The following is a guest post from Dean Quiambao, partner at Armanino. Opinions are the author’s own.
Artificial intelligence is transforming every corner of the executive suite from forecasting to compliance, and finance leaders are reaping the benefits. CFOs can now use AI to model tax scenarios, simulate investment outcomes and run predictive analytics. But as technology accelerates, one part of the CFO’s oversight too often lags: the tax adviser.
If you’re getting more strategic insight from AI than from your CPA, it may be time to ask a difficult question: “Is my tax partner strategically working with me, or just filing returns with the IRS?”
The truth is, not all CPAs have evolved for today’s corporate world. The best ones are both a lens of insight into working with other companies like yours and business partners involved in every decision, strategically shaping what’s next.
Here are six signs your tax adviser might be holding you back.
1. You’re talking more to AI than to your CPA
If you find yourself turning to ChatGPT for perspective before you call your CPA, that’s a red flag. AI is a powerful ally, but it can’t replace the human judgment and business understanding that come from a strong advisory relationship.
Your tax partner should be part of that technology conversation. They allow you to interpret what AI tools reveal, connecting them to your broader business strategy. A CPA with a modern mindset will help you make smarter, faster decisions. If your CPA isn’t comfortable discussing AI’s impact on tax or operations, they’re not keeping pace with you or your business.
2. They react to change instead of leading through it
Tax laws and business conditions shift constantly. But when your adviser’s idea of “thought leadership” is forwarding a generic tax bulletin, you’re not getting real insight.
A proactive CPA will take the extra step of putting change into context. They should sit down with you and say, “Here’s what this new regulation means for your business, cash flow and long-term strategy. Here’s what we should be considering right now.”
If you’re not hearing that level of tailored advice, your CPA is just checking boxes on a list of responsibilities instead of showing you opportunities to grow your business.
3. They operate in a silo instead of a system
Today’s CFOs don’t make decisions in isolation, and neither should their tax advisers. The tax function is interconnected with banking, legal and investment strategy, each influencing the others in real time.
Your CPA should be part of that collaborative ecosystem, not a disconnected specialist who shows up once a quarter. When your tax adviser partners with your broader financial team, strategic tax planning becomes a business growth lever.
4. They haven’t evolved with technology
Does your CPA still send static PDFs while your team runs on dashboards? Are they manually entering data that your systems already automate?
A forward-thinking firm is tech enabled and AI empowered. They use automation to eliminate busywork, freeing their experts to focus on value creation. The modern tax partner will harness AI to deliver faster insights and higher-impact strategies.
If your adviser hasn’t updated their processes in years, they’re holding you back.
5. They have no succession plan
Many CPAs are nearing retirement, and too few have developed the next generation behind them. For CFOs managing enterprise risk, this is a blind spot.
You wouldn’t accept a vendor with no continuity plan. The same should apply to your tax partner. Ask how they are investing in mentorship programs, teaching new leaders and integrating technology into every step of their lessons. You want a partner who will be there for your next 30 years, not just your next tax season.
6. They ignore the family balance sheet
For CFOs managing private or family-owned companies, the business and the estate are often intertwined. A capable adviser sees beyond the P&L and digs deeper to understand the family balance sheet. Trusts, estates, alternative investments and generational wealth influence family-owned businesses in a myriad of ways that aren’t always obvious.
A great CPA can bridge the business with the family office, preserving the legacy while minimizing risk. If your adviser only sees tax through the lens of the current year, they’re missing the big picture.
From taskmaster to strategist
The modern CFO deserves a tax partner who can think strategically, communicate collaboratively and leverage technology to drive growth. The next generation of CPAs will combine data intelligence with emotional intelligence.
In a world where technology can handle the transactions, it’s the human relationship that defines true advisory value. The CFOs who thrive will be those who surround themselves with advisers who look through the windshield, not the rearview mirror.
