Fourteen questions to ask before you buy practice management software

Search for practice management software for a CA firm and you will find ten listicles ranking the same eight products. Read a few and you notice they disagree completely, which is the tell: most are paid placements, and the ranking is the price list.

We build one of those products, so take this in the spirit it is offered — not another ranking, but the questions we watch firms fail to ask, and then regret. Ask them of us and of everyone else you shortlist. Several of them we answer better than our competitors and one or two we do not, which is rather the point.

About the work itself

1. Can a job be raised without a document, and a document logged without a job? Real offices do both. A client walks in with papers before anyone has decided what the engagement is; equally, a partner commits to work weeks before anything arrives. Software that insists on one order forces staff to invent placeholder entries, and placeholder entries are how a system starts lying to you.

2. What happens to recurring work? Most of a practice is the same jobs, every quarter, for the same clients. Ask to see next quarter's work raised — not created by hand, raised — and ask what happens when a client is added in the middle of a cycle.

3. Can you see where every job is without asking anybody? The honest version of this question is: at 6pm on a filing day, how many clicks to the list of what is not done. If the answer involves a report being run, exported and read, the firm will go back to WhatsApp inside a month.

4. Where do pending issues live? A job stuck on a missing bank statement is not a job in progress; it is a job waiting on a client. If the system cannot express that difference, every dashboard it draws will overstate how busy the office is.

About money

5. Can you bill several completed jobs on one invoice? And, separately, can you raise an invoice with no job behind it, or collect in advance and issue a receipt? Firms do all three. Software that only bills one job at a time turns a monthly bill run into an afternoon.

6. What does the system do about dues on its own? Chasing fees is the work nobody in the firm wants and everybody postpones. The right answer is automatic follow-up on a frequency and a threshold you set, so it happens without a partner deciding to be unpopular this week.

7. Does it know which work made money? Not billing — profitability. Fees against the time the job actually consumed, per engagement and per client. A firm that cannot see this is repricing blind at every renewal.

8. Multi-currency, and multiple invoice series? If you have clients outside the country, or more than one office, ask this early. It is expensive to retrofit and easy to fake in a demo.

About the people

9. How long does it take a junior to log a timesheet? This is the single best predictor of whether the system survives. Timesheets are entered by the people with the least reason to care; if it takes three minutes, the data will be fiction by the second month.

10. Can you tell who is overloaded before they tell you? Work occupancy per person, not per job. Every firm discovers its bottleneck eventually — the question is whether it discovers it from a screen or from a resignation.

11. What does a partner see in the morning without logging in? Ask whether yesterday's activity arrives as an email. The habit that makes practice software stick is the one that does not require a habit.

Questions people forget to ask in a demo

12. Whose data is it, and how do you get it out? Ask for the export format before you sign, not after you are unhappy. A vendor who cannot answer this quickly is telling you something.

13. Who answers the phone in filing season? Support in September is a different product from support in June. Ask existing users, not the salesperson — and ask about the worst week, not the average one.

14. What is the second year price? Per user, per module, per branch, and what happens when the firm grows from twelve people to twenty. Get it in writing while you still have leverage.

Two things more important than features

Demo with your own data. Not the vendor's tidy sample office. Ten of your real clients, your real engagement names, your real year end, your real currency. Most of the fourteen questions above answer themselves within twenty minutes of doing this, and almost nobody does it.

Ask who it was built with. Practice software written by people who have never sat through a filing season is recognisable within an hour of use — it is always the small things, in the wrong order. MyTask exists because practising Chartered Accountants asked for each part of it; you can read what that produced across the fourteen modules, from Time-Sheet & Cost Management and Digital Signature Management to Document Management and General Work Management & Notices.

Take the fourteen questions to whoever you are evaluating, including us. A vendor who is comfortable being asked them is usually the one worth buying from.