For one of his side projects, Chris Thile knew he wanted to form a string quintet composed of mandolin, violin, banjo, guitar, and bass with childhood friend and fiddler Gabe Witcher, but didn’t know which direction he wanted to take the band. At the Telluride Bluegrass Festival in Telluride, Colorado, Thile met banjoist Noam Pikelny and later commented that “every note he played was something I wish I’d played”. It was then that Thile realized that he wanted to “put [his] stamp on the traditional bluegrass ensemble”. Thile wanted to get five musicians together for a Nashville jam session in 2005, after he found talented bluegrass musicians that could fill the positions. The bassist Thile was searching for, Greg Garrison, was recommended to Thile by Pikelny, who had performed alongside Garrison in the Cajunjam bandLeftover Salmon. The guitar position was filled by Chris Eldridge famous as a member of the Infamous Stringdusters. The five musicians met up in Nashville one day in 2005 and decided that they needed to “do something musical together”. A few nights later, the group met again “just to drop a ton of money, drink too much wine, eat steaks, and commiserate about our failed relationships”. That night, they came to an agreement and formed a bluegrass band.
The quintet decided to make this project serious and record an album. The album was recorded over the course of two days in 2006 at Sear Sound Recording Studios in New York. The album was not recorded digitally, but rather on tape. In an interview with the United States magazine Guitar Player, Chris Thile explained the old fashioned style in which the album was recorded:
It was recorded at Sear Sound in New York using two vintage Telefunken ELA M 251 E mics into a Forsell Technologies FetCode preamp. Most of it was recorded onto the same Studer 1" two-track that was used to mix Sgt. Pepper's Lonely Hearts Club Band! Everything was tracked live, and I’ve decided never to record wearing headphones again unless I absolutely have to. Wearing headphones is bullshit, because you’re in your own little world playing to a mix that no one will ever hear but you. What’s the point?
How to Grow a Woman from the Ground was self produced by Thile, and had no guest musicians, just the quintet. Other than the band, which in promotion of the album was named the How to Grow a Band, the album had a fairly small production crew; an engineer, an assistant engineer, two mastering people, and an artist.
How to Grow a Woman from the Ground takes influence from different genres, “drawing equally from traditional bluegrass, progressive acoustic, and singer/songwriter traditions”, with one critic calling the majority of the album very “roots oriented”. The album has a bluegrass or progressive bluegrass core; bluegrass mandolinist Ronnie McCoury became the album’s official “bluegrass guru” to ensure that there was “someone who could make sure we didn’t do anything clichéd or trite”. In regard to the album’s style, Thile said that “All in all, How to Grow a Woman from the Ground is a bluegrass record. There are definitely some musical things that are out of the ordinary, but it sounds like a bluegrass record to me. It’s not all like “Brakeman’s Blues,” but “Brakeman’s Blues” doesn’t sound out of place, and neither does “The Beekeeper” sound out of place. It’s all related.” Much of Thile's work on the album was influenced by his divorce, and Thile claims that he could relate to the title of the album, a Tom Brosseau song. Thile said that he "got my ass kicked by the last relationship I was in. This girl just left. It created a pretty serious complex for me. I’ve always been able to talk to girls, but I’m scared of them. I just could relate to it. Like, man if I could just grow one, that would take care of a lot of problems."
How to Grow a Woman from the Ground received positive reviews from country and bluegrass music critics. Allmusic called it "fantastic", and JamBase described it to be "a tasteful string dinner" and stated that "this is only the beginning of great things to come". However, some critics found particular tracks to pale in comparison to the rest of the material. The Arizona Republic stated that the album was "amazing", except for "Dead Leaves and the Dirty Ground" because "Thile [couldn't] quite match Jack White's musical hysteria".Music Box also said that tracks like "Stay Away" and "I’m Yours If You Want Me" "completely fell flat". Regardless, the review still stated that "the bulk of How to Grow a Woman from the Ground is remarkably engaging".Bullz-Eye criticized Thile's vocal quality, saying that "his voice often lacks the strength and/or character to carry the song". On the contrary, the previously mentioned JamBase article complimented Thile's vocal strength, saying "it's the soul in Thile's voice and the heart and intensity of the musicianship that give the album its power."