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Questions to ask about software

What does it do?

What is the main problem it solves?

How does it solve that problem? Can you explain this in 1 sentence? 1 paragraph? 1 page?

Who is going to use it?

Who is the main audience?

Who are the secondary audiences? For example, moderators, admin users, customer support.

Are there things required to operate it outside of the main thing?

For example, admin tools, reports, automated maintenance?

For example, batteries, cables, WiFi access?

What is the maintenance or upkeep requirements?

Does the CMS need to be updated?

Will data become stale and need to be replaced or updated? For example, zip codes change frequently.

Are there APIs that will be upgraded and require changes?

Are there social plugins or other third party tools that may change or stop working? For example, Google Maps, Facebook Likes, etc.

Will the storage eventually fill up?

Will the database explode?

Will cost of some small component (email, text messages, database storage, etc) scale very quickly if successful?

How will required information get into the system?

For example, if a site will recommend restaurants, where will the list of restaurants come from? Where does the information that powers the site come from?

If from other users, when, how and why? Nobody wants to build a database for someone else.

Users

What requires login vs what can anyone do?

Are there different layers of being a user?

Are there relationships between users? Groups, friends, following, etc?

Content Management

Admin Tools

What sort of admin tools will be required?

What sort of customer support tools will be required?

Problem Solving

How will you debug problems?

What happens if offensive content is posted?

What happens if user is abusive?

What happens if security breach?

What happens if data loss?

What happens if server outtage?

If Social / User Generated Content

How will the first users get value before other users arrive?

For example, if my site is about showing me my friends activity, but none of my friends are on the site, what do I see that makes me want to invite my friends?

How will the first users find out about it?

Before something goes viral, it needs to find its first 100, 1000, and 10,000 users.

Do the math!

Signing up 10,000 users in 3 months requires that you sign up 100 people a day.

Signing up just 100,000 users over the first year is about 275 people per day.

How many people do you have to reach per day to get 275 to sign up? If you can convert at a respectable 3%, you need about 9500 people per day to have the chance to say yes. But converting 3% is really high! So you probably need 20,000 people per day to get 275 to sign up.

Paid advertising costs $1+ per click.