The Smart CEO's Guide to Hiring Beyond Your Skill Set

You need to make a hire, a big one. Maybe it's a CFO, a COO, a VP of marketing, head of sales, and you're sitting there thinking, I don't know what questions to ask this person. I don't know what to pay this person. And I definitely can't tell the difference between someone who actually knows the job and someone who's just really kind of pretty good at interviewing for the job. And look, I get it. I've scaled 8 companies past 8 figures. I've personally hired hundreds of people, and I can tell you from experience that hiring for a role you know nothing about is one of the most expensive and challenging mistakes a founder can make if you get it wrong. And heck, I once paid a CFO who was basically just a glorified bookkeeper $200,000 a year for 2 years because I didn't know any better. Now that single mishire cost me well over $1 million when you add up their salary plus the 2 years of growth that we basically left on the table just because they sucked. So Lemme walk you through the 4-step system that I use anytime I need to hire for a job that I've never done, so you don't make the same mistake that I made. Step 1, you need to name the role. Before you interview a single candidate, you need to be crystal clear on the actual role you're hiring for. Here's what I do now. So step 1, list out the specific tasks and activities that you actually need this person to complete. Not vague stuff like, Handle marketing. I want you to be specific. Write email campaigns, manage paid media accounts, oversee content production. Step 2, list the outcomes they need to own. What are they specifically responsible for? What are they actually delivering? Step 3, list the metrics they're gonna be measured by. Is it revenue? Is it leads? Is it conversion rates? Is it customer retention? If you can name the numbers, name the numbers. Step 4, get clear on the context of your business, the industry that you're in, the types of products and services that you offer. The size of your company, number of employees, revenue range, stuff like that. Then take your answer to all 4 of these questions that you asked and give it to Claude or ChatGPT with a simple prompt, something like, based on the following tasks, outcomes, metrics, and company context, what are the most appropriate job titles for this role? Provide 3 to 5 options with descriptions of each, including the typical experience level and salary range. And when you do this, what you'll get is a list of real job titles that actually exist with descriptions that actually make sense, ones that you can actually use, titles that real candidates will recognize, titles that have real compensation benchmarks on sites like salary.com and Glassdoor. Don't be surprised if AI tells you that what you think of as one role is actually two or three different roles. When that happens, believe it. This is the unicorn trap revealing itself, and the time to be creative and come up with your own roles is not when you're ignorant to the role that you actually need. Now, here's what's happening when you get this step wrong. Remember the CFO title I mentioned earlier, the one who cost me over a million dollars? This step, the one that I just went through, especially with the added benefit of AI, this is the step that I skipped because I just didn't know what a CFO actually did at the time. If I would have done this exercise, listed the tasks, the out comes the metrics. AI would have told me in 30 seconds that what I actually needed was a controller, not a CFO. Okay, so you got a real title and a real job description, but here's the thing: you still have no idea what someone who's actually good at this role looks like. Step 2: Learn the role. Before you interview a single candidate for the job, you need to fully understand the role that you're hiring for. And I don't mean reading a few blog posts or articles about it. I mean actually talking to people who are doing the job right now to find out what does a good person look like before you interview them. You got to get a picture of the right person in your brain. So, here's how I do it. I go to LinkedIn, I search for the job title I identified in step 1, which good news, because it actually exists, you're actually going to find people, and then I just start DMing people who are currently in that role. I'm not looking for job seekers, I'm definitely not looking for recruiters. I'm looking for people who are employed and winning in that role right now. Here's the key: I offer to pay them. When we were hiring for a content marketing manager years ago, I offered $100 an hour for a 30-minute conversation. That's $50 for half an hour of someone's time, and it completely changed the dynamic. First, it told people that I was serious. I wasn't some random person looking for free advice. I was a business owner willing to invest in getting this right. Second, it got me access to people I never would have reached otherwise. People who are great at their jobs, guess Guess what? They're busy and they're not gonna take random calls from a stranger. I went into those conversations thinking that I was hiring one person. I needed a doer, I needed an executor, someone who could really take the content marketing efforts that we needed on their shoulder and just run with it. But by the third conversation, I realized I was completely wrong. Every single person who was actually performing the job that I wanted to hire for had 3 to 5 people working under them. They had writers, they had designers, they had SEO specialists. They weren't doing a lot of this work themselves. They were leading a team that did the work. Now, that single insight, which sounds simple, changed everything. It changed the job description, it changed the budget, and it changed the candidate profile because now I knew that anyone who told me that they could do it all themselves probably didn't actually understand the role. What do you actually ask in these learning conversations? Here are 5 questions that I would recommend that you ask. Question number 1, walk me through a typical week in your role. Question 2, What resources or team members do you need to actually be successful in this role? Question 3, if you were hiring someone to replace you, what would you look for? Question 4, what does someone who's failing in this role look like? What are the early warning signs? And question 5, what should someone in this role accomplish in their first 30, 60, and 90 days in the job? Now, when you're doing this, you should absolutely talk to a minimum of 3 people, 5 to 7 is even better, because That's when the patterns really start to emerge. And remember, this is not recruiting. The moment you start selling your company is the moment that you stop learning. So keep these conversations about them and their role. If it turns into a recruiting opportunity, great. But here's where most founders still get burned, because knowing what good looks like and being able to spot it in a 60-minute interview, those are two very different things. And that's why you need step 3, protect the hiring process. Get an expert in the dang room. This is so important. And this is the step that would have saved me over a million dollars. When you're hiring for a role that you don't fully understand, you need someone on your interview team who has successfully hired for this role before. Not someone who's done the role, someone who has hired for the role, managed the role, led the role. This person will bring you 3 things that you just don't have. First, role-specific questions. The types of questions that you'd never think to ask because, well, you just don't have enough domain experience. They're gonna come up with technical follow-ups, they're gonna come up with scenario-based questions, you know, "Walk me through how you'd handle X, Y, and Z," things that separate someone who's actually done the work from someone who's just read about it. Second, they're gonna smell the BS. They're gonna pick up on the subtle stuff, the buzzwords without substance, the vague answers dressed up in confidence, the red flags that sound like green flags to someone who doesn't know any better. Third, and this is the most important one, they give you the authority and really the permission to say no. So, how do you get this expert? Well, there are 3 ways that I've done it in the past. Option 1, you can just ask a favor. If you're in a mastermind or a CEO group, or you just have friends who run businesses at your level, you can ask someone who's hired for this role already just to sit in on your final round interviews. Most people will do this as a favor if you ask and if you promise to do the same for them. Now, this is one of the biggest benefits, by the way, of being in a mastermind or CEO group that not enough founders take advantage of. Option 2, you can pay a consultant. So you can find a fractional executive or a freelance expert who's actually done this role Pay them for 3 to 5 hours of their time to review your job description, sit in on interviews, and give you a candid assessment. Trust me, it is worth every penny. Option 3: hire a recruiting firm. Now, for true executive, VP, or C-level roles, this is the route that I recommend going. They're gonna own the sourcing, the screening, the interviewing, and they're gonna give you that third-party objectivity that you're just not gonna get from your own team. Just make sure if you go this route that you're working with a firm that understands your industry and has actually placed people in the exact role that you're hiring for. Try to do reference checks beyond the references that they gave you. Go and look at their past companies, look who they're connected to at those companies, who they seem to have worked with, and do some blind reference checking on your own. By the way, if you want a structured way to evaluate candidates across all the dimensions that matter, not just skills, but culture fit, leadership potential, the whole picture, I built something that does exactly this. I'm gonna tell you about it in a minute, but just know it's completely free, and I, I dropped the link inside the description if you wanna check it out. Any point in time. Now you're down to your finalists. How do you actually make the final call? Step 4, test the fit. Now you need to do 2 final filters to make your decision. Filter 1 is the 30-60-90 plan test. So, remember the question 5 from those learning conversations back in step 2? Remember we asked, "What should someone in this role accomplish in their first 30, 60, and 90 days?" And I want you just to create a simple template in, in your mind. What What does a strong first 30 days look like? What about 60? What about day 90? You're not writing the plan yourself, you're compiling what the experts told you a plan should look like. Then, ask each of your finalists to create their own 30, 60, 90-day plan for the role as the last step in the hiring process. Depending on the role, you may need to pay 'em a little something to do it. If you do, it's fine, it's worth it. That's gonna tell you how they think. It's gonna tell you what they expect of themselves when they enter this role at your company. Now here's what a strong plan looks like. Number 1, it's specific. Specific to your company. Number 2, it should include a learning phase. Should say, "Hey, in the first 30 days, here's what I need to understand before I start making changes." This not just shows some humility, it also shows that they're not gonna fix things that aren't broken. It should mention the team and any other resources that they're gonna need. And it should prioritize. It should prioritize ruthlessly. They should be clear on the deliverables. They should be clear on the metrics-based outcomes that they would want to achieve. But you shouldn't expect them to promise to fix everything in the first 90 days. That's not just unrealistic. If that's what they're doing, then, then it likely has shown some immaturity on their end. If you compare the candidates' plan to one another, the candidates' plan to your template, you know, look at it. Where do they align? Where do they diverge? And look, divergences aren't automatically bad, but they should prompt a conversation. You can say something like, hey, I noticed your plan doesn't mention anything about X. If you hire this person and it doesn't work out, it's not working out, you basically have a built-in evaluation and accountability framework. Now, the second filter is what we call the tacos and tequila check. All right, this one is going to sound counterintuitive, but hear me out. You actually need to like this person. Right now, this is a role that you have never managed before. You don't fully understand the work. You're gonna need to do a lot of brainstorming and time spending with this particular person, learning, collaborating, figuring out how the role fits into the broader ecosystem of your company. And if you can't really evaluate their skill level and you don't enjoy talking to them, you got a double problem. My friend and fellow CEO Jonathan Cronstadt refers to this as the tacos and tequila test. He says, "If this isn't someone that I want to grab tacos and tequila with, then it isn't your person." Now, maybe tacos and tequila aren't your thing, and I'm not saying that somebody necessarily needs to drink alcohol. Please don't blow me up in the comments for that. So yes, hire someone whose skills complement yours. Hire someone who brings expertise that you don't have, but make sure they're someone who gives you energy. Make sure there's someone who you're going to be excited to see when you have a meeting with them on your calendar, someone who when you hang up the phone or get off a Zoom meeting you think, you know what, that was a good conversation. Now there may come a day when the company's big enough that you're hiring purely for competence and merit. You got professional managers all over the place, they can handle people they don't like, but for now don't sacrifice chemistry. Now I mentioned earlier that I built something to help with this entire process, it's called the Founder First Hiring Scorecard. It's actually a tool that we use internally to evaluate candidates holistically. So not just their skills, but also culture fit and all the factors that actually predict, you know, is this hire going to work out? They're going to be a good fit. It is totally free. Just click on the link in the description, put in your email address, and it's yours. And when you download it, I'm also going to give you access to a full 60-minute training that my co-founder Richard Lindner made walking through this entire thing step by step explaining how to actually use it. And by the way, if you got value from this, be sure to subscribe. I put out videos like this every week for founders who are building businesses that can actually scale, and I don't want you to miss the next one. Speaking of the next one, if you found this video helpful, then the next one I would watch is one on the 3 systems that you need to scale to $20 million and above. This is actually gonna break down the high-level roles that some of these systems wind up replacing, so you may not even need to make some of these hires. So check that one out, and I'll see you over there.