01
Which ChatGPT plan should a Montana small business buy?
ChatGPT Team. Full stop. $30 per seat per month, 2 seat minimum. Team includes the GPT-5 series models, custom GPTs, no training on your data, admin controls, and shared workspaces. Free and Plus tiers do train on your inputs unless you turn it off, and they lack the multi-user controls every business eventually wants.
ChatGPT Enterprise is for 150+ seat orgs with compliance requirements (HIPAA, GLBA, education) — overkill for most MT small businesses but the right choice for clinics, law firms, and CPAs.
- ChatGPT Free — fine for trying it out; not for any business data.
- ChatGPT Plus ($20/mo) — single-user upgrade; do not use as your business stack.
- ChatGPT Team ($30/seat/mo, 2-seat min) — the right answer for 95% of MT small businesses.
- ChatGPT Enterprise (custom pricing) — for compliance-heavy orgs and large teams.
02
The three workflows that always pay back first
Start with one. Add the others once the first one sticks.
- Customer email drafting — paste the inbound message and your bullet-point response; ChatGPT writes the polished email in your voice.
- Q&A over your own documents — upload your handbook, contracts, SOPs, or pricing sheets; ask questions in plain English.
- Meeting summaries — paste a Zoom or Teams transcript; get summary, action items, and follow-up email.
03
Custom GPTs — the unlock most MT businesses miss
Custom GPTs let you bake instructions, documents, and voice into a reusable assistant. A typical Montana small business has 3–5 of these by month two: 'Our Sales Email Writer,' 'Our Estimating Assistant,' 'Our Phone Intake Helper.' Building one takes 30 minutes; everyone on the team uses it from then on.
04
Data settings every Montana business should turn on
Out of the box, ChatGPT Team already excludes your inputs from training. Verify in admin settings. Also: enable SSO if you have Microsoft 365 or Google Workspace, set a data retention policy that matches your records retention, and require all sensitive client data go through a designated workflow rather than ad-hoc chat.
05
What never to put into ChatGPT (any tier under Enterprise)
Full Social Security numbers. Full credit card numbers. Protected health information (PHI). Privileged attorney-client material (use a privilege-aware setup instead). Anything that would be a fineable breach if it leaked. For these, use ChatGPT Enterprise, Microsoft 365 Copilot, or Claude Enterprise with the appropriate signed agreement.
06
30-day starter plan
Week 1: buy 2 Team seats, write a one-page AI policy. Week 2: 2-hour training session for the two pilot users on the three core workflows. Week 3: pilot users build a custom GPT for their highest-volume task. Week 4: roll to the rest of the team; measure hours saved per person.