Checklist · 9 minute read
IT due diligence when buying a business
Field testedThe technology questions to ask before the letter of intent, what the answers do to the price, and how integration goes when it is planned.
By Pete Weigel, Partner and CEO · June 2026
Buying a business? Ask the IT questions before the letter of intent. Every unlicensed seat and untested backup is a cost you inherit.
IT due diligence Gold Star survey"Another great job by Midwest IT. Our company just loves your fast response to our issues."
Client, 2024 surveyMore from the survey wallAsk before the letter of intent
What systems does the business run on, and who owns the licences? Where is the data, and is it backed up? Who is the IT provider and what does the contract say about termination? Are there records that must be kept, and for how long? Has there been a security incident? The answers affect the price, the timeline and whether the deal is worth doing.
What the answers do to the price
Unlicensed software is a cost you inherit. An unsupported server is a capital expense you inherit. A backup that has never been restored is a risk you inherit. A contract with a long notice period is a monthly fee you inherit. None of these are deal-breakers; all of them belong in the negotiation.
Planning the integration
Treat it like an onboarding: inventory, data mapping, a cutover date chosen around the business calendar, side-by-side operation before anything is switched off, and the acquired staff given the same written sequence a new client gets. Email addresses forward, phone numbers port, old systems are archived readable rather than migrated wholesale. We have consolidated three companies and nineteen years of accounting history into one, and merged four insurance agencies; both went to plan because there was one.
After the deal
Retire duplicate systems on a schedule. Standardize devices and security across all locations. Write down the playbook so the next acquisition is faster. Companies that grow by acquisition need a technology plan that expects the next one.
Proof it works
The stories where we did this, and what the clients said afterwards.
Three companies, one accounting system, nineteen years of records
Insurance · MergersMerging four agencies into one, without losing a renewal
Strategy · Multi-year roadmapGrowing through acquisition: a roadmap that unified five offices
Engineering firm · Cloud migrationGetting ahead of a vendor forcing everyone off premises
If a vendor tells you your setup is fine, ask them to put it in writing. The answer changes once it has to be written.
The ERP under a desk Small businessSunk cost is real. A backup server you bought last year deserves a plan before it goes in a dumpster because a move made it convenient.
Server or cloud, honestlyQuestions this guide gets asked
When should we call IT about an acquisition?
Before the letter of intent, if you can. Later is fine; earlier is cheaper.
The full answerCan the acquired company keep its IT provider?
For a while. Someone has to own the plan, and a plan with two authors is not a plan.
"As always, efficient, non-intrusive and complete!"
Kurt, concrete supplierMore from the survey wall- A technician who knows your setup takes every request. Not a dispatcher, not a queue.
- Every closed ticket is surveyed and a partner reads every response.
- 99.5% of surveys come back positive.
- Family-owned since 2005. 21 years in the same corner of Wisconsin, not going anywhere.
"Service is excellent, quick to respond and quick to complete. Thank you!"
Cheri, small businessTalk to a partner, not a sales script.
Tell us what is going on. A partner will call you back the same business day, look at what you have, and tell you honestly whether we are the right fit. No pricing pressure, no pitch deck.