Name: Lynette Guastaferro
Job Title and Description: Executive Director of Teaching Matters
College Name/Major: Columbia University, M.B.A. and Williams College, B.A.
Twitter Handle: @TeachingMatters
What does your current job entail? Is there such a thing as a typical day?
LG: I’d say there’s more of a typical week. My job entails running a group of about 50 folks. The core of the work is working with urban schools, essentially teachers that are going back into urban schools. But working for us is a non-profit experience — to provide coaching and support services in places that often have difficulty attracting and retaining a level of experienced talent that you need in order to really move kids.
The work entails a combination of working externally and working internally. Internally, we’re working with teams: looking at designing programs, looking at the results of those programs. Then, on the external side, it’s sort of promoting the work and helping people understand the reasons we have to provide all these services to urban schools. A lot of people don’t realize that urban schools have a much more challenging time attracting and retaining teachers. It’s a combination of communicating those ideas to people and then also getting people to fund the work.
What is the best part of your job?
LG: I really enjoy identifying challenges and opportunities in this particular mission—which is to help urban kids get access to great teaching— but also to have this opportunity to see the problem and see various opportunities to improve. The part that I really love is putting together teams of people based on their different talents, who then try to solve the problem. One of the things I credit myself on is that I don’t consider myself to be fantastic at anything: What I think I’m pretty good at is really honing in on people’s skills and strengths and figuring out how to position them so they can really do well in their talent set. To me, that’s the key to being a leader in the field.
I think a lot of times, when trying to be in a leadership role, people spend a lot of time trying to excel personally at various things. I figured out very young that the most important thing you have to do is really understand your own strengths and really hone in on your own weaknesses, get comfortable with them and understand them, and then find people that are way better than you in those things and surround yourself with those people. I think that’s the number one trick at being an effective leader.
What was your first entry-level job in your field and how did you get it?
LG: When I left college I ended up taking a job at Pricewaterhouse and became a management consultant. It was an “entry-level job,” but my first week they sent me to Florida to do a capacity analysis of the homeless service delivery system. I was thrown into the deep-end in terms of management consulting projects with a lot of autonomy and a ton of responsibility. I did this for three years and developed an enormous set of skills supported by people at Pricewaterhouse. As a management consultant, you’re not necessarily an expert, but you learn to look at things from the perspective of what’s efficient, what’s effective and what’s the best use of technology. I worked in homeless service delivery, human service delivery and education, so I had this amazing opportunity to be thrown into different parts of government and non-profits that were trying to support people in poverty. Having done that, I ultimately decided to leave this work and teach.
What words of wisdom do you find most valuable?
LG: My core philosophy is “what doesn’t kill you makes you stronger.” I really believe that, to grow, you have to experience serious struggle. We like to say in education that kids need productive struggle to learn. I think the real learning experience I’ve had is when I’ve had real challenges. I would especially zero in on those challenges that take you back a step or knock you down. How do I then go forward? I really believe you have to embrace and learn that every time something hits you [and it] seems too big, you have to see it as an opportunity for growth.
What has been the most surreal moment of your career thus far?
LG: For years in my work, I served in a role where I led 28 urban schools. I don’t want to paint this like it’s a typical situation when you’re leading urban schools, but I had a situation where I had 14 children die over the course of a year— for all kinds of reasons. A lot of times it was related to issues of poverty, where they weren’t getting what they needed in some way, shape or form. It was totally surreal to me that I was working with school communities trying to get them through this process of grief, almost on a monthly basis.
It helped me deeply understand that, when you’re in urban education, there’s a lot of pressure on teachers to perform. This is important but we must also work on improving our children’s educational experience. My experience leading a network of schools where so many children died made me realize that sometimes it’s incredibly hard to focus on the academic, for the very simple reason that you are getting the wind knocked out of you on a regular basis.
What was happening to me was unusual (and it’s not the norm) but it’s what can make urban education so challenging. [High poverty schools can encounter] a lot of crisis, and great educators can burn out really quickly because of that. So, it taught me to really rethink some of the ways that we support teachers and really focus on developing communities in schools where teachers work together in ways that they have each other’s back and they’re responsible for the kids.
What do you look for when considering hiring someone?
LG: The first thing we look for is that there’s always a set of technical skills that are important for the job. They have to have either the experience or skills to do the job and have demonstrated it. What I actually really look for in people when interviewing them? I look for an energy. For example, with some people, I can see when things get in their way that they know how to knock through them and they’re people that don’t wait for the solution to be handed to them. They have a desire and need to solve their own problems. I look for leadership— and it’s apparent in their energy level in how they describe problems and challenges and how they get through them. I look for people who can jump in the deep end and who can make it.
What advice would you give to a 20-something with similar aspirations?
LG: Specifically, for someone who is interested in leading a non-profit, it’s no easy task. The path that I took would be to spend some time in the for-profit sector and then get out of it. Go in, learn and leave, because you can get sucked in by the money. It really gave me an edge and has throughout my career made me different in how I lead a non-profit. I’m not one of those people who runs a non-profit and treats it like a business. I believe that having been in the for-profit sector for three years, I understand how decisions are made. People in the non-profit sector often are very focused on mission. And I’ve always run this organization in a sustainable way because I’ve always figured out how to do good while being mindful and smart about business.
Do the mission— but also think like a sustainable business. To summarize, if you’re passionate about non-profit work, don’t shy away from a few years in some sort of [for-profit] productive pathway in the for-profit sector. But don’t get sucked in, because you can forget why you did it and you can get stuck there.
What’s the one thing that’s stood out to you the most in a resume?
LG: I really look into the history. It’s not one particular thing. I want to see a narrative, I want to see that this person is jumping around, trying new things because they may be looking for different experiences to learn from and build, but I need to see a real narrative on how they’re creating their own destiny and career pathway. That’s really important to me because I think that’s how they’ll run their department or job: They’re going to take the bull by the horns and lead.