There are two types of decisions – big life altering ones and innocuous ones. The tough part is I dont know which decisions fall into either category. Like Steve Jobs said, you can only connect the dots in hindsight. The amazing part is these decisions are to be taken in every aspect of your startup – engineering, marketing, sales, finance etc.
Let me give some examples:
For BuzzGain, I had a good friend recommend a lawyer who he had worked with. Jim (Cooley) was a smart, very well connected and personable individual. Daniel and he helped me put together our initial structure, complete my 83B election. Being a tech and a sales guy I did not care too much about the 83B election. I was loathe to spend too much money speaking to Jim and Daniel (they are good, but charge by the hour) so I dismissed the paperwork as needless “waste of time”. 3 days after sending me the paperwork, Daniel called me to remind me to send it in. There was a decision I had to make – spend a few thousand dollars today or punt to a later day. Since I was bootstrapping, I was inclined to punt. A couple of days later, Daniels’ paralegal called me and reminded me again to file the paperwork. I did it and it turned out to be the best decision I made on exit.
When our alpha version was out in Sep, I had 15 pre-release customers who were trying out the initial version. The feedback from most was to continue to build the initial database of key reporters and bloggers with a focus on specific markets. I.e. to continue on our original vision and value proposition. Paul though was the only person with an alternative opinion. He asked me to look at his most recent blog posts and compare them to his posts from 6 months before. His focus had dramatically changed from finding and building blogger relationships to engaging on social media. He mentioned that although it would be a dramatic change in our product, it was where things were headed. The decision was rather scary at that point – continue down our path (based on 14 folks feedback) or change course (based on 1 person’s feedback). We chose the latter. Again, the best decision I have ever made.
Now, these decisions were not made in a vacuum. Both alternatives to the decisions had a ton of pros and cons. I needed to build a framework to think about how to think.
My first piece of learning was its always better to see the options and decision criteria in writing. Somehow I have found that writing it in paper (or on your computer) and hence being able to see it (with your eyes) brings a level of clarity that doing it in your mind (hence being unable to see it) does not.
My second piece of learning was that my framework was a tree. The depth of the tree would be the level that was needed to get to two states – Worst case situation and Best case situation. The rest were if-then-else statements.
The third part of my learning was to map out how to undo my decision if I figured out later I had made the wrong decision. If I spent as much time figuring out how to recover from a bad decision as opposed feeling good about a well made decision, I’d be okay.
Try it out. Let me know if it works. If you have learned something else, drop me a note.