8. If I Were You: The Next 90 Days
The single most important thing
Get 3 organisations on Microsoft Teams to pay for an anonymous all-hands question window before you build the bot.
- Buyer: the person who runs the all-hands or internal comms at an organisation of 100–2,000 people that works in Teams.
- Job: "Let our people ask leadership the hard questions without their names attached, and let us answer them in the open."
- How: start with a concierge pilot. Use an anonymous Microsoft Form, a moderation sheet, and an Adaptive Card that posts the ranked questions to a Teams channel. Charge for it (~$49 per all-hands). Automate only what you've done by hand at least 3 times.
The plan fits ~15 hrs/week. Full-time, compress weeks 5–8 into 3 weeks and run 5 pilots instead of 3.
Week-by-week
| Weeks | Goal | Exit criteria |
|---|---|---|
| 1–2 | Discovery. 10–15 calls with all-hands owners. Ask: how do you collect questions today (Forms, Slido, town-hall Q&A, nothing)? What went wrong last time? Who approves new Teams apps, and how long does it take? What would you pay per month? | You can write the top 3 pains in their words, and you know the IT approval path at 5+ organisations. |
| 3–4 | Concierge pilots. Run the question window by hand for their next all-hands: open the Form, moderate, group duplicates, post the ranked list, post answers back. | 3 paid pilots (5 full-time). If fewer than 2 will pay, the pain isn't real at this size. Change the buyer (internal-comms agencies), not the pitch. |
| 5–8 | Build the thin v1 (Teams only): anonymous post and reply, moderation queue, upvotes, question window with reminders, ranked host view, answers posted back, a rotating-hash design with no stored identity, Stripe checkout. Open Partner Center and start publisher verification in week 5. | Pilots move from the Form to the bot, installed through each organisation's own app catalogue. ≥2 run a second window. |
| 9–10 | Store and search. Create the SaaS offer and link it to the app. Submit to the Teams Store. Publish the "how anonymity works" page, the IT security one-pager and 4 guides for exact searches. Answer 10 existing Microsoft Q&A threads on anonymous posting. | Store submission accepted for validation. 4 guides live. |
| 11–12 | Measure and decide. | 3+ paying organisations (5 full-time), IT approval in ≥2 of them, ≥2 question windows per paying organisation. If you hit it, keep going. If you miss it, go back to discovery or try the agency buyer. |
Kill criteria (write these down now)
If at day 90 you have fewer than 3 paying organisations, or no pilot ran a second question window, the wedge is wrong. Don't respond by adding polls, kudos or a Slack version. Change the buyer or stop.
The one thing to stop doing
Stop keeping the ritual open, and stop assuming Slack first.
"We'll pick the ritual later" means no listing, no search term and no buyer to call. Slack first means launching into the most crowded version of the wedge (6+ anonymous apps), behind a 10-install minimum and a review of up to 10 weeks. Pick anonymous questions on Teams this week.
What stays on the long-term roadmap (only after proof)
- Answer archive tab, admin analytics and Excel/PowerPoint export.
- Publisher attestation (by month 6), then Microsoft 365 Certification only when an enterprise buyer asks.
- The Slack port, after the month-12 gate, as a second listing on the same backend.
- Per-event pricing, if subscriptions churn after one use.
- Translation for multinational tenants.