Self-Assessment

The SquareWave.ai
“Is Your Music Business AI‑Ready?”
Self‑Assessment

Taking Stock Before You Start

Our 12 Tasks guide lays out what’s possible: Twelve places where AI can take real work off your plate. This assessment is about you. Reading a list of possibilities is one thing. Knowing which of them actually apply to your business or team, and which to tackle first, is another. That’s what The SquareWave.ai “Is Your Music Business AI-Ready?” Self-Assessment is for: It is designed to turn that vague sense of “we should probably be using AI more” into a specific, honest picture of where you stand and where your fastest gains are hiding.

The thirty questions ahead are grouped into six areas, running from your everyday comfort with AI, through the day-to-day work of running a music business, to the deeper systems that separate light experimentation from real leverage. You will rate each statement from 1 to 5 based on how things truly work today. There is no passing grade and nothing to submit. The only audience is you.

Two things to consider when taking this self-assessment: First, answer the questions honestly, based on how your business actually operates rather than how you’d like it to, because a flattering score does nothing for you. And second, pay attention to which questions you react to, not just how you score them, since the ones that give you pause tend to point at your best opportunities.

By the end, you’ll have a score, a sense of your weakest area, and a short list of specific tasks and business areas worth your attention, each one tied back to a fix from the 12 Tasks guide. That’s the whole aim: Not a grand plan, but a clear and personal place to begin.

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Self-Assessment

30 Questions to Find Your Biggest Opportunities

Instructions

The “Is Your Music Business AI-Ready?” Self-Assessment should take approximately 10 to 20 minutes to complete. Read each statement and rate how true it is for your business today; not how true you would like it to be. Answer honestly; The value is in an accurate picture, and there are no wrong answers. Throughout, “we” means you and anyone on your team or within your organization. If you are a team of one, it just means you.

Rate each statement from 1 to 5:

  • 1 Not at all, we don’t do this
  • 2 Rarely, or just getting started
  • 3 Sometimes, or in a few areas
  • 4 Often, or in most areas
  • 5 Consistently, this is fully in place
  • N/A Does not apply to our business

Use N/A only when a statement describes something that does not apply to your business (for example, catalog tagging if you don’t manage a catalog). N/A answers won’t count against you. Your score is calculated automatically once every statement has a rating.

Group 1: General AI Awareness & Adoption

1We have a clear, current understanding of what today’s AI tools can and cannot do
2Someone here uses an AI assistant (ChatGPT, Claude, Gemini, or similar) regularly, at least a few times a week
3We’re comfortable writing a detailed prompt in order to get a genuinely useful result
4We actively keep an eye out for new AI tools and features relevant to our work
5Trying out AI tools is encouraged here, rather than ignored or put off
6When we use AI, we’re confident we can catch its mistakes before anything goes out via our manual review steps

Group 2: Content & Marketing

7We use AI to draft artist bios, one-sheets, press materials, or similar documents
8Our social captions and content calendar are drafted or planned with the help of AI
9We turn a single show or session into multiple pieces of content, rather than posting it once and moving on
10Our email newsletter is drafted with AI from activity and copy that we already have
11AI tools help us ensure that our written content holds a consistent voice across every channel

Group 3: Outreach & Client Communication

12We use AI to research venues, contacts, or opportunities in markets that we don’t know well
13Our pitch and outreach emails are personalized at volume with AI help
14We have an AI-assisted or automated follow-up process so that warm leads and other opportunities don’t slip away
15Repetitive questions (rates, hours, lessons, shipping) are handled by a chatbot, a self-serve FAQ, or AI-drafted replies
16We respond to inquiries quickly, even outside business hours, with AI helping us manage our after-hours workload

Group 4: Admin & Operations

17Notes and action items from sessions, calls, and meetings are captured, summarized, and published automatically
18AI helps us triage and prioritize our email inbox instead of reading every message cold
19Routine email replies are drafted by an AI tool for us to review and approve
20Scheduling sessions, calls, and rehearsals is handled by a scheduling tool or AI assistant
21Reminders and rescheduling run automatically, so no-shows and scheduling conflicts are rare

Group 5: Creative & Catalog

22When we are creatively stuck, we use AI as a sounding board to generate options to react to and ideas to branch from
23We use AI in our creative work in a way that keeps our voice, values, and final decisions our own
24Our music catalog is tagged with consistent, searchable metadata
25We use AI to help tag, describe, or organize our catalog for search and licensing

Group 6: Deeper AI Deployment

26We have one or more reusable AI setups (custom GPT, Project, saved prompts, automations) that we use regularly
27We use automations (Zapier, Make, or similar) that connect our tools and run tasks for us
28Our AI tools are loaded with our own information and context (brand voice, catalog, policies), not used generically
29When we find an AI workflow that works, we document it and share it across the team
30We have a rough plan for where AI could help the business over the next year, beyond one-off use cases

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