Finger Songwriter is designed to tell a story of dealing with loss. The opening line sung, “I’d like to learn how to lose,” serves as an indication of the emotional gamut, and variety of human conditions, that Siskind explores through words and music; from nostalgia, to denial, to madness, and eventually to resolve, optimism and hope.

Siskind chose a small ensemble to most effectively interpret this intimate, yet powerful music, featuring vocalistNancy Harms; "By a complete coincidence, I played on Nancy’s first gig in NYC when she moved here from Minnesota. She gave me an album that I listened to in my car and it stayed there for weeks and weeks and became one of my favorites. I wanted her on this project because she has an intense, focused, and captivating way of delivering a lyric. Plus, her voice has a beautiful, dark tone that’s perfect for the music", said Siskind; and saxophonist Lucas Pino; "I knew I wanted Lucas on this project the second I heard his sound – a warm, deep, and heartfelt tone reminiscent of Stan Getz. I like to say that he has the sound of Getz and a phrasing similar to that of Joe Lovano. Plus, he was wonderfully willing to work on some doublings that aren’t his usual fare."

The concept behind this group came mostly from Siskind's love of Norma Winstone’s recordings, specifically, Like Song, Like Weather and Somewhere Called Home (with piano great John Taylor), her work with Azimuth, Songs and Lullabies, with Fred Hersch, and two recent albums – Distances and Stories Yet to Tell (with Europeans Glauco Venier and Klaus Gesing). Siskind was specifically inspired by, "the warmth of the sound, the intimacy of the setting, and the emotional power of a lyric delivered against a subtly morphing acoustic backdrop".

Another powerful inspiration for the project came from the Siskind's love of words and wanting to create with them. Armed with a Masters degree from Columbia University in English and Comparative Literature, and having written a thesis on the nexus of music and words in song settings, the majority of the lyrics on Finger Songwriter come from a specific literary text, which was then paraphrased, rephrased, reworked, spliced, and Frankensteined to become a new lyric.

The album’s genesis also stems from Siskind's love of, and identification with, the singer-songwriter genre and the desire to make something that was as personal, intimate, and confessional as Joni Mitchell’s Blue or Nick Drake’s Five Leaves Left. Siskind also has great admiration for Tom Waits, Iron & Wine, Fionn Regan, Damien Rice, Paul Simon, Ray LaMontagne, Sufjan Stevens, Will Stratton, Laura Marling, and Leonard Cohen, to name a few. Siskind explains the title, "I wanted to call the record 'Finger­Songwriter' because I like the way that performer and composer/confessor are conflated into a single being, permitting emotional openness, in ways than don’t always permeate jazz. Although, sadly, I can’t be the singer and the songwriter, I’m still a composer-performer and I’ve shaped the whole process of each song’s interpretation."