Questions that trigger Advisory Conversations

When having a value conversation, there are two types of questions an accountant/advisory can ask: 1) Questions to uncover the potential value of the engagement based on what the customer wants you to solve for them? and 2) Questions that trigger issues that they have not even considered you to be a good person to help them solve (AKA. a potential Advisory Engagement) So, I am going to give you some examples:


  • Why Me? – Why are you talking me (or our firm) specifically?
  • Why This? – Why is this specific solution important to you?
  • Why Now? – Why not do it before or in the future?
  • Why Not? – What would happen if you don’t do anything
  • Is there a narrowly defined and objectively measurable result to be achieved by the firm? Or is the engagement very broad/dynamic?
  • What is the specific result you want us to guarantee?
  • In the event of an Audit (Internal, Government, Financial, or other 3rd party) what is the firm guaranteeing?  Do you need us to be 100% Independent and Objective?
  • Will the firm refund the client if result is not achieved? If so, how much?
  • If you have an accounting/tax question for us, how quickly do you EXPECT an answer? And HOW do you want that answer? e. fully disclaimed but brief e-mail, opinion memo (with court cases / code section citations), phone conversation, and/or combination of any
  • How important is it to you that we guarantee our results (and give a 100% money back guarantee)?
  • Ideally, when do you want us to START working? and by when do you expect to see either work in progress reports or final completed work?  Is there a deadline?
  • How do you want to pay? Upfront 100% or at the end? (maybe something in between?, like 50/50)
  • Are there users of my work, reports, etc… outside your organization? How involved do you need me to be if a 3rd party inquires about by work (like banks, investors, etc…)?
  • What are some things that we can do (or forget to do) that would be deal breakers for our relationship?
  • How would you define a successful relationship?
  • What could we take “off your plate” immediately, that will free you up to spend more time doing what matter most for your business?


  • Do you want a transactional relationship (call me when you need me, and we will work and charge you then)? or a proactive relationship (you expect me to alert you of industry/tax updates, remind you of important deadline, warn you about obvious risks to your business, etc…)?
  • If price wasn’t an issue, show would you describe our ideal role in your organization?
  • How much budget have you allocated to “Business Growth”?
  • What is the cost of ALL the technologies you are currently using internally?
  • Is your business currently setup to allow you to “disconnect? or take a vacation?
  • What does a typical purchase and sales process look like?
  • How do you manage documents?
  • What is the best way we can learn your business processes in-depth?
  • What does your cash flow look like and/or how do you think we can help you improve it?
  • What do you think we could do to help you reduce your expenditures, increase your sales, and/or increase the value of your business?
  • Are you happy with your current business model? Do you need an Advisor’s help to make changes/improvements at a high level?
  • Do you have well defined and well executed Purpose/Vision/Mission statements?
  • Do you believe your organization’s culture (how employees behave and make decisions when you are not looking) is in line with your vision/strategy?
  • Is your business attractive enough for external investors? Is it bankable (banks would easily lend to it at prime market rates)?
  • Does the business produce enough to fund your retirement plan?
  • Is your business on track for an exit strategy? (to be able to be sold or for succession)
  • Have you need able to attract and retain the top talent needed to ensure your business has sustaining growth?
  • Do you believe you BRAND as any value unto itself? If not, would it be value to work with someone that could help you increase the value of your brand?
  • Do you believe your company is focused on increase the value/price of your products and services? or are they just focused on increasing the sales/volume?

Some examples here:

If you are a small business owner and your accountant has never had a conversation with you like this, consider asking them for some ADVISORY-level services, and if they cannot provide it… decide what type of accountant do you want to have at your side.

Questions/Thoughts? [email protected]