A Deep Dive on Hiring

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A Deep Dive on Hiring In The Trenches

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Questions Asked

Randy Street (3:30)

Many of you will know Randy Street as co-author of the book Who: The A Method for Hiring, which introduced the now widely used Topgrading hiring method to the world. The book went on to become a New York Times, Wall Street Journal, BusinessWeek, USA Today, and Publishers Weekly best seller. Most importantly though, more than any other book of which I’m aware, this book acts as the “hiring bible” for countless CEOs across the world.

  • Where do you stand on CEOs interviewing every single new hire within their organization? Is this a sign of admirable dedication to people and culture, or a sign of ineffective delegation and a lack of trust in other members of the leadership group?
  • Is there a company size threshold that would dictate which of the above approaches is more appropriate?
  • Where do you stand on the use of personality profiles/tests as part of the hiring process? How reliable or predictive have you found them to be?
  • Should a CEO include members of her management team in the interview process when hiring new members of that team? What if she disagrees with the team’s consensus recommendation?
  • Many hiring mistakes seem to manifest when small companies hire executives from much larger companies. Why? Does this challenge or support conventional hiring wisdom?
  • What’s the more common hiring mistake: Right-person-wrong-seat, or wrong-person-right-seat?

Verne Harnish (22:39)

Verne Harnish is the founder of the Entrepreneurs’ Organization (“EO” for short), a global network of entrepreneurs and CEOs that boasts over 16,000 members worldwide. He is the author of multiple global bestselling books including Mastering the Rockefeller Habits, and Scaling Up, which has been translated into 23 languages and has won eight major international book awards.

  • It seems to be particularly hard for CEOs to hire a “#2” or “right hand” to take some of the day-to-day responsibilities off their plate. What advice would you give to a CEO currently contemplating (but struggling) to make such a hire? Why does this seem to be such a difficult hire for CEOs and entrepreneurs to make?
  • When filling these types of roles, why do internal hires tend to work out more frequently than external hires do?
  • Many CEOs want to make a key executive hire, but are worried that they don’t have the budget to do it. However, in some cases, the value that these new hires would generate could create the budget bandwidth that these CEOs are seeking. How would you counsel a CEO who currently finds herself stuck in this type of circular logic?
  • How do you recommend that CEOs structure “trial periods” when making key executive hires?

AJ Wasserstein (37:43)

AJ Wasserstein is currently a Professor at the Yale School of Management. Prior to his time at Yale, AJ was the CEO of two highly successful companies: His first company, ArchivesOne, grew to become the third largest records management company in the U.S. prior to being sold to Iron Mountain 17 years after its founding. His second company, Onesource Water, grew to become the third-largest bottleless water service business in the U.S. before also being sold, this time to Water Logic, a U.K.-based strategic acquirer, in 2016.

  • What are some of the generalizable lessons that you can tease out from the hiring mistakes that you made over two decades as a CEO?

Mike Zani (43:40)

Mike Zani is CEO of The Predictive Index, which serves more than 9,000 clients across 142 countries, helping businesses optimize their hiring and team composition decisions through data-and technology-based tools. Mike is also a best-selling author, having published The Science of Dream Teams, a Wall Street Journal Best Seller, in 2021.

  • Explain your “head, heart, and briefcase” framework for evaluating talent, and tell us where within that framework do most hiring mistakes tend to take place?
  • What are some of the hiring mistakes that you’ve made recently, and what generalizable lessons did you extract from those mistakes?

Steve Divitkos (52:27)

Steve Divitkos is the Founder of Mineola Search Partners, a firm that invests in Search Funds, the entrepreneurs who run them, and the companies that they acquire. Prior to Mineola, Steve was the CEO of Microdea, a document management and workflow automation software company serving the transportation and logistics industry. Steve acquired the business from its original founders in 2014, and successfully sold the company to a strategic acquirer in 2020 after having served as its CEO for approximately seven years.

Anthemos Georgiades: Hiring in High Growth Environments (1:12:50)

Anth Georgiades is the Founder and CEO of Zumper, an apartment rental platform that he founded in his second year at Harvard Business School in 2012. Zumper boasts over 250 employees, 75 million active users, and 17 million app visits per month. The company has raised over $150M in Venture Capital from investors that include Andreessen Horowitz, Greylock, Kleiner Perkins, and Blackstone, among others.

  • Did your company “outgrow” some of its early hires? If so, how did you deal with the reality of having to move on from people who helped you grow so rapidly?
  • Was there something in particular that you looked for in your early hires to see whether or not these people had the ability to rapidly scale alongside the company?
  • You recently hired a very experienced executive to be your President and COO, a very difficult hire for a lot of Entrepreneurs to make. When considering this hire, what worried you the most? What did you consider as some of the possible pros or cons of making it?

Nicholas Andrews: Hiring for the Finance & Accounting Function (1:27:09)

Nicholas Andrews is Founder of The Aspen Consulting Group, a company that performs finance, accounting, and operations consulting for a wide range of small and medium sized businesses.

  • What is the difference between a CFO and, say, a VP or Director of Finance & Accounting?
  • How does a CEO know whether or not she needs a CFO versus, say, a Controller or a Director of Finance?
  • What should CEOs look for in the resumes and interviews? And are there any red flags to be aware of that might be suggestive of a potential bad hire?
  • How do you know that a newly hired Finance/Accounting leader is doing a good job? Are there any metrics that might better inform this question?

Rich Mironov: Hiring in Product Management (1:42:40)

Rich Mironov is one of North America’s preeminent Product Management thought leaders. Rich has spent 40 years in the software industry in numerous capacities, and currently acts as a Coach, Consultant, and Interim Executive for CEOs and Heads of Product across Canada and the United States, advising them on a diverse range of issues spanning product, marketing, engineering, and sales.

  • What should CEOs look for when hiring their Product Management leader, and what should they ask in the interview?
  • How do you weigh industry experience vs. general Product Management experience, assuming that it’s hard/rare to find somebody who has both?
  • How involved should a Head of Product be in the day-to-day of Product Management (gathering requirements, writing user stories, etc.)?

Dave Prusinski: Hiring in Sales (1:55:20)

Dave Prusinski spent 10 years as the Executive Vice President of Sales and Marketing at FleetComplete, a technology provider to fleet-owning businesses around the world. Under Dave’s leadership, FleetComplete grew their annual revenues by ~25x, achieving a ~50% revenue CAGR for 9 of his 10 years. Dave now spends his time as a Revenue Coach to several SMBs, working directly with their CEOs and Heads of Sales to optimize their sales and revenue generation processes.

  • What are the most common mistakes that CEOs make when hiring a Head of Sales?
  • How do you hire a Head of Sales who can scale while also avoiding “over-hiring” risk?
  • How important is industry experience when hiring individual sales reps?
  • When should a CEO expect a new sales hire to pay for themselves?
  • How do you evaluate new sales hires if your company has very long sales cycles?
  • How do you translate a revenue goal into a quantifiable activity goal for each rep?    
  • If building a sales team from scratch, who should you hire the first? Leader or individual contributors?
  • How do you most effectively ramp/onboard newly hired sales reps?
  • Should CEOs utilize their existing reps to help onboard newly hired reps?  

Thanks to our Sponsors

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