The Fruit Story: Leadership Pre-Alignment Interviews
Interview your leaders and surface their pet ideas before building strategy, so reviews don't become fruit rejection.
- Difficulty
- Easy
- Time to result
- ~weeks to results
- Steps
- 3
- Confidence
- 90%
A pre-alignment ritual inside the preparation phase: before building a strategy, systematically interview the leaders who will review it about what success and failure look like, and ask for their pet ideas. The 'fruit story' is the cautionary parable — presenting a mango, then an apple, then a banana to a reviewer who rejects each in turn — that this avoids.
Origin
Chandra Janakiraman's framing, illustrated with his own 'fruit' parable of frustrating strategy reviews.
Core principles
- 01Engaging leaders before you build is cheap insurance against a wasted review cycle.
- 02Asking leaders what they want is a sign of strength and humility, not weakness.
- 03Leaders almost always have a pet idea they're shy to volunteer for fear of seeming like a micromanager — asking removes the mystery.
- 04These conversations energize leaders because they're more fun and creative than their usual meetings.
How to run it
- 1
Divide and conquer the leaders
Assign each relevant leader to a member of the strategy working group so the interviews happen in parallel.
- 2
Ask the core questions
For the specific product/feature, ask: what does success feel like, what does failure look like, what's the measure of success, and what principles should be kept in mind through the process.
Watch out Keep the questions centered on the specific product being worked on, not strategy in the abstract.
- 3
Ask for their pet ideas
Explicitly invite each leader's favorite or pet idea. It gives them a creative outlet and takes the guesswork out of what they secretly hope you'll build.
Pro tip Also pre-flight the emerging pillars with your own manager on Day 2 of the strategy sprint so there are no surprises at rollout.
In the wild
You bring a mango — 'I don't like mangoes.' You bring an apple — 'I stopped eating apples last year.' You bring a banana — 'I've hated bananas since I was a kid.' Each round frustrates both sides.
→ The lesson: had you simply asked the reviewer what fruit they like before presenting, the whole review would have gone far better.
Common mistakes
Assuming interviews waste leaders' time
People fear engaging senior leaders is a burden; Janakiraman found the opposite — leaders welcome it and bring positive energy.
Is it for you?
Best for
A PM about to invest 8–12 weeks in a strategy who wants leadership buy-in baked in rather than fought for at the end.
Not ideal for
Contexts where leadership access is impossible, or where the strategy is deliberately bottom-up with no reviewer to align.
From the transcript
“what does success feel like for for the leader what does failure look like you know what is the measure of success what are principles…”
“yeah and also like I think ask them for their favorite or pet ideas”
“it's actually a sign of strength and humility to ask your leaders what you want”
“there's a bit of grade of Truth there which is you know imagine how frustrating that is for both the reviewer and the person like…”
From the episode
An operator’s guide to product strategy
Chandra Janakiraman (CPO at VRChat, ex-Meta, Headspace, Zyng