates or reaches the next level.
Sequential discovery-then-delivery (waterfall wearing agile clothes)
Designers going off for a month and lobbing the result over the wall to engineers means all the assumptions get tested at build time, when changing them is most expensive.
Pushing the risk down to the team
Big swings are the less safe choice. If the leader doesn't sit in the hot seat and absorb the downside, the team has no permission to fail and will retreat to predictable work.
Is it for you?
Best for
Product leaders and heads of product running teams that keep shipping safe, incremental work and can't explain why nothing innovative ever ships.
Not ideal for
Pure execution phases (a committed launch date, a compliance deadline) where the roadmap is already de-risked and the job is delivery, not discovery.
From the transcript
“this idea of having dual track agile going, where you're doing discovery and delivery simultaneously, and doing it in a way that's not waterfall”
“and actually prioritizing those first in terms of product discovery and figuring out what can you do to start de-risking because if you constantly put…”
“accountability, so if some of these things don't pan out, it's on you and not on your team and kind of give your team permission…”
“It reminds me of this piece of advice that people call eat the frog”
From the episode
Monetizing passions, scaling marketplaces, and stories from a creator economy vet
Camille Hearst (Spotify, Patreon, Apple, YouTube)