At 9:17 on a Monday morning, Daniel opened an email from HMRC and immediately regretted leaving his tax return until the weekend. He had income from freelance design work, a small online shop and a part-time job. His spreadsheet contained three different versions of his expenses, one missing invoice and a transfer he could no longer remember making.
The accountant he found through a quick online search seemed affordable. The first conversation lasted ten minutes. The accountant asked for his HMRC login details, promised to “sort everything out” and gave him a price before asking what kind of work he actually did.
That was enough for Daniel to look elsewhere. A Self Assessment return is not just a form to be completed as cheaply as possible. The quality of the advice depends on whether the accountant understands your income, your records, your deadlines and the systems you will have to use in the coming years.
Start with the shape of your finances, not with the accountant’s advertised price. A sole trader with one bank account and a handful of invoices may need a very different service from a landlord with rental income, a consultant with overseas clients or a company director who also earns freelance income. Make a short list of every type of income you receive and the expenses you expect to claim. An accountant should be able to discuss those details without making you feel as though you have brought them an inconvenient puzzle.
Ask how much experience they have with clients in a similar position. “We handle Self Assessment” is not a particularly useful answer on its own. Ask whether they regularly work with freelancers, tradespeople, landlords, online sellers or whichever category best matches your circumstances. The right experience often shows up in the questions they ask. Someone who understands your work will want to know how you use equipment, where you work, how clients pay you and whether personal and business spending have become mixed together.
The conversation should also cover what is included in the fee. Some accountants prepare and submit the return but offer little help during the year. Others provide bookkeeping, reminders, tax estimates and advice about payments on account. Neither arrangement is automatically better, but you need to know which one you are buying. Ask whether the fee covers queries after submission, amendments, registration for Self Assessment and help if HMRC asks for supporting information. Find out whether VAT, payroll, rental income or capital gains work is charged separately.
A low initial quote can become expensive if every short email costs extra. A higher fee may be sensible if it includes regular checks that prevent mistakes, but the accountant should explain the difference in plain English. You are not looking for the most impressive package. You are looking for a service that matches the amount of complexity and support you actually need.
Deadlines are another useful test. For the tax year running from 6 April 2025 to 5 April 2026, an online Self Assessment return must be filed by 31 January 2027. A paper return has an earlier deadline of 31 October 2026. If you are filing for the first time, registration with HMRC is usually required by 5 October 2026, while any tax due for the 2025–26 tax year is payable by 31 January 2027.
An accountant who treats deadlines as an afterthought is not a good fit. Ask how they gather information from clients and when they want it. Some firms use a secure portal; others prefer email, shared folders or accounting software. The method matters less than the discipline behind it. You should know what documents to provide, who checks them and how you will be told about the final figures before the return is submitted.
A proper professional relationship also requires formal authorisation. Your accountant should use the appropriate HMRC agent authorisation process. For online representation, the agent needs an agent code, registration with HMRC and your authorisation to act for you in relation to Self Assessment. You should receive a clear explanation of what access you are granting and why.
Never hand over your HMRC sign-in details. An accountant should not ask for your Government Gateway password or other login credentials, and HMRC specifically warns taxpayers not to share them, including with a tax agent. The accountant should act through the authorised agent system instead. This is not a minor technical distinction. Your login gives access to your personal tax account, and keeping control of it is part of protecting your identity and your tax records.
You can ask a prospective accountant directly how they handle authorisation, document storage and communication. A trustworthy answer will be routine and unexciting. They will explain their process, tell you what they need from you and avoid dramatic claims about “guaranteed” tax savings. Be cautious around anyone who suggests hiding income, inventing expenses or claiming costs that do not relate to your work. Aggressive advice may sound clever in a sales conversation and look very different when the records are examined.
The most revealing questions are often ordinary ones. Who will prepare the return? Will a qualified accountant review it? What happens if that person leaves the firm? How quickly do they respond to messages during January? Do they keep a copy of the submitted return and calculations? How will they tell you what to pay, and will they explain payments on account if those apply to you?
You should also ask whether they are comfortable working digitally. Making Tax Digital is changing the practical side of tax reporting for many self-employed people. From 6 April 2026, it becomes mandatory for people with qualifying income above £50,000. The threshold falls to above £30,000 from 6 April 2027 and above £20,000 from 6 April 2028. If your income is likely to reach one of those levels, ask the accountant how they will support you through the change.
That question needs a specific answer. Will they help you choose compatible software? Will they keep digital records for you, review quarterly information or simply submit the annual return? Does their fee change once MTD obligations apply? An accountant who still treats digital reporting as a distant issue may leave you trying to learn a new system while dealing with a tax deadline. The right adviser can explain what will change for your business and what will stay the same.
Compatibility matters more than people expect. You may be comfortable sending neatly labelled monthly records, while your accountant may insist on a particular bookkeeping platform. Perhaps you want a short video call every quarter, but the firm only communicates through a ticketing system. Neither preference is wrong. The problem appears when the working relationship becomes a daily irritation. Tax is already an area where small delays create larger problems; a process you dislike will make those delays more likely.
Look for someone who can explain rather than merely announce. If the accountant tells you that an expense is allowable, ask what makes it allowable. If they advise you to change how you take money from the business, ask what assumptions the advice depends on. You do not need a lecture on tax law, but you should leave the conversation understanding the decision well enough to repeat it in your own words.
A good first meeting may include uncomfortable questions about missed records, late registration or income you have not yet reported. That is preferable to false reassurance. An accountant cannot fix a problem they have not been told about, and a serious professional will be more interested in an accurate picture than in winning the engagement at any cost.
Before appointing anyone, compare two or three conversations rather than collecting a long list of prices. Notice whether each accountant listens, asks relevant questions and explains the next step. Check the engagement letter carefully, especially the services, fee, payment terms, responsibilities and arrangements for ending the relationship. Keep your own copies of returns, calculations, invoices and messages; changing accountants should never mean losing access to your financial history.
If an authorised agent causes a problem and you need to check the proper process, HMRC’s Agent Dedicated Line can be reached on 0300 200 3311, Monday to Friday from 8:00 to 18:00. That does not replace choosing carefully at the start, but it gives you somewhere to turn when an authorised representative is no longer dealing with your affairs properly.
Daniel eventually chose an accountant who spent most of the first meeting asking questions. The fee was not the lowest, and the accountant did not promise a magical reduction in his tax bill. Instead, she separated his income streams, explained which records were missing and showed him how future digital reporting might affect his routine. His tax return became less mysterious because the person handling it had first taken the time to understand the business behind the numbers.