One Question to Ask an AI-Obsessed Boss, According to TroopHR's Founder

"How many times did you use ChatGPT last week?" is the signature phrase of a new workplace archetype: the AI-obsessed boss. That's the opening diagnosis from contributing writer Mita Mallick, whose essay lays out how leaders consumed by all things AI derail their teams — and what employees can actually do about it.

Mallick identifies a specific pattern of behavior. The AI-obsessed boss, she writes, is the one who is "consumed, hyper fixated, and quite frankly possessed by all things AI." The symptoms read like a clinical checklist. In her telling, prolonged exposure produces the following side effects.

• The boss is always ready to green-light the next AI trend, while ignoring the other seven AI initiatives still in progress.
• They copy and paste from ChatGPT and label it "my thoughts" in response to direct questions.
• They misuse buzzwords regularly, including "agentic," "what's our AI strategy," "AI proof," "human in the loop" and "let's automate."
• They confidently declare an AI-generated plan is perfect, then ask you to fix parts of it.
• They forget how to brainstorm as a team, and their default mode is "Let's ask ChatGPT."

The core problem is volume without direction: seven initiatives running at once, none finished, while a new one launches. Mallick frames the whole piece around a single corrective question.

What's the one question that resets the conversation?

"When they come to you excited to roll out yet another AI initiative, start by asking your boss this simple question: Can you help me understand what's the goal here?" says Tracy Avin, founder of TroopHR, a community for modern HR leaders. Her advice continues: "Help your boss pause, ground them back to reality and focus on what actually needs to be done now, and what can wait."

The question works because it forces prioritization without confrontation. It doesn't challenge the boss's enthusiasm for AI. It challenges the absence of a stated objective — which is usually the actual problem.

How do you manage up effectively?

Avin's guidance, as relayed by Mallick, comes in three parts. First, focus on the facts, not the feelings. Mallick's verdict is blunt: you can have plenty of feelings about an AI-obsessed boss, but "save those for your diary." Bring specific examples to discuss instead.

Second, lead with what's working. "Make sure to also highlight the wins you have seen with AI. This builds credibility. When you do come with areas of opportunity, your boss is more likely to listen," Avin says. Credibility first, criticism second — the order matters.

Third, go to trusted colleagues, including your boss's peers, for advice. Avin says to position the conversation from a place of wanting to better help the boss and better serve the team. Mallick's read: the boss's AI obsession is probably "the worst kept secret in the company," and colleagues who have witnessed the behavior may be willing to help.

Is the boss coping rather than leading?

Mallick brings in her own book, "The Devil Emails at Midnight: What Good Leaders Can Learn from Bad Bosses," to argue for empathy. She admits she has been a bad boss herself — "and chances are, so have you." Her diagnosis of the AI-obsessed boss is that they might be struggling with a loss of control in their personal life, worried about job security, and scrambling to keep up with the pace of change.

The AI fixation, she suggests, may be a coping mechanism — an attempt to feel productive, engaged and valuable during what she calls "a bad boss era they are stuck in." Understanding what the boss is going through, she argues, helps employees survive the situation.

There's a boundary, though. Mallick warns employees not to get sucked into the AI frenzy themselves, "because it's contagious." Her closing instruction doubles as the essay's thesis: don't outsource your brain to AI. Keep thinking for yourself, she writes, and maybe your boss will be inspired to do the same.