Undercover Dean
A Commentary from Dean of Students David Tuttle
Monday, April 12, 2021

As David Tuttle, Dean of Students, retires after more than three decades at Trinity, we asked him to reflect on the lessons he’s learned about leadership during his tenure at the University.


In the television show Undercover Boss, a CEO wears a poor disguise and then works various jobs among his or her employees. The boss ultimately finds their staff is working in poor and easily correctable conditions, reveals their identity, and then rewards the hardworking people they met with perks and announces that company problems will be fixed pronto. It’s like Gilligan’s Island. After an episode or two, the pattern repeats.

Here is the sad part: Many organizations operate like those on Undercover Boss. I have spent countless hours in campus meetings (time I obviously could have spent watching TV) strategizing around aspirational vision—only to be disappointed when that vision isn’t executed across the broader campus. On the whole, though, we implement vision and strategy pretty well through the strength of leadership and the hard work of the faculty and staff.

I recall seeing a prominent ex-general as a distinguished speaker on campus. I don’t remember his canned remarks on leadership. I’m therefore well aware that my words may land like the tremendous sleeper show Patriot—you can ignore them, but you might be missing out.

Leadership, Tuttle-fied

The qualities of the best leaders are pretty simple, and they’re ones I try to follow and have observed from countless people at any level on campus. Leaders, undercover or otherwise, have creative vision, they are implementers, they make difficult decisions, and they are good supervisors.

Have creative vision. I have a couple mantras. The first is to look at what others are doing, and do the opposite. It doesn’t always work, but watching leaders who don’t follow a formula can be enlightening. Second, look at what can be, rather than what is. This requires asking the question: What if we could build it from scratch?

Execution matters. Leaders who can also execute, usually with a strong support team, are invaluable. I am not a patient person, and I operate a lot off of intuition. Once I have an idea, I know how I want the finished product to look, even if the details are murky. My deficiencies usually involve things in the intellectual realm. Because of that, I surround myself with people whose strengths are in technology, finances, and eye-rolling. Implementers have to be relentless—and bosses need to let them be that way.

Be comfortable making the tough decisions. Being a leader means making difficult decisions and having support from above. It never feels good to push back against others. But part of being a leader is accepting some people will really, really not like you. Have the courage to determine what is best for the greater good versus the individual.


Make the workplace more like Ted Lasso and less like C-SPAN.

David Tuttle

Be a supportive supervisor. Employees want to be appropriately paid, to have their work recognized, and to not be micromanaged. Now, I know some of my former Residential Life employees may do a spit-take on the last one. Is it too much to ask that the wood grain on the tables in the study lounges all run the same direction? I think not, and I stand by that. But the best way to be a good leader is often to get out of the way while mentoring, coaching, and holding people to standards of excellence.

Make meetings efficient and fun. And this might seem as minor as Chuck on Happy Days (you’ll have to Google it), but running effective meetings is really important. Be prepared, do advance work, have a charge, have a goal, and summarize progress. And if I don’t leave a meeting without having some fun, then I see it as a failure. Make the workplace more like Ted Lasso and less like C-SPAN.

Finally, I like to reference Rudolph the Red-Nosed Reindeer (the claymation version). A lot. Many of the characters are flawed: Sam the Snowman is a self-serving gossip; Yukon Cornelius is incompetent; and the Head Elf (he doesn’t even have a name!) is a horrible boss. You get the idea, and we haven’t even addressed Rudolph’s dad, Donner. On the other hand, Rudolph is selfless, forgiving, and ready to lead; his mom is warm and assertive; Clarice is brave and compassionate; Hermey is true to himself; Mrs. Claus, though a tad crabby, is the engine that makes things run; and the Doll on the Island of Misfit Toys is a total team player (and why is she there, anyway?). If Santa had the chance to go Undercover, he would see the obvious: He’s got work to do, but he’s in good company because leaders are everywhere—good ones and bad ones. Finding leaders is easy. They are out in the open. You just need to know what you are looking for.

David Tuttle came to Trinity University in 1987 as an area coordinator in Residential Life. He says he always felt bad for the poor sap who would have to follow Coleen Grissom as dean of students. He has been in ten offices on campus and four residences and says he has longevity here, if nothing else.

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