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Rick Hess Straight Up

Education policy maven Rick Hess of the American Enterprise Institute think tank offers straight talk on matters of policy, politics, research, and reform. Read more from this blog.

Education Opinion

RHSU Classic: 10 Questions to Ask Your Friendly All-Star Supe

By Rick Hess — February 03, 2020 3 min read

This month marks the 10th anniversary of Rick Hess Straight Up, making it a propitious time to revisit some favorites from the past decade. For each of the Top 20 which run this month, I’ve offered a quick reflection or thought as to why it remains a personal favorite.

The first throwback in our countdown reminds me of how different the education landscape was when I launched this blog in 2010. See, a decade ago, as I was musing on the thoughts that would soon become The Cage-Busting Leader, the education landscape looked very different. For one thing, “reformers” still thought I was more provocative than unhelpful. For another, we were still a ways from sinking into the wagon-circling that’s so prevalent on every side and in every camp today. That all explains how it was that I came to be asked to interview a couple of celebrated superintendents during the ceremony for the old Broad Prize for Urban School Districts. Now, onto number 20, originally published on October 19, 2010.

I was in New York this morning to moderate a panel preceding the Broad Prize announcement. I was given the chance to chat with the superintendents of two recent Broad Prize winners: New York’s Joel Klein and Wanda Bamberg of Aldine, Texas.

I was musing last night on what I’d really like to talk about with these acclaimed district chiefs. A series of chats in recent weeks with supes and state chiefs in a number of locales have got me thinking that we often don’t ask the right questions. Here are the 10 that I found myself most inclined to ask:


  1. Davis Guggenheim, director of “Waiting for ‘Superman’,” recently said we’ve “cracked the code” when it comes to educating low-income students and that we now know what we need to do and it’s only a question of will. Do you think that’s true? If so, given that most urban districts still have thousands of low-performers, why haven’t you set matters straight?
  2. We hear a lot about the virtues of data-driven decisionmaking, but I know that I’ve seen some really dumb decisions made with data. What’s the dumbest way you’ve seen data handled or misused, what lessons can we take from that, and what does it take to ensure that data is used smartly?
  3. We also hear a lot about “best practices,” but any number of ideas that are hotly contested today—including mega-high schools, social promotion, and forgiving disciplinary policies—were once deemed best practices. How can we tell the wheat from the chaff?
  4. How big a problem is the collective bargaining agreement, really? What’s a specific example of where you’ve sought to act and it has stopped you from doing what needs to be done?
  5. If the statutes, collective bargaining agreements, and associated policies governing staffing, evaluation, and pay went away tomorrow, what exactly would you do differently? Would your teams be up to the challenge?
  6. Given that we’re looking at a new era of flat or even declining per-pupil spending, how do you drive improvement without new dollars? What’s the toughest cost-cutting measure you’ve adopted on your watch and what was the toughest thing about making that happen?
  7. What’s the most inefficient, wasteful, or unproductive thing your district does? Why haven’t you yet zeroed this out?
  8. What’s the most important thing that your supporters and community backers get right? What’s the one thing they get most wrong or that it’d be nice if they did better?
  9. Recently, there’s been a bit of a media frenzy over the D.C. superintendency. What does the media get mostly right in covering schools and what do they get dismally wrong?
  10. Finally, in D.C., we’ve seen enormous attention to the question of whether former Chancellor Michelle Rhee was too abrasive and too willing to go it alone. Just how focused on consensus, “buy-in,” and collaboration do you think a district leader ought to be?

Anyway, those were mine—or at least the best I could do at the moment. Would love to hear reader thoughts on which of these aren’t all that interesting, how they might be asked better, or what else should be in there.

The opinions expressed in Rick Hess Straight Up are strictly those of the author(s) and do not reflect the opinions or endorsement of Editorial Projects in Education, or any of its publications.