[2] Q felt that "A couple of other tracks veer too close to pastiche, but taken as a whole, this is a rich, brave, eloquent piece of work",[2] while Uncut pointed to the length of the songs (three of the eight being under five minutes) as making them "a little ponderous, but clearly, our expectations are of little concern".

But this time, the melodies are performed on a variety of vintage synthesizers and rhythm machines, many of which give this album a sound that's sleek and evocative, but a decade or three out of date".

[3] Reviewing the album for PopMatters, Christopher Laird described Guesswork as Cole "going electropop", writing that it "offers a new palette of sounds that deepen the impact of his wordy ramblings".

[1] Phil Mongredien of The Observer concurred with Deming regarding Cole melding the two sides of his work, finding it to "combin[e] the two strands, with conventional song structures fleshed out by synths" and that while it "starts promisingly, with the honourable exception of the sparkling 'Moments and Whatnot' the second half of this front-loaded album is a little underwhelming, its songs needlessly extended when a more succinct execution might have worked better".

[4] Pete Wild of The Skinny called Guesswork a "keyboard-heavy record that doesn't hit all the right notes" with occasional good moments but that "for the most part, it feels like a pedestrian Morrissey album (without, of course, the taint of dubious politics).