Tuesday, December 9th, 2025 | 74 Reads
Tax laws change every year but 2026 is shaping up to be more than just another filing season. Tax specialists are pushing harder into AI, data analytics, and digital filing.
In Canada for example, the Canada Revenue Agency (CRA) is preparing automatic filing options for taxpayers starting with the 2026 tax year and building on its SimpleFile program. And while offering these services, the CRA is investing heavily in machine learning and AI tools to detect non-compliance and suspicious activity more quickly.
That means the accountant you pick for 2026/2027 needs to be more specialized and comfortable in a data-driven, tech-heavy environment instead of just knowing how to key numbers into a tax form.
Continue reading for a breakdown of the key points you should consider if you’re looking for a new tax accountant.
They Should Be Up-to-Date on 2026 Tax Rules and Digital Changes
Every single year the core principles of tax law haven’t changed but the fine details do.
A 2026 tax accountant that stays up-to-date should:
- Track annual tax law changes in your country and region.
- Understand new or expanded credits, benefits, and deductions for the 2026 tax year.
- Know how digital initiatives and new filing tools work.
Specifically ask your tax accountant if:
- They attend professional training.
- They follow official tax guidance.
- They adjust their processes before each tax season starts.
Asking these questions should give you a good idea as to the level of knowledge they have regarding emerging technology, and if they’re up-to-date enough to take on your 2026 and 2027 tax filing needs appropriately.
Accountants Should Be Exploring Tech Like AI and Cloud Accounting
Tax accounting in 2025/2026 is being reshaped by cloud software and AI. Surveys show that the vast majority of professionals are now using AI for research, summarizing complex rules, and delivering more proactive advisory services.
In 2026 you want a tax accountant who:
- Works comfortably with cloud bookkeeping platforms like QuickBooks, Xero and Sage.
- Can securely connect to your financial systems and banking data where appropriate.
- Doesn’t substitute the use of AI and automation for professional judgment.
- Is willing to explain how they use the technology and what controls they have in place.
The right accountant will be able to combine their tech fluency with professional skepticism, and be able to use automation for speed and depth without blindly trusting it.
They Are Specialized to Match Your Situation
Even though designations like CPA, CA, or CMA convey a foundational competence in an accountant, you also want an accountant who regularly works with clients like yourself. Specialization in certain fields ensures they understand the slight nuances that can affect the outcome of your return.
The basics still matter:
- They have a recognized designation like CPA, CA, or CMA.
- They’re in good standing with the relevant professional body.
- They have a clean disciplinary record.
In 2026 you should be working with a tax accountant that has experience in situations similar to yours. Because taxation is becoming more specialized, you want someone who has already navigated returns like yours versus someone who’s learning on your file.
Proactive Advisory versus Once-a-Year Compliance
A key trend going into 2026 is the shift from pure compliance work like simply filing returns to advisory services like planning, strategy, and decision support. As with our firms, many accounting firms are reporting rising demand for financial planning, business strategy, and technology-driven advisory and are restructuring their services around those needs.
Before the tax season starts an, up-to-date tax accountant will:
- Talk with you before year-end to get ahead of the curve.
- Help you structure transactions so you’re not surprised by a huge tax bill.
- Show you different what-if scenarios using AI-powered tools to model tax outcomes and risks.
- Identify all existing and new government incentives, credits and grants relevant to your situation.
If all you’re receiving is a once-a-year email asking you to upload your slips, you’re getting 2010 service in a 2026 world.
They Utilize Strong Data and Privacy Security
As everything is constantly moving online, data protection and privacy become as important as tax knowledge itself. Tax authorities and professional bodies place strong emphasis on safeguarding personal and financial data.
In 2026 a tax accountant should:
- Use secure client portals and encrypted file-sharing.
- Have documented policies for data retention and document destruction.
- Use multi-factor authentication in their systems where necessary.
- Be transparent about where your data is stored.
- Explain how they use and manage AI tools and how confidentiality is preserved.
If an accountant cannot answer these basic security questions, you should be cautious.
Provide Clear Fees and Communication Style
The tech and regulatory environment might be getting more complex, but your experience as a client should also become much more simpler.
An up-to-date accountant will cut through the noise and make the process more clear and manageable from the first conversation to the final filing.
The following are some questions you can ask your 2026 tax accountant:
Do they offer transparent fees?
- Flat fees vs. hourly rates?
- What’s included in their services?
- Are there extra costs for complex planning or amended returns?
- Do they charge extra for audit support or CRA/IRS inquiries?
- Are planning sessions or year-round consultations included or billed separately?
Defined response times
- Do they reply to emails promptly?
- Do they handle urgent issues during busy season?
- Do they respond to issues in the evening and weekends?
- What’s their response time during peak of tax season?
Clear communication you can understand
- Do they explain decisions and trade-offs without industry jargon?
- Are they willing to walk you through your return and show you where the numbers come from?
- Can they give you a summary of key takeaways after preparing your return?
- Will they explain how specific deductions or credits apply to your situation?
- Are they comfortable explaining filing strategies when there’s more than one option?
- Do they adjust their communication style based on your comfort level?
You need to feel comfortable asking these types of questions and not feel rushed or dismissed because your money is on the line and regulatory compliance is an absolute must.
Which Accountant is Right for My Situation?
When you’re interviewing accountants you can use 2026-specific questions which will give you enough information to tell you if any particular accountant is right for your situation.
How are you preparing for planned tax changes in 2026 and 2027?
Look for references to new digital tools, automatic filing initiatives for certain taxpayers, and enhanced data-matching or AI-driven compliance checks. If they seem unaware of these developments, they may not be proactively adapting to the evolving compliance environment.
What technology and AI tools do you use and how do you review the output?
You want a clear explanation of how tools support their work. Ask how they ensure accuracy and oversight when using automation, especially for decisions that affect your tax return.
How often will we talk outside of tax season?
This question helps you gauge whether they’re more of a year-round advisor or a once-a-year filer. Regular check-ins throughout the year can help you compel them to take advantage of planning opportunities before it’s too late.
What types of clients do you mainly serve?
Check that your situation fits comfortably within their usual workflow. Someone who routinely handles clients like you will likely spot issues and opportunities that others might miss.
How do you protect my data and documents?
You’re looking for specifics like a secure portal, encrypted storage, access controls, and defined retention policies. Try to make sure their approach is aligned with current best practices and complies with privacy laws.
Who will actually work on my file?
Will it be partners, staff or outsourced specialists that contribute? You should know who is responsible for the final review and signature. By knowing who’s behind the work, you will feel more confident in both the quality and accountability of the process.
Bringing It All Together
The goal is to hire an accountant who combines current technical knowledge, thoughtful use of AI and/or digital tools, and has a practical, proactive approach to accounting that fits your real life or business.
If you do business in Simcoe or the surrounding regions of Niagara, Haldimand and Norfolk County, you can visit our tax services page for more information on ways we’ll help your business succeed in the years to come.
