How I Approach Coaching First Time Entrepreneurs

Criticism is about what was. Coaching is about what could be

Every once in a while I get requests from friends and collaborators about mentoring someone. Last week I was contacted by a teacher from a local University who wanted to introduce me to one of her students; a aspiring entrepreneur with a love for technology.

The teacher wanted me to listen to his ideas, help him figure out what to focus on and how to proceed. I get these types of requests quite often, so I’ll spare you the details about our conversation. What I want to focus on is on the mistake I’ve seen people make when coaching others: criticizing.

Criticizing is about what was. Coaching is about what could be.

It’s quite common for people who are in their first crack at entrepreneurship to ask: do you think this will work?

This is not the correct question. If you’re motivation depends on hearing a “yes” from someone else to validate your thoughts then you might as well stop what you’re doing. It doesn’t matter what I think. What matters is that you’re committed to whatever it is that you want to do.

When someone asks me for feedback or advice, I don’t criticize their ideas. I focus on listening, providing insights and amplifying up their perspective. In the case of this 19 year old student, I listened intently to his ideas and never once remarked about the value I saw in them. Rather than focus on their idea, I focus on their intention.


Because there are a few things you can count on to be true when it comes to people and their ideas:

  • People will mostly come up with ideas that already exist;
  • They’re motivated to make money, not to solve a pressing problem for people;
  • Their ideas will be either too simple or very complex.

Remember: Brilliant thinking is rare and courage is in even shorter supply.

With that said, if you take my criteria for innovation – new, surprising and radically useful – you’ll understand that I’m likely to put someone down if I focus on their idea. So, I don’t tell them what to do. I help them figure out how make it more new, surprising and radically useful; and then how to do it.

Below are three key principles I encourage people to focus on:

  1. Don’t make an idea more complex for the customer or user; make it harder for someone else to copy you.
  2. Ideas can be too complex or too simple; but you can always make them easier to adopt.
  3. Do what are others unwilling to do.

The last point is The Golden Rule of Strategy.

Strategy is hard because it requires making tough choices. And my experience with first time entrepreneurs reflects that because they rarely think about making them. Rather they want to focus on the easiest path to profit; there isn’t one.

To conclude, I help first time entrepreneurs be more ambitious and clear in their thinking. People of different occupations seek for career coaching in New Jersey and beyond. Are you an Attorney looking to switch careers? Julie Han can help.

Ping me on Twitter or send me an email if you’re a first time entrepreneur and want to brainstorm ideas with me 😉

Also published on Medium.

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