Ep. 509 - Unlock CFO Success Secrets No One Tells You About Hiring

Summary

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Podcast Summary: Second in Command with Cameron Herold

Episode 509: Unlock CFO Success Secrets No One Tells You About Hiring
Date: September 11, 2025
Host: Cameron Herold

Episode Overview

In this episode, Cameron Herold and his guests deep dive into the complex process of hiring a CFO—a pivotal moment for many growing companies. They focus on real-world challenges: how to spot and address red flags during hiring, why direct questioning is crucial, the importance of honesty and ownership in leadership, and how outside expertise (like fractional CFOs) can help set both new hires and current leaders up for success. The conversation is candid, practical, and full of actionable insights for COOs and business leaders navigating the hiring of top financial talent.

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Key Discussion Points & Insights

1. Addressing Red Flags in CFO Interviews

• Incident Under Discussion: Damon shares a concern about a CFO candidate who delayed a leadership dinner and gave what sounded like a flimsy excuse, even though he aced the formal interview. There's underlying worry that this could signal future reliability issues.

  • Damon [02:01]:

    “He fucked around with getting here and we were supposed to have a leadership dinner... and it just sounded like an excuse. Right? I hate it when people make up an excuse to be late to anything, especially for an interview.”

  • Lacy confirms the candidate was on time for the main interview, but tension lingers over the missed dinner.

• Cameron's Guidance: Direct Confrontation

  • Cameron Herold [03:23]:

    “Have you had the, like, the quick discussion with them going, hey... there's this one thing, though, that's really bugging me. Can you just speak to this? Yesterday, like, what happened? Did you really have an accident or were you just late?... I’m worried that this is the way you're going to be showing up. Can you address that with me right now?”

  • His advice is to ask candidly and assess the response: If the candidate admits fault and displays accountability, it’s a positive sign.

  • Cameron Herold [05:06]:

    “Yeah, I just didn't. I didn't. I didn't leave enough time. I fucked that one up and I own that.”

• Respect for Honesty (Lacy’s Response)

  • Lacy [06:24]:

    "I can respect like, even if he gave that…answer, like it’s not the answer I want to hear, but it’s still like the truth. I respect it and he can understand my expectations moving forward that he's got to own his."

2. Drawing on Past Experiences (Notable Story)

• Cameron's Anecdote:
  • He shares a story about his sister being asked if she was a 'quitter' for retiring from elite ski racing.
  • Cameron Herold [00:00 / 03:55]:

    “My sister looked at him and said, I'd say, you have no idea what it's like to ski at an elite ski level or compete in anything in your life. So if you want to address it that way, you have no idea what it takes to compete.”

  • The moral: Sometimes the direct question must be asked, and the strength or candor in the answer can reveal character more than the situation itself.

3. CEO-CFO Relationship & Setting Up for Success

• Damon’s Challenge:

  • This CFO hire is especially critical as his last experience—years ago—didn’t go well.
  • Damon [06:43]:

    “What is that [CFO-CEO] relationship really? It's a new position for me where I haven't had that position for probably three or four years and that guy was a piece of shit.”

• Leverage Outside Expertise:

  • Cameron suggests using experienced CFOs or accounting firms to help clarify what success and expectations look like—especially when founders/CEOs may not have deep financial expertise.
    • Cameron Herold [06:57]:

      "I would make sure you have either a couple of CFOs from some other mid sized companies give you some advice and direction on what this guy needs to be doing over the next 12 months. I would maybe even have your accounting firm come in because often we don't really have the financial acumen to know what somebody seasoned in a very particular role should be doing or should be good at."

  • Cameron adds that a fractional CFO or an external advisor should participate in the interview and onboarding process, to check for real financial skill and fit.
    • Cameron Herold [07:40]:

      "You can interview for culture, you can interview for general aptitude. But in terms of like, does this person really know the CFO side of finance and accounting? Often that's outside of our purview of expertise..."

• Practical Takeaway:

  • Don’t go it alone: Bring in domain experts to vet CFO candidates and set up their first-year roadmap. This ensures expectations are realistic and aligned.

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Notable Quotes & Memorable Moments

• Facing Red Flags Head-On:
  • “Can you address that with me right now? Like, just.” — Cameron Herold [03:23]
• Candor Over Perfection:
  • “I would rather him tell the truth, even if it was like I didn't take enough time and I own it.” — Cameron Herold [05:05]
• Peer Validation:
  • “Often we don't really have the financial acumen to know what somebody seasoned in a very particular role should be doing or should be good at.” — Cameron Herold [06:57]
• Respect for Owning Mistakes:
  • “...even if he gave that answer, like it’s not the answer I want to hear, but it’s still like the truth. I respect it...” — Lacy [06:24]

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Timestamps for Key Segments

• [02:01] Red flags in CFO interview—lateness and excuses
• [03:23] How to confront candidate about reliability, honesty, and handling hard questions
• [03:55] Anecdote about confronting tough questions and measuring authentic responses
• [06:43] CEO-CFO relationship: learning from past mistakes, setting up new hires for success
• [06:57–07:40] Bringing in outside CFOs and financial experts to set expectations, participate in the hiring process

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Tone & Language Notes

• Frank, candid, at times blunt—mirroring the challenging realities of executive hiring
• Relatable, story-driven, with practical advice and a touch of humor
• Fosters an open environment for learning from mistakes

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Summary Takeaways

• Don’t ignore small red flags in the hiring process for strategic roles—directly address them and value honest responses.
• Leadership (especially in finance) requires both skill and accountability; honesty about mistakes can create trust.
• Engage external experts (fractional CFOs, accounting firms, peer leaders) in hiring and onboarding to ensure right-fit and clarity—don’t go it alone if you lack deep domain knowledge.
• Ultimately, a culture of openness, clear expectations, and mutual respect for candid communication define successful CFO (and broader leadership) hires.

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For more episodes and resources, visit COOAlliance.com.

Transcript

[Cameron Herold]

Would you do if I told you that I felt like you were a quitter and you'd be a quitter in business because you quit at ski racing? And my sister looked at him and said, I'd say, you have no idea what it's like to ski at an elite Ski Rebel or compete in anything in your life. So if you want to address it that way, you have no idea what it takes to compete. He goes, okay, solid answer. It's just like, like, you know, like. But he had to ask because he was like, do you, did you give up on things? When her response was so clear and so vivid so you. That he's like, got it. I stepped on some turd. I own it. Right? So maybe this guy can just come back and go, no, I really, I really actually had a accident. Like, it really actually was real. Or, or, or. Yeah, I just didn't, I didn't, I didn't leave enough time. I that one up and I own that.

[Podcast Announcer]

Welcome to the Second in Command podcast, produced by the COO alliance and brought to you by its founder, Cameron. In the second in command podcast, we talk to top COOs who share the insights, strategies and tactics that made him the chief behind the chief. And now, here's your host, Cameron Herald.

[Podcast Narrator]

The search for a CFO can be a critical pain point for many businesses. In this episode, we delve into the nuances of hiring for this pivotal role. Learn how to directly address red flags like scheduling issues or tardiness during the interview process, getting honest answers about commitment and ownership. We also explore the invaluable role of outside experts, such as fractional CFOs or accounting firms, in helping to define clear expectations and set a new CFO up for success, especially when the CEO may not possess deep financial acumen. Don't miss these essential hiring insights.

[Damon]

Sure. I have a question. Yeah, we interviewed a CFO today. It's been one of our pain points over the last fucking probably 5 years. Anyways, good guy. As far as his answers, I feel like they were in alignment with myself, with Lacy, with the rest of leadership. No big red flags, but there was a little bit of a scheduling issue where Lacy in her head maybe just built up a little bit. I think we tried to schedule it quickly because he has maybe two or three other offers out there and he seems like a good candidate, but he fucked around with getting here and we were supposed to have a leadership dinner with him last night, for example. I wanted the whole team to meet him outside of, you know, the four walls of the office and he pothole or this. And it just sounded like an excuse. Right? I hate it when people make up an excuse to be late to anything, especially for an interview. Kill you and. But this guy passes every other test. He did show up to the interview on time, but he around with that. What? Lacey, you're muted.

[Lacy]

He showed up on time today.

[Cameron Herold]

Today.

[Damon]

That's what I said.

[Cameron Herold]

Yeah, yeah, yeah, yeah, yeah. So have you had the, like, the quick discussion with them going, hey, lots of what we've interviewed for. We really, like. There's this one thing, though, that's really bugging me. Can you just speak to this? Yesterday, like, what happened? Did, like, did you really have an accident or were you just late? Like, did you not schedule this? I'm worried that this is the way you're going to be showing up. I'm worried that this is the kind of the way that you approach everything. Can you address that with me right now? Like, just.

[Damon]

Lacey, do you want to own that?

[Lacy]

Yeah, I will do that.

[Cameron Herold]

Because they might come back and just say, you know what? Yeah, I fucked up. I didn't leave enough time and I'm. I was stupid and I'm whatever. I would just ask the question and trust it. I had a guy one time ask my sister. This is going back a long time, but my sister was ski racing at a very elite level. She'd won the Canadian championships, and she finally retired from skiing at 21 or 22. And this guy was interviewing her and said, you know, what would you do if I told you that I felt like you were a quitter and you'd be a quitter in business because you quit at ski racing. And my sister looked at him and said, I'd say, you have no idea what it's like to ski at an elite ski revel or compete in anything in your life. So if you want to address it that way, you have no idea what it takes to compete. He goes, okay, Solid answer. It's just like, like, you know, like. But he had to ask because he was like, dude, did you give up on things? When her response was so clear and so vivid and so you. That he's like, got it. I stepped on some turd. I own it. Right? So maybe this guy can just come back and go, no, I really. I really actually had a accident. Like, it really actually was real. Or, or.

[Damon]

Or.

[Cameron Herold]

Yeah, I just didn't. I didn't. I didn't leave enough time. I fucked that one up and I own that. Hey, it's Cameron. I hope you're loving today's episode. Quick question for you. Does your company have a strong leadership training program in place to grow the skills of everyone who manages people? If you want to help yourself and your company grow, get everyone who manages people learning from my Invest in youn Leaders online training program. There are 12 core leadership skills that I cover online and they're all going to really grow. CEOs pay me $78,000 a year to coach them one on one, and now you can all benefit for 1% of what they pay me. These are the same leadership skills that I created and certified everyone in at 1-800-got junk when I was there as COO. Go to investinyourleaders.com today and use promo code podcast10 before the end of the month to get 10% off each manager you sign up. Now back to the show. I would rather him tell the truth, even if it was like I didn't take enough time and I own it because that can set a very clear bench, very clear, I guess, guideline going forward. Lacey, are you going to say something?

[Lacy]

Yeah. I mean I can respect like, even if he gave that, like that answer, like it's not the answer I want to hear, but it's still like the truth. I respect it and he can understand my expectations moving forward that he's got to own his. Yeah, yeah, I like that. I'm, I'm alive.

[Cameron Herold]

And then it's an easy way to deliver it that way too.

[Damon]

My second question with that, Cameron, is the relationship of the CFO and the CEO. What is that really? It's a new position for me where I haven't had that position for probably three or four years and that guy was a piece of shit.

[Cameron Herold]

So I would make sure that you have either a couple of CFOs from some other mid sized companies give you some advice and direction on what this guy needs to be doing over the next 12 months. I would maybe even have your accounting firm come in because often we don't really have the financial acumen to know what somebody seasoned in a very particular role should be doing or should be good at. But that can, you know, somebody as an outside expert can help us set that up. Lacy, you can talk to Tyler, who is the COO of a, a fractional COO or CFO firm. Like they have tons of fractional CFOs. I'm sure he could give us, you guys, a little bit of guidance.

[Lacy]

He's our fractional right now. Taylor is.

[Cameron Herold]

Yeah, I would, I would have him set this guy up for success, did he? Was he a part of the interview process?

[Lacy]

Not yet.

[Cameron Herold]

I would. I would make sure he does an interview to see if this person has the skills to do what you need them to do, too. You can interview for culture, you can interview for general aptitude. But in terms of like, does this person really know the CFO side of finance and accounting? Often that's outside of our purview of expertise. Outside of mine, anyway. So when we were hiring senior people, we used to go for outside advisors to help us with the interviews.

[Damon]

Damon, I wanted to ask you something about more on the personal side. You mentioned you're going into Paul, so I've had my agency for 18 years.

[Podcast Announcer]

You've been listening to second in command, brought to you by COO alliance founder Cameron Herold. If you enjoyed this episode, please be sure to like, share and subscribe to us on Apple Podcasts, Spotify and our other podcast streaming platforms. For more best practices from industry leading COOs, visit COOAlliance.com.

[Lacy]

SAM.