I once paid a "CFO" $200,000 a year for 2 years…

The problem? He was a glorified bookkeeper.

I didn't know any better.

CFO, controller, bookkeeper...they all sounded like "money people" to me. So I picked the title that felt right and paid the salary I thought a CFO was supposed to make.

That single mis-hire cost me well over a million dollars when you add up his salary plus the two years of growth we left on the table because our finance function...sucked.

And I know I’m not alone.

Hiring for a role you've never done yourself is one of the most challenging tasks a Founder/CEO can do. (And it can trigger one of the most expensive mistakes you can make.)

So let’s talk about how to make a BIG hire for a role you know nothing about…

Step 1: Name the Role

Before you post a listing or call a recruiter, you need to know exactly who you're looking for. Most founders skip this step and fall into one of three traps.

  1. The Unicorn Trap. You collapse four jobs into one fantasy role. "Head of Revenue and Operations who manages the team AND does customer success." That person doesn't exist.

  2. The Generalist Trap. You default to a vague title because you don't actually know what you need. TIP: If you think you need a "COO" or an "Ops Manager"...you probably just don't understand the specific role you actually need.

  3. The Loyalty Trap. Someone on the team raises their hand, and you decide it’s only “fair” to give ‘em a chance. Instead, ask this question: "If this person didn't already work here...would they even be considered for this role?" If the answer is no, be honest with them, then continue with your search.

So how do you find the right title?

  • Open Claude or ChatGPT.

  • List out all the tasks, outcomes, metrics, and anything other details that define the job to be done.

  • Add context about your company: size, industry, geography

  • Ask AI for 3 - 5 real job titles with experience levels and salary ranges.

That CFO I just told you about?

If I'd done this exercise, AI would have told me in thirty seconds I needed a Controller...not a CFO. Oops.

Step 2: Learn the Role

Knowing the job title isn't the same as knowing the job itself. So before I interview a single candidate, I go to LinkedIn, search for the title, and DM people currently in that role.

Then I offer to pay them.

When we were hiring our first Content Marketing Manager, I offered $100/hour for a 30-minute call. Fifty bucks. It told them I was serious...and got me access to people I'd never have reached otherwise.

My goal? Talk to at least 3 people. 5 - 7 is better. When you talk to 1 person you get an opinion. When you talk to 5 you start to get at the truth.

Here are some questions to ask:

  • Walk me through your typical week. What does an average day look like for you?

  • What resources and team do you need to win in this role?

  • If you were hiring your replacement, what skills and experiences would you say are non-negotiable?

  • What does it look like when someone is struggling or outright failing in this role?

  • What should they accomplish in their first 30, 60, and 90 days?

(That last one is the biggie… you’ll see why in a bit.)

When I did this for the Content Marketing Manager role, the very first call rewrote the job description.

Every person actually doing the work had 3 - 5 people under them. I wasn't hiring an executor, I was hiring a team leader.

Good thing I asked…

It seems obvious now, but that single insight changed the title, the budget, and the candidate profile. It also saved me from making an expensive, momentum-killing mishire.

Step 3: Protect the Hire

This is the step that would have saved me a million dollars…

When you're hiring for a role you don't understand, you NEED someone on your interview team who has successfully hired for this role in the past. Not someone who's done it… someone who's HIRED for it. Big difference.

This person brings three things you don't have:

  1. Real questions the candidate can't deflect

  2. A BS detector for buzzwords dressed up as substance, and most importantly...

  3. The confidence (and accountability) to say “No.”

Here's what that accountability is worth.

That “CFO” I told you about before… the bookkeeper with the $200,000/yr salary… he lasted 2 years.

$400K down the drain… OUCH.

But here's the part that really stings. During those two years, the business desperately needed a line of credit. We were inventory-heavy and capital intensive. But every time we applied, we got denied because our books were a mess and because our "CFO" had zero banking relationships.

The day I got the right person in place, we secured a $2 million line of credit and doubled the business in twelve months.

The $400K in wasted salary hurt. The two years of stalled growth cost 10X that.

So how do you find one of these experts?

Three ways: 1) ask a peer in a mastermind or CEO group to do you a favor, 2) pay a fractional executive for a few hours of interview help, or 3) use a recruiting firm that's actually placed people in this exact role.

Step 4: Test the Fit

Once the initial round of interviews are over and you have your finalists, there are two final filters before you pull the trigger:

FILTER #1: The 30-60-90 Plan. Use the answers from your Step 2 conversations to build a template of what a strong first 30, 60, and 90 days should look like in YOUR business. Then ask each finalist to write their own.

A resume tells you what someone's done. An interview tells you how they present. But a 30-60-90 plan tells you how they THINK.

A good 30-60-90 Plan should be 1) specific to your company, include metrics and milestones, and prioritize ruthlessly. Weak plans are generic and could be submitted anywhere.

And as an added bonus, this 30-60-90 Plan gives you a built-in evaluation framework for your new employee after they’re hired.

FILTER #2: The Tacos and Tequila Test. Everybody says you should hire for skills… not chemistry.

Eventually that's true. Not now.

Remember, you don’t fully understand this role, so you’re going to need to spend A LOT of time with this person to get them integrated into the business.

That’s why it’s so important that you actually LIKE this person.

You don’t need to be best friends and you don’t need to hang out every day after work, but they should be able to pass what my friend and fellow CEO, Jonathan Cronstedt, calls the “Tacos and Tequila Test.”

❝

"If this isn't someone I'd want to grab tacos and tequila with, it's not our person."

That may sound petty and selfish, but there’s a method to the seemingly immature madness…

At this stage, the culture of your company is a function of YOU. Every person you add either strengthens it or dilutes it. So don't sacrifice chemistry… not on a role this important and with this many unknowns.

Remember, you don't need to become an expert in a role before you hire for it…

…you just need to stop being ignorant about it before you sign the offer letter.

⚡ Action Step: Think of a role you know you need but don’t fully understand. Open Claude or ChatGPT. List the tasks, outcomes, and metrics. Ask it for three to five real job titles with salary ranges. Whatever it gives you...that's where you start. The role you've been avoiding is likely costing you more than the hire ever will.

Give it a shot and let me know how it works…

-Ryan

Ryan Deiss
Co-Founder and CEO, The Scalable Company

P.S. If you want a structured way to evaluate candidates across all the dimensions that actually predict whether a hire works out...not just skills, but culture fit and leadership signals...grab my free Founder-First Hiring Scorecard here.

It's the same scorecard we use with our 1-on-1 clients, and when you download it you'll also get a 60-minute training from my co-founder Richard Lindner walking you through how to use it.

P.P.S. I'm looking for 5 business owners who want to work 1-on-1 with my team and me to install a custom "operating system" so your business can scale and so you can exit the day-to-day. Click here for the details.

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