If you only hear from your IT provider when something breaks, during tax season, or when it is time to renew, you are not getting enough value.
Technology is not a one time setup. Your staff changes. Your tax software changes. Your bookkeeping systems change. Client expectations change. The risks change too.
That is why a quarterly IT review matters, especially for accounting firms, CPA practices, tax professionals, bookkeepers, payroll providers, and financial service organizations.
Most firm owners and partners know they should be checking in, but they are not always sure what to ask. That is normal. You run an accounting firm. You should not have to speak IT for a living.
Here are six simple questions your IT provider should be able to answer every quarter, in plain English.
1. What security problems need attention right now?
Every firm has weak spots. The goal is not to pretend they do not exist. The goal is to find them early and deal with them before they turn into downtime, fraud, data loss, or a major mess.
That matters when you are handling client financial data, tax returns, W-2s, 1099s, payroll records, bank statements, and financial statements.
Ask your provider:
Are any systems missing security patches?
Have there been unusual login attempts?
Are any users, devices, or processes creating extra risk?
Are there security alerts we should know about?
Are remote access tools, portals, and file sharing systems properly secured?
You do not want a vague answer like everything looks good. You want specifics.
A good IT partner should be able to tell you where your top risks are, what has already been fixed, and what still needs attention.
2. Have our backups been tested recently?
A backup only matters if it works when you need it.
Plenty of firms think they are covered because a backup system exists. Then a server fails, ransomware hits, a tax file is deleted, or a bookkeeping database gets corrupted, and everyone finds out the recovery plan was never tested.
That is not the time to figure it out.
Ask:
When was the last full recovery test?
How long would it really take to restore our systems?
Are backups stored separately from our main network?
Are Microsoft 365, Google Workspace, QuickBooks files, tax software data, and other cloud apps included?
Who is responsible for restoring what during an outage?
Could we keep serving clients if this happened in February, March, or April?
You need a tested plan, not hope.
3. Where is technology slowing our team down?
Not every IT problem feels like an emergency. Some problems just drain time all day long.
A computer takes too long to start. A tax application freezes. A scanner jams during document intake. A bookkeeping system lags. A payroll platform does not sync correctly. A staff member stops using a system because it is too painful.
Those issues cost money, even if nobody opens a ticket.
Ask your provider:
Are we seeing repeat performance issues?
Are any computers or servers aging out?
Which systems get the most complaints?
Are we outgrowing any software or hardware?
What should be optimized before it becomes a bigger problem?
Are our remote workers getting the same performance and security as the team in the office?
Technology should help your team move faster. It should not train them to work around problems, especially when deadlines are stacked up and clients are waiting.
4. Are we still meeting compliance and insurance requirements?
Compliance is not something you check once and forget.
Accounting firms and financial service organizations have a real responsibility to protect client data. Cyber insurance requirements, IRS guidance, FTC Safeguards Rule expectations, client contracts, payroll requirements, and industry standards can all shift over time. A firm that was in good shape last year can fall behind without realizing it.
Ask:
Have any requirements changed recently?
Do our policies and documentation still line up?
Do employees need updated security training?
Are there controls we need to strengthen?
Would we be ready if an auditor, insurer, regulator, or key client asked for proof?
Are we documenting how we protect client financial data?
The cost of falling behind is not just a fine. It can affect insurance claims, legal exposure, client trust, and your ability to win or retain business.
5. What should we budget for next quarter?
Good IT planning keeps surprises off your desk.
Your provider should be tracking what is coming, not just reacting to what broke this morning.
That includes:
Aging computers and servers
Expiring warranties
Tax software renewals
Bookkeeping and payroll platform changes
Microsoft 365 or Google Workspace license changes
Network upgrades
Security improvements
Upcoming vendor price increases
Quarterly planning gives you time to make smart decisions. It lets you spread costs out, avoid rush purchases, and keep technology aligned with your firm’s goals.
No managing partner, firm administrator, or business owner likes surprise IT expenses. Most of them can be prevented with better planning.
6. Where are we falling behind?
This is the question that separates a basic IT vendor from a real partner.
You need someone who can look at your firm and say, here is what is changing, here is what matters, and here is what we recommend next.
Ask:
Are there tools or automations we should consider?
Are we behind on cybersecurity best practices?
Are other firms our size doing something we are not?
Have cyber threats changed in a way that affects accounting, payroll, or financial services firms?
Are we using our current systems as well as we could?
Are we prepared if a key system goes down during tax season?
Technology moves fast. Cybercriminals move faster. Firms in St. Louis, the Greater St. Louis region, and the Metro East are not too small or too local to be targeted. In many cases, attackers go after firms because they know how much sensitive client information is inside.
Your IT provider should help you keep up without burying you in technical talk.
If these conversations are not happening, that is a red flag.
If your IT provider cannot answer these questions clearly, or if they are not asking to meet with you quarterly, you may not be getting the support your firm needs.
You need more than someone who shows up after something breaks.
You need a partner who helps prevent the break in the first place.
At Tigerhawk, we believe accounting firms, CPA practices, tax professionals, bookkeepers, payroll providers, and financial service organizations deserve clear answers, practical planning, and local support that actually understands how the firm runs. IT should protect your clients, support your team, strengthen cybersecurity, and help keep the business moving when things get busy.
If you want a second set of eyes on your current setup, we can help.
For more information, schedule time with Tigerhawk.