How-To Guide: Tax Season

Your Guide to Managing Cash Flow and Holding your CPA Accountable During Tax Season

As the April deadline draws closer and closer, you might be having unpleasant flashbacks of tax seasons past. Specifically, you may be remembering the unpleasant surprise of discovering you owe much more than you had anticipated – not to mention the unpleasant and complicated fallout. While horror stories abound, it is possible to meet tax season head on with the proper planning and forward-facing perspective. In addition to being completely transparent with your CPA and financial advisors, there are other ways to ensure you’re fully prepared for that deadline.

  • Consider Corporate and Personal Tax Returns
    Many small businesses, including dental and medical practices, are filing their tax returns as S Corporations. This allows the owners to pass company income, losses, deductions and credits on to their personal returns. Before you sign your tax return, have your CPA explain how your business income from net profits/losses, W2 wages and dividend/owner’s draws affects your personal return. If you are taking owner’s draws, ask your CPA to confirm that you have the tax basis for taking them. This will help minimize the risk of calling attention to an audit by the IRS.
  • Don’t Forget Your First Quarterly Estimate
    For many small business owners, April 15th is not only the deadline for personal taxes, but also for quarterly estimates (with the next estimate due on June 15th). Don’t forget this important overlap, as you can be penalized for late estimate submissions. Learn more about quarterly estimates, including due dates and payment instructions, on the IRS website.
  • Plan Ahead
    Always remember that your CPA is your tax compliance expert, but you should look to your CFO for help with managing cash flow requirements. Ask your CPA for a projection of the current year’s tax liabilities and have them give you quarterly tax estimates when you sign your tax return for 2019. These estimates can then be used to forecast and model future cash requirements.
  • Use a Forecasting Tool
    Cash flow forecasting software such as Total Cash Clarity™ can help you project up to 8 months into the future. They will help you see shortfalls in projected cash that may be needed when you have to pay your estimates. These kinds of tools can help manage time as well as money, and often include access to supplementary information and materials that can help you gain control of your finances.
  • Don’t Silo Your Specialists
    Be proactive in managing your meetings with your CPA and make sure your CFO is included. Don’t silo your CFO out of tax planning meetings. Try setting a meeting with both parties in June or July with the intention of finding out how much money you’ll owe and create strategies to get more money in your pocket.


Tax season can be a stressful time for business owners, but much of the anxiety can be eliminated through diligent and practical planning. If you have more questions about navigating tax season or wish to learn about our outsourced CFO service, give us a call at 303.835.7992.

Time to Get Naked

It’s time to get naked – but before you go reporting this post for inappropriate content, hear us out. We’re only asking you to get undressed financially. What this means is that you operate with complete and unflinching transparency when it comes to sharing financials with the relevant specialist (e.g., accountants, financial advisors, outsourced CFOs and cash flow experts). These experts are equipped to help you strengthen your finances, but they can only do so if they understand them. Without your total honestly, it hinders the expert from doing their job and effectively wastes your money on a service that cannot reach its full potential. Don’t worry, it’s not these experts’ jobs to judge you, your choices, or your expenditures. It’s their job to work for you to make your business as great as it can be.

We know it’s easier said than done, but trust us: it’s worth it. It’s also important to go into business with a financial specialist that you can trust. Trust is a two-way street, and if you can’t pave both lanes then your business partnership isn’t likely to have a bright future.

Finding a trustworthy advisor
This is an important first step in building a relationship that’s not only long-lasting, but maximizes revenue, savings, cash flow efficiency or any number of other financially oriented goals. Here are a few things to look for:

  • Experience
    This may seem like a given, but it’s an area that is all too often overlooked – especially when it’s hidden behind a flashy sales pitch or tales of recent successes. Ideally, you’ll want someone with decades-long experience. This can say a lot about a person, including A) they’re good enough to have stayed in business this long with the same name B) they’ve seen trends come and go and understand best practices C) they know how to work with all kinds of people and how to approach each unique relationship.
  • Multiple Roles
    Someone who’s held multiple roles has an elevated understanding of a business’s financial standing and knows how to view it from multiple angles. They are better equipped to think critically than somebody who’s only looked at finance through the same unmoving lens for their entire career. These well-versed individuals can think on their feet and offer valuable and unique insights.
  • Has Operated a Successful Business
    This is easy to check, as any successful business operated by a financial specialist will be prominently displayed in either their website bio or LinkedIn profile. It’s also one of the most straightforward litmus tests of their abilities – real-life proof of their operational abilities.
  • Public Speaking
    When they have public speaking on their resume, specifically as a guest speaker at events and seminars or on podcasts, it tells you that they not only know what they’re talking about, but that business leaders trust them enough to risk their reputations by inviting them to speak. It means that their knowledge has value to others, knowledge that is actively sought after.