New INC. Magazine column from Howard Tullman

 MONEY

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

MAR 17, 2026

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.

NEW INC. MAGAZINE COLUMN FROM HOWARD TULLMAN

 

Beware These Retention and Recruitment Mistakes That Will Hurt Employee Engagement

Investing in your people is the highest and best use of any entrepreneur’s time and energy.

EXPERT OPINION BY HOWARD TULLMAN, GENERAL MANAGING PARTNER, G2T3V AND CHICAGO HIGH TECH INVESTORS @HOWARDTULLMAN1

Dec 16, 2025

 

The vast majority of the heated headcount conversations taking place in businesses across the country are primarily focused on workforce reductions, with companies thinking purely short term and trying to “save their way to success.” Sadly, this is both a pipedream and a fool’s errand. It’s still the rule that you’ve got to spend money to make money. Simply cutting back broadly and indiscriminately on your people across the board in a frantic panic designed to please your directors and bankers isn’t the way to build your business for the future.

You’ve spent time and plenty of dollars finding and training these folks, and their experience and specific product and service know-how isn’t going to be that easy to replace when things get better. The general stupidity of the DOGE people in their wholesale dismissals and especially the work of the wrestling moron running the Department of Education (who is now begging dozens of key employees who were abruptly dumped to return to their jobs) is a great example of exactly what not to do.

The next most frequent discussions relate to the need for rapid recruitment of new employees with an over-emphasis on AI-first prospects. Of course, virtually every profile on LinkedIn has already been modified to describe AI chops and vast abilities in that area. And while it’s undoubtedly true in theory that it’s easier today to teach an AI jock about marketing than it is to teach an experienced marketer all about AI, mastery of the new tools and techniques is only an important part of the new job requirements and not the be-all and end-all of the story. It’s a lot more efficient and actually less costly to pair some of your key experienced people with some really smart young people with the right attitudes who can use the new methods to amplify and extend the business’s experience base and increase productivity without the pains and delays of trying to learn the ins-and-outs of a whole new industry on the fly. Leave the rocket science to the rookies, but don’t bet the whole business on a bunch of whiz kids. As my mother used to say: “Hire a young carpenter, but an old physician.”

So, companies should feel free to recruit away, but not at the risk of angering, frustrating or demotivating their current team members. They need a story and a vision that works just as well inside as outside the company. But this juggling act is a lot easier said than done, which is why far too many companies end up overlooking and failing to incorporate it into their overall HR strategies. This puts a substantial premium on retaining their key employees, regardless of tenure, instead of basically taking them for granted and ignoring their own needs and desires.

It’s too late to fix an unhappy situation or retain a key member of the team once they’re already out the door. The best time to keep an employee is before he or she leaves. And the scariest and most unfortunate part of the problem is that the best people aren’t interested in conflicts or complaints. They just make up their minds one day and leave. This is why you can never afford to leave well enough alone. It pays long-term benefits to pay attention all the time.

The risks in our businesses that leave us most vulnerable are the ones we fail to foresee. But today there are cost-effective and relatively easy ways to build yourself and your HR team your very own “crystal ball” to give you a realistic and practical view of the future. I have to admit that when I first looked into this area, I was very skeptical that the data (captured anonymously) and the underlying algorithms could be sufficiently predictive and instructive to be of real value. However, we have watched for more than a decade the growth and success of Balloon, which has built a powerful employee survey and suggestion system based on anonymous inputs which clearly adds immediate value to its users.

One leading company in this new space is Holistic, which provides a comprehensive program called SafeAhead. As you might expect, this system will help you move your team from a painful past of simply reacting to the bad news of unexpected employee departures to a process of proactive actions based on predictive data (customized to your company) which will let you anticipate, intercept and proactively interrupt employee departure plans effectively before the targeted employees even begin planning to leave.
 
Holistic provides a company-wide analysis and set of reports that specifically identify the levels of departure risk associated with each and every team member based on where they are located in the company (departmentally and geographically), their tenure, their levels of management responsibility, their compensation, and various external considerations which are also relevant to their overall attitudes such as changes in their management, missed advancement opportunities, and relocation challenges. As an example, we know that people may hire on because of a company’s reputation or vision, but they regularly leave because of management—especially very early in their employment.

Holistic’s broader reports roll up to provide small actionable target groups of high-risk employees along with specifics regarding each person’s issues and concerns as well as suggestions for management as to how these problems can be addressed and remedied in real time in order to prevent costly and disruptive departures. Visual aids and matrices let senior management see at a glance where in the business the greatest problem areas are located and just how many employees in each given department or division are at various degrees of departure risk.

Responding and reacting to these reports which are predicated on numerous variables like degrees of employee engagement, changes in performance levels, and other supervisory and management issues lets senior management get ahead of the game and stay ahead of inchoate problems by taking affirmative and specifically responsive actions in each case.

I call this approach “preemptive empathy” and every business can use far more of it. Caring for and investing in your people is the highest and best use of any entrepreneur’s time and energy. The real trick is to train your employees well enough so that they could leave; but treat them well enough so they don’t want to.

 

New INC. Magazine Column from Howard Tullman

 

Lead

How to Hire When Your Startup Needs to Grow Up

Many ‘lateral hires’ are complicated and expensive—whether they work out or not.

EXPERT OPINION BY HOWARD TULLMAN, GENERAL MANAGING PARTNER, G2T3V AND CHICAGO HIGH TECH INVESTORS @HOWARDTULLMAN1

Sep 8, 2025

In the life of most startup entrepreneurs whose businesses survive to the ripe-old age of three years, or who have hired more than 100 employees (or both), the inevitable discussions begin around that anniversary or significant benchmark about hiring “grownups” to supplement the founding management team. Occasionally these conversations are initiated by the CEO who understands that he or she needs help, but in the far more typical instances, it’s the investors, board members and sometimes worried key customers who want to be sure that the team is functionally complete and up to the task of managing the obstacles ahead.

To say that these “lateral hires” are complicated, expensive, and very risky is an understatement. In dollar terms, they’re expensive whether they work out or not. But the real cost is in management time and also in the various impacts on the rest of the team that are always part of the process. Balancing egos, adding titles, juggling job descriptions, and finessing actual operating authority are all massive tasks. Just keeping the peace is a challenge. A huge percentage of these sincere attempts and fraught experiments fail miserably and, sadly, rarely soon enough to avoid damaging some critical relationships inside and outside the company.

Causes for the failure can vary widely, but typically focus on blaming the newbie—for obvious, but not necessarily accurate, reasons. Other reasons include (1) a quickly-emergent and readily apparent lack of energy (stamina) and/or little enthusiasm for the day-to-day aspects of the business; (2) a weak connection to and empathy for the rest of the employees; (3) an early tendency to criticize the way the current team has run the business in the past; and (4) a focus and excessive interest in and emphasis on financial and compensation issues.

Sometimes, it’s the CEO’s own lack of interest, support and endorsement that brings about the new hire’s demise. And, of course, there are plenty of cases where the best laid hiring plans get blown up because the critical fit simply isn’t there—neither side of the deal looked deeply and clearly enough into the prospective arrangement to see the most obvious pitfalls. Leaping before looking leads to plenty of subsequent angst and severe remorse.

This is especially true right now when the market is flooded with men and women in their 40s and 50s with tons of documented and valuable experience who’ve been abruptly cut loose by Trump and his rotten DOGE flunkies. Far too many corporate executives and government managers have read the glossy books and seen the heroic movies, but they haven’t got the slightest clue as to how brutal life can be in a rapidly growing startup and how radically different it is from everything they’ve experienced before.

It’s ultimately on the CEO to do his or her best to make these personnel matters work out as swiftly and smoothly as possible, especially because hiring and retaining the right additional talent is absolutely critical to the company’s future. There are two primary concerns about the actions and reactions of the rest of the team that always require attention and some active involvement by the boss.

Youthful passion versus patience and planning

All successful startups are customer-centric and everyone in the place is told by the CEO from day one that being empathetic, attentive, reactive and responsive to the customer’s needs and demands is the most important operating rule for the business. Everything for the customer needs to be done “yesterday” and every problem or hiccup is an absolute emergency where everyone’s running around freaking out. This mindset might work when there are 12 of you sitting in a house somewhere, but not when there are hundreds of employees spread all over the country.

The older and more experienced “newbies” know this—that patience and process are essential even in a crisis—and that, even when your hair’s on fire, you don’t use a hammer to put it out. But the younger team members confuse this considered response with ignorance or indifference. You hear that the new guy “doesn’t get it”—he or she doesn’t understand “our” culture—they don’t fit. And this perception quickly spreads across the company.

The CEO needs to step in and make it clear that this is not a matter of a bad attitude or any lack of passion or interest in the business. It’s a response governed by a more important longer-term consideration. There’s a plan and a purpose, there’s a process in place, there’s a new measured approach to emergencies, and there’s an underlying idea and acknowledgment that if everything’s an emergency, then ultimately nothing gets done.

Let bygones be bygones

New, experienced team members are usually brought in—at least in part—because the systems and programs which had been in place from the beginning need to be strengthened and hardened in order to support the company’s growth. Documentation, for example, is almost always deficient. This requires change, and change is always uncomfortable, but it’s rarely personal. This is another area where the younger old-timers take great offense and umbrage. Every suggestion, each comment and especially observations about the old ways that things were done is taken personally and regarded as an affront and attack.

The team feels that it’s necessary to stick up for the past, that it’s somehow disloyal to suggest that the CEO didn’t get everything right from the get-go, and that saying that things need to be different going forward is blasphemy. They’re offended on behalf of the founders and management team. But the sad truth and the joke is that the CEO doesn’t really care.

As we all get older, it’s so much easier to get over slights, to avoid getting angry or offended by insignificant actions, to forgive and forget about little mistakes, and to not hold grudges. Attention to detail is a critical earlier tenet of startup discipline and nobody likes to see errors or mistakes, but as the business gets bigger and far more players are involved, some problems are going to be inevitable and unavoidable. The focus needs to be on fixing them and not being frustrated about them.

Here again, the CEO needs to speak up and let the team know that, while their pain on his behalf is appreciated, it’s not necessary or useful. Everyone needs to learn from the past but not live there, and they need to get on with building a better and stronger business. The past is a resource, not a residence. If the boss doesn’t give a damn about something, it’s not on you to carry the cross of grievance for him or her. Life’s too short and there are far more important things to address. Let bygones be bygones.