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.
