How To Hire A Simplifier

The pass/fail interview guide that tests for my #1 leadership quality

A few months ago, I wrote about Simplifiers and Complicators - the two types of people you’ll inevitably run into at work. Simplifiers make things clear. They cut through noise, take a stance, and drive action. Complicators? They make things murky. They create friction, add steps, and somehow leave you with more questions than you started with.

That article turned out to be my most-read post of the year. Turns out, a lot of people agreed with the idea that work moves faster (and feels better) when you’re surrounded by Simplifiers - and that nothing grinds progress to a halt quite like a Complicator who conflates complexity with competence.

But after I published the piece, I kept getting asked the same question: How do you find these people? How do you spot a Simplifier before you hire them—and more importantly, how do you avoid letting a Complicator slip through the cracks during an interview process?

My friend Carlos, CEO of accounting automation company Tesorio, put it best when he asked:

Great question. And as someone who has accidentally hired Complicators before (painful) and seen firsthand what happens when you bring on a world-class Simplifier (a joy), I’ve got an answer.

Maybe I’m giving away a bit of a secret here, but I also think the way I test for Simplifiers in interviews is almost impossible to cheat—if you dig deep enough and ask the right follow-up questions.

My approach boils down to a simple two-part interview guide, designed to test whether a candidate can first simplify and then execute.

The Simplifier Interview Guide

Question 1: Can You Simplify?

The first question I ask is:

“Tell me about the 3–5 metrics you look at every week to gauge the health of your part of the business.”

This isn’t a trick question, but it is revealing. It’s designed to see if the candidate can distill complexity into something clear, actionable, and meaningful. A good answer is all about focus. You’re looking for a short list of metrics that tell the truth about how the business is actually doing. Bonus points if they include at least one leading indicator, showing they’re tracking what’s coming, not just what’s happened.

Here’s a few other notes on what I’m looking for - and what to watch out for:

• Good answer: They take a stance. They’ve clearly thought about their KPIs and which ones are most important. They can rattle them off without hesitation, and it’s clear these numbers aren’t theoretical - they’re burned into their brain. They can explain why these particular metrics matter, how they track them, and what the numbers tell them about the state of the business. You can tell by the way that they talk about them that they don’t just present them in board meetings - they’re talking about them with their team every week.

• Bad answer: A laundry list. They mention “all the usual ones” like revenue, bookings, new logos, etc., without any clear sense of priority. It’s clear they either haven’t thought deeply about their metrics or haven’t developed the discipline to track the business in a meaningful way. Worse, they default to trailing indicators, which are useful for keeping tabs on results but less so for staying ahead of the curve and alerting them when their part of the business is heading off-track.

Another thing to listen for here: Simplifiers think in terms of signal, not noise. And their answers reflect that.

Question 2: Can You Execute?

Once we’ve gotten through the list from Question 1, I hit them with the follow-up:

“Ok, now tell me about a time you noticed something in those numbers, dug into what you saw, and made a change as a result. Be specific about what you noticed, what you dug into, and what you did.”

This question shifts from simplifying to taking action. Simplifiers don’t just spot the signal. They do something about it. They roll up their sleeves, figure out what’s going on, and do the work that’s needed to move an important number in the right direction.

Here’s what I’m listening for:

• Good answer: They’re specific. They can clearly describe what they observed in the numbers (and in the real world), what triggered their curiosity, and how they dug into the issue. That “digging in” part is critical. Simplifiers are clear, but they’re also curious. They don’t just notice things - they do the extra work to understand why those things are happening. They can also clearly articulate the changes they decided to make based on what they noticed, why it made sense, and the results they achieved. Even better, they can explain how they ensured the solution stuck - whether it was through a process, a system, or personal reinforcement.

• Bad answer: Complicators will talk in abstractions and concepts, avoiding specifics at all costs. Their response is long-winded, filled with buzzwords and qualifiers, but doesn’t get to the point. They might try to hedge, hoping I’ll give up and move on. If you find yourself feeling impressed (at the volume of work, complexity of the problem, or how badly the deck was stacked against them) but also confused (at what they actually did and why) while they’re talking, that’s your Complicator radar sounding its alarm. Pay attention to it.

How to Spot a Complicator in the Wild

There’s this Doc Rivers quote that I love (and probably reference way too often):

“Average players want to be left alone. Good players want to be coached. Great players want to be told the truth.”

Most Complicators just want to be left alone. Which is exactly what they’re trying to get you to do during an interview. They want the stories they share to seem so messy, so complicated, so difficult that you lose track of what they actually did and whether it worked. It’s like they’re playing a video game on hard mode - narrating every obstacle, every unfair battle, every impossible challenge - so that by the end, you’re too exhausted to ask the only question that matters: Did you actually win? Like an outmatched prizefighter, their only hope is to get you to chase them around the ring, hoping that you’ll eventually run out of steam.

Simplifiers, on the other hand, do the opposite. They take a stance. They make the complex feel obvious. They aren’t afraid of being specific, because they’ve put in the work to refine their thinking and reflect on the decisions they’ve made. And once you know what to ask and pay attention to, you can improve your ability to spot this dynamic playing out in real time. You can actually see the Simplifiers float to the top of your hiring process.

Here’s a nuanced way to start honing your simplifier-spotting ability. Interviews are hard for everyone. Everyone struggles to tell their story in the right way. But next time you’re interviewing someone, pay attention to how they struggle. If they’re working hard to answer your question as directly and thoughtfully as possible - that’s a good sign. That person is probably a Simplifier.

But if they’re working hard to dredge up “all of the things” - the obstacles, the drama, the dozens of variables that made it all so hard - odds are, they’re a Complicator. It’s like they think the sheer weight of their struggle should count as an accomplishment. Spoiler alert: It doesn’t.

And this pattern doesn’t stop once they’re in the job. Just like in the interview, Complicators don’t actually want to deliver results. They want to deliver just enough confusion that you don’t notice they aren’t delivering results.

Final Thoughts

Hiring well isn’t just about finding high performers. It’s about finding the right kind of high performer. You don’t want people who do a lot—you want people who do the right things, do them well, and can clearly articulate what they’re doing and why. That way, they can (a) get others on board and (b) help their team get better.

I’m a big believer in growth mindset and people’s ability to evolve, but this is one of those qualities I rarely see change. Either someone naturally cuts through the noise, or they create more of it. It’s hardwired.

Simplifiers can’t help but simplify. Complicators can’t help but complicate. And while it might not always be obvious who’s who at first, don’t worry: If you ask the right questions, they’ll show you exactly who they are.

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Author’s Note: I spend a lot of time on hiring and working on how to do it well. If you’d like to learn more about how I think about hiring, I hope you’ll check out the ParkerGale Capital Hiring Handbook - linked here.