His decision to retire at the end of June comes with a year left on his current employment contract with the board of education.
“There’s been no pressure from anyone,” he said. “This has been solely my decision. It’s been on my mind for awhile, but I wanted to take the time to make sure this was what I wanted to do.
“It’s time for someone else to grab the reins and, as they say in these hills, take the mule on up the mountain.”
Saylor’s tenure as Harlan County’s superintendent has been the longest of recent vintage. No one since the late James A. Cawood served more than seven years. During the 1980s and 90s, the county system had several leaders who only lasted two or three years, some due to either internal political strife or running afoul of state authorities.
Saylor said he sought to bring unity and stability to the system. Students who entered first grade when he was hired in 2000 graduated last week. The coincidence was not lost on Saylor. And while he had his own set of challenges in the job, now looking back on them, he can’t think of anything he’d have done differently.
“I thank the members of the Harlan County Board of Education for the tremendous opportunity they gave me,” he said. “This office had been a revolving door. I admit I was scared of that and somewhat skeptical at the time.
“But when you are in a leading role, you are only as good as the people around you, and I’ve had the privilege to work around a lot of very good people who have given their hard work and dedication to our students, our schools and our school system throughout these 12 years.
“I am thankful for the many people who supported me in this time, but mostly I’m thankful for the students and their accomplishments. Students are what this job is all about and I’m proud of the progress we’ve been able to make.”
Since 2000, curriculum offerings have expanded. Facilities have been updated. Consolidation has been largely successful. As the district has contracted in size, it has also come together, Saylor noted.
Liaisons for each school have worked to improve staff skills, communication and cohesion across the district. Enhanced public relations have showcased student talent and accomplishment in the community. Students have greatly improved their performance on standardized tests.
“We had poor test scores and consolidation was looming,” Saylor said. “It was like we were in quicksand and slowly sinking. At the very least we were not moving forward. I took it as a professional challenge to get us on solid ground and start to move up the mountain, and now I feel like we’ve accomplished at least some of that.”
Looking around Saylor’s office you see lots of photographs of family and friends, and they’re facing toward you, not him. The view is that of a man at work surrounded by loved ones, all looking in the same direction. The trophies on his walls are from a lifetime of work — plaques, certificates and, being an old coach, of course there are game balls of past triumphs.
The wallpaper is decorated in motivational quotes from the great and famous, as well as the obscure.
“I’m just a quote guy,” Saylor noted. “When I took this job I used an old RFK (Robert F. Kennedy) saying: Great change dominates the world, and if we don’t move with change we’ll become a victim.
“I refused to allow us to be a victim here and the biggest obstacle was trying to get everybody working together,” he recalled. “It was a real battle to overcome all that and get all of us on the same field. Being a leader, you have to make decisions and some of them are very difficult. People get hurt. They’re disappointed. Some you make mad. Often that can’t be helped, but I never tried to intentionally hurt anyone. It was always about the business of doing what was in the best interest of the students and the school system.
“I hope, at the end of the day, people will say ‘He tried to improve the quality of education available to the kids in this county.’ Personally, I’ve been nothing but blessed. I’ve worked 30-plus years at a job I love, and I’ve always had a job. I’ve been healthy and benefited from a lot of good help. I’m thankful for all of that.”
Saylor does have some regrets, though — often around those issues over which he had little control. Continued financial difficulties in the system prevented the staff from receiving raises, while consolidation and facility priorities have thus far prevented the Wallins community from getting a new school.
“The job’s been like a giant roller coaster,” he said. “Things move fast and there are dips and jerks, valleys and hills. It’s a wild ride. I hate heights, but when the family goes to parks I force myself to get on them and at the end I let go, raise my fists and say ‘Man, I rode that thing!’ — but I never rode one twice.”
For a man who thought he’d be a football coach his entire career — “And at heart I still am,” he says — Saylor expressed his surprise at where he wound up. The leadership requirements of coach, teacher, and superintendent are largely the same and that was a lesson he said he learned from his father, Needham Saylor.
“Being a teacher and coach is how I started and it’s the way I wound up,” he said. “I revered my dad and, though I didn’t plan it that way, I followed almost exactly in his footsteps.
“As a coach, you put a game plan together, and I always tried to stick to that game plan, and hire good people — good assistant coaches — to help us win. I want Harlan County Schools to continue moving forward and I know the board will hire the right person to do that.”
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