The blog article below recently featured on Hacker News. It has a nice list of questions that can be further adapted for use in the context of FOSS movement, esp. the FSDL stage where sustainable income becomes important.
And the related HN Discussion that among others poses a 4th fundamental question to answer:
Would it make sense to quote the questions here to guard against link rot?
Cynical answers:
How do we get customers in the door?
Pay them (how Paypal got started, and effectively the same with all the subsidized money-losing startups like Uber et al)
How do we get customers to the âwowâ moment quickly?
Spectacle and gimmickery, but they have some âwowâ just from the low-cost anyway
How do we deliver value as often as possible?
Just keep the low cost for enough time that it surpasses normal human short-term time reference (Uber et al operate for years while losing money)
Most of the rest of the questions could just as well be considered at Uber et al too, except for âAre we fighting gravity?â
Okay, to be fair, most of this can still be useful to a normal, responsible business. I just am expressing a wariness of framings that work for corrupt businesses. A test to consider is whether some framing is unusable if your basic business model is unsustainable.
Yes, the question certainly need to be adapted. But many of these questions, when reformulated to match FOSS-based sustainable business, have relevancy. It is perfectly okay to have a FOSS project as pure volunteer or hobby project, but too often once popularity comes and strains on maintainers grow, the question arises âCan I keep this going?â If the answer is âYes, if I could get an income from my work so I can dedicate fully to the projectâ, then a whole new world beyond technical concerns needs to be waded through. Where I havenât found too much good material beyond listings of the usual revenue models that a FOSS developer can choose from.
I reformulated Gabriel Maysâ article Business questions worth asking to be a better match for Sustainable FOSS. From here the questionaire can be further improved and additional questions added.
 In this questionaire âsustainableâ refers to:
- Financially healthy to support most work people do.
- Community-based and inclusive to all its participants.
- Focused on the entire lifecycle of solutions that are built.
- Collaborative within larger FOSS-based ecosystems.
Terminology changes:
Other changes:
 Key questions
1. Which pain of our client does our solution remove?
2. How do we quickly delight clients, convey the "wow" factor?
3. How do we reach our clients?
4. How do we deliver most value early and as often as possible?
 Providing value to clients5. How does our solution make things easier or serve clients better?
6. How do we ensure clients using our solution are significantly
better off than before?
7. When clients use our solution, how do we want it to change them?
How do we convey that vision to get them to switch?
8. What value does this deliver to our clients?
9. Are we doing whatâs right for the client? Always? No matter what?
10. Where do clients want to spend money? What encourages them
to keep doing so?
11. How do we understand what people think they want and translate
the value of our solution into their terms?
12. Are we building our offering around solution clients love to use?
13. Are we starting with technology or with client's needs?
We should start with the client and work back towards the tech,
because tech is just a tool to solve a client's problems.
14. How do we put focus on the innovation, not the solution?
 Strategic introspection & key abilities15. Projects positioned in the way things used to be and predicated on old
assumptions may not survive. What assumptions is our solution based on?
Are they still true? Will they continue to be?
16. There are vision problems, sustainable business model problems,
and execution problems. Which do we have?
17. FOSS projects succeed when they focus on what is truly unique to them.
What can we be uniquely good at?
18. Are we differentiated, or are we more like the low-barrier choice?
19. Do we have small objectives, or big ambitions? In other words,
are we chasing field mice or hunting antelope?
20. Are there any places we succeeded because a strong demain for our
solution allowed us to be strategically inept?
Find examples of similar projects that never had to do the hard work of
1) understanding what made them successful and
2) building a real sustainable model until it was too late.
21. What things about our [audience/clients] will never change?
Are we giving enough attention to those?
22. Assume itâs one year from now, and we failed at our goal. What went wrong?
23. What would my replacement do if I would hand over my tasks?
24. Culture is a microcosm of the community member's psychology.
How is our culture shaped by the collaborative?
25. Are we listening enough to the people on the front lines?
26. Are we putting enough importance on making the âimportant thingâ good?
27. Are we involved in too much loose talks (waving our arms)
and not enough true commitment (earning trust)?
28. For project/solution-related services: Are we maximizing our
addressable audience?
29. What fair advantage distinguishes us from unfair business competitors?
 Needs discovery30. How do we embrace the transition to [focus on needs] and adequately
[satisfy needs] for the long term?
31. What needs are we best positioned to satisfy?
32. How will we (financially) sustain ourselves in the future
(satisfy our own needs)?
33. Whatâs the future state of the world, and what changing needs will
people have because of it?
34. If applicable: How do we thrive in a post [past need relevancy] world?
35. Is our positioning realistic, or are we fighting gravity?
 Opportunities & adaptive strategy36. From our current state what would a "delightful" solution look like?
How would we start over? What is the clientâs fundamental problem,
and how do we solve it this way?
37. What big assumptions are we making?
38. What would (holistic) sustainability look like if it were easy achievable?
39. How can we apply commodity services as building blocks for
higher-level services?
40. Complex systems canât be designed. They can only evolve. What synergies
can we ceate around our project, community and ecosystem and all
the people involved with them?
41. Where should we tinker with objectives vs. tinkering with alternatives?
Sometimes related: Itâs often easier to change the our collaborative
framework than to change our fundamental nature as a sustainable
project / business.
42. Are our efforts aligned with our opportunities?
43. If success is achieved by going to extremes, should we even do this?
How would a sustainable project or business do this and stay
true to its values?
 Experience & differentiation44. Are we fully dedicated to removing friction for our clients?
45. Are we thinking about the full lifecycle of the social experience
(from inception to end-of-life) our solution provides?
Do we objectify people as "users" and more narrowly consider only
the UX/UI? Features donât create differentiation, experiences do.
46. Does every solution we have complement the rest of our solutions and
make them more attractive?
47. How can we pull modular components together into solutions around
our client's problems and needs?
 Alignment48. Are incentives (expectations/motivations) across the project, community,
ecosystem and solutions well aligned?
49. What outcomes are we incentivizing? Collaboration is about balancing
a series of incentives where people are motivated and encouraged to do
the right thing because itâs in their best interest, corresponds to their
passions and the values they hold dear.
50. Do we have clear tasks and goals, clearly communicated,
with clear and frequent measurement?
51. Strategy is about decisions and trade-offs: Are we moving one step in 20
directions or 20 steps in one direction? Favor focus over compromise.
Strategy is also about what you donât do.
 Efficiency52. Long term sustainable FOSS depends on many aspects. Sustainability
is a holistic concept. What are the sustainability criteria of our project
and how do we measure them?
53. Where can we turn our efforts to best use to achieve
holistic sustainability?
54. How do we get 80% of what we want for 20% of the work?
55. Are we spending effort, time or money where it does not sufficiently
address our needs and those of our clients?
56. Over the long run, sustainability involves inherent efficiency.
How efficient are we relative to our peers? How do we make continuous
small improvements part of the process to become more efficient?
57. Do we celebrate progress, even if only small steps forward, as a habit?
Today, @aschrijver wrote
FYI Emily Omier wrote a nice e-book (PDF) on Positioning FOSS Projects
I started reading it and I agree that itâs good. Iâm going to extract some gists myself and would like to document them here. Do I need a wiki page or can I update this answer?
Iâm going to take notes in my private Zim wiki until I see a response here.