Your IT person is retiring: how to hand over properly

Our IT guy is retiring, what should we do?

Use the notice period deliberately, because a cooperative handover is the easiest transition in this business and it only happens once. When somebody has looked after an office for years, most of what they know is in their head rather than in a file, and the whole exercise is about moving that knowledge into a place the business owns before the person walks out the door.

Compare it with the alternative. When a provider simply stops answering, an office spends weeks proving ownership of its own domain, resetting things blind and rebuilding configuration by observation. That recovery is described in what to do when your IT guy stops answering, and it is a far more expensive month than the one you are about to have. A retirement gives you a person who wants to leave things tidy. That is genuinely valuable.

The plan has four phases, and it fits comfortably inside a typical notice period:

1. Collect the accounts, passwords, documentation and vendor contacts, in writing, into something the business owns.
2. Interview for the knowledge that is not written anywhere, which is usually the most valuable part.
3. Overlap the new provider with the retiring one for two to four weeks of ordinary work.
4. Verify everything yourself for a couple of weeks after the last day, by testing rather than trusting.

If the notice is short, compress the phases rather than skipping one. The verification phase is the one offices most often drop, and it is the one that catches the problem you would otherwise discover during an emergency six months later.

What should we collect while they are still available?

Collect every account the business depends on, with the login, the recovery method, the billing arrangement and the renewal date, into a password manager the company owns. That last point is the one that matters most. Credentials emailed as a list are out of date the moment someone changes one, and they leak. A password manager in the company's name, with two people able to reach it, is the destination for all of this.

Work through a written list and tick items off as they arrive rather than accepting a single bundle at the end. Ticking as you go is how you find the missing item while there is still someone to ask.

1. Domain registrar login, the registrant details, and the renewal date and payment method.
2. DNS hosting, which is sometimes at a different company from the registrar, plus a copy of the current records.
3. Microsoft 365 or Google Workspace global administrator account, licensing details and who the reseller is.
4. Website hosting, the content management login and where the site backups are.
5. Firewall, switch and Wi-Fi administrator passwords, and the current configuration exported if the device allows it.
6. Internet service account number, contract end date and the support number that actually reaches a human.
7. Server and local administrator credentials, plus any service accounts and what each one runs.
8. Backup console login, what is protected, where copies are stored and the date of the last tested restore.
9. Endpoint security or antivirus console, and whose subscription it is bought under.
10. Line-of-business software: practice management, agency management, accounting, design tools, and the support contacts for each.
11. Phone system administration, the account details and how numbers are ported if that ever becomes necessary.
12. Printer and copier lease details, service contacts and the administrator passwords on the devices.
13. Any software licenses or subscriptions purchased in the retiring person's name rather than the company's.

That last line is worth a specific conversation. Independent IT people often buy things under their own reseller account as a convenience, and those subscriptions need transferring or repurchasing in your name before they lapse. The general principles of what belongs to whom are set out in who owns your passwords, domain and equipment.

What knowledge is only in their head?

The undocumented knowledge is usually the reason the office runs smoothly, and it is lost by default unless somebody sits down and asks for it. Passwords are the easy part. What is hard to replace is the accumulated understanding of why things are set up the way they are, which quirks are normal, and which vendor to call for which problem.

Book a proper session for this, an hour or two, with the new provider present and somebody taking notes. Ask open questions and let the answers wander, because the useful material tends to arrive as a side remark.

1. What breaks most often here, and what do you do about it?
2. What have you been meaning to replace or fix, and why has it not happened yet?
3. Which computer, cable run or piece of software do you worry about?
4. Is anything held together in a way the next person would not expect?
5. Which vendor is genuinely helpful, and which one needs a specific person asked for by name?
6. What did you try in the past that did not work here?
7. Which member of staff needs a different approach, and why?
8. What happens at month end, quarter end or during a busy season that changes the load?
9. If you were staying another year, what would you do first?

That last question is the most productive one I know. A person on the way out has no reason to protect a recommendation, so the honest answer arrives immediately, and it usually tells the new provider more about the state of the systems than a week of inspection would. Write the answers down in the same document as the account register, because in a year nobody will remember who said what.

How long should the overlap be, and what happens during it?

Two to four weeks of genuine overlap is the sweet spot for a small office, because it covers a full cycle of ordinary problems. Shorter than that and you only see the systems at rest. Much longer and you are paying two providers to watch each other. The point of the overlap is not training sessions; it is the new person handling real tickets while the old one is still reachable to explain something odd.

Run it in a defined order rather than letting it drift:

During the overlap the new provider should also be installing what it needs to support you: its own management software on the computers, its own backup running alongside the existing one, its own security tools if the current ones are leaving with the current person. Running two backups for a few weeks costs a little and removes the only genuinely dangerous gap in a transition.

Introduce the new provider to the office in person during week one, so staff have a name and a face before they need help. That single half hour prevents most of the friction people expect from a change. If you want a sense of typical timelines, how quickly a new IT company can take over covers the practical minimum.

What should we verify in the two weeks after they leave?

Verify by testing rather than reading, because a handover document is a claim and a test is evidence. Set aside the fortnight after the last day for a short list of checks, each of which either works or does not. Every item that fails is far cheaper to fix now, while the retiring person will still take a phone call, than during a real incident.

1. Log in to everything yourself. Every account in the register, one at a time, including the ones nobody uses. A password that was correct at handover may have a two-step prompt going to a phone that no longer exists.
2. Test a restore. Pick a real file and a real mailbox item, restore both, open both. Then ask what a full server restore would involve and how long it would take.
3. Rebuild one computer. Take a spare or a leaving employee's machine and set it up from scratch. This exposes missing license keys, undocumented software and the printer driver nobody could find.
4. Add and remove a user. Run the full joiner process and the full leaver process on a test account, so both are proven before a real person needs them.
5. Test the after-hours path. Call the number your staff would call at seven in the evening and see what happens.
6. Check what is still pointing at the old provider. Alert emails, vendor account contacts, domain notices, the ISP portal contact, the alarm or door system if IT ever touched it.
7. Confirm the old access is gone. Remote access software removed, accounts disabled, keys and door codes returned, and their address off the administrator lists.
8. Re-read the documentation. Have somebody who was not involved try to follow it. If they cannot, it is not documentation yet.

Do the alert-email check carefully. Backup failure notices, disk warnings and security alerts frequently keep going to an inbox nobody reads any more, which means the office believes it is being watched when it is not. Redirecting those is a ten-minute job that prevents a bad surprise.

How is a friendly handover different from a hostile one?

The steps are the same; only the sequencing and the tone change. In a friendly exit you collect openly, in a defined order, over weeks. In a hostile or absent exit you secure the top of the tree first and worry about completeness afterwards, because the risk is not that knowledge is lost but that access is abused.

There is a middle case worth naming: the person who is retiring but has quietly stopped doing much for a year or two. The exit is friendly, yet the systems have been drifting, so the new provider finds outdated equipment, missed updates and a backup that has not been tested. That is not a betrayal, it is what happens when someone is winding down, and it is better to expect it than to be indignant about it. Budget for a small catch-up project rather than assuming everything is current. For a planned move between companies rather than a retirement, how to switch IT companies without downtime has the contractual side.

Who should we hire to take over in Dallas, and what should we ask them?

Hire whoever can describe your handover back to you in specifics before you have signed anything, because that is the test of whether they have done one before. A provider who answers with generalities about onboarding will run a generic transition and miss the things that matter in your office.

Ask each candidate the same questions and compare the written answers:

1. What exactly will you collect from the retiring person, and in what order?
2. How long an overlap do you recommend for an office this size, and what will you do during it?
3. Where will the documentation live, and does the business own it or do you?
4. What will you test after the last day, and will you tell me what failed?
5. What do you expect to find that needs fixing, and roughly what would that cost?
6. Who does the work day to day, and who answers the phone at six in the evening?
7. How do I leave you, if it comes to that?

For my part: I am Anthony Omini, the owner of Cross River Tech, a small IT company in Dallas, with over 15 years of IT experience across many industries, supporting small businesses onsite across Dallas–Fort Worth and remotely anywhere in Texas. Managed IT is quoted per user or per device after a short conversation, month-to-month with no lock-in. During a handover I do the collection and the interview myself, write the documentation into a password manager you own, and run the verification list above in the weeks after the exit. Because there is no ticket queue and no account manager, the person who learned your office stays your point of contact afterwards, with my team handling the routine monitoring and updates behind me.

The honest limits: onsite visits are by appointment, and I work remote-first because it resolves most things faster. If your systems lean heavily on Microsoft 365, the day-to-day administration side is on the Microsoft 365 and Google Workspace page, and the security settings worth reviewing during a handover are in Microsoft 365 security for a small business. The ongoing service is described under managed IT services. If you have a retirement date in the calendar, send me the date and I will lay out what the weeks before and after should look like.

Questions people ask

Written and reviewed by

Anthony Omini, founder of Cross River Tech

Over 15 years in IT across many industries, now running Cross River Tech, a small owner-led managed IT company in Dallas. Every article is written from his own client work and checked by him before it is published.

Have a retirement date in the calendar? Send me the date and the size of your office and I will map out the collection, the overlap and the checks for the weeks afterwards.

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