By Jennifer Garrett | Photo by Hillary Schave
Janet Piraino’s resume reads like a who’s who of Wisconsin politics. Recently retired (for the second time), Piraino has been a strategic advisor to just about every prominent Democrat in recent memory: Tammy Baldwin, Mark Pocan, Dave Cieslewicz, Russ Feingold, Tom Barrett and Peter Barca. And, she also squeezed in leadership positions at the University of Wisconsin System and Overture Center.
Over the course of her career, Piraino has amassed a sizable fan base among other women working behind the scenes in politics. Known for her accessibility, generosity and warmth, Piraino has served as a role model for many and an official mentor for a few, including Sarah Smith.
Smith is by all accounts — including Piraino’s — a rising star among Wisconsin Democrats. She has already served in elected offices twice — the first time as the state chair for the Young Democrats of Wisconsin and the second time on the Dane County Board of Supervisors. She also holds an appointment at the Office of the Commissioner of Insurance (OCI), a cabinet agency in Gov. Tony Evers’ administration. And she did this all before turning 30.
Piraino and Smith began a formal mentorship in 2019 when Smith was wrapping up a six-month leadership institute with the Wisconsin chapter of the New Leaders Council.
The program paired participants with experienced leaders for formal mentorships as the official program wound down.
While Smith says some of the mentorships did not survive the first conversation, her relationship with Piraino has endured. In the five years since their first meeting at the Tipsy Cow, Piraino and Smith have continued to meet, talk and connect as Smith built her career as chief of staff for State Treasurer Sarah Godlewski and later as communications director for Sen. Patty Schachtner.
Smith specifically credits Piraino for helping her secure her current OCI position in the administration.
“If you had asked me at the beginning of 2020 if I would be working for the Commissioner of Insurance at the end of the year, I would have not believed it,” Smith says.
Yet when the position opened up at the end of 2020, Smith was intrigued. The opportunity to work in Gov. Evers’ administration was too good to pass up, even though she felt like it was a long shot. Naturally, she turned to Piraino.
“I don’t know why she thought that,” Piraino says, adding that she believed Smith was an ideal candidate. “She has this great experience. She has such a great personality. She is incredibly bright.”
Looking back, Smith acknowledges she had a tendency at the time to overlook her strengths and focus on what she perceived to be challenges or barriers.
“I think that is actually one of the things that I’ve learned, and one of the things that Janet has helped me learn, is that I may be imagining things that are in my way,” Smith says.
Piraino explained how she uses role-playing and probing questions to help Smith and other women she mentors to see and amplify their strengths and qualifications.
“The first few times I mentored, I remember walking to the lunch or coffee, and I wondered what I [was] going to say. I hope there’s some wisdom in there somewhere that’s going to be useful,” Piraino reflects. “But then the more I did it, the more I realized that really what I try to do is hold a mirror up … help the [mentee] see what I see.”
Smith says the tactical exercises with Piraino helped her build confidence for her interview and land a job that she still feels fortunate to do every day. But to her, the key to making it all work was her approach to the relationship itself.
“Getting as much out of my time with Janet as possible meant that I needed to be … as vulnerable and open as I could, which I’m not good at generally,” Smith says, “but Janet makes it easy. She was genuine, and I could tell early on that she just wanted the best for me.”
It is true, Piraino says. She does want the best for women like Smith who have bright futures ahead of them.
She also wishes more women would recognize how much they have to give — and how much they stand to gain — from mentoring.
“It’s pretty selfish. I get at least as much out of it, and I mean that,” Piraino says. “I know it sounds like a cliché, but it brings me incredible joy. To have somebody like Sarah look up to me and actually trust me? That is a gift.”
