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Executive Search

The 5 Critical Questions To Ask When Hiring Your Next CEO

Nick Cromydas
4 min read

Few decisions hold as much weight and significance as selecting the right CEO or President to lead a company. For startups and growth-stage companies, this decision can either propel teams toward unprecedented success or lead them down a path of missed opportunities. The complexities and nuances involved in hiring a CEO are vast, requiring a careful examination of various factors to ensure a seamless fit between the executive, the market, and the organization’s needs.

So much hinges on making the right decision. But every company and what a business needs is different — it can be difficult to assess what the right fit looks like without some helpful tips and blueprints. Our Search Team has developed a comprehensive framework that aids in assessing the "Who" and aligning with the right CEO candidate. This framework revolves around five key questions that set the stage for a successful CEO search.

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A Helpful Framework When Hiring a CEO

CEO recruitment is a complex endeavor that, without a helpful framework, can quickly tailspin. Here are 5 questions our Search Team uses when helping companies determine top-tier candidates and with their decision-making. With this framework, we’re better able to help growing companies identify and hire the best-fit leader for their CEO role.

1. What is the company’s current profile? 

Whether declining, flatlining, growing steadily, or experiencing exponential growth, the demands on the CEO differ significantly depending on the company’s current profile. Understanding where it is is crucial in identifying the right leader who can navigate the specific challenges and opportunities presented by the organization's growth stage.

2. What is the “shot clock” set at to meet key milestones?

Time is a precious resource. Determining the "shot clock" for achieving desired outcomes — be it 12 months, 24 months, or in perpetuity — becomes a crucial filter in selecting the right leader. This consideration helps us identify candidates with the material experience and expertise to drive results swiftly and effectively while nurturing a culture of collaboration and long-term success.

3. What is the most important priority the company can accomplish in years 1, 2, and 3? 

A company must know its one "Most Important Thing” at any given time. To ensure clarity and focus, we advocate setting one key objective for each year of the CEO's tenure. For example, if Year 1 is fundraising and Year 2 is product innovation, the "who" behind a CEO role will look totally different than if Year 2 is in a "grow the core business" stage. Having a singular focus helps in tailoring the candidate search and finding an individual with the right skill set and track record to accomplish that set goal.

4. What are the strongest and weakest leaders and functions in place today, and how important are the weakest functions to a company's overall success?

A successful CEO has to understand the existing leadership landscape. From leaders to departments to functions, it’s helpful to have a comprehensive picture of the strongest and weakest areas. Identifying the strengths and weaknesses provides valuable insights into the areas that require specific attention and expertise. 

This helps us align when a candidate may need a "major spike" in a certain functional area. For example, if commercial growth has flattened, the next CEO may need to come through GTM origins and have lived through this type of revenue stage. By gauging the importance of these weaker functions to the company's overall success, we can align our candidate search with individuals who possess the necessary strengths to fill those gaps effectively.

5. What persona does the company culture need to be successful?

Sometimes, organizations require a change agent who can shake things up and drive transformation. Other times, team members just need a leader who can skillfully manage the game and align the team toward a specific outcome. Both are different personas. Recognizing the specific cultural needs and expectations helps in identifying the right persona and leadership style that will enable the company to thrive.

So, which one do you need?


More Than a Framework: 5 CEO Archetypes To Know

We don't just look at the business model, industry, stage of company experience, and outcomes. We find the above 5 questions set the stage, then we break down specific archetypes of "who" to help draw an even clearer picture.

Here are the 5 most common archetypes we see for a "joining CEO" at a $10-200M business.

  1. The Capital Allocator: A leader with deep strategic financial experience and acumen who can determine where and how to make investments, run capital markets processes, and more.
  2. The GTM Specialist: A strong customer-facing leader with deep expertise in marketing & the CS experience, which can help catalyze growth where things have stalled.
  3. The Product Guru: A general manager who has come up through engineering, product management, and, innovation, who understands how to continue to innovate to delight with strong adaptability.
  4. The Customer Visionary: An industry leader who has strong domain expertise, external relationships, a talent following, and is credible among stakeholders in the strategic and investor landscape.
  5. The Integrator: A strong cultural fit who can manage the game and scoreboard, as well as drive impactful cross-functional harmony and operational discipline across your teams.

A final tip: There’s a lot to consider with many moving parts in executive recruitment. Before starting the search process for hiring a new CEO or rather than swapping out a leader, it can be helpful to just put your founder/CEO on a sabbatical, and when they return, give them another shot on goal. It's hard to replace someone who knows every inch of a business.


Additional Resources To Help Hire a CEO

Need additional help and tips when hiring a new CEO? Explore our CEO-related blogs or get started today to learn more about how Hunt Club can help you throughout the hiring process and connect you with potential candidates.


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