“I think I know when I’ve written a great song. But I don’t necessarily know when I’ve written a hit, because there are so many variables. The record has to be made fantastically. It has to be performed by an artist who’s in the right place at the right time. Then the song has to be released in the right order.” Reflecting on the Faith Hill single “This Kiss,” for which she and co-writers Beth Nielsen Chapman and Robin Lerner won 1999 CMA Song of the Year and ASCAP Song of the Year, Roboff asks, “What if it had been the fourth single on that Faith record instead of the first? If a song gets released after an album is already considered a hit or not, you might have a hit song that’s totally wasted.” She laughs, and adds, “But you do know when you’ve written a piece of crap, that I can tell you!” The Nashville-based songwriter started out performing with New York a cappella ensemble the Bondinis, with whom she appeared in the movie and TV show Fame. After the group broke up, Roboff turned down a record deal designed to make her a Madonna-style pop artist. “I considered myself a keyboard player, not a dancer and performer,” she explains. Instead, she developed her arranging and orchestration chops by composing TV music. “Until that point, I had always felt the weakest part of my musicianship was that I couldn’t tell a band how to play what I was hearing in my head,” says Roboff. “So when I was offered the choice between the record deal and the chance to learn arranging, I jumped at the chance of learning how to arrange. In the long run, that’s what I thought would make my career either happen or not.” She went on to compose themes for ABC, CBS and TBS football, presidential election coverage, the 1984 Olympics, and ABC's broadcast of Prince Charles and Princess Diana's wedding. Roboff relocated from Los Angeles to Nashville in the mid-90s. Within three months of her arrival, she’d co-written her first #1 hit, Diamond Rio’s “Walking Away,” with Craig Wiseman. One secret of Roboff’s success: Slick-sounding song demos. “My demos sound like records,” she says. “Sometimes if a song is poignant enough and short enough, with an incredible singer accompanied by just a keyboard or guitar, you can get the point across—but those situations are few and far between. Plus, the songs I write usually demand elaborate demos. My songs aren’t based on the usual I-IV-V progressions, but on more complex harmonies that change over melody. That’s just the way I hear things. Without an elaborate demo, people can’t tell what’s supposed to go where.”

Most Roboff songs begin at the keyboard. These days her favorite writing instrument is the Yamaha PSR keyboard. “It’s incredible,” she says. “It allows me to travel like a guitar player. I can take it anywhere, plug it in and write a song. For example, ‘This Kiss’ was written on the porch of a beach house in Malibu. I often start songs with a bass part and a groove, then start thinking about chords over it, so I love having a traveling instrument that allows you to write that way.” “I can’t tell you how many songs I’ve written on the PSR: ‘This Kiss,’ the Dixie Chicks’ ‘If I Fall You’re Going Down With Me,’ Beth Nielsen Chapman’s ‘Happy Girl’–it just goes on and on. If you combine the PSR and the Motif, I’d say more than half of my records have been written on them.” Though she uses live musicians on her final demos, Roboff often retains the portable keyboard sounds from her initial songwriting sessions. “For example,” she says, “the portable keyboard’s drawbar organ sound makes it onto the final demos all the time because it has a nice flat sound that just comes through. And it doesn’t take up the space that a regular B3 would!” Roboff also appreciates the PSR’s ease of use: “There was a time when I had to decide whether I wanted to get more into programming and writing, or focus on pure songwriting. And I realized that if I went heavy into programming, I’d barely write at all. So I purposely stepped back in terms of programming. That’s why the PSR and the Motif are such great instruments—Yamaha has already gone through all the years of getting the best sounds, so you can just focus on the songwriting.” Some songs almost write themselves, Roboff says. “Believe it or not, sometimes a songwriter will come to me with what I think is the obvious song already written, and they can’t hear it for their life. Those are your lucky days, when you just go in and finish it.