Ann Dolin had always been drawn to teaching. But, during her first year as a young teacher with Fairfax County Schools, she began to have doubts about her capabilities. The duties of a teacher were seemingly inexhaustible; the workday continued long after school hours ended. Every night, Ann stayed late grading and preparing for the following morning’s lessons. Even so, she questioned whether she was keeping up with everything, even as she continued to invest more and more time and energy in her students.

On top of her day-to-day responsibilities, Ann began to take leadership roles at the school. She created a math committee, and a math resource room stocked with tools and materials the students could check out. In spite of all her success, her insecurities still haunted her.

Then one night, the school Principal, Dr. Ross, came to speak with her. Dr. Ross was both pleased with and astonished by the level of commitment Ann had shown as a first-year teacher. “He told me, you have a lot of leadership capabilities,” recalls Ann, “’I really see you going places in life.’ And I thought, wow, you see that in me? Very few people had been encouraging to me when it came to academics, and I felt very empowered. It was probably just a two-sentence compliment that he gave me, but he really helped me think about what I wanted to do with my career, that maybe I could do more than I’d planned, that maybe Dr. Ross could see something that I hadn’t been able to see in myself.”

“He told me, you have a lot of leadership capabilities,” recalls Ann, “’I really see you going places in life.’ And I thought, wow, you see that in me?

That brief exchange helped shape the course of Ann’s future; she was able to let go of her self-doubt and begin thinking about how to best make use of her talents and leadership skills. And from that exchange, she experienced first-hand the impact a boss, teacher, tutor, or peer can have simply by encouraging and empowering another.

Today, Ann’s staff of 170 tutors empower hundreds of students across DC and Northern Virginia every day. Ann is the Founder and President of Educational Connections Tutoring and Test Prep, commonly known as EC Tutoring. For over 21 years, Ann has worked tirelessly to build one of the most successful and well-respected tutoring companies in the Washington DC Area, growing from a simple home business to a $2 million company.

EC Tutoring offers three major services to clients. The first is subject area support; working with kids who need help with a specific topic, like Calculus, Physics, or English. The next is SAT and ACT prep for high school students applying to college. Finally, EC Tutoring offers a rather special service, what is called Executive Function Coaching. This arm of the business helps set Ann’s company apart from competitors. “We often find kids who are very smart, but for one reason or another they’re struggling with organization, time management, and study skills,” explains Ann, “We work with the kids on their soft skills, things that aren’t always taught in schools.” Teaching kids how to manage time, organize a workspace, and avoid procrastination are important components of a healthy learning experience, but one that most tutoring companies fail to consider.

EC Tutoring also distinguishes itself from the competition in other ways. Their competitive hiring practices also set them apart from the pack. Tutors at EC Tutoring are not college students, which is typical for some tutoring companies. EC Tutoring tutors are professionals, usually former teachers, who are always required to pass a diagnostic test in the subject they tutor. Eighty-five percent of tutors at EC Tutoring hold graduate degrees. Only about 5-10% of applicants are ever hired for a position, making a role at EC Tutoring a competitive undertaking indeed. “They need to know how to break things down, make them digestible for the student,” nods Ann, “there are a lot of smart people out there, but that doesn’t mean they will make a good tutor. You have to have a knack for making a hard thing seem easy.”

Once hired, EC Tutors undergo rigorous professional development as well, with Saturday workshops keeping staff up to date about new research in executive functioning and best practices in the field. Additionally, EC Tutoring sends tutors directly to the homes of students, rather than working out of a central location. Tutoring centers are common in the field, but Ann is adamant about the advantages of teaching in the home. “People really value someone willing to come to their home, they are willing to pay more for that,” asserts Ann. “The value of working in someone’s home is, you’re helping the student set up their study area, you’re making sure they’re equipped with everything they need for the homework process, and you’re also working with the family in the home. If a parent just drops a kid off, you don’t get to build that relationship with the parent, but really, it’s not just about the kid, it is about the parent as well. The home piece has become an important part of our culture.”

Lastly, EC Tutoring takes the process of matching tutors with specific students very seriously. Students and tutors are assessed on four compatibility criteria: the subject area of expertise, location, availability, and personality, which Ann considers the most important of the criteria. “We look at, from the pool of tutors who can, let’s say, go to McLean and tutor a fourth grader in reading, we’ll determine who is the best personality match for that particular child,” explains Ann, “It’s a lot of work. That’s the most difficult part of our business model, there’s a tremendous amount of work upfront to find the right match. But in terms of results, it is certainly worth it.”

The students tutored at EC Tutoring run the gamut; certainly, there are straight-A students struggling with a single subject, and over-achieving Class Presidents hellbent on achieving a certain SAT score. But Ann holds a particular affection for the kids who experience deeper struggles in academia. She was initially trained in Special Education, and she’s never lost her passion for working with the kids who try hard, but fall behind.

Early on in the development of EC Tutoring, Ann tapped into a referral source that few tutoring companies make use of; psychologists’ offices. Local psychologists were seeing scores of students struggling with ADHD, dyslexia, learning disabilities, and other mild learning difficulties sure to impact the kids’ academic potential. Ann knew that these kids would benefit greatly from the resources offered at EC Tutoring: learning to build soft skills like organization, making check lists, managing time. “I went and spoke with psychologists and other people in the field,” explains Ann, “And I realized this was a very underserved niche. There were so many general tutors out there, but so few who specialized in work with kids on things like reducing procrastination.”

“When I think of my years of teaching, I don’t think about the straight-A students, the ones that were easy,” Ann reflects, “the thing I loved about teaching was working with kids no one else believed in. I always loved them, because they were so misunderstood.”

Despite her pride in the Class Presidents and student leaders who seek out EC Tutoring, Ann holds a special admiration for the kids who had previously struggled academically. Her prize possession is a gift from a student: an apple paperweight with her name engraved on it. She can’t remember the student’s name; she’s seen thousands over the decades, but to Ann it represents all the students who came to her struggling and walked away empowered. “When I think of my years of teaching, I don’t think about the straight-A students, the ones that were easy,” Ann reflects, “the thing I loved about teaching was working with kids no one else believed in. I always loved them, because they were so misunderstood. They were kids with so much potential, who simply lacked motivation. The apple reminds me of students that I really clicked with, the ones I so love to work with. I saw myself in them.”

Back in elementary school, math was a particular challenge, and Ann remembers her otherwise mild mannered-father getting frustrated as to why she could not grasp the steps to long division. But generally, she considers her childhood in a tiny Florida town called Indialantic to have been about as idyllic as they come.

Ann, her parents, and her younger brother spent time outdoors, exploring their little island home on the central East-coast of the state. Gorgeous weather and proximity to beaches meant a sun-kissed childhood spent swimming, exploring, and collecting shells. Ann’s father, an entrepreneur himself and something of a career role model for Ann, ran a successful engineering business, while her mother stayed home to raise the kids.

At the age of ten, Ann was already demonstrating a pre-disposition to teaching. A neighbor couple adopted two little girls from Korea, ages 4 and 2. The girls spoke no English, so Ann took it upon herself to help them adjust to life in America. She put together worksheets for them and turned her book collection into a library. Her mother bought library card holders for the back of her books, so she could check the books out to the girls as in a real library. She taught them English, but also cultural lessons, like when she gave them a worksheet to help them learn which colors belonged with which holidays. Red and green mean Christmas, she explained. Black and yellow is for Halloween. For years, the lessons continued, and Ann keeps in touch with the girls to this day.

Tutoring the neighbor girls wasn’t the only leadership role Ann took on. Within no time, she became the ringleader of the neighborhood kids, setting up summer camp-like activities at her house and recruiting her friends as the campers. Her plans were so ambitious that at one point, her mother had to intervene. She said we couldn’t have any more kids over at the house, laughs Ann, “You can’t teach all of these kids swimming, for liability reasons. So that squelched my dreams of running this huge summer camp program at home.”

Ann’s parents also taught her the value of a hard day’s work. From the age of 16, Ann held a job; all through high school and college she found work at restaurants and in retail.

When Ann was in fourth grade, her parents employed a tutor to help her with math. “Once a week I’d ride my bike to Mrs. Lewis’s down the street,” Ann recalls fondly, “and I remember after that summer, going into fifth grade thinking, this is the best I’ve ever felt in my life academically. I’m not lost anymore, I feel so confident, so good about myself. That’s the first time I realized the power of tutoring. I was the example of the transformation that can occur, from someone feeling terrible, hating school, hating math, to feeling great and confident and actually liking numbers.”

Ann’s parents also taught her the value of a hard day’s work. From the age of 16, Ann held a job; all through high school and college she found work at restaurants and in retail. Her first job was selling popcorn at a stand in the mall. And as a young child, she even engaged her entrepreneurial talents, painting seashells down at the beach and selling them to tourists.

Her father was known for his exacting nature. Ann recalls walking into his home office the day after he passed away and taking in a scene of impressive organization. “Everything was so precise,” she recounts admiringly, “every pencil, exactly 10 centimeters apart. The scissors were laid perfectly, the calculator framed the desk perfectly. The glass was on a coaster exactly in the middle of the coaster, not off to the left or right. Everything was pristine. That’s how he lived his life.” Ann’s mother gravitated more to the social side of life, instilling in Ann a respect for the importance of relationships. “She was so outgoing,” states Ann, “I think I got that from her. I’ve always built my business by networking, getting to know people, instead of advertising.”

Ann loved her time in Florida, but after high school, she was desperate to move on. Although she’d been reluctant to consider a small all-girls school, she ultimately decided to attend Pine Manor, outside Boston, when her parents pushed her to give it a shot. Initially, she planned to transfer after sophomore year, but she soon considered it a second home. At college, her passion for optimizing the studying process led her to develop new tools. “I created new note-taking methods, figured out how to predict what the professor would put on tests,” affirms Ann, “I started to create study guides, and soon the other students asked me whether they could use them. At first, I let them, but soon I realized I could offer something better. I taught them how to make their own study guides.” The school was small, and Ann was able to thrive in other ways, too. She played soccer and served on the President’s Council.

After graduating from Pine Manor with a degree in Psychology and Education, Ann went on to Boston College for graduate school to pursue a degree in Special Education. It was there that she solidified her interest in students who need a little extra, personalized help. After graduation, Ann visited a friend in Washington, DC, and immediately felt drawn to the city. She spent the weekend at the exciting Gold Cup horse races. Having heard Fairfax schools had 15 positions open to new teachers, she decided to apply. She nearly fell out of her chair upon hearing the real figure. “Honey, we have 1500 jobs,” exclaimed the interviewer.

In 1992, Ann began teaching at North Springfield Elementary. It was there she had the fateful conversation with Dr. Ross. After leaving North Springfield Elementary, Ann taught at Forestville Elementary in Great Falls. In 1998, after 6 years of teaching, and with a baby on the way, Ann began to consider her options. For years, she’d been tutoring as a side hustle, and she found working with kids one-on-one to be extremely rewarding. She wondered if she could turn her passion for tutoring into a home business.

The conversation was a turning point. Spurred on by her father’s own success in business, Ann began bringing on staff. The transition was a difficult one, but EC Tutoring was profitable from day one.

At first, the business was simply Ann at her kitchen table, but within a year, things had escalated. Ann’s husband, Chris, was supportive, but he also pointed out that he never knew when some kid would come racing into the living room or pop up in the kitchen! The driveway was always blocked and even the neighbors complained. Not only that, Ann was burning the candle at both ends, tutoring six days a week plus a half day on Sunday. She hated saying no to anyone, but something had to be done.

It was Ann’s father who presented her with a choice about her future. “He told me, you have a decision to make,” remembers Ann, “you can either have the complete quality control you have now and keep doing everything yourself, or you can hire people to work for you and relinquish some of the control you have. You have to decide: do I want to stay the same or get bigger.” The conversation was a turning point. Spurred on by her father’s own success in business, Ann began bringing on staff. The transition was a difficult one, but EC Tutoring was profitable from day one. After a few years , EC Tutoring employed 40-50 tutors, and annual revenue had climbed to $550,000.

Ann considers herself to be more of a visionary leader than an executor. Identifying her strengths and weaknesses has been a learning process, too. Initially, she gravitated toward hires who shared many of her strengths, but today she looks for those who mesh with her by bringing the skill sets she lacks.

She advises college kids looking to begin their careers to remember that, at times, everyone has to do things they don’t want to do, and those things serve as valuable experiences. “Don’t be quick to quit, quick to make decisions emotionally,” advises Ann, “you need to think, what do you want to be doing in five years? What kind of hard work now can help me later on? Be grateful every day, always find the goodness in your job, try to find happiness in whatever you do.”

To entrepreneurs, she has other advice: surround yourself with other entrepreneurs. As a member of a group called Entrepreneur’s Organization, or EO, Ann has become a part of a community where she can share with and learn from peers. “Having someone to talk to is extremely important,” says Ann, “I’m surrounded by people who can be sounding boards, they provide valuable experiences, they encourage me to make it to that next level.” Unsurprisingly, Ann pays that encouragement forward to her staff and their clients, empowering students all over DC to reach their next levels, too.