tmatthewj

I think one way for them to realise is through situations that put them in a position to seek advice and when prescriptive advice goes wrong for them. This need not be in startups but in any wicked environment. I think that could force many prescriptive advisors to reflect on what they dole out in the form of advice.

Glad you liked it.

I hear your rationale to flip the rating for novice-reflective and expert-prescriptive advisors. In fact that’s how I started putting the framework together.

However after talking to a few founders and reflecting on my own experiences I felt there is more value in having an expert in the domain - considering the benefit of contextual stories you get to hear from them on how they handled similar situations. I just feel the merit of this experience though from a prescriptive advisor wins narrowly over the merits of being with a novice advisor even if the person has a reflective method. But I can imagine situations that warrant a scoring like what you suggested. I just hope people who read this note can try and be aware of these aspects to enrich their intuition when choosing advisors.

Agree with you. Very few expert advisors can fight the urge to impose their solutions (prescribe), and give time to reflect on the problem with you.

This is built on the notion of wicked environment defined by psychologist Robin Hogarth, and which was popularised by David Epstein in his book Range.

It was towards the end of 2017 that I got my hands on Principles a book written by Ray Dalio, CEO of the biggest Hedge Fund firm in the World — Bridgewater Associates. I had already read the summary version of Principles by then and was a big admirer of his efforts to build a team based on meritocracy. But one of the best parts of the book that I could relate with was the section under “Work Principles” where he explains how he tried to build a culture in which it is okay to make mistakes and unacceptable not to learn from them.

He goes onto elaborate how his company ended up losing to the tune of hundreds of thousand of dollars because of a careless mistake by one of his employees. He understood that letting the person go would build a culture that’s averse to failures and came up with a public log where everyone should list down the mistakes they commit, explain how it impacted the customers / company in detail and with reflection on how it could be avoided in the future. Everyone is expected to read the error logs and this has helped them avoid recurring mistakes or failures while also building a culture that encourages the team to move fast and break things. More about our adaptation of error logs in the blog post.

Thinking, Fast and Slow - Daniel Kahneman

The Richest Man in Babylon - George Samuel Clason

Zen and the Art of Motorcycle Maintenance - Robert M. Pirsig

How to Win Friends and Influence People - Dale Carnegie

This is such a beautiful thread!

The closest is convertible equity, adopted by a good number of startups during their seed stage. You can read about SAFE by YC and KISS by 500 Startups, 2 informal instruments / agreements used to do convertible equity.