There’s something valuable in the way these lessons keep returning to character, honesty, and judgment rather than credentials alone. The line “Remember to be human” feels like the clearest summary of the whole piece.
Thank you! I listen to too much content about the UK business market haha. You’re probably the one person who will read this essay and know that company. I’d love to try their stuff. I have a whole list of companies to check out and restaurants to try next time I make it back there!
And yes, I think kindness is underrated. I definitely have had many moments of not living up to my own standards, but it was something I really tried hard to instill with my team in the past.
Interesting! That sounds really cool. It’s funny because that totally sounds like the kind of event that would never work, but I’m sure they did a great job!
Great article. I’ve hired people over my career - never on the scale you discuss. I always looked for the people who take ownership. I do it myself. I’m the guy that stays until 2am to get the work ‘right’ and I want others who do the same. It’s always served me well. I take ownership. My last job, I was working on a project and my boss (I didn’t meet her until I was a week in) stuck her head in the office and said “It’s 4:30. Go home. The project will be here tomorrow.” I’d never heard that in 30 years. I could have kissed her.
That sounds like a great boss! I had to do the same thing with my team a few times. Some of them basically refused to take breaks. Sometimes I’d even selfishly say “you’re worth more to me tomorrow if you’re well rested” haha. (Maybe not the best thing to say but who knows…)
I really enjoyed these lessons and reflections, man!! I always usually go with my gut when hiring more than experience..sometimes it works for me, and sometimes it backfires lol.
Thank you, @Danielle Wright! And thanks for your help reviewing it. Haha yeah I feel like I always lean to hard one way. I either go with my gut maybe more than I should, or I totally second guess myself.
This was great - more than almost anything else, I think hiring and firing are things that are hard to learn to do well without making real 3D mistakes. Thanks for sharing yours, sharing wisdom, and normalizing the learning process.
What stood out to me is that you asked every teacher the same two questions. That consistency is a big part of why the answers told you so much, because you could compare them across hundreds of interviews. On lesson 4, the best way I've found to respect a "too good to be true" feeling without letting it turn into bias is to turn it into one more concrete question, like asking them to walk through a past project that slipped and what they did about it, and asking every finalist the same thing. Looking back, is there a question you wish you'd asked Candidate 1?
Hi Kat! Thanks! I wasn’t always so consistent, but I got to a system where I had an interview script I followed for a few years. It was definitely super helpful to be able to compare everyone’s answers on the same questions!
Yeah, I definitely asked things like that, and I did love that Candidate 1 seemed to have a real heart for students. I think perhaps the red flag I could have noticed is that he already had his own thing going sort of on YouTube and he had some pretty good experience with the government.
Sometimes, you have to be skeptical of people who are sort of mercenaries for hire (for lack of a better term) rather than people who are super committed to working at a particular company they really love. We often had success hiring people who had slightly less experience but who really liked our mission. They were often so grateful we gave them a chance that they’d stay for a few years.
I don’t know if there really is another question I would have asked! He answered pretty much all the questions well from what I remember. I think I was scared of being biased toward Candidate 2 because I simply liked her better as a person. But sometimes that counts for something!
This is really good! As a school director, I’ve interviewed and hired a lot of teachers over the years, and your points are spot on. I especially appreciated the fourth one. Almost every hiring mistake I’ve made involved something feeling a little off, but I convinced myself that the person’s experience or credentials made them the right choice. I’ve also learned that character and personality ultimately matter much more.
I didn’t realize you were a school director! That’s so cool. My experience was weird because I never taught and ran a kind of unusual program so I’m not even sure how a school would view my experience. But I’m a board advisor for another EdTech startup now called Electus, so it’s been nice to get back into the education world.
At what kind of school do you work? Did you ever teach?
I have been running a preschool and kindergarten for the last 16 years. Prior to that I taught high school and middle school for 7 years. I also run camps for elementary and middle school kids. It sounds like you work on some cool stuff!
500 interviews made me laugh because I think I’ve done the applicant-side version of this in applications alone. At some point it stops being a job search and becomes field research.
The bit about treating candidates like humans really lands for me though, because people absolutely remember the process. I have forgotten job descriptions. I have not forgotten the companies that made me feel like I was applying to join a secret society with no contact information.
And your Candidate 2 story is exactly why I think honesty is underrated in hiring. “This year is going to be a nightmare” is somehow much more trustworthy than the usual “fast-paced environment with exciting opportunities for growth” 😂
Also, every hiring manager should be forced to read the line about rejected candidates becoming future customers, collaborators or critics before they hit send on a generic rejection email.
Haha… that’s a lot of job interviews! I’m glad I haven’t had quite that many on the application side!
Yeah… I have a tendency to be honest (sometimes too honest!). Sometimes it’s bitten me, but a lot of times it ends up being really helpful. I think in the case of hiring, being honest means you get someone who really wants the true job, not the shiny fake version of the job.
And yeah, I don’t get why some companies don’t seem to care about that! I think they get so arrogant they think “well, we’ll still have other people who like us…”
But imagine if that famous author’s team had treated me better in the interview process! I’d probably still be going around talking about how cool they are, even after getting rejected!
I wonder if “gut” sometimes becomes the word we use for information we’ve noticed but can’t yet articulate. You clearly detected something that didn’t fit, even though you couldn’t explain it. I’d be curious what repeated experience does to that gap between noticing a signal and being able to name why it matters.
I’m sure that experience shortens that gap between the two! I think it’s kind of an example of system 1 and system 2 thinking, with the pre-frontal cortex vs. the limbic system.
I think one thing about modern culture is that we really tell people not to listen to their intuition, because that sounds like bias (which most of the time people interpret as a bad thing). Obviously, we don’t want to be biased and rule out candidates for arbitrary or discriminatory reasons, but I think sometimes we end up not even trusting our own intuition when something seems off.
Somehow I think we need to get back to a point culturally where we are more comfortable using both data/logic and intuition.
I think the experience piece is what interests me most here. I’d be a little careful mapping System 1 and System 2 directly onto the limbic system and prefrontal cortex, because the neuroscience is more distributed than that. But experienced pattern recognition is fascinating. Sometimes we may detect that something doesn’t fit before we can identify which cues produced that judgment. The hard question then becomes: when has experience produced useful pattern recognition, and when are we simply feeling the pull of a bias?
I value character as well, but I also think skill matters just as much. I believe a balance of both is better than character alone. I even applaud you for treating applicants as people. More hiring managers need to practice this method.
Thanks, Erin! I’ve found for a lot of not as specialized jobs like customer service, you can train a lot of skills, but you can’t really train character or personality. And then for more specialized jobs like finance, the skill is kind of just a minimum requirement for the job. So if they didn’t have that, I wouldn’t consider them. But if they did, I’d be evaluating them on character.
Great article. During my 25+ corporate career, I could not count how many candidates I have interviewed. I would say this is a good list. Particularly point 2, I would not stress enough how important “culture fit” is in corporation, especially for major corporations.
Thanks so much! Wow, I can imagine you have a ton of good stories too! Do you have any examples of particularly important hiring lessons you learned in your career? Or especially good/bad hiring stories?
Thank you! I actually have a few hiring lessons that have stayed with me over the years. I’m writing a series called “25 Lessons in 25 Years,” and some of my hiring reflections will be part of it.
A couple that immediately come to mind: I like to ask candidates about their five-year plan. It tells me a lot about what they’re looking for and whether the role and organization can genuinely support where they want to go. I also like asking them to describe their “perfect coach.” That helps me understand how they learn, what kind of support brings out their best, and, importantly, how I can better support them once they join the team.
For me, hiring has never just been about finding the person who can do the job. It’s about understanding what they need to thrive—and whether I can create the environment where they will.
I’m looking forward to it! Definitely send it to me one you post it. Yeah, the 5 year question is interesting. I often wonder if people answer it honestly. I think a lot of people don’t totally know what they want to do in 5 years (or they might be envisioning themselves at a different job!)
I really like the perfect coach question! That’s a really interesting way of seeing how a person wants to be communicated with and what they’d find encouraging.
“ The perfect coach “ question is a steady one I have used for years. It helped me find good hires, also helped me adjust my approach accordingly as different people need different supports.
Many of my mentees are now in leadership roles, they found this question helpful in recruiting as well.
Thank you for the restack @Jason Stevens!
There’s something valuable in the way these lessons keep returning to character, honesty, and judgment rather than credentials alone. The line “Remember to be human” feels like the clearest summary of the whole piece.
Thanks so much! I’m so glad those themes came through and that you liked the essay!
That's a brilliant anecdote about the Bold Bean Company.
A great reminder that being genuinely kind to folk is always good business.
And I can also give a first-hand verification that their produce is spot-on - I buy it every week!
Thank you! I listen to too much content about the UK business market haha. You’re probably the one person who will read this essay and know that company. I’d love to try their stuff. I have a whole list of companies to check out and restaurants to try next time I make it back there!
And yes, I think kindness is underrated. I definitely have had many moments of not living up to my own standards, but it was something I really tried hard to instill with my team in the past.
100%, decency tops everything in business.
And yes, it's really the company of the moment, they just hosted a bean pop up in Soho!
Interesting! That sounds really cool. It’s funny because that totally sounds like the kind of event that would never work, but I’m sure they did a great job!
Great article. I’ve hired people over my career - never on the scale you discuss. I always looked for the people who take ownership. I do it myself. I’m the guy that stays until 2am to get the work ‘right’ and I want others who do the same. It’s always served me well. I take ownership. My last job, I was working on a project and my boss (I didn’t meet her until I was a week in) stuck her head in the office and said “It’s 4:30. Go home. The project will be here tomorrow.” I’d never heard that in 30 years. I could have kissed her.
That sounds like a great boss! I had to do the same thing with my team a few times. Some of them basically refused to take breaks. Sometimes I’d even selfishly say “you’re worth more to me tomorrow if you’re well rested” haha. (Maybe not the best thing to say but who knows…)
I really enjoyed these lessons and reflections, man!! I always usually go with my gut when hiring more than experience..sometimes it works for me, and sometimes it backfires lol.
Thank you, @Danielle Wright! And thanks for your help reviewing it. Haha yeah I feel like I always lean to hard one way. I either go with my gut maybe more than I should, or I totally second guess myself.
This was great - more than almost anything else, I think hiring and firing are things that are hard to learn to do well without making real 3D mistakes. Thanks for sharing yours, sharing wisdom, and normalizing the learning process.
So glad you liked the essay, Kristin! I think I agree. Hiring and firing are one of those things that you can’t really learn from a book.
I guess it’s a good thing I went through so much (and made so many mistakes!) so that I’d be able to share.
What stood out to me is that you asked every teacher the same two questions. That consistency is a big part of why the answers told you so much, because you could compare them across hundreds of interviews. On lesson 4, the best way I've found to respect a "too good to be true" feeling without letting it turn into bias is to turn it into one more concrete question, like asking them to walk through a past project that slipped and what they did about it, and asking every finalist the same thing. Looking back, is there a question you wish you'd asked Candidate 1?
Hi Kat! Thanks! I wasn’t always so consistent, but I got to a system where I had an interview script I followed for a few years. It was definitely super helpful to be able to compare everyone’s answers on the same questions!
Yeah, I definitely asked things like that, and I did love that Candidate 1 seemed to have a real heart for students. I think perhaps the red flag I could have noticed is that he already had his own thing going sort of on YouTube and he had some pretty good experience with the government.
Sometimes, you have to be skeptical of people who are sort of mercenaries for hire (for lack of a better term) rather than people who are super committed to working at a particular company they really love. We often had success hiring people who had slightly less experience but who really liked our mission. They were often so grateful we gave them a chance that they’d stay for a few years.
I don’t know if there really is another question I would have asked! He answered pretty much all the questions well from what I remember. I think I was scared of being biased toward Candidate 2 because I simply liked her better as a person. But sometimes that counts for something!
This is really good! As a school director, I’ve interviewed and hired a lot of teachers over the years, and your points are spot on. I especially appreciated the fourth one. Almost every hiring mistake I’ve made involved something feeling a little off, but I convinced myself that the person’s experience or credentials made them the right choice. I’ve also learned that character and personality ultimately matter much more.
Thanks so much! I’m really glad you liked it!
I didn’t realize you were a school director! That’s so cool. My experience was weird because I never taught and ran a kind of unusual program so I’m not even sure how a school would view my experience. But I’m a board advisor for another EdTech startup now called Electus, so it’s been nice to get back into the education world.
At what kind of school do you work? Did you ever teach?
I have been running a preschool and kindergarten for the last 16 years. Prior to that I taught high school and middle school for 7 years. I also run camps for elementary and middle school kids. It sounds like you work on some cool stuff!
That sounds really interesting! We should do a zoom call sometime next you’re free
Would be great to connect!
500 interviews made me laugh because I think I’ve done the applicant-side version of this in applications alone. At some point it stops being a job search and becomes field research.
The bit about treating candidates like humans really lands for me though, because people absolutely remember the process. I have forgotten job descriptions. I have not forgotten the companies that made me feel like I was applying to join a secret society with no contact information.
And your Candidate 2 story is exactly why I think honesty is underrated in hiring. “This year is going to be a nightmare” is somehow much more trustworthy than the usual “fast-paced environment with exciting opportunities for growth” 😂
Also, every hiring manager should be forced to read the line about rejected candidates becoming future customers, collaborators or critics before they hit send on a generic rejection email.
I’m so glad you liked the essay!
Haha… that’s a lot of job interviews! I’m glad I haven’t had quite that many on the application side!
Yeah… I have a tendency to be honest (sometimes too honest!). Sometimes it’s bitten me, but a lot of times it ends up being really helpful. I think in the case of hiring, being honest means you get someone who really wants the true job, not the shiny fake version of the job.
And yeah, I don’t get why some companies don’t seem to care about that! I think they get so arrogant they think “well, we’ll still have other people who like us…”
But imagine if that famous author’s team had treated me better in the interview process! I’d probably still be going around talking about how cool they are, even after getting rejected!
I wonder if “gut” sometimes becomes the word we use for information we’ve noticed but can’t yet articulate. You clearly detected something that didn’t fit, even though you couldn’t explain it. I’d be curious what repeated experience does to that gap between noticing a signal and being able to name why it matters.
I’m sure that experience shortens that gap between the two! I think it’s kind of an example of system 1 and system 2 thinking, with the pre-frontal cortex vs. the limbic system.
I think one thing about modern culture is that we really tell people not to listen to their intuition, because that sounds like bias (which most of the time people interpret as a bad thing). Obviously, we don’t want to be biased and rule out candidates for arbitrary or discriminatory reasons, but I think sometimes we end up not even trusting our own intuition when something seems off.
Somehow I think we need to get back to a point culturally where we are more comfortable using both data/logic and intuition.
I think the experience piece is what interests me most here. I’d be a little careful mapping System 1 and System 2 directly onto the limbic system and prefrontal cortex, because the neuroscience is more distributed than that. But experienced pattern recognition is fascinating. Sometimes we may detect that something doesn’t fit before we can identify which cues produced that judgment. The hard question then becomes: when has experience produced useful pattern recognition, and when are we simply feeling the pull of a bias?
Haha fair enough. I’m definitely writing as someone who actually knows nothing about neuroscience.
I think that’s the tough part. I’m not sure if anyone has the answer to the bias vs experience question. Maybe it’s just a line we all have to walk.
I think that’s exactly it. Maybe the point isn’t to eliminate that tension, but to get better at noticing when we’re walking that line.
I value character as well, but I also think skill matters just as much. I believe a balance of both is better than character alone. I even applaud you for treating applicants as people. More hiring managers need to practice this method.
Thanks, Erin! I’ve found for a lot of not as specialized jobs like customer service, you can train a lot of skills, but you can’t really train character or personality. And then for more specialized jobs like finance, the skill is kind of just a minimum requirement for the job. So if they didn’t have that, I wouldn’t consider them. But if they did, I’d be evaluating them on character.
Great article. During my 25+ corporate career, I could not count how many candidates I have interviewed. I would say this is a good list. Particularly point 2, I would not stress enough how important “culture fit” is in corporation, especially for major corporations.
Well done Colin.
Thanks so much! Wow, I can imagine you have a ton of good stories too! Do you have any examples of particularly important hiring lessons you learned in your career? Or especially good/bad hiring stories?
Thank you! I actually have a few hiring lessons that have stayed with me over the years. I’m writing a series called “25 Lessons in 25 Years,” and some of my hiring reflections will be part of it.
A couple that immediately come to mind: I like to ask candidates about their five-year plan. It tells me a lot about what they’re looking for and whether the role and organization can genuinely support where they want to go. I also like asking them to describe their “perfect coach.” That helps me understand how they learn, what kind of support brings out their best, and, importantly, how I can better support them once they join the team.
For me, hiring has never just been about finding the person who can do the job. It’s about understanding what they need to thrive—and whether I can create the environment where they will.
I’m looking forward to it! Definitely send it to me one you post it. Yeah, the 5 year question is interesting. I often wonder if people answer it honestly. I think a lot of people don’t totally know what they want to do in 5 years (or they might be envisioning themselves at a different job!)
I really like the perfect coach question! That’s a really interesting way of seeing how a person wants to be communicated with and what they’d find encouraging.
Thank you Colin. I actually posted Lesson 1 this week. Please take a look when you have a chance. I am posting one lesson each week.
https://yingquietmillionairestudio.substack.com/p/25-lessons-in-25-years-the-glass?r=25ep7i&utm_medium=ios
“ The perfect coach “ question is a steady one I have used for years. It helped me find good hires, also helped me adjust my approach accordingly as different people need different supports.
Many of my mentees are now in leadership roles, they found this question helpful in recruiting as well.
Ok great! I’ll go give it a read! Yeah, if I get back into hiring, I may have to start using that question!