Under a proposed deal announced Dec. 10, Diana Sirko, superintendent of the Roaring Fork School District, will remain at the helm for two more years before handing the post to Rob Stein, her second-in-command.
Under a proposed deal announced Dec. 10, Diana Sirko, superintendent of the Roaring Fork School District, will remain at the helm for two more years before handing the post to Rob Stein, her second-in-command. Credit: Kelley Cox / Aspen Journalism

Whatever your role and whatever side you’re on, the board of the Roaring Fork School District faces a big decision on Wednesday, Dec. 10.

In a meeting now scheduled at Roaring Fork High School in Carbondale — where there’s room for a larger-than-normal crowd — the board will consider a three-year extension to Superintendent Diana Sirko’s contract with the district. Hiring or re-hiring the district’s top executive is always an important matter, but it’s especially important for this district at this time.

Ever since the school board terminated former Superintendent Judy Haptonstall’s contract in early 2012, most would agree the district has been in a state of transition. Board members, administrators, employees and parents are engaged in a broad effort to improve academic performance, upgrade facilities and equipment, sharpen instruction and revitalize the organization.

“We stand united as a team and proud of the work we are accomplishing as a district,” said a recent letter from the district’s executive team to staff members.

But the question of who leads the district for the next 3-5 years has inadvertently pitted members of the executive team against each other. Diana Sirko, the district’s current superintendent, has requested a three-year extension to her contract (which expires in June), but a vocal group of parents is backing her assistant superintendent, Rob Stein.

As parent Julie Comins Pickrell stated in a recent letter in The Aspen Times, “a contract extension for Dr. Sirko, especially one that stretches three years, would have significant ramifications for the district, including the potential (perhaps likely) loss of the visionary Rob Stein.“

Stein is known as a skilled educational reformer and leader, due mainly to the turnaround he orchestrated several years ago at Denver’s Manual High School. His current title in the Roaring Fork district is chief academic officer and assistant superintendent, but he was originally hired by the district in 2012 to succeed Haptonstall as superintendent.

A family emergency forced Stein to step down after just a few weeks on the job, however, and Sirko, a former Aspen superintendent with several decades of public school experience, took Stein’s place as the district’s chief executive. She later brought on Stein in his current position, and most observers give Sirko credit for assembling a top-tier team of administrators.

Board president Daniel Biggs said recently that he feels as though “the Dream Team” has occupied the district offices.

“As a board of directors looking at our executive team, we say ‘wow, we’re well-positioned,” he said.

In his assistant superintendent role, Stein led the creation of the district’s long-term strategic plan, which now guides most district-level decision-making. Shannon Pelland, the district’s longtime financial officer, has also become an assistant superintendent under Sirko, and is leading a planning effort to upgrade the district’s school buildings and other infrastructure. Meanwhile, Technology Director Jeff Gatlin is overseeing a “one-to-one” initiative in which the district aims to equip every student with a Google Chromebook computer.

In recent letters to local newspapers, the Stein fans have thanked Sirko for her interim leadership, but they clearly want Stein at the helm when Sirko’s contract expires in June. For her part, Sirko is a Stein fan as well; she hired him. But she’s quick to point out that every step the district takes is a team effort.

“None of this happens without a lot of people on the same page and moving in the same direction,” Sirko said this week. “Rob does a great job, but none of us do anything by ourselves.”

From a purely procedural standpoint, Stein isn’t part of Wednesday evening’s discussion, which will include public comment beginning at 5:45 p.m. The decision before the board involves only Sirko’s proposed contract extension. Nobody else has applied for the job yet, so any formal discussion of other candidates — Stein or anyone else — will have to wait.

Still, the public discussion over the last couple of weeks has underscored the broader context of the decision about Sirko’s contract — the strategic vision for the district’s future and how to maintain the sense of momentum.

Former school board member Richard Stettner was on the board when both Sirko and Stein joined the district. He said this week that Sirko has done “an amazing job” as superintendent, and that assembling today’s executive team was a cornerstone of her tenure.

“I think they’ve got a phenomenal leadership team in place, and I’d like to see the school board find a way to keep everybody on that team,” Stettner said.

Stein has politely declined to comment publicly on the matter. Sirko said this week that she wants to continue the work she started in 2012, and she hopes she can do so with Stein’s help.

“We sincerely hope that he will agree to continue in that position if the board approves my contract renewal,” Sirko said.

Aspen Journalism’s Education Desk is collaborating with The Aspen Times on schools coverage. The Times published this story on Dec. 10.