Dave Watkins


I first met Dave Watkins when he was appointed Chief Financial Officer of Chicago Public Schools in October 2011.  He was the second CFO in as many years and everyone in the Finance Department was anxious to find out how our new leader would interact with the staff.  Everyone who encountered him before I did stated how sharp, approachable and candid he was in his interactions.  After meeting Dave myself, I’ve added “witty, engaging and shrewd” to his list of attributes.  He’s a working example of authentic leadership and proof that one does not need to lose themselves in a role in order to be successful.

I interviewed Dave over tea in early July 2012.  Despite what I already knew about his communication style, I was still surprised by his candor and humor in sharing aspects of his personal and professional life.

Before joining the Chicago Public Schools as CFO, you enjoyed a long and successful career in the private sector.  How did you come to join CPS? 

One former colleague and a former client of mine both reached out introducing me to the opportunity and recommended that I consider giving the search firm handling the assignment a call.

Have you retired at any point in your career?

Absolutely not! I don’t think it’s in my DNA and after 35 wonderful years of marriage, I wouldn’t want to jeopardize that by staying home on a daily basis.

I’m sure many would like to know the interview process for a Chief Executive.  Can you describe the most typical and most unusual interview processes you have experienced? 

The most typical are one-on-one interviews with members of Senior Leadership.  Generally you have been vetted for your technical and functional skills by this time and the real test is in the intangibles or the leadership/chemistry/style aspects and those are most easily assessed in a one-on-one setting.  The most unusual is the tag team or group interview which I have done twice, earlier in my career.  Of those, one back in 2007 was an interview with eight board members and the CEO which lasted four hours straight! That tops my list of the most unusual and most demanding.

What are the biggest challenges of joining an organization at the C-Level?  Particularly one such as CPS which is going through such a monumental shift in culture. 

For me, the biggest challenge is learning the unique aspects of the education industry with all of the rules, regulations, intricacies and the cause and effect impact of various programs.  It’s also additionally challenging because many of the typical measures you use to evaluate investments and/or strategic initiatives by, (i.e. ROI, ROE etc.) are much more difficult to measure when you’re evaluating learning programs with students, and when the top priority is providing resources to the classroom in order to drive student achievement.

I’m not sure if you know this but you are much admired by many at CPS.  In addition to your reputation as a leader and finance expert, many I’ve spoken to have mentioned your approachability and candor.  Are these traits you honed while working overseas?  I imagine a lot of emotional intelligence was needed in dealing with the vastly different. 

I appreciate the compliment, but I really think those traits or personalities were really established in my youth by my parents. I’ve always tried to lead by example, hold people accountable but never ask them to do something you wouldn’t join in and do yourself. And sometimes, to a fault maybe, I jump in and participate in a project more than one might expect. Europe, where I spent a good deal of my career, was a fascinating experience, and being a good listener early on in the assignment served me well as it grounded me in the different cultures from England to Germany to France and Spain. Each of these is singular, and I needed to understand their culture and needs so that I could figure out how to motivate them and drive them towards the common goals we were trying to achieve. I wouldn’t trade that experience, albeit often a real challenge, for anything.

Describe your typical day at CPS. 

That’s the fun and challenge; I don’t believe there is a typical day at CPS. I generally start my Sunday evening with a prioritization of the areas I need to focus on for the upcoming week — it might be anything from analyzing the different potential impacts of pension reform for CPS to reviewing quarterly financials or part of the CAFR during the annual audit season. I start with the list but every day is usually filled with “audibles” that come from any direction. Requests range from team members seeking time or advice to a request for financial data to supplement a response to the media and many other things that seem to just “drop in”. The day generally flies by and depending on the audibles, you really need to prioritize which areas you devote time towards to ensure that you are driving real change here at the District.

How would you describe your leadership style? 

I guess if I would have to describe my style it would be collaborative.  After my time in Europe, my philosophy centers around getting people to rally around a cause or strategy.  When you get buy-in, your chances of success increase dramatically. It also requires you to dig for the root cause of a challenge and   identify the key metrics or factors that drive an issue or process.  It really boils down to determining what elements are really necessary to success. Once you get people on board and excited, empower them and stand back and watch the results. When you do that, you have to know how to balance empowerment and accountability because you need both, and being able to balance them is generally the key to success.

Thinking back to the beginning of your career, where did you plan to be at this point? 


It appears as though you stayed true to the Finance field throughout your career.  Were you tempted to deviate at any point, and if so, which direction do you think your career would have taken? 

When I left public accounting after 20 years, it was partially driven by the desire to try something new.  When I assumed the Chief Operating Officer roles I played at Maritz, while I maintained my grounding in finance, it allowed me to expand my reach to oversee operations, sales and marketing as well as such things as human resources, all of which were interesting and different challenges that I enjoyed getting involved with.  Having done that for a period, yes, I returned more to my core strengths and interest: finance.

How long have you been married and do you have any children? 

I’ve been married to my wife Deb for 35 years.  We met my senior year in college and married a year and a half later after she graduated.  She has been a great partner and a wonderful Mom often picking up the slack for me as I my schedule was pretty hectic with travel a routine theme.  I do remember how she routinely planned family activities with a focus on “quality time”. We are blessed with two wonderful daughters: the oldest one single and living in Calgary, Canada, much to her Mother’s and my chagrin, while the youngest is currently starting her 6th year in a combination MD-PHD program at University of Alabama – Birmingham where she is actively directing her Mother, who is planning her upcoming fall wedding here in Chicago to another Doctor she met at medical school.

You are from St. Louis.  When did you move to Chicago and why? 

After graduating from the University of Illinois, my business career took me to St. Louis where we stayed until the girls were out of high school and when the Europe opportunity presented itself.  We were just outside of London for almost three years, toggling back and forth to primarily Boston and Houston where our daughters were at the time and occasionally a return trip to St Louis where our Corporate Headquarters was located.  Fortunately, when we sold the European Division, I had the back half of the round trip ticket for Deb, me and our furniture and we had to make a decision as to where to land.  Deb was raised in Bellwood, Illinois and we have always loved Chicago and given the business and economic climate of St Louis it seemed logical to choose Chicago, so we moved to Lincoln Park in the summer of 2007.

What do you do in your spare time? 

I spend a lot of time on the rooftop deck and taking walks with our three dachshunds — yes three.  With three, (we call them “the Pack” and all different colors), we are quite a spectacle and they enjoy it.  The rest of the time is spent biking, golfing and going to movies/theaters and spending time with Deb’s side of the family out in Downers Grove.

What would you tell someone to give them clear insight into how they can aspire to a leadership position within their profession?  

As my career progressed, I always tried to evaluate and compare each of my numerous bosses and in essence, take notes on the positives and negatives of each.  As I moved into various manager levels I tried to emulate some of the positives that I valued the most.  In leadership style, there is not a “one size fits all,” so my recommendation to aspiring leaders is to develop their own style which is an art, not a science, and is generally formulated over time and refined as they grow in their professional career.


Interview by Sherry Clayton on May 23, 2012 in Chicago. Sherry is a Project Manager by day and blogger, mentor and volunteer whenever inspiration calls.  Sherry can be reached at sherryclayton78@gmail.com.

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  1. Executive Interview: Dave Watkins, CFO of Chicago Public Schools «

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