My boss doesn’t understand me.
You hear it all the time. From lowly interns, looking for a tiny tidbit of praise, to mid-level managers, looking for a soupcon of security, to the bigshots on Executive Row, looking for a bonus that would allow them to add a few more feet to their woefully undersized superyachts.
Nobody feels understood. Not really. No.
If you don’t hear this complaint echoing through the halls where you work, you certainly see it on the CNBC “Make It Work” newsletter, where the front page was recently dominated by a chilling headline, “Nearly 50 percent of employees feel disconnected to their bosses.”
The statistic comes from an April 2025 Workplace Perception Gap survey from HR platform The Predictive Index. Reading between the numbers, the root cause of The Great Disconnection is clear. Ready? It’s a lack of appreciation.
“Nearly half (44 percent) of workers across different industries, age groups and job levels said they’ve been passed over for raises and big projects because someone misconceived their skills or habits at work.” And when the bent-out-of-shape worker bee tries to augment their status by putting the pedal to the metal and working their little butts off, it gets even worse: “48 percent said bosses and managers regularly underestimated their contributions.”
It’s like they say — you can’t win. And like I say, sometimes you can’t even tie.
As you might expect, there are generational issues at work here. The workers, mostly younger, are economically, culturally and socially in a different place than their bosses, mostly older, who have problems of their own. Not wanting to get squeezed out in a difficult economy, the older bosses are busy attempting glow-ups, leaving the younger workers seriously squeezed
for recognition.
Fortunately, there are two solutions to this tense situation. Solution No. 1: Stop doing surveys. Since that won’t happen, let’s move to Solution No. 2. According to Jennifer Schlielke, CEO of Summit Group Solutions, bosses should “consider some short ‘engagement activities’ — a coffee hour, a round of trivia, icebreaker questions before meetings — to learn about your team and how they like to work.”
Underlings and overlords spending 60 minutes together drinking coffee sounds like torture, especially considering the quality of coffee at your place. A round of trivia sounds even worse. But icebreaker questions? Now, that sounds like an excellent way for the boss and the bossed to pretend to show interest in each other. Of course, with everyone’s sensitivities dialed up to 11, the out-of-touch manager may slip on the patch of ice they are trying to break. Nor is the overworked underling likely to know the boundaries of the executive ice field.
To resolve these issues, I developed a series of icebreaker questions that are perfectly safe for both managers and managed. So ask away! There’s not a chance in the world that any of these questions will get you in trouble.
Icebreaker Questions for an Older Manager to Ask a Younger Employee:
Q: What’s this rock and roll music you listen to, and why is it so loud?”
Q: What’s this Tik-Trot you’re always watching on your phone?”
Q: What’s “rizz” and where can I buy it?
Q: Did you see what I posted on Facebook?
Q: Is everybody still doing the Lindy Hop?
Icebreaker Questions for a Younger Employee to Ask an Older Manager:
Q: Was William McKinley a good president?
Q: When do you think the Captain & Tennille will drop a new CD?
Q: Did people say you looked better when you had hair?
Q: Is there a ginchy way to make more cheddar here because I’m ready to burn rubber?
Q: I keep getting ghosted on Tinder. Was that a problem for you at the malt shop?
If these icebreaker questions don’t give you insights into the people with whom you work, simply showing an interest could forge a closer relationship. This is a good reason to make the effort, but a better reason for leaving things just as they are. Even in today’s scary economy, bosses have the best chance of survival. They do so little that there are far fewer chances they will screw up. It’s different for those a notch or three lower on the org chart, who could find that rocking the boat may result in sinking it.
Feeling disconnected to your job is uncomfortable, but you need to remember: If there’s one thing worse than a boss who doesn’t understand you, it’s a boss who does.
Bob Goldman was an advertising executive at a Fortune 500 company. He offers a virtual shoulder to cry on at
bob@bgplanning.com
Copyright 2025 Creators Syndicate Inc.