Hire the Right Boss for You

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Three co-workers talking
by Cynthia Woolbright

People leave their boss, not the institution. Be prepared to hire the right boss.


Based upon his research in leadership, Michael Watkins, associate professor of business administration at Harvard Business School, cautions, “the root cause of transition failure always lies in a pernicious interaction between the situation, with its opportunities and pitfalls, and the individual, with his or her strengths and vulnerabilities.” We simply don’t consider that we are hiring our boss, just as the organization may potentially hire you.

People leave their boss generally, not the institution. How can you hire the right boss? Here are some things to consider when you’re looking for the right fit for you:

Know thyself. When did you last complete a self-assessment? Have you asked for constructive feedback – inside and outside of work? Have you assessed your leadership style? What is your work style? Your strengths? How do you perform under pressure? How do you best learn? In what type of organization do you perform best – highly structured, wildly flexible or somewhere in between?

Read the environment. How can you assess your potential boss and the board? What is the organization’s resources, culture, and politics? What about relationships? Can you recognize and read patterns and common themes such as ethics, values, team? What are the common threads that you learned from your interviews? How does it match your skills and style? Are your values aligned? How might you contribute? What is valued here?

Ask real questions. This may feel risky but it’s worth it, notes Ron Carucci, Forbes Magazine (February 16, 2016). He advises us to ask:

  • “What can I expect in our relationship?
  • “If I asked others on the team about what it’s like to work for you, what would they tell me?” They’ll probably say, “You should definitely ask them” and you should. It signals to the potential boss that the relationship matters enough to ask.
  • “How do you make decisions and how do you engage your team in them?”
  • “How regularly do you give feedback to those on your team?” Probing specifically into how they lead will give you clearer indications of what you can expect.

While not a complete list, the above steps can begin to lay the groundwork for hiring your boss. You should read, ask and listen to whatever you can about the organization and our potential new leadership. Check out the mission, vision, strategic plan, campus publications, leadership profiles, budgets & financial reports, and, donor relation reports. Ask others about the institution, consult with colleagues, etc.

When it’s all said and done, ask yourself, “Do I want to hire this boss?” And, if you’re the person making the hire, ask yourself if you’re prepared to be interviewed by potential candidates.

Learn more about The Woolbright Group’s talent management services visit or read other talent management articles.

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