http://en.wikipedia.org/wiki/Four_stages_of_competence

Using that model, I’d say that many of the entrepreneurs I’ve worked with are at the level of unconscious incompetence. They simply do not realize how little they know. Many have had limited business or web experience, yet they assumed their creativity and intelligence would make up for their lacks.

They think they have a clear idea of what they want, but once I start asking detailed questions, there certainty begins to dissolve. And yet, I would be unreasonably conservative if I simply told them not to proceed.

Many of them end up buying themselves an expensive education – they spend $200,000 and at the end of that they know much more about web development than they did before. That’s okay so long as the money wasn’t crucial to their standard of living. That is, they could afford to lose that money. Possibly their next attempt will be more successful. The history of business has a long tradition of the entrepreneur who fails at their first venture but then later succeeds. An example:

John Bayer tried to run a distillery, but he went bankrupt. Then he fell in love with a woman whose father was suffering from severe arthritis, and who therefore was dealing with the pain by drinking large amounts of willow bark tea (at that time, it was the only source of salicylic acid). At dinner one night, the father complained that the bitterness of the tea was burning his mouth and throat. Bayer then decided to run the willow bark tea through his distillery equipment, producing a powder than could be made into a pill and therefore more easily swallowed. This was the beginning of Bayer Aspirin.

Some of the entrepreneurs I’ve worked with might end up like that.

Also, all of us face severe limits of knowledge relative to the future. “Clarity of thought” runs into definite limits when you are running a startup – circumstances arise that could never have been seen ahead of time. Flexibility is needed.

At the moment, my current (but always evolving) ideal for start-up leadership is clarity of thought, informed by experience, and balanced with flexibility, which must also be informed by experience.

On the matter of disorganization I wonder what options we have. The cost for everything to be organized is impractical. Possibly the client has other aspects of their business affairs perfectly in order and in balance it is worth paying the designer/developer double because they aren’t paying the CFO double to keep the books in order. In a perfect world every functional area would be orderly but one must prioritize.

I think the answer is to make the client aware of the cost and allow them to prioritize. Ideally we can even be rational about what we leave disorganized.

Thanks Duane!

-Ron