How to Effectively Work with your Accountant

As a financial planner and business owner, I know firsthand how important it is to have strong financial professionals on your team. One of the most important relationships you need to cultivate, especially as a business owner, is your relationship with your accountant. For many business owners, dealing with taxes is a constant challenge. Having a trusted accountant will help ease the stress of navigating your taxes. Make it a priority to work with an accountant who is proactive in filing, organizing, and reducing your tax bill.

This month, I was excited to talk with one of the trusted accountants in my circle on all things taxes, JD Greenberg from Paisley Pike, CPA and how to work successfully with your accountant.

JACKIE: Clients tell me they are never sure what to ask their accountant about taxes. Are there specific questions they should ask to get a sense if the accountant they have is the right fit for their business?

JD: There are several questions they can ask. Potential questions include:

  1. Do you understand my business?
  2. Do you have clients in my industry?
  3. What can you tell me that’s important for people in my industry to know?
  4. How often will we communicate?
  5. What should I expect from you?
  6. What are your expectations for me, and how will you hold me accountable?

JACKIE: From a client perspective, what questions should my accountant ask me before taking me on as a client?

JD: Prospective clients should be asked the following questions:

  1. Tell me about your tax situation?
  2. What is happening with your current taxes, and what do you want to do differently with me? What I am listening for, as their potential new accountant, is to figure out if it is a reasonable or aggressive request. Also, are there opportunities that have been missed before that can now be captured if we go back in time? For example, were there missed deductions that were never claimed but the client is entitled to? I would look at adjusting the previous year’s tax returns.

Finally, I would ask them, what are you looking to achieve with your taxes? They might need someone to help them figure out how much they should be taking from their corporation; they might need to do succession planning and need advice on tax effectively transferring shares to the next generation. Depending on what services they tell me they need, I can determine if there is a fit and vice versa.

JACKIE: How often should clients be speaking with their accountant? 

JD: You should be on year-round discussions with your accountant to effectively plan. Not a good idea to be in touch with your accountant as you come up against a tax deadline as it leaves you very little wiggle room to strategize around paying as little tax as possible. Keep in mind there are so many filing deadlines: Corporate taxes, payroll taxes, HST, personal taxes and different ones have different deadlines and different reporting processes, which make taxes a year-round challenge.

JACKIE: How do you Respond to CRA challenges on behalf of your clients? What should clients understand when it comes to CRA disputes, and what expectations should they have on how it will be handled by their accountant? 

JD: They need to feel a level of comfort that their accountant is competent enough to put together a strong set of documentation to support the position you have taken with the dispute.

It is also my responsibility to explain and educate the client what options they have in dealing with the dispute and to clearly articulate what the options mean so that the client understands the level of risk they are taking in moving forward with the dispute.

JACKIE: Have you had to defend clients with the CRA? What’s your level of comfort and experience doing this? 

JD: Yes, I have represented client interests and opinions to the CRA. I will often have a discussion to make sure we are on the same page when it comes to the tax rules around the dispute, what I am comfortable with and what they may want me to do. This is why it’s important to determine goals around taxes, the level of risk a client wants to take around the tax rules to ensure we are a fit. 

JACKIE: What about working with a bookkeeper?

JD: Have your accountant review your bookkeeper’s work on a regular basis to stay on top of the numbers. You should be checking in regularly, maybe every month or two, on your books and verifying the expenses entered, especially in the first couple years. This will gage your comfort level with the work your bookkeeper is doing.

The bottom line: Top Three Takeaways to Work Successfully with Your Accountant.

  1. Go with your gut when choosing an accountant. If you don’t feel like you can talk freely to them about your financial circumstances, chances are they are not a good fit.
  2. Ensure you have an accountant who is available year-round and not just a seasonal tax filer. In fact, October is a great time of the year to be checking in with your accountant on strategies to reduce the taxes you will pay before filing. You can even prepare a mock return based on estimating what income will come in by the end of the year and what you can do now to reduce taxes owing.
  3. Ask for referrals. Potentially from business colleagues or your financial advisor. In my practise, I am always on the lookout for top notch accountants who I can refer my clients to and who are willing to take a collaborative approach to financial planning, like JD.

I want to thank JD Greenberg for agreeing to this interview and lifting the curtain on what every business owner should know when working with their accountant.

Take charge of your money today, and let us help you build your financial fortress in these uncertain times. We are happy to have a 30-minute conversation where we delve into a customized retirement plan for you. Please reach out to Also, feel free to share your questions with us here or on our social platforms.