How to hire for a role you know NOTHING about

A Simple System for Making Smart Hires for Jobs You've Never Done Yourself...Without Overpaying, Mis-Hiring, or Getting Out-Sold by a Great Interviewer  ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌

Read online 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. 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. 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. 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: Real questions the candidate can't deflect A BS detector for buzzwords dressed up as substance, and most importantly... 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. Quick Hits Here’s some other content from the Scalable network, plus some other cool stuff I liked and thought you might like, too: Tool of the Week: This free "Founder-First" Hiring Scorecard ensures you only bring on team members you LOVE working with. (Hiring Scorecard Template) Free Training: I just FIRED myself (and then rehired myself) and why you should, too. (YouTube) Getting Off the Org Chart (Part 2): How to find, compensate, and onboard the CEO that replaces you. (Business Lunch Podcast) This is what I would do differently if a time machine dropped me back into my first day as CEO. (LinkedIn) Want to increase your profitability? Read these books. (Instagram) How'd you like today's newsletter? ❤️ Love it! 🫤 Meh...it's ok 👎 Not my favorite   Update your email preferences or unsubscribe here © 2026 The Scalable Company 4330 Gaines Ranch Loop, Suite 120 Austin, Texas 78735, United States Terms of Service

Stuart Stevens join us live Monday at noon ET - we have an awful lot to discuss

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	Forwarded this email? Subscribe here for more Reflections On The Return Of Our "Barbarous Ancestors" And The Need For Us To Build Something New Stuart Stevens join us live Monday at noon ET - we have an awful lot to discuss Simon Rosenberg May 3   READ IN APP   Happy Sunday everyone. Sundays at Hopium are rest and reflection days, take it easy days, do some gardening, take long walks kind of days…. The big news here at our house is that an old bird house just outside the window where I write each morning was re-occupied this spring for the first time in a long time. So I am now greeted each morning with the new parents scurrying around taking care of their chirping chicks. Here’s a close up of my view: Here’s mama bird standing watch: We need these moments of joy, peace and renewal to help counter the deep sense of betrayal and disbelief that we all rightly feel from Trump, John Roberts, and the malicious extremists doing so much harm to our country and our democracy. For an American governor to try to cancel an already underway election by declaring a state of emergency is a breathtaking expression of tribalism and racism…… Honestly, I am still reeling that something this like this could happen in America, in 2026, and articles about the Civil War never ending are coursing through my various social media feeds this weekend….. Upgrade to paid From this outrage must come a deeper commitment to fight and defeat this dark and dangerous political movement that has seized power in America. I felt that resolute commitment at the Maine Democratic Party Convention this week. In my remarks to the Convention on Friday I read the entire Gettysburg Address for inspiration, and share it here once again for its words still speak to us 163 years later….. Four score and seven years ago our fathers brought forth on this continent, a new nation, conceived in Liberty, and dedicated to the proposition that all men are created equal. Now we are engaged in a great civil war, testing whether that nation, or any nation so conceived and so dedicated, can long endure. We are met on a great battle-field of that war. We have come to dedicate a portion of that field, as a final resting place for those who here gave their lives that that nation might live. It is altogether fitting and proper that we should do this. But, in a larger sense, we can not dedicate -- we can not consecrate -- we can not hallow -- this ground. The brave men, living and dead, who struggled here, have consecrated it, far above our poor power to add or detract. The world will little note, nor long remember what we say here, but it can never forget what they did here. It is for us the living, rather, to be dedicated here to the unfinished work which they who fought here have thus far so nobly advanced. It is rather for us to be here dedicated to the great task remaining before us -- that from these honored dead we take increased devotion to that cause for which they gave the last full measure of devotion -- that we here highly resolve that these dead shall not have died in vain -- that this nation, under God, shall have a new birth of freedom -- and that government of the people, by the people, for the people, shall not perish from the earth. I also draw inspiration this weekend from these words from Thomas Jefferson: I now more than ever believe that our pro-democracy movement must make explicit our goal of overcoming and defeating white supremacy itself. Here is something I wrote in October of 2020 about my hopes for a possible Biden Presidency: Of all the big things we have to do in the coming years there is one more – to honor and build on the work of FDR American leaders should forcefully denounce white supremacy in all of its forms. We have to make clear that American, Western, liberal, Four Freedom values are universal values, values of all people everywhere, regardless of race, religion or country of origin. They belong to all of us. White supremacy is not just a malicious legacy belief system from our racist and colonial past, it’s also profoundly anti-modern; for who could, after seeing the advances and potential of the people all over the world over these past fifty years ever believe that any race or religion or culture was somehow not capable of extraordinary things, and the people of all nations not deserving of the opportunities and freedoms we cherish. Trump’s white supremacy must be returned, aggressively, to the dustbin of history, where it belongs. And I am deeply encouraged by the parade of polls we’ve seen these past few weeks showing Trump dropping further, reaching new levels of rejection and repudiation. The latest comes from ABC News and The Washington Post this morning. Just look at this astonishing chart, documenting how much the nation has turned on Trump and his ugly political movement, how much people now see and understand this to be a failed Presidency: In my weekly talk and post I talked about how post-Callais Democrats were going to have build something new, a new politics suited to the moment and the new opportunities and challenges we now face. I don’t exactly know what this new politics is going to be, but listen to James Talarico here talk about rot and corruption. This feels new, and powerful, and where we are headed, and not where we’ve been: Stuart Stevens is coming by tomorrow at Noon ET for our monthly catch up. Register here to join us live, and I will be sharing a recording of our discussion Monday afternoon. Catch my weekly talk and post for my thoughts about we should be thinking about our politics now, post-Callais, and feel free to spend time with some of our wonderful and courageous candidates today if you want to lift your spirits a bit. Links can be found below…….. Now, my friends…… It Is Time To Get Work Everyone!!!!!!!!!!!!!!!!!!!!!!!! Winning The Midterms, Competing In Red States and Red Places, Expanding The Map Rallying For Jordan and Rankin For Georgia Supreme Court - This is our next big opportunity to make good trouble all. The Election is May 19th, early voting has begun, and we have 2 great candidates, Jen Jordan and Miracle Rankin, who have a serious shot at flipping two GOP-held Supreme Court seats. Watch our new interview with Jordan and Rankin, donate to their campaign, and volunteer no matter where you are! In just one day we’ve already raised $22,900 towards our $50,000 goal! We can do this people!!!!!!!!!!!!!!!!!!!!!!!!!!!!!! Hopium’s Winning The House Campaign (2026) - $633,600 raised, $1,000,000 goal (new ambitious, audacious even, q2 goal) - Donate to all twelve of our endorsed House challengers with one click | Get to know Jamie Ager (NC-11), Christina Bohannan (IA-01), Paige Cognetti (PA-08), Rebecca Cooke (WI-03), Sean McCann (MI-04), Jo Mendoza (AZ-06), Chaz Molder (TN-05), Janelle Stelson (PA-10), Shannon Taylor (VA-01), and Sarah Trone Garriott (IA-03) by watching our recently recorded Hopium interviews. Interviews with Jonathan Nez and Elaine Luria coming soon! If you are looking for inspiration watch a few of these interviews - I promise these great candidates will get you excited about our opportunities this November! For it is simple - if we win these twelve races the House flips. Period. James Talarico For Texas - $64,300 raised, $250,000 - Donate | Volunteer and Learn More | Enjoy my inspiring interview with Rep. Talarico as he fights to turn Texas blue Mary Peltola For Alaska Senate - $88,200 raised, $250,000 goal - Donate | Volunteer and Learn More | Enjoy my uplifting conversation with Mary Peltola as she fights to turn Alaska blue Winning Ohio - $133,300 raised, $250,000 goal - Our new campaign splits contributions evenly among Sherrod Brown, the Acton/Pepper ticket, and the Ohio Democratic Party | Donate today and help us turn this critical 2026 battleground blue | Watch my new discussions with US Senate candidate Sherrod Brown, Lt. Gov candidate David Pepper, and Ohio Dem Chair Kathleen Clyde This total includes $21,000 sent by a Hopium community member directly to each of our three Buckeye State partners! Hopium’s Audacious Expansion Fund - $547,900 raised, $1,000,000 goal (new stretch goal) - Join our campaign that has helped expand our map by investing in the Democratic Parties of Alaska, Florida, Iowa, Maine, and Texas, all now central battlegrounds in the 2026 election | Catch interviews with the five intrepid state chairs leading their troops into battle this year - will get you fired up! | Contribute to all five state parties with one contribution split evenly among these five new battlegrounds Many thanks to two generous Hopium community members who have audaciously donated $20,000 to each of our five state parties over the past two years. Roy Cooper for NC Senate (2026) - $108,500 raised, $250,000 goal - Donate | Learn More | Volunteer | Enjoy my new discussion with Gov. Cooper as he fights to turn North Carolina blue Jon Ossoff GA Senate (2026) - $172,400 raised, $250,000 goal - Donate | Learn More | Volunteer | Enjoy my inspiring conversation with Senator Ossoff Advocate For The Hopium Agenda/Pass Resolutions Of Condemnation In Your Community/Winning In An Evolving Battlefield There are a few more ways to go to work in the coming days - call your leaders and advocate for elements of our working, ever evolving Hopium Agenda; bring resolutions that condemn our Mad King and lets facts be spoken to a candid world to your state or local government; and learn how you can help us win in evolving political and electoral battlefield this year. Here’s our working Post-Iran Disaster Agenda: Work to end this new gulf war and Trump’s Imperial global ambitions Support Ukraine and Europe, not Russia Roll back the new, illegal tariffs Rescind the Trump tax cuts, claw back the extra ICE funding, fund the IRS so it can collect the taxes the rich are hiding from us Launch a major anti-corruption, renewing democracy campaign, one that ensures accountability for the crimes and treason committed, limits the political power of our emerging oligarchy, and strengthens democracy here and everywhere Make the US a clean energy superpower, fight for true energy independence, and lower utility and energy prices for the American people Rein in ICE, end Mass Deportation End Trump’s destructive war on science, research, our health scare system and our public Health Make clear to American farmers that we want to end the failed war, repeal the terrible tariffs, find legal pathways for farm workers, and make health care and energy more affordable Please use the paid subscriber chat to self-report the good trouble you make each day. Keep working hard all. We have a country to save and elections to win, together! - Simon Upgrade to paid Share Leave a comment You're currently a free subscriber to Hopium Chronicles By Simon Rosenberg. For the full experience, upgrade your subscription. Upgrade to paid   Like Comment Restack   © 2026 Simon Rosenberg 5185 MacArthur Blvd, NW #600, Washington, DC 20016 Unsubscribe