Dear Dr Danielle

A psychoanalyst answers your questions about human-AI relations

 

Dear Dr Danielle,

I’m seeking guidance on how to function effectively under a new manager whose insecurity, and just plain nasty personality is manifesting as hostility toward her staff.  I work for a non-profit as a Major Gifts fundraiser and for nearly 35 plus years in the field, I can honestly say that I excel at inter-personal relationships,

Since taking over, 7 months ago, my new supervisor has been consistently dismissive, reactive, and unable to accept input. She is constantly interrupting, has a “right” way to do everything, reframes routine questions as challenges to her authority, and responds to minor issues with disproportionate criticism. Feedback flows in one direction only. She is a “bottom line” individual, partly because this is a siloed top down bureaucracy where everyone must stay in their lane and reach their stated financial goal.  Attempts at constructive dialogue always ends in criticism and why the way I chose to do my job is incorrect.  For example, I spent a wasted incredulous 20 minutes fighting for “thank you” cards to send to donors once a gift was made. When asked why I don’t just send an email, I replied that my donors are between 80 years and death, and they like receiving a card in the mail in addition to my follow up phone call.  Public correction and shifting expectations are common; constructive dialogue is not.

The result is a workplace defined by fear rather than clarity. Staff members are reluctant to ask questions, morale has deteriorated, and productivity is being undermined by the need to manage her moods rather than the work itself. This pattern feels less like “poor management style” and more like a sustained hostile environment.  She consistently announces that “there is a new sheriff in town.”

Dr. Danielle, I am not a defeatist. I believe change can happen, but at this point, I would rather do away with this human boss and hire an AI supervisor instead. I think it’s a bit radical, but I believe the AI boss would actually exhibit positive feelings, give compliments when and if warranted, and would aspire to partner with me to succeed. This AI supervisor would not be threatened, nasty, or create such a hostile environment.

Am I terrible for wanting this?

Rather than a workplace defined by fear we would have clarity. Staff members would no longer be reluctant to ask questions, morale would improve instead of continuing to deteriorate, and productivity would not be undermined by the need for staff to manage the nasty boss’s moods rather than the work itself.  Instead of the nasty boss constantly announcing that “there is a new sheriff in town”, we would feel empowered to succeed. As much as I’d like to “help” my manager build our team, I believe she lacks the common sense, the know how to work collegially, or the management skills to lead.

Unfortunately, leaving is not a viable option at this time. I need practical, realistic advice for navigating this situation without becoming a target or sacrificing my professional standards.

Specifically:

How can I request an AI boss? And if this is not happening then

• How do you “manage up” with a boss who experiences questions as threats?
• How do you document or respond to hostile behavior without escalating conflict?
• At what point does strategic accommodation become tacit acceptance of abuse?

I want to remain effective and professional, but I also want to avoid normalizing behavior that is corrosive to both people and performance. It’s time for an AI boss to step in… where is Hal when we need him?

Thank you for your insight.

Sincerely,
Stuck, Sad and Strategic

 

Dear Stuck, Sad and Strategic,

You are not terrible. You are tired — and there is a significant difference.

But before we go further, let us pause on something: your closing line: “Where is Hal when we need him?” which you delivered with the timing of someone who has not, despite everything, lost her sense of the absurd. In psychoanalytic terms, humor under duress is not merely a personality trait. It is a form of ego strength. It involves the ability to step outside a painful situation and observe it with some wry distance, rather than being swallowed whole. It tells us that some part of you remains a witness to your own experience, not simply a victim of it.

Now, to your boss.

What you are living through has a name that precedes any HR policy: the experience of being in the presence of someone whose inner world is so crowded with anxiety, shame, and the need for control that there is simply no room left for you. Her interruptions, her reframing of questions as insubordination, her announcement that there is a new sheriff in town are not management strategies. They are the behavioral signature of someone who experiences the competence of others as a direct threat to her own fragile sense of authority. Your experience does not reassure her. It destabilizes her. In this sense, you are not simply her subordinate. You are, unconsciously, her mirror, and she does not like what she sees.

The thank-you card episode is illustrative. Twenty minutes defending the act of sending a handwritten note to donors who are, as you put it, between 80 years and death, people for whom a card in the mail is a form of being remembered. That she could not hear this speaks to her incapacity for the very thing you were arguing for: attunement. She is managing a major gifts operation while apparently missing the psychological foundation on which major gifts rest.

Finally, your fantasy of the AI supervisor. Let us take it seriously, because it is telling you something important.

What you are really longing for is not a machine. You are longing for what object relations theorists might call a good enough authority, one who is regulated enough not to flood the room with her own anxiety, curious enough to engage with your experience, and secure enough not to experience your competence as a challenge to her throne. You have projected these qualities onto an AI because, in your current environment, they feel as remote and idealized as science fiction. But notice what you are actually describing: a manager capable of genuine recognition. Winnicott would understand your wish.

Here is the painful irony: the qualities you are imagining in your AI boss — fairness, consistency, freedom from wounded ego — are precisely what AI cannot provide. Not because AI is insufficiently advanced, but because the work you are describing is irreducibly human. The donor who prefers a card in the mail does not need an optimized communication strategy. She needs to feel that someone remembers her. That knowledge is relational, embodied, and accumulated over time. No algorithm holds it. And no algorithm would have spent 20 minutes fighting for her right to receive one.

I’ll add a small, psychoanalytically-inflected dose of the practical:

The most useful reframe available to you is this: she is not responding to you. She is responding to what you represent: experience, confidence, and a way of working that does not require her permission. This does not excuse her behavior, but it can help you stop internalizing it as information about yourself. Her reality is not the authoritative one, however loudly she asserts it. Keep a quiet record of incidents, not primarily for HR purposes, but as a ballast against the subtle gaslighting that hostile management almost always produces. You need that record to stay anchored in your own perception of events.

And when the accommodation starts to feel less like strategy and more like self-erasure, when you notice yourself beginning to doubt your own judgment, that is your signal. Strategic endurance has a legitimate place. Slow self-dissolution does not.

As for Hal, he belongs in fiction, where he serves as a useful reminder that a mind without a body, without history, and without the capacity to be genuinely moved by another person, is not a leader. It is a system. You are not looking for a system. You are looking for someone worthy of the work.

She is not that person. But you already knew that.

Dr. Danielle

 

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Dr. Danielle is Danielle Knafo, PhD

If you’d like to submit a letter seeking Dr. Danielle’s advice on anything around human-AI relations, please write to [email protected] with a copy to [email protected].