The Top Five Ways to Mess Up Hiring the Right CEO

There are few board responsibilities more important than hiring the right chief executive, as any board member who has had to remove the wrong one knows. And yet, even smart boards mess up the hiring process.

Mark Goulston, Executive Coach/Advisor to Boards
Patricia Romboletti, President, Sage Executive Search, LLC


Here are five common mistakes, ranging from least to most problematic, and tips on how your board can avoid making them.


5. Turn to friends and family.

While this approach works to raise money, it doesn’t work when hiring a chief executive. Unless your friends and family have done solid due diligence — defined the business issues, challenges, and opportunities, and understand all of the dynamics around the current executive team and board — they cannot connect you to the right candidate. Most often, they will recommend a person who most needs the job, not a person who best fits the job.

4. Overreact to the weaknesses of the predecessor.

Let’s imagine that your last chief executive, a consensus builder, didn’t work out. So, this time, one thing seems clear: You need someone who will take command and control the organization. But, wait a minute. Maybe consensus-building wasn’t the problem; maybe it was something else. If you haven’t performed a thorough post-mortem, you don’t really know. You are just fleeing from the fire and looking for the first bucket of water to throw back over your shoulder.

Instead, you should dig a fire ditch — in other words, stabilize the organization, perhaps by hiring an interim chief executive — and analyze why the previous chief executive failed. And don’t forget to put your organization, your board, and your external environment under the microscope as well — not because you want to point fingers but because you need to make an honest assessment of the current situation before moving forward.

3. Fail to define necessary attributes.

If you don’t know what you want in a chief executive, you won’t know when you have found it. When the management and coaches of a baseball team discuss what it will take to get their team to the World Series, you can bet recruiting talent is on the list. But they don’t just say, “We need another pitcher.” They have looked at films of the games, watched the practice sessions, analyzed why they lost, and assessed the pitching staff. Then, and only then, do they send out their scout to find the “right-handed, fast-ball, relief pitcher who has a track record for pulling out wins in tight games against left-handed batters.”

General descriptions, such as “an outstanding leader” or “someone who is able to articulate a clear vision,” will not help you locate the right chief executive. If you want your chief executive to be successful, take the time to clearly define what you want. Getting as much input as possible, answer the following questions:

  • What are the organization’s top three to five objectives for the next 12 months?
  • What are the internal and external obstacles to meeting those objectives?
  • What skills, talents, and expertise already exist on the senior team?
  • What is missing?

Now, you can scout for a candidate who has the desired qualities. And later, when you have a new chief executive in place, you will have a roadmap that both of you can follow.

2. Cast a small net.

A few years ago, Patricia attended a photography workshop presented by world-class photographers. They said one thing really made the difference between them and amateurs: They were willing to burn through 100 rolls of film to get one fabulous shot.

Cast a wide net. For an average search, Patricia’s research will identify between 50 and 75 potential candidates based on broad criteria, such as size of organization, years of experience, etc. From there, she will have meaningful discussions with about 20 people, meet with approximately 10 to 12, and then present three to five to her clients. Organizations that conduct their own searches usually have much smaller numbers. So, burn a lot of film. It’s worth it.

1. Rush the process.

There is a lot of wisdom in the old adage, “Marry in haste and repent in leisure.” You cannot get to know someone in one interview. Both Patricia and I urge our clients to use the “Colombo” approach to interviewing candidates. Colombo, a television detective popular many years ago, would talk with crime witnesses multiple times in an effort to catch them off guard. This is the most effective interview tool. Candidates show up for the first interview fully prepared and ready to counter any concerns you might have. The best tactic is to leave the elephant in the room at the end of the first meeting. Don’t ask the most obvious uncomfortable question, such as why the candidate has a history of short tenures or a long lapse between positions. Instead, follow up by phone or in person again and again, each time drilling down more and more until the elephant has been identified. Meet at different times of the day, at different venues, over a meal. By the fourth meeting, Patricia and I are confident we have gotten behind the résumé to the real person.

If you are thinking you don’t have time for this, stop and add up the hours you have spent trying to work through your issues with the wrong hire, devising a way to replace that person, and meeting with your legal counsel. And don’t forget to add in the lost opportunities and the impact on staff. Now, think back to how long you took to vet that person. These two numbers provide an important part of the answer to why the last chief executive didn’t work out.

Take your time. The right hire can easily make up for a few weeks. But the wrong hire will cost you months of lost time, not to mention lost opportunity and momentum.


The Top Five Ways to Mess Up Hiring the Right CEO
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101 Resource | Last updated: July 10, 2017

Resource: Chief Executive Transitions: How to Hire and Support a Nonprofit CEO