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In this essay (11 min. read)
The worst hiring decision I ever made and how I recovered from it
Why you should let your employees eat ice cream while taking calls
Why everyone should hire more like a bean company in the U.K.
An unconventional question to find out if a candidate is kind
The worst mistake I ever made hiring.
Picture this.
You’re 24 years old, managing an online high school program with 1600 students and nearly 100 teachers.
You hired someone who looks incredible on paper. Stellar credentials. Has a portfolio of real work posted online. Kind, easy-to-get along with, seems like a good guy.
The only problem?
It’s a few weeks before classes start, and this guy’s basically suckered you out of thousands of dollars. The product he delivered is absolute garbage, only half-done. And he’s not answering your calls or emails.
The only way you’re going to fix this is to go back to your second choice, the person you wanted to hire for his position but for some reason didn’t.
Hat in hand. No excuses. Beg for help.
What do you do?
This is what I learned about hiring from doing roughly 500 job interviews.
Let’s get this out of the way first. The credibility issue.
You might be asking yourself, how is it possible to do 500 job interviews? Are you the most rejected candidate of all time?
No, but thanks for asking.
I did roughly 325 interviews hiring teachers for an online education program that I used to run. Those were just the ones I counted in my last year or so of 3 years of hiring, so I think the number is a bit higher.
Then, I did roughly 90 interviews or informal interview networking calls in connection to grad school or my time in banking. That’s between applying for jobs in grad school, looking for roles at the bank, or interviewing candidates who wanted to work at the bank.
Plus roughly 75 practice consulting case interviews in grad school.
And then all the other random interviews I’ve done applying for other jobs.
So do those all count? And is it really 500?
Who knows? I say close enough.
For now, I’m going to focus on the perspective of hiring managers. But I’m sure I’ll do another piece sometime from the perspective of interviewees.
Ok, enough preamble. Let’s dive in.
Lesson 1: Find out who the candidate admires. That’s who they’ll be.
When I hired teachers, I’d always ask two things. Who their favorite teachers were. And how they’d help a struggling student.
The answers always corresponded. And while the questions may seem obvious, the answers never were.
The truth is, of course I didn’t actually care about their favorite 4th grade math teacher Mrs. Johnson. What I cared about was what kind of person Mrs. Johnson was.
Because that’s who the candidate wanted to be. And that’s exactly who they would be toward their students.
Whenever teachers answered this question, I’d learn what they really thought made a good teacher. I’d learn if they were strict and mainly valued the rules. I’d also learn if they were kind and compassionate toward students who were struggling.
It sounds so simple, but I can’t tell you how many teachers looked excellent on paper and were rejected because of their answers to these two questions.
Job candidates can fake their way through almost anything.
But most people don’t think about faking their heroes.
Lesson 2: Hire for character and personality. You can train skills.
One of the best people I ever hired is my friend Joseph (name changed). He’s now a highly regarded professor and a well-liked writer on Substack.
I’ll always remember two things about him.
First, he used to take customer service calls in a broken desk chair that allowed him to recline almost flat on his back. He’d sit there, reclined all the way, eating Chick-fil-A ice cream he got at lunch.
How he did this without spilling, I’ll never know. How he did this while still sounding completely professional on the phone was an even greater mystery.
But he was great on the phone, so I wasn’t too worried. Parents and students loved him, and everyone in the office thought he was a joy to work with.
What made Joseph such a nice guy? Well, partly I think that’s just his personality.
But I think it’s also important that he worked at a McDonald’s located at a rest stop on a busy interstate highway in Tennessee. There’s something about working in a crazy, busy, fast-paced environment that just makes you good with people.
The second thing I remember about him was that on his first week of the job, I needed help working at the office until about 10 p.m. on an incredibly boring, tedious project. Printing out and mailing every student’s final grades.
Later we decided this was utterly ridiculous. Students could just look at their grades online.
But, at the time, that’s what we did. And what I remember is that Joseph was the only employee who volunteered to do it. Everyone else refused.
I had other employees who would watch the website crash at 5 p.m. and say “Well, that’s not my problem. I’m heading home.”
Not Joseph.
You can train someone to do calls. You can train them to do Google Ads. You can train them to write marketing emails
You can’t train someone to go the extra mile.
You have to hire for that.
Lesson 3: Treat your job candidates like real people. They are.
Earlier this year, I had two interviews to run marketing for one of the biggest authors in the world. I’m serious. This person has written many books and is a well-known public figure.
I was told I was in the top 4 candidates.
The day after I had my second interview, everyone on the team re-posted the job on LinkedIn. (Yes, I admit I looked them all up!)
Then, I got ghosted. Even after I sent a follow-up email to ask about next steps… nothing.
I used to be a huge fan, but honestly, it will be difficult to listen to or read that author again.
Contrast this with another experience I had.
When I was first out of college, I was rejected to be a legal assistant at an education-focused law firm.
Later, I applied to work for that law firm’s online education program. The lawyer who rejected me put in a good word for me. He didn’t think I was the right fit to work for him, but he thought I’d be a good fit for this role instead.
Not every door needs to shut at once.
Or, just this week, I heard about a famous brand doing a great job of following up.
Amelia Christie-Miller has gained some fame in the UK food market for her company Bold Bean Co. Against all odds, she’s found a way to make beans seem a lot cooler, through clever branding, marketing collaborations, and unique cookbooks.
The brand went viral on LinkedIn for sending a thank-you note along with a gift of gourmet beans to job candidates who made it to the final round but weren’t hired.
It’s a simple gesture. But who really thinks of doing that level of expensive follow-up with rejected candidates?
It’s easy to think that once a candidate is out of the hiring process, that person no longer has a relationship with your company. But that’s not true. They could be a potential future customer, a fan, or a future collaborator.
Hiring managers have the power to create their own fans or their own brand’s worst critics.
A rejection doesn’t have to be a burned bridge.
Lesson 4: Consider the data. Go with your gut.
As we start to wind down, I want to get back to the opening story.
What happened with that guy I hired? And did he actually rip me off?
Well, we were trying to hire a course developer and 4 teachers for an online chemistry course. If you think teaching online is tough, trying teaching online and including science labs.
I think we went through at least 50 interviews just in the first round of hiring.
Candidate 1 was a guy who had great experience teaching, had his own science channel on YouTube, and who had even done scientific research for the U.S. government.
Candidate 2 was a qualified scientist but had only about 2 years of teaching experience and had never taught online.
I asked the whole team, and they said hire Candidate 1.
Pretty obvious decision, right?
The problem is that I liked Candidate 2 better.
I just couldn’t really explain why. She just seemed like who I’d choose to teach my own kids. She was a bit more humble and easy to get along with.
Candidate 1 seemed fantastic, but somehow I just knew he was the wrong choice. He seemed too good to be true. And those kinds of situations bother me.
But it was all so subtle, it was difficult to put into words.
I spent about a week spiraling and overthinking.
After too much deliberation, I hired Candidate 1 to develop the course. Candidate 2 would be one of the 4 teachers.
Well, the months kept slipping by and I kept checking in on the course development. He kept turning in subpar work (or no work!) but continued asking for his next check.
Instead of just standing up to him, I kept mailing the check.
I figured he’d get it together eventually! I’d seen what he could do! He was just having family troubles this summer!
I think in part I was overwhelmed. We were developing 10 new courses that year, hiring dozens of people, and revamping both our internal and external websites.
This guy was a professional. Why did I have to hold his hand? He’d get it done eventually.
Or so I thought.
About 2 or 3 weeks before the classes started, none of the other teachers had heard from him. I couldn’t reach him either. And he wasn’t done developing the course.
Finally, I got a hold of him on the phone.
I told him, “This isn’t working out. I’m going to have to let you go.”
Oddly enough, he seemed kind of surprised.
He asked, “Have you ever had to fire someone before? I know that must be hard…”
Internally, I was thinking, what the heck is wrong with you, you condescending jerk?! Did you really just ask me that?
Here I was as the manager, and I’d never felt like more of a child.
Even worse, I was out somewhere between $6,000 to $8,000.
He was great on paper. Everyone liked him. There seemed to be no red flags.
Except that weird feeling that I was making a mistake.
I went with the data, but I ignored my gut.
Maybe the best way is to combine intuition with data. I suppose that’s what 90-day probation periods are for.
Podcaster Dan Pope likes to talk about 2-D lessons and 3-D lessons. You learn a 2-D lesson when you read a principle in a book. You learn a 3-D lesson when you live through it.
Like when you lose thousands of dollars over a bad hire.
I guess this was a 3-D lesson.
Lesson 5: Protect your brand. Be honest in the hiring process.
After I got off the phone call, I had only one option. I had to go back to Candidate 2.
There simply was not enough time to find anyone else.
I had to tell her everything. How I wanted to hire her, but he was more qualified on paper. How I’d made a mistake and I needed her help cleaning up the mess.
She wasn’t going to be teaching a pre-developed Chemistry course. Easy peasy.
No, she was going to be building the airplane while flying.
She was going to have to learn teaching online for the first time, manage two other teachers, teach an extra class section, and develop a course from scratch, a week or two ahead of the actual class. Meaning, as we were on week 3 of the class, she’d be writing the material for week 4 and 5.
In short, it was going to be an absolute nightmare.
I told her, “This is going to be an awful year, and you’re going to have to work really hard. But I have no other options, or I have to refund all these students. I really need your help.”
She said yes.
Talk about eating humble pie.
I was right. The year was a nightmare.
The next spring, she told me she wasn’t coming back. I don’t blame her.
Then, I had to hire for Chemistry all over again. Another 40 or 50 interviews.
We did hire again. We found two excellent course developers who tag-teamed to redevelop the course and knocked it out of the park. It just cost us 2-3x as much to develop Chemistry as it should have.
There was a silver lining. I’m pretty sure a year or two later, Candidate 2 actually came back and taught again for another year. So, at least she didn’t hate us.
Midway through that school year, I remember her telling me something important.
“If you’d lied about how hard it was going to be, I wouldn’t have accepted. I’m glad you told me it was going to be awful.”
The moral of the story? If you want someone to walk through a storm for you, tell them about that storm that’s coming. Never hire under false pretenses.
Or simply, in the words of David Beckham, “Be honest.”
Concluding thoughts
I’m writing all this down about a decade after it happened. Hopefully, a little older and wiser.
There’s so many other things I could share, but I thought I’d start with these five.
A lot of them may seem like obvious takeaways, but I’m a big believer in 3-D lessons, so I’m hoping the stories help.
To recap the 5 lessons:
Find out who someone’s heroes are. That’s who they’ll become.
Hire for character over skillset. Skills can be developed.
Treat your job candidates like human beings. Even when you reject them.
Use the data, but trust your gut. Better yet, use both.
Never hire under false pretenses. Hire people who will willingly walk into a storm.
If you’re not a hiring manager, a lot of this may not seem applicable to you. Don’t worry! I’ll probably write a follow-up piece for job seekers too.
But I think it’s helpful for all of us to remember that hiring managers are real people trying to solve real problems. And a lot of the time, they don’t get it right.
Then again, employees don’t always get it right either.
If I had to choose one principle for both employees and managers, it would be this:
Remember to be human. Forgive people for when they are.
. . .
But seriously, if the website crashes at 5:00 p.m., please don’t just go home.
Want to read more like this?
Here’s a few of my favorites.
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.