September 6th, 2024

Work with people who tell you when you're stupid

Greg Kogan reflects on his early consulting days, realizing the importance of comfort in business travel and encouraging open communication about financial decisions, leading to improved travel standards.

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Work with people who tell you when you're stupid

In a reflective piece, Greg Kogan recounts a lesson learned during his early days as a consultant regarding business travel expenses. On his first trip to San Francisco in 2014, he opted for the cheapest accommodations and flights, believing he was being frugal and responsible by not billing the company for his expenses. Despite the value he provided to the client, Scalyr, he declined reimbursement offers from the CEO, Steve, insisting he was fine with his arrangements. A subsequent conversation with a fellow consultant revealed the impracticality of his approach, as the friend emphasized the importance of comfort and convenience in business travel, which included billing clients for expenses. This realization prompted Kogan to reassess his travel standards and foster open communication with peers about financial decisions. He now encourages a culture where colleagues can candidly point out unwise choices, whether in travel or marketing strategies, and has since adopted more reasonable travel practices.

- Kogan initially believed frugality in business travel was commendable.

- A conversation with a peer led to a change in his approach to travel expenses.

- He now values open communication about financial decisions among colleagues.

- Kogan has set higher standards for his travel arrangements since the experience.

Link Icon 11 comments
By @exabrial - 4 months
Thomas Sowell — "When you want to help people, you tell them the truth. When you want to help yourself, you tell them what they want to hear."
By @acheong08 - 4 months
I do agree. I’ve been working on a month long hackathon recently with a team & one of the issues we have is that since none of us know each other well, we’re a bit more reserved. This has meant that some team members have gone down really stupid paths or coded with extremely bad style (tons of magic numbers, xyz as variable names, no type hints, etc) with nobody to stop them. I wish I had the ability to call them out but when they’re an Oxford graduate and you’re just a Cardiff nobody, it’s hard to say anything without angering the whole group.
By @biomcgary - 4 months
I'm fortunate to work in a biotech startup where the CEO actively encourages people to push back on him and he seems to relish it. In fact, one of my colleague's unofficial job titles is "devil's advocate", particularly around statistical claims (e.g., anti-p-hacking).

It helps that the team members are all fairly experienced, have a previous history of working together, and are generally mature individuals. I'm not sure it works without that filter, which is possible for us because our CEO is a serial founder with a deep network of competent people.

By @huhkerrf - 4 months
I want to be nice, but there is "write bad code" stupid, and then there is "pay for your business travel yourself" stupid. How did his manager never pull him aside and tell him to stop it?
By @toofy - 4 months
i agree, however, because ive seen people unironically argue otherwise, i’d expand it a little: work with people who are intelligent enough to give constructive criticism.

i have more than enough experience building teams to know with confidence that if alice is naive enough to tell bob, mallory and eve they are stupid—no matter alice’s skill level—the majority of time her team will not perform as well as the other team where david has learned how to give constructive criticism.

criticism is one of the key mechanisms a team needs, but someone skilled at delivering that criticism is every bit as valuable as the unicorn.

By @Jemm - 4 months
No! You have it all wrong. We have to be positive all the time and never ever say anything that might be construed as negative or critical.
By @hirvi74 - 4 months
People telling me I am stupid would be redundant information. I already know this, and I do not try to come off as anything superior. I am only concerned with how I can harness the same stupidity for improvements.
By @more_corn - 4 months
The people who most need to hear this cannot hear this.
By @wiskinator - 4 months
Yes and, I hate working with people who think this means you can literally say “you are stupid” and that this the same as providing helpful feedback.

If you are blunt to the point of being rude, then any communication you’re attempting is going to get lost behind the other person getting angry. People, generally, don’t think productively if they feel attacked, diminished or insulted.

You’ve gotta phrase what you want to say in a way that won’t elevate someone’s emotions beyond the point that they can actually hear your real feedback.

By @AnimalMuppet - 4 months
As long as they can take it too.

That is: When I decide you're being stupid, it's not always you who's being stupid. Sometimes it's me. Sometimes when I tell you you're being stupid, it turns out that I am. If I'm going to tell you, I need to be open to finding out that, no, actually I'm being stupid on this question.

By @WarOnPrivacy - 4 months
> Work with people who tell you when you're stupid

...and who you trust to deliver that info: re ++knowledge, --agenda

Other info (like having bad breath or taking-up-1.2-parking-spaces-in-a-full-lot-is-bad) can be trusted from anyone.