The process of ensuring that a candidate will be a good cultural fit for your organization can be roughly divided into three steps. Ideally, the first two steps should be completed before you even start reviewing resumes. The third should be done once your have identified several strong candidates. The three key steps are:

  1. Assess your organization’s culture

  2. Define what you are looking for in a senior manager beyond just the description

  3. Learn about a potential candidate’s personality and work style

Step 1: Assess your organization’s culture

When you think about finding the right people for your organization, you need to first understand your own organization’s culture and work style. At a bare minimum, asking the following questions about your current organizational culture can help clarify what type of work environment your organization offers to potential candidates:

Work Style:

  • How do we get our work done? How do we make decisions?

  • How do we communicate? What are our meetings like?

Professional opportunities and advancement:

  • What types of people tend to do well here? How are we structured?

  • How do we reward people who do well? What happens when people don’t perform well?

Work hours and commitment to work:

  •  How many hours a week do we expect senior management to work on average? How does this expectation match up to reality?

  • Do we provide flexible work schedules or allow for telecommuting, or do we prefer people to work set hours?

  • How much travel do we expect of senior management?

  • Do we expect senior management to be available and accessible after work hours?

  • Are we looking for someone who will be here for a certain number of years or as part of a succession plan for senior management?

Architecture, aesthetics, and atmosphere:

  • How are our offices set up? How do we dress? How do we have fun?

Once you’ve done an assessment of your current organizational culture and work style, you can then think about whether you want the new senior leader to contribute to the existing culture or to be a part of changing the culture of the organization going forward.

Step 2: Define what you are looking for in a senior manager, beyond just the job description

​It is critical to balance your search for fit with your goal of building a team with a diverse set of backgrounds, experiences, ideas, and working styles. Some categories of questions you might want to consider in developing your list of fit criteria include:

  • What adjectives would we use to describe the people who have been successful in our organization?

  • What kind of decision-making style do we want this new senior leader to have?

  • What kind of leadership style are we looking for in this position?

  • What types of personalities work well with the various stakeholders we interact with and what characteristics will this person need to have in order to be successful in these interactions?

These kinds of questions will help you identify what types of personalities and work styles will fit best with your goals for the senior leadership position.

Step 3: Determine the candidate’s fit with your organization

Some aspects of “fit” and personality are more easily assessed than others. Here are some ways to get the information you need to determine how well a candidate will fit with your organization:

Maximize interactions during the interview process

During the formal interview process, it is immensely helpful to have a 360-degree view. This means having candidates interact with not only the people they will report to, but people who will be their peers, and the people who will report to them. Scheduling a day of a long series of meetings with a candidate can ensure that any facades are worn through. Be sure to ask the receptionist, the person who scheduled the interviews, and anyone else who interacted with the person for their assessment of the candidate. Candidates for senior level jobs will probably also meet with board members, allowing you to get feedback about them from the board’s point of view.

Ask a lot of good questions

In order to assess fit, ask questions such as, “What did you enjoy most about the last place you worked? What did you not enjoy?” or “When you think back on your favorite job, what was it and why?” and “Describe your favorite and least favorite bosses.” The types of answers you hear will help inform how well the candidate’s favorite work experiences match up with the kind of work environment and personalities at your organization.

Ask candidates what they like to do for fun. This can be a great way to ask a personal question without violating any employment laws. In addition, invite the candidate to ask questions as well. You can tell a lot about people based on the type of questions that they ask — whether they are insightful or not, big picture versus detail-oriented, process versus people-oriented.

Seek out informal interaction opportunities with the candidate

If possible, try to find ways to spend time with the candidate outside of the formal interview process. It is perfectly acceptable to invite a candidate for a senior position to attend a brown-bag lunch, participate in a staff meeting, or come to an upcoming fundraising event. In each of these situations, you can learn a lot about the individual. Take the opportunity to ask candidates about their impressions of the event they attended. Take note of how critical or constructive they are in their suggestions. Observe what kinds of things they observed. The manner in which the candidate answers these questions can tell you a lot about whether or not s/he will fit with your organization’s culture.

Do the airport test

When interacting with job candidates, one good way to test for this “likeability index” is something called the airport test. Imagine that you are traveling for work with the candidate and you discover your flight is delayed. How do you feel about being “stuck” with this person for two-plus hours in an airport with not much else to do? Can you imagine being happy about this, neutral, or do you think you’ll dread it? Just asking this simple question can help clarify how you really feel about a candidate and his or her fit with your organization’s culture!

Pay attention to your gut instinct

After interviewing the candidate, spend some time reflecting on how the interviews went form a fit perspective. Ask yourself questions such as: “Can I imagine the candidate working effectively with our team?” and “Would I be able to work with this person?” and “Would I enjoy working with this person?” If there are fit criteria that the candidate does not meet, think long and hard about whether those criteria are still important to you and whether this candidate offers sufficient trade-offs to warrant putting them aside. When you’ve done your research and looked at how a candidate stacks up against your organization’s fit criteria, step back and listen to your gut before you make a final decision.


Finding the candidate who is the best cultural fit for your organization can be a very challenging task. It requires insight into your own organization’s culture and keen observation of the candidate’s personality and work style. By proactively developing a list of ideal fit characteristics that go beyond the job description, and maximizing opportunities to learn more about candidates through formal and informal interactions, you can have greater confidence in finding the right senior manager for your organization.

Source: “Making the Right Hire”