Meet Matthew DeGreeff

Matthew DeGreeff
Dean of College Counseling and Student Enrichment
Middlesex School (MA)

How did you become the dean of college counseling and student enrichment at Middlesex School?
In the fall of 1989 after graduating from college, I found a job in the financial aid office at my alma mater through the recommendation of a classmate. Over time, I discovered that I loved working with students, and I also grew up professionally in the office as I was surrounded by some of the best folks in the business. When I hit my thirteenth year, I was the assistant director of financial aid and a senior admissions officer, and my wife and I were running a freshman dorm while raising our newborn son and our beloved Chesapeake Bay Retriever. It was time to look for my next opportunity, and I was fortunate to land at Middlesex School in 2002. Besides my role in the college office, I have coached girls’ basketball, and I am head of a boys’ dorm in which my wife and I have raised our four children. In my 30 years in this business, I have never driven to work!

What is your favorite part of the job?
When students trust me enough to share their personal stories, their families’ histories, or their financial circumstances, and then we work together to tell their narrative to the colleges in an authentic way. It is a profound gift to have such a bond with a young person as they are about to embark on the next phase of their life. I also love to tell good stories!

How has NACAC played a role in your career?
NACAC has been a vital part of my professional development because of the incredible networks I have developed over my career. The relationships that I have developed through NACAC interact, overlap, and intersect in my life in so many ways that it is hard to even measure it. We are in a people business and the people are what make NACAC so powerful.  

What do you think is the biggest challenge facing new counselors?
The college process is like a multi-dimensional puzzle or an elusive amoeba that has constantly moving surfaces that require you to always listen and watch for the changes that are happening. New counselors must develop a network of friends and allies who are great sources of information, sounding boards, and professional feedback.

When you aren’t working, what do you like to do?
Play my electric bass, read detective novels, watch the Celtics, spend time with my wife, and play with my kids.

If you could be any fictional character, who would it be and why?
Commissario Brunetti from Donna Leon’s Venetian detective series.

Describe yourself in five words.
Tall, thorough, kind, genuine, patient.

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