How can a hacker ask for startup advice so they get the most value?

The last few weeks I had the opportunity to talk and chat with several (engineer) entrepreneurs who were in various stages of their company. While most entrepreneurs are fairly clear and specific on the problems they are facing, a few are unable to clearly articulate where they could use help or advice. There are several “categories” of  questions and issues that an entrepreneur has. Some questions are procedural – “how do I do this”, others are “introduction”, still others are “transaction-al”.

The most difficult ones for both parties are the “What should I do?”.

Any mentor / advisor will not have enough context (regardless of how much time they spend with your company) to help you by giving the “right answer”.

For these class of questions there is really no right answer.

The right answer does not exist because it comes down to what the entrepreneur wants to do. What she is comfortable with, what her biases are and what her motivation is.

The only thing a good advisor can do is to provide a “framework” for your question.

The only other thing an advisor can do is to give the entrepreneur confidence in herself so she can best utilize the framework to her benefit.

A simple way to think about the “framework” is a set /series of “if-then-else” statements, with <then> and <else> colored with the advisor’s experiences.

E.g. When faced with this issue like <a>, I responded with <b>, but the alternative is <c>.

So, if <you believe “a” is true> and <you also think “b” will happen> then <you should do “c”> else <the other thing you can do is “d”>

The framework is not just one if-then-else. Its a series of them.

Can it be that simplistic you ask?

Yes. That’s it.

The best advisors / mentors listen and ask a lot of questions, with each answer leading to more questions. The questions are to help the entrepreneur think, not for the advisor to assess.

So the next time, as a hacker you are looking for some advice on a question “What do I do?”, then remember to keep a note of the conditional construct.

P.S. For those that know me as a hard-core sales guy and nothing else, I did study DES based cryptography algorithms under Dr. Sherman, who I am sure is absolutely disappointed that I ended up a sales guy in a tech company.