Asking yourself the "what happens if..." questions

[Ewan McIntosh]

Rick Segal came to Scotland a few years ago and spent some time (along with Shel Israel) researching who was doing what with social media. He has been a programmer and VC, and is one of the most incisive questioners I've had the privilege to know, cutting to the chase and asking about the things you hoped would just sort of, well, pan out in the end.
He recently wrote a post which applies almost every time to companies filling in their first ever specification for their 4iP idea: people who forget to ask the "what happens if..." questions always ...:

Let’s say that an investor and a founder agree to a two stage funding scenario. This isn’t me, by the way, just an example I’m making up as I type this. Chunk one on closing, chunk two based on milestones. Now, typically, both sides will know they need to create the measurable milestones which would be the added to the financing documentation. Both sides agree on language with respect to obligation or right but not obligation, etc. Then, off to the lawyers.

The smart lawyers all start with the what if questions. What if the investor doesn’t want to fund. What happens if only one of the seed guys fund and not the other 3? What happens to board seats, the founders equity, etc. When both sides have their own legal teams, it gets expensive fast because each side is walking their client through what if scenarios and why one flavor is better or worse for their side. Lawyers push back, a little posturing, yadda yadda and eventually you and the investor get a punch list and walk through the issues to varying degrees of compromise. This is expensive and that punch list should be done upfront.

Read more: http://ricksegal.typepad.com/pmv/2009/07/eyodf-part-two-the-l-word.html#ixzz0NVrNe3dR

Today I was with a group of newly graduated new media-istas, going through the process of using a boring, dry specification as a means of asking all those tricky questions as we form and develop ideas, rather than forming the idea and then shoehorning it later into a specification to keep your investor or funder happy. It'll be interesting to see how this approach, rather than aiming roughly in the 4iP direction, might help form more sound business ideas.

What do you think? Taking these questions into account, as we do, means that the process of commissioning a new company or idea takes more time than simply running into it and worrying later. Should creativity behind fresh ideas be unbridled or does the addition of those "what happens if..." questions at a much earlier stage sound like the kind of thing that might help us come up with better ideas that people really want?

[Coll Maclean]

"What if" is too late......................."if what"............is what we do here,"if what" we have agreed is our best pitch lets go for it...the what ifs come from the client at the first pitch ideas...................Here I am not talking Web Design but our Branding we do for Clients here & overseas & our own Produced Products.......................maybe it is the same !!

[Karen Doherty]

Agreed Colin. I'm not a naturally patient person and a too much talk/too little action switches me off totally. I don't mind addressing small things as we progress through a project but the big questions should be always addressed at the outset.
I also believe that the best creativity comes from hitting the right mix of people for a project. It's rarely a one mind product. Creativity is a tapestry of concept and collaboration. Or am I mixing my metaphors too much - a tapestry coin??? There's a thought... ;-)

[Colin Gilchrist]

Karen my thoughts exactly. "What if questions" are essential to ultimately develop the project into the final offer.

However as Guy Kawasaki mentioned at the event in Edinburgh earlier this year - if you see the idea has potential get on with it, maybe phase 1 isn't perfect but you know what, it'll never be perfect...

[Karen Doherty]

I think creativity and "what if" questions are two sides of the same coin. Creativity needs a "what if" framework to ensure sustainability or a terrific project can be scuppered very early on. The best creators are able to allow ideas to seep in during a shower, a daydream whenever but, crucially, can also generate the best circumstances for success by asking those "what if" questions rather than firefighting later. Often, non-contractual "what if "questions can be a stimulus to creativity, The contractual "what ifs" should be seen as a mutually protective measure - sometimes frustrating and costly but necessary.

The tricky thing is balancing and spinning the creativity/what if coin on its edge because, let's face it, that's the fun part.