Let’s Roast.
A music school tries to hire a woodwind instructor… by posting a job ad that keeps hiring for drums. Jen and Paul break down what copy/paste chaos signals to candidates, and why “it’s just a gig” isn’t a free pass for a sloppy posting.
Follow along with the full job ad here :
The Bigger Picture
How do you design a job post that reduces uncertainty instead of creating it… especially in contractor roles where clarity about expectations, pay logic, and “who this is for” is the whole point?
A posting isn’t just a listing; it’s your first trust-building artifact.
At a Glance: The Job Profile
Job Title: Part-Time Woodwind Instructor
Report-to Title: Unknown
Company Size: 1-50 Employees
Industry: Education & Training (Arts & Music)
What do they do?: Individual music lessons for all ages & levels in voice, piano, guitar, drums, bass, violin, cello, brass & wind instruments, recording techniques, engineering, studio production and more. The music school also offers a dynamic Rockband and Ensemble program as well as group classes, clinics and workshops on a variety of music related subjects.
Head Office Location: Toronto, Ontario, Canada
Job Location: Toronto, Ontario, Canada
Geographical Operating Area: Toronto, Ontario, Canada
Job Type: Part-Time, Freelance (Independent Contractor)
For the Job Seekers
Did you come across a job ad like this? These questions might help you shed some light on what working there is really like:
What instrument(s) are they actually hiring for, and can they confirm it in writing before you invest time?
Is this truly contractor work (invoicing monthly), and are staff meetings paid or unpaid expectations?
How is pay determined across lesson types (private vs group vs admissions prep)? Is there a rate card?
Who are the students… kids, teens, adults, audition-track? Does your teaching style match that demand?
What’s the real schedule reality: “set schedule,” “Mondays needed,” and “5–6 hours/week” don’t mean the same thing.
What value does the school add (space, demand-gen, admin, referrals), and what are you expected to do yourself?
For the Job-Seeker Seekers
Are you writing a job ad for a similar role? Consider these hidden issues that might impact the success of your recruitment campaign:
Instrument confusion (woodwinds vs drums vs piano) → Outcome: qualified candidates self-select out, credibility damage. Fix: slow down, proofread, and validate the role title + every instrument reference.
“Seasoned” + low floor pay → Outcome: attracts underqualified applicants or creates resentment. Fix: align pay band language with expectations; explain pay-by-lesson type plainly.
Contractor role + mandatory meetings → Outcome: misclassification vibes, friction, no-shows. Fix: state whether meetings are paid and how often; keep contractor obligations tight.
Benefits section that isn’t benefits → Outcome: reads unserious. Fix: replace fluff with real value: access to studio space, admin support, marketing/referrals, paid PD, free rehearsal hours, equipment stipend.
No employer/student-body story → Outcome: you attract random talent, not the right talent. Fix: describe the student mix and teaching mission (adult enrichment vs performance-track prep).
Unclear scheduling model → Outcome: candidates can’t assess fit, churn risk. Fix: define “Mondays now” vs “growth later,” and how hours expand (waitlist? seasonal? enrollment-driven?).
The Verdict
Jennifer Houle: 5 / 10
“This is a very different one because it’s for a contractor, and it’s part-time. I think it had the information that it needed to have, but it was a bit jumbled up. It had those hilarious mistakes of is this… woodwind or drums? Who are we hiring here? It also tells us nothing about the organization, and maybe it doesn’t matter. A gig is a gig. But, I still felt like it was lacking substance.”
Paul Austin-Menear: 6.5 / 10
“Feels a bit like this is Uber for Music School… we’re hiring a contractor, but the employer wants the instructor to attend staff meetings. Is that paid time? It isn’t clear. The job ad didn’t give me a great sense of what the organization was all about. Maybe that doesn’t matter for gig work, but it was still a miss for me.”
Roast the Post is a passion project of Jen Houle and Paul Austin-Menear. The show helps job-seekers and employers get dud job ads out of their lives. We use tips to help pay for our production costs, and donate anything raised beyond our costs to charity.
