I Ran A Search For a Job I Ended Up Getting [Field Notes #6]

My first (and only) recruiting switcheroo

“What do you think? Would you work for any of these people?”

January 2020. I’m on a Zoom with my new boss, reviewing candidates who are interviewing for the role of becoming my “new” new boss.

On paper, they were all great. Well-experienced. They’d done the job before. They could probably survive in the crazy, chaotic environment we were in at the time.

But none of them blew me away. None of them were going to.

They were doing the job I was going to do next.

Even if they had been in the Director role for a few years, they didn’t feel that far ahead. How many 11th graders are all that impressed by a 12th grader?

The people were smart, but the conversations were the opposite of inspiring. For every good idea I heard, I’d listen to three (or ten) things I’d do differently.

My boss told me she put me on the search because I had a high bar. I was her recruiter — the one who brought her into the company. She knew how I operated.

But I still wonder if she saw it before I did (she usually saw things before I did) — nobody who wasn’t named Mike Radice was getting my endorsement unless they were the Recruiting Director equivalent of Derek Jeter.

The Silent Pattern

This has been the pattern through 17 years of recruiting and nearly a decade leading: the most qualified people aren’t a lock to get the job.

I know because I found people with better credentials than mine, presented them to my boss, and watched her choose differently.

I know because I’ve regularly passed up talented people with sexy resumes for people with scars and bruises.

Here’s the brutal truth (he said, longing for the days before AI ruined that phrase): it doesn’t matter how qualified you are on paper. Hiring managers will hire the person they feel they can work with. Enough skills to do the job. Room to grow. Coachability. A personality they’re comfortable with. Their vibe. Someone they can put in front of other stakeholders without getting a call later asking, “Why’d you hire that dipshit?”

I was presenting impressive candidates — she’d have known if I was sandbagging the search. They just weren’t impressive enough, not for what the company needed, and most definitely not what I needed in a boss.

We needed someone who could elevate the team. I saw myself as that guy, even if I hadn’t done it at this scale yet.

My boss had an inkling I wanted the job. I think that conversation confirmed it.

Mind The Gap

The external candidates had done the job. I hadn’t. And in hindsight, I credit that gap for most of my success.

I’ve stepped into roles where the job was familiar. After the newness wears off and you settle into the new routine, it’s the same gig — just different scenery and different toys to play with. Outlook instead of Gmail. This ATS instead of that one. Once you settle in, you realize: I’ve already done this.

But when you move into a role you’re not fully qualified for, you’re trying to prove something — to your manager, to yourself, to the voice inside that’s hounding you like a bleacher creature in the Bronx. You don’t know what you’re doing. You’re gonna fuck this up. You should’ve just stayed where you were. Know your place. There’s a hunger to learn, a willingness to be coached, a desire to become worthy of the new seat. That’s an element you find less frequently in people who’ve been there, done that.

I cringe to think of the leader I was back then. I remember a couple of ego-fueled team meetings in particular, chest-thumping and shit-talking, that still make my skin want to slither off my body. But you have to start somewhere.

Attitude and coachability beat hard skills. Every time. Because at some point, every hard skill atrophies. The skill that made you lethal ten years ago might be obsolete today. The person who can learn is always the safer bet, even if they have to learn a few things to handle the bigger job.

The “Prove It” Months

She told me straight: You could be the guy to run this department. But you’ve got a long way to go. There are gaps in your game, and we’re going to have to work on it together.

So that’s what we did.

Some weeks, it felt like I was progressing. I felt my mind stretching. My beliefs were being challenged. Sometimes, I’d get punched in the face — often in public settings — and have to think about where I went wrong to allow the blow to land. I’d do a better job with a direct report in a tough situation and know that, six months earlier, I’d have bungled it.

Other weeks, it felt like I was shredding fresh powder in Breckenridge, smooth heel-to-toe transitions while kicking up clouds. Dialed in. Executing at a high level. Popping my head up to see if anyone was noticing — and, oh shit, boss is out of office today.

Then a recruiter called.

In recruiting, it’s all about timing. Call someone on the right day and they’d never think of leaving. Call them the next day after a bad week and they’ll take every call they get. I wasn’t at “fuck this place” yet. But I was definitely at: is this promotion ever actually going to happen?

So I went through the process. Got all the way to an offer — better money, equity, the whole nine yards. The hiring manager seemed like a dude I could work with. It gave me something to think about.

In the end, I turned it down. I liked my boss, and believed she’d be true to her word — even if it wasn’t on my timeline. I also liked my team. And as crazy as the company was at the time, I knew my way around it, and I was working directly with C-level leadership. I’d seen enough candidates jump for the wrong reasons, just to find out the grass isn’t always greener.

So I kept chewing the grass I knew for another month.

Then I got promoted.

You Got What You Wanted. Let’s See If You Really Wanted It.

My loyalty was rewarded — the numbers were better than if I had jumped ship. (The guy who was going to hire me at the other company left a month later, too...so it goes).

Almost immediately, the peers who all wanted the same job — friends I had been through the wars with for years — started leaving, one by one. Within six months, they were all gone. I had to rebuild my leadership team from scratch and learn every department underneath me at the same time.

Another perk of the promotion: minimal air cover. I was appropriately deemed the “throat to choke” for all things recruiting, and everyone who had issues came to me. I didn’t realize how many issues there were.

(Much later, I’d come to understand that a leader’s job is mostly dealing with issues. For those who strive for the top spot in their org, leadership is summed up perfectly in this 2-minute scene from The Wire).

Tech Founder/CEOs are passionate about all parts of their business, so I’d occasionally link up with ours to talk about candidates. I’d get a Slack ping at 11pm with a “Mike, good to connect?” The next message (whether I responded or not) would be a Zoom link. Most often, this was to go through candidates that had applied to roles. Scrolling through our Applicant Tracking System, I’d have to walk through why one candidate got an interview while another didn’t, what the status was of a certain candidate, and so on. I never had context. I don’t think that really mattered.

There’s a real gap between wanting a thing and being ready for it.

I thought getting the title was going to make me feel a certain way. Like I’d “made it,” at least for a minute. That had been a milestone I had been working towards.

Instead it was: Welcome to the show. Let’s see if you know what the hell you’re doing. And if not, we’ll go find someone who does.

So you do the job. You get battle-tested. You do indeed fuck things up, but you also get a few things right. People see you’re trying. Some even want to help you. And you find out your CEO had a pretty good sense of humor at 11:30 at night.

Discomfort is Not Optional

The best advice I have for someone who wants to move up?

Get comfortable being uncomfortable.

I emphasize this for two specific reasons.

First, good leadership is all about the willingness to have difficult conversations. That includes the discussions that you have with your manager about getting into leadership. You need to speak up.

When my boss asked what I thought of those candidates, I could have told her the truth: I think I’d do better than any of these people and you’d get me for cheaper. But I didn’t. I waited for her to suggest it because I didn’t want to seem like my ego was too big. (She got to know it well, and it was too big. I have a tattoo to prove it.)

Still, that was stupid. You have to raise your hand and say, out loud, that you want to enter the ring. It’s going to change the relationship dynamic. You gotta be OK with that.

Second, when you’re stretching into something new, you’re going to have to become a version of yourself that doesn’t exist yet. That takes...as long as it takes. The missing 20% doesn’t sound like a huge gap to cover, until you remember that the last 10% of a project takes 90% of the time. It’s gonna be a minute until you’re good at the gig.

You learn as you go - meeting by meeting, situation by situation. You make some good calls and blow others. People like working for you — until some don’t. There will be gaps. You will fuck up. You’ll lose some sleep. You’ll learn from your mistakes.

That’s the point.