Troublesome hiring, missed Amazon shares, and how to improve your judgment

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Ashley Friedlein is the CEO & Founder of Guild, a messaging app for professional groups, networks, and communities. He's also the Founder of Econsultancy, a community for marketers learning about digital marketing.

Biggest fuck up

Not going through with my purchase of £1k worth of Amazon shares when they floated in 1997… they’d be worth £1.2m now! I have a hatred of filling in long forms and gave up on the application form near the end. Oops.

But generally, there isn’t a single moment. As an entrepreneur, you have highs and lows, successes and failures, crowning glories and fuck ups almost every day. Hourly even.

Your emotions can swing from elation to despair surprisingly quickly. On the whole, I’ve made good decisions and had good judgment.

Ashley Friedlein is the CEO & Founder of Guild - No Wanky Bollocks

The exception is around people. I sometimes say business would be easy if it wasn’t for customers and staff 😉

Staff are more troublesome than customers usually. Despite reading endless advice on how to interview and how to run a recruitment process, I still don’t feel any closer to getting that right reliably. And then it is too easy to bury your head in the sand about a people problem rather than confront it properly.


Lack of personal integrity. Not meaning what you say, not doing what you say.

Sometimes this exhibits itself in the disingenuousness of ‘office politics’, sometimes in hollow ‘management speak’, but mostly it is just when people don’t have the courage or honesty to say what they actually think or feel.

Life is too short to waste time in this way. Politicians are the other obvious candidates, of course. Actually, people tend to respond well when politicians appear to be honest – at least in the sense of saying what they really think. Trump is perhaps able to get away with so much because he is, well, Trump, and you can’t say you’re surprised by his behaviour?

Integrity is also about taking responsibility, being accountable, getting stuff done, and admitting when things haven’t worked. There is still too much ‘arse covering’ or people who avoid pulling their weight.

Useful advice

The most important thing for success is good judgment. Making the right decisions and getting the timing right. But there are very few rules, or best practices, around improving your judgment.

I have found over the years that if you’re sure about something, or even 75% sure, you should act quickly and decisively.

“A good plan, violently executed now, is better than a perfect plan next week”

George Patton

However, if you have doubts, then you should just wait. Be honest with yourself that you don’t know – waiting is a decision in itself. It is amazing how problems seem to resolve themselves or go away if you just wait.

My other observation on good judgment is borne out in these three quotes.

Listening to feedback but also making decisions based on a more nuanced understanding of intent and psychological drivers behind what people say.

“Remember: when people tell you something’s wrong or doesn’t work for them, they are almost always right. When they tell you exactly what they think is wrong and how to fix it, they are almost always wrong.”

Neil Gaiman

“You should listen to your customers but you shouldn’t do what they say. You should understand why they’re saying it.”

Alessandra Bellini, Chief Customer Officer, Tesco

“We are stubborn on vision. We are flexible on details. […] The thing about inventing is you have to be both stubborn and flexible, more or less simultaneously. The hard part is figuring out when to be which!”

Jeff Bezos


  1. “Remember: when people tell you something’s wrong or doesn’t work for them, they are almost always right. When they tell you exactly what they think is wrong and how to fix it, they are almost always wrong.”

    This reminds me of the Dunning–Kruger effect, the people who are trying to actively convince you of the ‘truth’, don’t know the truth!


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