Skip to content

Hiring C-suite executives: 6 essential questions


Selecting senior leadership team members is among the most significant – and perhaps transformative – choices a company can make.

Whether yours is an up-and-coming business or an established organization facing a critical pivot point, hiring C-suite executives is an opportunity to take a closer look at your organization’s top priorities and hire accordingly.

To guide you through this process, here are six key questions to consider:

1. Whom should you hire first?

For small or startup companies, typically the founder has the title and function of CEO. In businesses rooted in a partnership, titles may be shared or divided in a way to reflect individual strengths and experiences.

The traditional first C-suite executive hire

Assuming the founding leadership has specialized knowledge outside of money matters, often the first new leader to be on-boarded or promoted through the ranks is a chief financial officer (CFO).

At least that’s how things have been done traditionally.

More recently the financial duties typically tied to the CFO have been assigned to a controller, a certified public accountant (CPA) or even a consultant.

If bookkeeping practices are kept in reasonable order and someone can manage the books, tackle closing and financial reporting, then there’s no requirement that the most senior financial person have a C-suite title, saving you a permanent post and a corresponding salary.

Larger, established organizations may discover the departure of a CFO is a great time to reconsider the post and its necessity. Outsourcing financial oversight responsibilities may both make sense for your workflow and save money.

The CFO job duties have recently shifted to focus more heavily on M&A, due diligence, treasury and initial public offerings (IPO). If your need does not include any of these factors, then an individual with the title of CFO may not be needed in your organization. 

The modern first C-suite executive hire

For many modern companies, it may be wiser to invest significant money and energy toward securing a chief technical officer (CTO) or chief information officer (CIO).

A great CTO or CIO:

  • Understands the ins-and-outs of your organization
  • May be charged with ensuring the reliability and implementation of automated accounting, procurement and sales customer relations management (CRM) tools
  • May have responsibilities that cut across several areas, making the position more mission-critical than a CFO

Beyond the areas of finance and information technology, the nature of the work and size of the company will dictate whether or not additional C-suite positions are needed for operations, marketing, compliance, human resources or general counsel.

Similar to the CFO role, many companies find outsourcing these positions can keep overall costs lower than the salary and benefit packages that individual C-suite officers might reasonably expect. Potential savings can be used in all sorts of ways, from research and development to expanding your sales team.

2. How do you attract top-notch C-suite executives?

Frankly, whether you’re looking for a CEO or any other C-suite positions, the work of recruiting, hiring and retaining a great employee begins long before a job announcement is drafted.

Developing a clear sense of mission and building a culture that genuinely reflects that purpose is vital. If your culture doesn’t authentically reflect your overall objectives and vice versa, it can be difficult to attract great candidates.

People in every industry talk amongst themselves and word can spread if there are negative behaviors or a short-sighted vision in place. A rapid succession of departures from key posts by well-regarded individuals can be red flags to outsiders, even if existing leaders believe they’re making changes for the greater good.

At the same time, a company with an excellent reputation within their industry may find themselves inundated with applications from top-notch candidates.

Your C-suite executive recruitment process

Assuming your mission and culture are in sync and your reputation is solid, let’s consider who needs to be involved in the recruitment process.

Depending upon the structure of your company, essential stakeholders may include everyone from direct reports, members of the board, private equity group members, and those currently in top leadership posts. If your C-suite employee is retiring, it is good to have them involved in the process as well.

When you initiate your search, it’s critical to consider who will be involved in the initial screening of candidates, interviews and making the final offer. This cadre of professionals likely have opinions – perhaps strong ones – about responsibilities, deliverables and other functions for the new staff member.

Welcome their input about:

  • What the company is currently doing well
  • What are some of the challenges facing the company
  • What are the goals and vision for the future
  • What is needed from the new hire to fulfill those goals and that vision

By clarifying expectations and setting some parameters, you can define precisely whom you’re seeking and present a more united front to interviewees.

Your C-suite job description

It’s time to craft a captivating job description. Do your homework to benchmark with industry leaders and competitors, if only through a Google or LinkedIn search for recent, similar job postings.

(Note: It’s important to track and update job descriptions over time, not just in the heat of recruiting. They can be helpful for employee reviews, performance management as well as future recruiting efforts.)

Keep in mind that the description should reflect characteristics suitable not only for the position but also for where the organization is in its life cycle.

For example, if yours is an early-stage startup company, you may think you need a dynamic, entrepreneurial personality for your C-suite post. What you may actually need is someone who has prior experience smoothing out processes and planning for the future.  

Meanwhile a turn-around company working to replace someone in an existing position can fall into the trap of thinking they need a clone of the person who just left. Again, having conversations with key stakeholders about needs and goals can provide some clarity around the ideal candidate’s character.

3. Where will you find great C-suite prospects?

It’s possible that your next C-suite hire is working for a competitor, in a different field or even in the workspace down the hall. You won’t really know for certain until you start recruiting. With a clear job description in hand, it’s time to begin sharing it in hopes of building a rich, dynamic applicant pool.

Just as job seekers are encouraged to look within their networks for job leads, companies should look within professional networks for great employees. This process can take a lot of different forms, including:

  • Talking to peers in your industry
  • Reaching out to alumni at your alma mater
  • Tapping your own board members for potential leads
  • Looking internally

Wise leaders also look to diversify their pool. Look beyond your existing networks to professional organizations and leaders who can help a forward-thinking company uncover more diverse talent.

Foster an environment that can enhance your company, your brand and your product’s appeal to a wider array of clients and customers in an increasingly global marketplace. Indeed, the issue of diversity in C-suite hiring is so important that it has its own separate question (see below).  

Once you’ve got your job description in hand, you’ll want to post it to your company website, relevant professional organizations and on public job boards like LinkedIn and specialized sites unique to your field.

Utilizing a recruiter to manage this part of the work can free you up to focus on your business as they identify and engage qualified candidates that meet your organizations goals and objectives. 

4. Whom should you avoid hiring?

It may seem counter-intuitive, but serious thought should be given to whom you don’t want in a leadership role, especially for an essential role like those in the C-suite.

A good hire knows that the executive team isn’t there to lead in a top-down fashion. They appreciate that a productive workplace runs on collegiality and a sense of shared responsibility.

Conversely, a bad hire in the C-suite may not share the same vision and values as the rest of the organization.  Many times these executives are focused more on the top-down approach instead of the current collaborative workplace already established.       

In a worst case scenario, a bad senior hire can:

  • Damage productivity and morale
  • Collapse even the healthiest company culture
  • Lead to a mass exodus of employees that cripples the company, perhaps permanently

Hoping to avoid this kind of scenario? The key is to remember that sometimes bad leaders interview well and look great on paper. A polished veneer coupled with extraordinary communication skills can mask poor leadership abilities.  

Vetting a candidate thoroughly requires:

  • Probing behavioral interview questions
  • Follow-up interviews or assessments
  • Identifying a candidates EQ (emotional intelligence)
  • Thoughtful conversations with previous supervisors and, if possible, recent subordinates

Look for evidence of substance over style. If other team members express reservations, hear them out – even if their intuition runs counter to your own.

Remember: Just because a candidate has previous or similar experience at another company doesn’t necessarily mean that their leadership style will work well with your business culture.

Good leadership requires trust, and if a new hire can’t spark trust because they put their agenda above that of the company’s mission, then your business’s long-term success may be placed in jeopardy. 

5. How do you build a more inclusive C-suite executive team?

Hiring C-suite positions is an ideal opportunity to not only bring in fresh perspectives at the top of the org chart, but also signal to the world that you welcome diversity at all levels.

A strategic hire in your C-suite may help you diversify talent at other levels, too.

Inclusive hiring practices require intentionality and a willingness to work a little harder to ensure things like position announcement keywords and your company’s digital footprint reflect the fact that you have – or seek to build – an inclusive culture.

Your C-suite position job description keywords

Getting the words right in the job description and public posting of the vacancy can help or hinder your efforts.

For example, the phrase “code ninja” is popular in some tech field position announcements, but the phrase has a decidedly masculine tone that can be off-putting to the wider array of candidates you are trying to entice.

To set a more inviting tone, use the language of your job announcement to indicate interest in hiring employees from diverse backgrounds. One simple way to do this is to include an official company statement on diversity and inclusion.

Your social media presence

It’s important to remember your company’s social media footprint can send off-putting signals, too.

In an increasingly visual culture, social shares send messages beyond intended branding and invitations to click a specific link.

The faces and spaces that your marketing team highlight in images, the way your marketing and website text reads and even the references that you make to holidays or current events can widen or narrow your potential applicant pool accordingly.

Your existing workforce

Finally, if you’re truly committed to nurturing diversity, consider promoting from within the ranks of your current staff.

A great company culture is one in which a pipeline of talent is nurtured continuously. If team members reflect the diverse leadership you aspire to put in place, then consider the fact you may have someone waiting in the wings, ready to step into the C-suite spotlight in the company’s future.  

Such a hire may help you attract an even wider talent pool moving forward, especially as like-minded industry professionals take notice of your choices.

6. How do you prepare for future hires?

The final question you should ask as your company contemplates a C-suite executive hire is how to prepare for succession.

Times have changed and the days when an employee would stay with a single company for decades is waning. Movement is to be expected. Advance preparation can smooth the process and ensure some degree of continuity, if desired.

Prepare by:

  • Creating a system for storing and updating job descriptions
  • Monitoring changes in responsibilities within your company and the industry at large
  • Collecting business cards for talent you might want to recruit in the future
  • Maintaining your own LinkedIn page and connecting with other professionals in the field

The work of determining objectives, crafting a job description, recruiting and interviewing the next hire can seem overwhelming – let alone planning another step or two ahead. This is where partnering with a good recruiter can alleviate much of these burdensome tasks. 

It’s never too early to think about and plan for future leadership shifts, especially if you aspire for your company to easily promote internal candidates to top posts or attract the best and brightest minds in the workforce.  

Many great companies have C-suite and leadership roles that will be vacated due to retirement in the coming years. Establishing succession plans and investing in your current employees will pay dividends when the time comes to fill these critical roles.

From creating the right workplace culture to developing and maintaining accurate job descriptions, there’s much that can be done to make future hiring processes run more smoothly. Insperity’s own guide to succession planning can help you get a jump on those future needs.