They were the only two people in a New Orleans diner, the kind with peanuts on the floor and not much on the menu. Gail Anderson and Michael Barrett were there for a conference to represent the Ontario Public School Boards' Association (OPSBA), where she was executive director and he the trustee elected as president.
Alone in the restaurant with four young servers — "the place was a dive," Barrett admits — Anderson struck up a conversation with the youth that the Oshawa trustee says he'll never forget.
"She asked them about their dreams and aspirations and education, and talked to them for ages about their opinions. I think those kids walked away feeling they were the most important people in the world," says Barrett, struck by how the seasoned education bureaucrat took such interest in the young strangers.
"That's the soul of Gail I saw, right there in that little roadhouse in the middle of nowhere. I won't forget it."
As she prepares to retire after 20 years at OPSBA's helm and even longer in the sector as a whole, people point to the personal touch Gail Anderson has brought to the business side of schooling. That gift for forging relationships — "she has a genius for being one of the people Malcolm Gladwell calls Connectors," suggests long-time friend Susan Cook — has helped make Anderson one of the power brokers of Ontario education.
She may not be known to the general public, but this friendly extrovert believes that trustees should speak for the organization. Since helping found OPSBA in 1988, the master networker with the golden Rolodex has helped steer Ontario's public English-language school boards through decades of rocky change, using back channels and friendships to build bridges.
Her connections have smoothed the way in midnight labour talks and daytime lobbying. Her input is there in every OPSBA position paper and new initiative, from curriculum support to student well-being. It was largely Anderson's brainwave to have school boards push for bulk discounts on electricity. The School Energy Coalition that OPSBA formed with other education groups saves school boards some $10 million to $15 million a year.
Also a staunch believer in professional development for trustees — the organization now offers a cluster of training modules — Anderson herself has saved many a rookie OPSBA leader from putting their foot in their mouth, recalls grateful former president Rick Johnson. "She's honest, even if it's something you don't want to hear," says the Lindsay-area trustee and former Liberal MPP. "But then, she's a child of the '60s. She's a free spirit."
Anderson is candid even with colleagues who have risen to education minister. Michael Barrett remembers when the province introduced a new policy without consulting trustees "and we had a meeting scheduled with [then education minister and former OPSBA president] Liz Sandals.
"Only Gail could walk in and say to the minister, 'What on earth were you thinking?' and get away with it."
From big political fish to the fish in her backyard pond, Anderson strives for a meeting of minds. She tells friends she can lie on the ground, dip her fingers in the water and actually commune with her koi.
"She has us rolling on the floor, she's such a good storyteller," says Toronto trustee Gerri Gershon, another former OPSBA president. "She's fun to be with, which makes people comfortable around her."
With a master's degree in education administration from the University of Toronto, Anderson has worked her way from banging out committee reports for the old Toronto school board to overseeing the largest trustee group in the province. "There has never been an OPSBA without Gail; she came to it with a passion for public education and that makes such a difference," observes Guelph MPP Liz Sandals, who was president of OPSBA before being elected to Queen's Park and becoming education minister. Sandals now serves as president of the Treasury Board.
"These (The Harris years) were tumultuous times in education," Sandals reminisces. The Harris government changed education from top to bottom, merging school boards and centralizing everything from funding to curriculum. The bombshells rocked local school boards — at least three were taken over by the province for not balancing their books — and it fell to OPSBA, with Sandals and Anderson at the reins, to defend their interests and help them weather the storm.
"It would have been easy for the organization to get fractious; boards were facing such different circumstances [amid the upheaval]," Sandals recalled, "so it's a tribute to Gail that OPSBA came out stronger."
Still, it's the personal stories that keep popping up. She's a master schmoozer. She never made a friend she hasn't kept, and some relationships go back to grade school. She's the best listener, in private or in the boardroom. She's a nurturing friend; when Johnson lost a bid for re-election to Queen's Park, one of the first texts he got that night was from Anderson, asking, "Are you okay?" When Barrett had a health scare, Anderson was a shoulder to lean on.
"She's one of my favourite humans — and a lot of people might underestimate her because she's so beautiful, but she backs up that charm with brains," says NDP MPP Catherine Fife, who, like so many trustees who have served as OPSBA president, still counts Anderson as a friend. Fife brought her leek and potato soup after Anderson had hip surgery.
"Gail has been breaking barriers for years. She was often the only woman in a room full of male directors of education and superintendents, but she can hold her own, let me tell you," says Fife with a laugh. "She stays true to who she is and has surrounded herself with strong, principled women."
Veteran educator Fiona Nelson, who met Anderson decades ago at the old Toronto board and worked with her later at OPSBA, says she'd like to see Anderson give management tips to men.
"She runs the happiest shop in town. She's relaxed, kind but firm, and is a stickler for procedure," recalls Nelson. "She has a mind like a steel trap — she's very smart."
As CEO, Anderson deftly juggled the often conflicting interests of different school boards, "solving problems before they fester," agrees veteran communications chief Jeff Sprang. Running such a diverse organization is a "complex role," he says, "but her strength is hiring teams that work well together, and then letting them do their work."
But while she has a positive outlook, "it pays you well not to mistake her for a lightweight," warns Susan Cook. If a discussion veers off track and the interests of students are being lost, Anderson will rein people in with her trademark "Frankly, Scarlett" quip. It works, says Cook, because Anderson cracks the whip so rarely.
She actually copes well with upheaval, marvels communications veteran Ross Parry, who worked with Anderson at the Association of Large School Boards of Ontario (ALSBO), one of three former trustee groups that joined to create OPSBA. Anderson went from being ALSBO's executive director to associate executive director of the new OPSBA, and before long she took over the reins.
"She's not afraid of chaos, because if you are, you won't get through change well," notes Parry, who continued to work with Anderson in the early years of OPSBA. "It wasn't a job for the faint of heart, but she has a tremendous sense of perseverance that served her through the [trustee groups'] amalgamation and political turbulence," he says.
Besides, there's her secret weapon, he says: "her phenomenal sense of humour, which you need to survive that amount of change. At the end of the day, she knows how to laugh."
Louise Brown is a long-time education reporter for the Toronto Star, now retired.