Field notes on IT Strategy.
Every OSH post tagged IT Strategy: practical write-ups from real engagements, not vendor decks.
Everything filed under IT Strategy
Posts from OSH engineers working in IT Strategy. Migrations that went sideways, configurations we have learned the hard way, and the practical decisions worth writing down.
Controls You Should Never Give Up as a Business Owner
Nine controls every business owner should keep in their own name, even when fully outsourcing IT. Domains, tenants, admin accounts, …
Read field noteHow to Lock Down Your Reseller From Owning Your Stuff
Stop your reseller owning your tenant. The Microsoft GDAP setup, Google reseller mechanics and the five contract clauses that keep your data …
Read field noteMost Break-Glass Accounts Won't Work When They're Actually Needed
Most break-glass accounts are a tickbox. They fail on the day they're needed. Here is what working emergency access looks like on M365 and …
Read field noteReseller or Direct? When to Buy Cloud Software From a Partner vs the Vendor
Should you buy Microsoft 365, Google Workspace and Bitdefender direct from the vendor or via a reseller? An honest 2026 partner-vs-direct …
Read field noteSecurity Audits: What Good Looks Like in 2026
What a proper SMB security audit covers in 2026: the 7-domain checklist (identity, endpoint, email-auth, data, MDM, backup, IR), and when to …
Read field noteSuccession Planning for SMBs: How to Not Lose Your Business to Your IT Provider
How South African SMBs lose access to their own tech stack when an IT provider quits, sells or hikes prices, and the account-ownership map …
Read field noteThe Unlucky Teacher Problem: Inheriting IT You Didn't Ask For
You did not sign up to run the network. The previous person left. Now it is yours. A survival pattern for the accidental IT owner: first …
Read field noteWhy Your IT Partner Should Be Offering You This (And What to Ask If They're Not)
Nine things a competent 2026 IT partner should be doing for you, and the questions to ask if your MSP isn't, without burning the …
Read field noteYou Knew This Vendor Would Hold Your Data Hostage. You Signed Anyway.
The vendor data hostage pattern is documented, predictable, and entirely preventable. Five contract clauses. Write them before you sign.
Read field noteGot a it strategy problem we haven't written about?
If you are stuck on something we have not covered, tell us. The next field note is usually a client question we did not have a tidy answer for yet.
