Hiring someone to set up your accounting software: what to confirm they'll deliver

You've just bought Xero or Sage. It's sitting there, blank and waiting. You could stumble through setup yourself, but your chart of accounts, VAT configuration and bank feeds need to be right from day one—errors compound fast. So you're looking for someone to do it properly. The question isn't whether you need help; it's who will actually deliver what your business needs, not just tick boxes and hand it back half-working.

Setting up accounting software sounds straightforward until you realize two setups for the same business can look completely different. One person might build you a chart of accounts that matches your tax year; another might follow a generic template that makes year-end reconciliation harder. One might integrate your bank feeds and test them; another might skip it, leaving you puzzled why transactions aren't flowing through. The difference between adequate and fit-for-purpose often depends on how well the person asking your questions understands your actual operations.

Their grasp of how you actually work

The best signal isn't their software certification (though that matters). It's whether they ask you specific questions about your business before proposing a setup. Do they ask how you invoice? Whether you hold stock? If you operate across provinces? Whether you have employees and contractors, or just one? How you currently track expenses?

Someone who dives into configuration without asking these things is building a generic solution. They might set up a system for retail when you're a service business, or configure payroll tracking when you don't have staff. When you mention it later, changes become add-ons and extra fees.

Ask them: what do you need to know about my business before you start? Listen to whether they ask follow-up questions or seem to be following a checklist. The checklist person will get you to "go-live" faster. The curious person will get you to a setup that actually works for you.

Experience with your specific software and industry

There's a gap between knowing Xero and knowing Xero for a professional services firm, or a retail business, or a not-for-profit. Each has different rhythms: invoicing patterns, tax considerations, reporting needs.

When you're vetting someone, ask them directly: have you set this package up for businesses like mine? Don't accept a vague yes. Ask for a specific example—what did they configure, what was tricky, how did they solve it? If they've genuinely done it before, they'll have a story. If they're improvising, they'll hedge.

Also confirm they've been doing this for long enough that they've learned from mistakes. Someone who set up five systems a month for two years has real depth. Someone who dabbles in setup alongside general bookkeeping might wing it when something unexpected appears.

What they'll actually hand over and test

After setup is complete, what gets delivered? This is where promises often fall short. Some people will leave you with configured software and a wave. Others will provide a setup document, walk you through how to use key features, test your bank feeds, and stay available for questions in the first few weeks.

Before you engage, ask: what's included after go-live? Will you test the bank feeds? Will you run a test transaction? Will you provide documentation or training? Will you be available if something doesn't work in week two? Get clarity on what "done" means to them. If they're vague, you'll likely end up figuring out problems alone.

Also ask them to confirm in writing what they're setting up: your chart of accounts structure, VAT configuration (if applicable), which bank feeds they'll integrate, any automation they'll build in. This prevents drift during the job and gives you proof of what was agreed.

Verifying they're qualified and insured

Check whether they hold a relevant qualification—many software providers maintain listings of certified advisors and bookkeepers. This isn't a guarantee of quality, but it does mean they've studied the software formally and stay current with updates. Ask for their certification number and verify it if possible.

If they'll have access to sensitive data—your bank credentials, client lists, financial records—confirm they have professional indemnity insurance. This isn't bureaucracy; it's protection. If something goes wrong (a data breach, configuration that breaks your records, or lost information), insurance covers liability. Ask to see a copy of their insurance certificate.

When you're ready to move forward, look for someone on Strove who combines proven experience with your software, genuine curiosity about your operations, and clarity on what they'll deliver. The few extra minutes spent finding the right person saves you months of headaches later.