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Q&A: Former Superintendent Reflects on Life as a Headhunter

December 16, 1992 3 min read

Kenneth J. Underwood had been a superintendent in one district or another for 23 years when, in 1975, he resigned as superintendent of the Charleston, W. Va., public schools. Five years ago, after teaching at the Virginia Polytechnic Institute and State University, he decided to help school boards look for people like himself, and bought a majority share of Harold Webb Associates, one of the largest superintendent-search firms in the nation.

Although his business is based outside Chicago, Mr. Underwood lives in a Maryland suburb of Washington, D.C., and spends much of his summer working out of a house trailer in northern Minnesota, near some of his favorite fishing holes.

He shared his personal insights into the superintendency, and life afterwards, with Staff Writer Peter Schmidt.

Q. What made you decide to buy a superintendent-search firm?

A. I had worked with Harold for a number of years, just kind of on the side, and one, I enjoyed it, and two, I think it is worthwhile doing it for boards and it is a valuable service. Basically, I am working with the same kinds of people I have worked with and enjoyed my whole life, that’s boards and superintendents. ... I understand their problems and can sympathize in some cases. ...

I feel like I am a matchmaker. That is really what this job is. A particular board, a particular school system, needs a particular kind of superintendent at a certain time in terms of the experiences they have had over the years as well as their personal attributes, and I enjoy matchmaking. Remember, I have always worked with young people coming up.

Q. Having been a superintendent, what do you look for in superintendents?

A. It depends on the system. That’s really what it amounts to. It isn’t so much what I look for specifically as much as it’s what does that particular school system need at that time?

Q. What are the key things that you consider in matching a superintendent with a district?

A. The first thing, I guess, you look for is, where is the district at that particular time? What particular issues are in the forefront? Where are they in terms of particular stages of change via site-based management, via completely going into the effective-schools movement? ...

Then you look at the board in terms of personality matches, and then at what kind of personalities are needed at that particular time. Usually, what will happen is, school systems, if they have had a very strong, domineering superintendent, in many cases will look for kind of the reverse, someone who will work in a collaborative fashion. Many times the reverse is true also.

And then you look at the experiences that various people have had and been successful at, and whether they will match a particular school system at that time.

Q. How do you judge success or failure?

A. That’s a very good question. Someone can fail doing one thing in one school system and be a complete success doing the same thing in another school system. Success or failure is measured by the perceptions of that particular school system.

Q. Describe your life now and how it has changed. Do you think you made the right choice in leaving the superintendency?

A. I have no question I made the right choice. I have no question at all.

Let’s talk first just about lifestyle. I have a definition I have used for years of a superintendent, and that’s an egomaniac with a death wish. No matter what you do as a superintendent, there are some people who are going to be displeased with it. No matter what decision you make.

And, I think, for yourself as well as your family, living in what is a complete fish bowl--you know, the public eye--has its down side.

I think of the constant, and I mean constant, drain on your personal energy--if nothing else, we won’t talk about the issues and the decisions that have to be made, but the drain in terms of time. You are on the job 24 hours a day, seven days a week.

Q. How do you see the field changing, in terms of the job of the superintendent, since you left?

A. I think when I was a superintendent, many boards’ primary interest was the school building, the fiscal management, things along those lines. I think now, yes, those things are still important, but I think more and more boards now are talking about the superintendent and the experience they have had with instruction, with community building, things more along those lines than the hard business of management.

A version of this article appeared in the December 16, 1992 edition of Education Week as Q&A: Former Superintendent Reflects on Life as a Headhunter