Dolly was one of a kind - in addition to her music, movies, Dollywood, philanthropy... she also teaches us a lot about how to be a leader.
by Janet Ply, PhD · The Practical Leadership Newsletter · September 1, 2026
On August 25th, Dolly Parton left us, leaving a hole in the world’s heart. We’re mourning an extraordinary entertainer and humanitarian. I also believe we lost an extraordinary leader whom we can all learn from.
Several years ago, I was fortunate to see Dolly in concert in Tulsa, OK - second row seats near the center. She was so talented, playing multiple instruments and singing with a voice that only she has. She didn’t have a backup band, the concert started right on time, and the venue was filled with energy from the start. She played and sang for an hour and a half before a short intermission. She came back out and sang for another hour.
For two and a half hours, she sang, told stories, and made thousands of people feel like we were spending the evening with her on her front porch.
Leadership is revealed in how people use their abilities, influence, and resources to improve the lives of others. By that measure, Dolly was one of the finest leaders of our time.
Her life offers lessons worth carrying forward.
A guy in drag who dressed up as Dolly had a front row, center stage ticket at the concert I attended - big blonde wig, stilettos, lipstick, sequins - the works. At one point during the concert, Dolly said to him, “It takes a lot of work and money to look like this, doesn’t it?” It was probably the highlight of his night.
She could’ve ignored him but instead, made it a point to make a drag queen feel included.
As leaders, we need to be inclusive of everyone on our teams and make them feel welcome. We are all different and we all bring our perspectives and beliefs to work. It doesn’t mean someone is right or wrong - they’re different from us. Diversity is needed to bring forth our best thinking and ideas.
During a 1977 interview, Barbara Walters asked Dolly a question that was condescending even by today’s standards:
“Dolly, where I come from, would I have called you a hillbilly?”
Dolly replied that Walters might have considered the description natural, although she “would have probably kicked your shins or something.”
The humor drew a boundary. Then Dolly addressed what was behind the question.
She explained that the people she grew up with were proud people with class. “It was country class,” she said, “but it was a great deal of class.” Many had little formal education, yet they were smart, and had common sense (horse sense, she called it).
Dolly could have used the moment to distance herself from her upbringing. Instead, she chose to defend the people who had shaped her.
Leaders are often confronted with assumptions about their backgrounds, abilities, teams, or people. Dolly demonstrated how to respond: remain composed, establish the boundary, correct the assumption, and protect the dignity of the people you represent. There’s no need to throw anyone under the bus or distance yourself from what shaped you.
In the same interview, Walters questioned why Dolly wore blonde wigs and extreme clothing when she was already naturally beautiful.
Dolly’s response was classic: “I would never stoop so low as to be fashionable. That’s the easiest thing in the world to do.”
She explained that her appearance was intentional. It attracted attention, and once people got past the initial shock, they might discover that there was something underneath worth appreciating.
She knew exactly what she was doing. She owned her entire story. She never allowed someone else’s limited view of where she came from to determine how she saw herself.
As leaders, how often do we try to fit in by wearing similar clothes as our managers or others in the company or acting as we think others expect us to act?
Dolly defended her choices without apology. She could also laugh at herself without feeling insecure.
She was with her hair dresser in the Los Angeles area one time and learned about a Dolly Parton look-alike contest at a Los Angeles drag event. She thought it would be funny to enter, which she did - with bigger hair, bigger makeup, and a bigger beauty mark.
The other contestants apparently assumed she was simply another performer.
The real Dolly received the least applause and she joked that even that was from her hair dresser. She thought it was hilarious.
People who constantly protect their image become exhausting to lead and difficult to follow. Every mistake feels threatening. Every disagreement becomes personal.
Dolly’s confidence gave her the ability to laugh at herself and leave her ego out of it.
When leaders are preoccupied with protecting their image, people spend more energy managing the leader’s ego and less energy speaking honestly about the work. Mistakes get hidden, feedback gets softened, and disagreements become unnecessarily risky.
Leaders become more approachable when they can laugh at themselves. They create an environment where people can be candid, acknowledge mistakes, and be human without worrying about bruising the leader’s ego.
At 31, Dolly told Barbara Walters that she wanted to become a superstar. She said it plainly and clearly, without mincing words or soft-pedaling her intent.
I can only imagine what Walters was thinking, especially after her hillbilly comment to Dolly.
Dolly understood that reaching that level required moving beyond one part of the music industry and connecting with many kinds of people. She had a vision for her life long before the world could see what she saw.
Her ambition was connected to contribution. She wanted her work to make people happy, and she repeatedly used her success to create opportunities for others.
The more she achieved, the more she could build, employ, fund, give, and influence.
Dolly dreamed big enough for herself and then kept expanding the dream to include others. As leaders, we can do the same: dream big not only ourselves but for those we influence and lead.
Dolly’s big break came when Porter Wagner offered her an opportunity to be on his televised country music show, which helped launch her career. After seven years with him, however, Dolly knew it was time to move on.
Porter resisted. Their discussions became contentious, and Dolly struggled to make him understand that her decision was final.
So she communicated in the language she knew best.
She wrote “I Will Always Love You,” took it to Porter, and sang it for him.
He cried.
The song allowed her to communicate two truths at the same time: she appreciated what he had done for her, and she still had to leave.
Many leaders struggle with that combination. Some postpone necessary decisions to preserve a relationship. Others deliver decisions with little regard for the people affected.
Dolly demonstrated that clarity and compassion can coexist.
Gratitude does not create a permanent obligation to remain in a role or relationship you have outgrown. Strong leaders help others develop into bigger roles, even when that means leaving their team or company.
When Dolly accepted her first movie role in 9 to 5, she didn’t have any acting experience. And because she didn’t know how actors prepared for movies, she memorized the entire screenplay, not only her own lines, but also everyone else’s.
She showed up ready, watched how the professionals around her worked, and paid attention to the activity on set.
Dolly didn’t assume that success in music made her an expert in movies. She entered unfamiliar territory prepared to learn, then applied what she already did exceptionally well.
Experienced leaders need that same combination of confidence and humility: know what you bring, respect what you don’t know, and prepare before you act.
Dolly’s confidence also allowed her to collaborate with other exceptionally talented women and men.
When she recorded the Trio albums with Linda Ronstadt and Emmylou Harris, the three rotated the lead and arranged each song around the voice that served it best. Linda and Emmylou sometimes wanted Dolly to sing lead on everything.
Dolly didn’t want that.
Their working styles were very different. Dolly described Linda as a perfectionist and herself, memorably, as “a butterfly on duck dung.”
Ronstadt brought extraordinary studio and arrangement discipline. Harris had a remarkable ear for finding songs. Dolly brought songwriting, spontaneity, Appalachian authenticity, and her unmistakable voice.
When the three sang together, their voices created something different from anything any of them could’ve produced alone.
Their collaboration involved scheduling problems, hurt feelings, and disagreements. Still they figured out how to accomplish the work they valued.
The best leaders know when to take the lead and when to harmonize. They bring their strengths, allow other people’s strengths to improve the work, and stay focused on what they are creating together. No need to hog the spotlight.
In a 2022 interview with organizational psychologist Adam Grant, Dolly described herself as a “professionalist.”
She worked hard, maintained high standards, and stayed with the work until it was as right as she knew how to make it.
She also understood that technical perfection could drain the life from a performance. If the first recording of a song contained the right heart and emotion, she might keep it even when every detail was not technically flawless.
Dolly wanted to enjoy her work and for the people around her to enjoy it too. She knew that working for a perfectionist wasn’t much fun - in fact, it’s quite frustrating.
She also understood how to recover when something went wrong. Some of her best concert moments came after a mistake because the audience saw that she was human and watched how she handled it.
Dolly examined criticism for any truth it contained, made improvements, and moved forward. She did not waste energy continuing to beat herself up for mistakes.
Leaders need high standards. They also need to recognize when perfectionism is creating delays, rework, micromanagement, or unnecessary pressure for the team.
Professionalism improves the outcome. Perfectionism can become an obstacle to it. Progress over perfection.
Dolly’s father, Lee Parton, never learned to read or write.
In 1995, she created the Imagination Library to send free books to young children in her home county. The local initiative grew into an international system that has distributed more than 300 million books.
Dolly took a problem that was personal and built a mechanism capable of helping millions of families. She brought together publishers, community organizations, funding partners, and distribution systems to place books directly in children’s homes.
Caring about a problem creates intention.
Leaders demonstrate what they value through their own behavior. They create a lasting legacy by building those values into how the organization operates.
If developing people matters, make it part of how work is assigned, leaders are evaluated, successors are prepared, and promotions are decided. If accountability matters, establish clear ownership, visible commitments, regular follow-through, and consistent consequences.
Then teach other leaders why those practices matter and give them responsibility for carrying the work forward.
A leader’s behavior influences the people who see it. A leadership system allows that influence to continue across teams, successors, and generations.
After wildfires devastated parts of East Tennessee in 2016, Dolly created the My People Fund.
More than 900 families who lost their primary residences received direct financial support each month for six months, receiving $10,000 each.
Dolly trusted people who had lost their homes to best know what they needed. Research conducted after the disaster found that recipients considered the cash more helpful than donated food, clothing, and other goods. The money gave families the flexibility to buy what they needed instead of taking what other people thought was important.
There is a lesson here for every leader who genuinely wants to help.
Begin by understanding what people need. Provide practical support. Let the people who are closest to the work use their own judgment to get the desired outcomes. They are likely more informed than the leader and have better ways of solving a problem or achieving an outcome.
Whitney Houston’s recording of “I Will Always Love You” took Dolly’s song and her financial success to another level.
Dolly later explained that she used some of the royalties to purchase an office complex in a historically Black Nashville neighborhood. She called it “the house that Whitney built.”
She freely acknowledged that Whitney had expanded the song’s reach and value. She expressed her gratitude by connecting part of that success to a community associated with Whitney’s legacy.
She followed that pattern throughout her life.
She built businesses that created jobs in the region where she grew up. Dollywood offered employees opportunities for fully funded education. She supported scholarships, hospitals, medical research, disaster recovery, and children’s literacy.
Her values consistently produced action. Values become credible when they affect how leaders use influence, make decisions, and treat people.
As leaders, we should be looking for others who can take our work to the next level - and we don’t need to take credit for it. We can provide opportunities for team members to shine and get the recognition they deserve.
Very few public figures are almost universally known by their first name. Even fewer are loved across generations, political beliefs, economic classes, geographic regions, and musical genres.
Dolly accomplished that while remaining unmistakably herself.
She knew who she was.
She dreamed big.
She worked extraordinarily hard.
She protected what she created.
She made difficult decisions with humanity.
She knew when to lead and when to harmonize.
She took care of people in practical ways.
And she turned generosity into systems that will continue serving others for generations.
I am grateful that I had the opportunity to see her perform from the second row. Yet the most impressive view of Dolly Parton comes from stepping back and looking at the full scope of her life.
She showed us that authenticity can coexist with ambition, kindness with judgment, confidence with humility, and extraordinary success with extraordinary generosity.
That is a life worth celebrating.
It is also leadership worth learning from.
So, in Dolly’s honor, pour yourself a cup of ambition.
Choose one of these lessons and put it into practice. Own your story. Have the difficult conversation. Protect something valuable. Invest in someone’s future. Build something that will keep helping people after you are gone.
Then tell us: What did Dolly Parton mean to you?
And which part of how she lived will you carry forward?
Janet Ply, PhD
Author, Practical Leadership ~ Creator, Leadarity AI Thinking Partner and the Practical Leadership System