When Taylor Swift was first starting out in her career, she looked to Tim McGraw and Faith Hill as a guiding light.

Reflecting on his relationship with Swift, who is featured on the cover of PEOPLE’s Most Intriguing People of the Year issue, the “I Like It I Love It” singer opened up about the conversations they had 16 years ago when she opened for his Soul2Soul tour.

“We had long conversations with her in Faith’s dressing room about always being open to listening, but always know that you’re the leader, that you’re the one making decisions, that you will know what song is going to work or not and that you are the captain of your ship,” McGraw, 56, tells PEOPLE in this week’s cover story.

Swift, 34, who named her 2006 debut single after McGraw, had many heart-to-hearts with the McGraw and wife Hill.

“I remember thinking this girl has so much talent and so much moxie, and she’s so curious,” McGraw adds. “We both absolutely fell in love with her instantly, as an artist and as a person — just a fellow professional that you realize totally knows what they are doing.”

In addition to her professionalism and drive, McGraw admires her ability to navigate the spotlight: “She knows when, where, how to promote [her work], but she also knows when, where, how to be normal and be a human just living her life,” McGraw says of Swift. “I think she has brilliantly navigated that line.”

Taylor Swift on the cover of PEOPLE. 

In 2021, McGraw spoke candidly about being the inspiration behind Swift’s breakout hit in an interview with Apple Music Country for Apple Music Essentials.

Detailing that he was impressed with the song, McGraw further admitted that he was “a little apprehensive” about the track when he first heard it.

“I thought, have I gotten to that age now to where they’re singing songs about me? Does that mean I’ve jumped the shark a bit? Is everything still cool?” he explained to host Alecia Davis. “And then I realized that somebody had told me that she was in her seventh-grade math class when she wrote the song, so it made me feel a little bit better about that because she was so young writing it. So I didn’t feel like I was that terribly old.”

“Tim McGraw” was released in 2006 as Swift’s first-ever single from her self-titled debut album and peaked at No. 40 on the Billboard Hot 100 and No. 6 on Hot Country Songs.

Back in 2007, while attending the 42nd Annual Academy of Country Music Awards, Swift performed a live rendition of the song and met McGraw for the first time during the ceremony. “It’s so nice to meet you,” Swift said as she held onto her guitar and greeted the country star and his wife.

Years later, in 2018, the superstar couple also joined Swift on stage during her Reputation World Tour to perform the 2006 single as a trio.