How to Know If the Experts Advising You Are Still Qualified for Today’s Business Reality
God forbid they’re using ChatGPT for lawyers or accountants to help write your tax returns.
EXPERT OPINION BY HOWARD TULLMAN, GENERAL MANAGING PARTNER, G2T3V AND CHICAGO HIGH TECH INVESTORS @HOWARDTULLMAN1
Photo: Getty Images
Entrepreneurs and small business owners of a certain age face an interesting dilemma regarding the various professionals they’ve employed and relied upon for decades as they’ve built their businesses, lived through countless ups and downs, paid their taxes, and presumably matured. The personal bonds that have been built over the years are far beyond transactional and more often are powerful friendships and loyalties that time and change can’t break. These connections offer stability, security and levels of comfort that are often missing elsewhere in many new business builders’ lives. Severing these relationships for whatever good and sufficient reason still often feels like something between abandonment and betrayal.
Sadly, even the best professionals – lawyers, consultants and accountants in particular – necessarily age out over the years. Time has a way of turning all of our most important assets into liabilities. Some of the members of your personal support team may even have the gall to retire and move to warmer climates. Doctors and other medical professionals are in a category all their own. All I can say is, if your doc is still using a flip phone and a fax machine, you may have waited too long to update your team. How these men and women can even attempt to keep up with the daily changes in medicine seems like an impossible task and a foolish expectation on the part of their patients.
Apart from simple age and ability issues, skill sets and current knowledge diminish ratably over time, regardless of diligent efforts. Constantly changing technology is also a major concern for these folks. As time passes, memory fades and adjusts to console us and conform to what we think we remember. And, if and when we’re being honest, we know in our hearts that we’re losing a step or two, and that we should begin to think about stepping away to be fair to all concerned. You start by lying about yourself. Eventually, you begin lying to yourself. But it’s a very hard decision and there’s a tremendous amount of identity tied into the mix as well.
If your professionals belong to a large firm or a group or boutique practice, they are likely to attempt to hand you off to a younger partner or another practitioner who may or may not be great but, for sure, the newbies will have no idea of your habits, quirks, shortcuts, record-keeping practices, or even what’s happening with your company or in your industry. They may know a lot about many things, but they really don’t know you.
But even in these cases of uncomfortable and sometimes abrupt transitions, the much bigger question is what the new professionals actually know. And what are their strategies and processes for staying current in an environment of constantly changing rules and regulations? God forbid they’re using ChatGPT for lawyers or accountants to help write your tax returns.
As you might imagine, as tax time rolls around, these aren’t random or hypothetical questions. These days, the basic comprehensive Tax Code is somewhere between 7,000 and 9,000 pages in length. If that wasn’t intimidating enough, when you add the related rules, rulings, regulations and case law, you’re looking at over 70,000 pages. And forget about asking anyone at the IRS about pretty much anything. You’ll be on hold for an eternity.
The DOGE kids – with Trump’s encouragement and blessing – got rid of more than 25 percent of the total IRS workforce and almost 38 percent of the groups that focused on large businesses, the internet and high-net-worthindividuals. Their ultimate goal before they were booted was to cut 40,000 to 50,000 jobs at the IRS. I realize that in some ways the reduction in auditors (around 3,600 experienced experts) is a mixed blessing for those who would just as soon never be audited, but smart and prudent businesspeople don’t relish rolling the dice and would like to be able to rely on proper advice and guidance in making certain choices and decisions. Suffice it to say, that won’t be coming any time soon from the government.
So, we’re back to trying to figure out what exactly the people sitting across the desk from you “know” and just exactly how they claim to know it. This is not an easy question to ask – especially when you’re dealing with new people and new relationships – but it’s an inquiry that every smart entrepreneur and owner needs to make before you put the fate of your business and your own assets at risk. And to be clear, age and experience cut both ways in this conversation. In medicine, we say we want relatively young surgeons trained on the latest procedures and mainly old, experienced psychiatrists because Freud will always be Freud.
But what criteria should you use and what questions should you ask of the new teams of accountants taking over your case? Have you even thought about this issue at all? Size, brand and reputation are all useful indicators and word-of-mouth recommendations from peers you respect are also helpful, but remember that no one ever admits that they were in the bottom quartile of their class at business, law or medical school.
The circumstances and situations are so diverse and complicated in each case that I’m reluctant to try to even offer specific areas of inquiry, but I think that the best strategy is to simply have a conversation with the lead professional dealing with your case and ask him or her – somewhat naively and sympathetically – exactly how they can possibly keep up with the massive changes every year. Their answers and your reaction to them will be the best test of your comfort level.
