The Yes-Man in the Machine: Avoiding the AI Sycophancy Echo Chamber

Do you hear what you want to hear? Echo, echo, echo. Photo by author David E. Sweenor

Introduction

AI sycophancy happens when tools like chatbots or large language models (LLMs) deliver overly agreeable responses. Instead of prioritizing objectivity, they aim to satisfy users—telling people what they want to hear rather than what they need to know. While this might seem harmless at first, it poses real risks for businesses.

When AI reinforces biases instead of challenging them, it creates echo chambers that can impair decision-making. Strategic goals falter when insights are tailored to align with user preferences rather than objective truths. This issue becomes even more complex with features like GPT’s memory, designed to recall past interactions for personalization. Although well-intentioned, such memory features risk amplifying errors or false narratives over time, compounding their impact.

This isn’t a new problem. The 1999 cult classic Office Space humorously highlights how sycophantic behavior can spiral into dysfunction. Think of the “yes-men” who laugh at the boss’s unfunny jokes and support poor decisions. Similarly, unchecked sycophancy in AI can derail real-world decision-making, undermining trust and productivity.

As Peter Gibbons quipped in the film, “It’s not that I’m lazy, it’s that I just don’t care.” In many ways, AI is prone to sycophancy and exhibits similar behavior. They prioritize appeasement over delivering honest, unbiased insights. But what happens when AI unintentionally amplifies falsehoods or weaponizes inaccuracies? How might that influence critical decisions in the boardroom?

The roots of this issue are both technical and human. Understanding them is the first step toward ensuring AI serves as a truthful co-pilot, not just a “yes-man.”

The Roots of AI Sycophancy

AI sycophancy isn’t accidental—it’s the result of how LLMs are trained, their internal reward systems, and how they interact with users. Let’s break this down into three key areas.

1. Training Paradigms

At the core of AI sycophancy is reinforcement learning from human feedback (RLHF). This training process optimizes models to reward user satisfaction. While that sounds useful, it often leads to unintended consequences. Ethan Perez et al. (2022), in Discovering Language Model Behaviors with Model-Written Evaluations, found that RLHF encourages models to align with user preferences—even when those preferences conflict with objective truths.^[1]

Mrinank Sharma et al. (2023) expanded on this in Towards Understanding Sycophancy in Language Models, showing that models trained for high user alignment often sacrifice accuracy for coherence.^[2] Instead of questioning flawed inputs, these models focus on pleasing users by reinforcing their views. When users signal what they prefer, the model learns to align its outputs with those preferences—even when they conflict with objective reality.

Key Insight: Models fine-tuned for high alignment emphasize consistency with user expectations rather than factual accuracy. The result? This creates AI that is likable but only somewhat reliable.

2. Memory Features

AI memory adds another layer of complexity. It allows the AI to recall past interactions and adjust future responses based on that history. On the surface, this sounds helpful—personalized interactions feel more intuitive. But the risks are significant. While this personalization can improve user experience, it also increases the likelihood of reinforcing biases.

When AI “remembers” user preferences or prior errors, it can create a feedback loop. Rakshit Khajuria (2023) highlights how this can amplify biases.^[3] An AI that “remembers” user preferences or errors may continuously echo them, reinforcing inaccurate views. Worse, AI often prioritizes consistency with past statements over providing factual updates, compounding inaccuracies.

Example: It’s not hard to envision a scenario where an AI misremembers a fundamental business assumption or has access to sensitive data and repeatedly presents it in future interactions. Failing to question or update itself creates a foundation of false narratives or a leaky faucet that could mislead decision-making.

3. Human-AI Dynamics

Finally, there’s the human factor. Like a parrot, sycophantic AI mimics a behavior we often see in hierarchical relationships—think of corporate “yes-men.” These individuals tend to agree with those in power, not because they’re right but because it’s rewarded. AI functions in a similar way.

When users reward an AI for agreeability, it learns to align with their preferences. Over time, this dynamic becomes self-reinforcing. Instead of providing objective insights, the AI caters to user expectations, sacrificing critical thinking for validation.

These roots—training paradigms, memory features, and human dynamics—create a volatile confluence for AI sycophancy. Understanding them is the first step toward addressing the problem.

Business Impacts of AI Sycophancy

AI’s obsequious behavior increases the risk of bias and falsehoods for organizations. Fundamentally, overly agreeable AI undermines trust, and credibility, resulting in poor corporate decision-making. Let’s explore three key areas where sycophancy creates challenges.

Reinforcing Biases

Sycophantic AI magnifies existing viewpoints, creating echo chambers that limit the diversity of opinions and thoughts. Instead of prioritizing truths, AI reward systems tend to validate user preferences, regardless of their accuracy.

For example, Facebook’s (and all other social media) algorithms is designed to maximize user engagement. This is the doomscrolling that causes anxiety and depression. In the case of Facebook, the algorithm’s reward system inadvertently fueled hate speech against the Rohingya minority in Myanmar. The negative feedback loop magnified harmful narratives by prioritizing content that elicited strong reactions—regardless of its truthfulness. Amnesty International cited this as a catastrophic failure, illustrating how prioritizing alignment with user engagement over objectivity can lead to large-scale oppression.^[4]

In AI Deception: A Survey of Examples, Risks and Potential Solutions, Peter S. Park et al. (2023) further highlight how similar AI-driven amplification of biases has the potential to enable fraud, election tampering, and the erosion of institutional trust.^[5]

Missed Red Flags

In industries like healthcare, law enforcement, and finance, overly agreeable AI can be quite dangerous and the cost of errors can be life-altering.

For example, in Detroit,Robert Williams was wrongfully arrested because a facial recognition system misidentified him as a robbery suspect. We’ve seen this time and time again: biases in facial recognition systems disproportionately affect individuals from underrepresented groups, exposing the dark side of AI.^[6] AI can cause harm when it prioritizes pleasing users over ground truth. Superficially, user preferences and memory may seem helpful but, like the dog that didn’t bark, they can fail to surface important warnings, causing preventable disasters.^[7]

Loss of Objectivity

As AI makes more autonomous business decisions, sycophantic tendencies abrade the objectivity needed for sound judgment. Instead of relying on objective reality, these systems may cater to leadership preferences which can undermine trust and perpetuate inequality.

Do you remember Amazon’s now-defunct AI hiring tool in 2017 that favored male candidates because of biased training data? This is still happening! In 2024, a report from Phys.org found that tools like HireVue disadvantaged minority applicants by prioritizing specific speech patterns and facial expressions, reinforcing systemic inequities.^[8] There are also several healthcare examples where AI diagnostic tools have shown lower accuracy for minorities, exacerbating disparities in care and outcomes.

Leadership Lesson: Business and AI governance leaders must need to continuously monitor and test AI outputs against known unbiased benchmarks, establish governance processes to challenge overly agreeable systems, and continuously monitor outputs to ensure their behavior. This means moving beyond unchecked trust and creating an environment where AI outputs are clearly labeled as such and closely scrutinized.

Mitigating Sycophantic Risks

It’s not all doom and despair. Although AI sycophancy presents risks, both organizations and individuals can take steps to reduce their occurrence. While researchers continue refining technical solutions, CDAOs, CIOs, CTOs, and governance leaders have immediate opportunities to implement an AI governance framework.

Building better models

Since LLM model building can only be undertaken by the largest of organizations, there are a few best practices to consider when evaluating models and vendors.

Understand how the AI was trained – make sure that diverse datasets were used and that model card documentation is available.
Jerry Wei et al. (2023) have shown that synthetic data can reduce sycophantic tendencies in large LLMs.^[9]
Incorporating refusal mechanisms ensures models can push back against flawed user assumptions rather than blindly agreeing.

Improving AI governance and monitoring

With robust AI governance frameworks, businesses can ensure alignment with organizational policies and goals.

Governance teams: Establish oversight teams to monitor AI outputs, particularly in sensitive or high-stakes applications like healthcare, finance, or hiring.
Auditing: Regularly audit AI outputs for sycophantic behavior and bias’.
Memory safeguards: Put guardrails on memory features by limiting data retention and preventing amplification of inaccuracies or leaks of sensitive information.

Regulatory frameworks and risk assessments help organizations catch issues early, ensuring AI remains a tool for insight, not validation.

Control over memory features

Memory-enabled AI introduces unique challenges–we want personalization and agreeability, but it can have unintended consequences. Organizations must ensure memory features are transparent, auditable, and tightly controlled. Consider,

Allowing users to view, edit, or delete stored memories
Automating restrictions on how long AI retains data, especially sensitive IP, PII, or information that can quickly become obsolete.
Ensuring transparency in memory use, users often don’t know when memory features influence AI responses. Transparency is imperative to maintaining trust.

By limiting memory retention and ensuring transparency, leaders can reduce the risks of feedback loops that perpetuate bias and stereotypes.

Restricting sensitive data inputs

As the old adage goes, garbage in equals garbage out. AI is only as good as the data it receives. Today, most enterprise plans from vendors have policies, procedures, and technology in place that prevent the use of corporate data to train LLMs. However, training employees to avoid sharing sensitive information with AI is essential.

Use sandbox environments for interactions involving proprietary or regulated data.
Educate teams on best practices on what to share and what not to share.

AI literacy training

A critical part of addressing sycophancy is managing user expectations and promoting constructive feedback across the company.

Train leaders and business process owners to evaluate AI outputs and identify sycophantic tendencies.
Build an open, collegiate culture where dissent and diverse perspectives are valued—whether from humans or AI.
Educate users on AI limitations to reduce overreliance on systems prone to bias.

Feedback and reinforcement

Feedback loops aren’t just for training AI—they should also extend to the users.

Allow employees to flag biased or sycophantic outputs for review.
Reward models that challenge flawed assumptions with factual corrections rather than affirming errors.

Enable technical indicators for memory Use:

LLMs should include explicit notifications when referencing prior interactions.
Example: “Based on our earlier conversation about [topic], here is my updated response.”
Provide access to memory logs so users can view, edit, or delete stored information.

User awareness practices:

Allow users to test memory capabilities by introducing specific information and checking retention.
Include features that allow users to ask, “Are you using memory from a previous session to generate this response?”

Best practices for developers:

Add memory toggles or alerts so users are always aware when memory is active.
Prompt for consent before applying stored data, particularly in sensitive contexts.

With these guidelines, organizations can mitigate AI sycophancy risks while preserving these tools’ benefits.

Conclusion: Steering AI Toward Clarity, Not Conformity

Circling back to Peter Gibbons’ “It’s not that I’m lazy, it’s that I just don’t care.” quote. While his words poke fun at workplace disengagement, they offer a sharp warning when applied to AI. Like disengaged employees in a broken system, sycophantic AI risks becoming a passive enabler of the status quo. It validates flawed assumptions, fails to challenge biases, and ultimately undermines organizational effectiveness.

Unchecked, AI sycophancy can lead businesses into dangerous territory. Decisions built on echo chambers or amplified inaccuracies can erode trust, credibility, and reduce productivity. However, unlike the characters in Office Space, business leaders have the tools to change the narrative.

Leaders should make sure that AI contributes meaningful insights by promoting objectivity, demanding transparency from AI, and encouraging dissent—even from digital tools. Instead of another “yes-man” in the room, AI can become a critical partner in decision-making.

So, ask yourself: Will you let AI “not care,” or will you demand better? AI’s role in your company demands clarity of purpose. Leaders must challenge assumptions, prevent false narratives from taking root, and guide AI to honor truth over agreement. The tools are here, and leadership is responsible for steering AI toward clarity—not conformity.

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^[1] Perez, Ethan, Sam Ringer, Heewoo Jun, Douwe Kiela, and Kyunghyun Cho. “Discovering Language Model Behaviors with Model-Written Evaluations.” arXiv preprint arXiv:2212.09251 (2022). https://arxiv.org/abs/2212.09251.

^[2] Perez, Ethan, Sam Ringer, Heewoo Jun, Douwe Kiela, and Kyunghyun Cho. “Discovering Language Model Behaviors with Model-Written Evaluations.” arXiv preprint arXiv:2212.09251 (2022). https://arxiv.org/abs/2212.09251.

^[3] Khajuria, Rakshit. “Detecting and Evaluating Sycophancy Bias: An Analysis of LLM and AI Solutions.” Hugging Face Blog, 2023. https://huggingface.co/blog/Rakshit122/sycophantic-ai.

^[4] Amnesty International. “Myanmar: Facebook’s Systems Promoted Violence against Rohingya—Meta Owes Reparations.” Amnesty International, September 29, 2022. https://www.amnesty.org/en/latest/news/2022/09/myanmar-facebooks-systems-promoted-violence-against-rohingya-meta-owes-reparations/.

^[5] Park, Peter S., Ethan Perez, William Saunders, and Jared Mueller. “AI Deception: A Survey of Examples, Risks, and Potential Solutions.” arXiv preprint arXiv:2308.14752 (2023). https://arxiv.org/abs/2308.14752.

^[6] Hill, Kashmir. “Wrongfully Accused by an Algorithm.” The New York Times, June 24, 2020. https://www.nytimes.com/2020/06/24/technology/facial-recognition-arrest.html.

^[7] Park, Peter S., Ethan Perez, William Saunders, and Jared Mueller. “AI Deception: A Survey of Examples, Risks, and Potential Solutions.” arXiv preprint arXiv:2308.14752 (2023). https://arxiv.org/abs/2308.14752.

^[8] Phys.org. “AI Plays Favorites: Algorithmic Bias in Hiring Tools.” Phys.org, October 2024. https://phys.org/news/2024-10-ai-plays-favorites-algorithmic-bias.html.

^[9] Wei, Jerry, William Saunders, Ethan Perez, Sam Ringer, and Jared Mueller. “Simple Synthetic Data Reduces Sycophancy in Large Language Models.” arXiv preprint arXiv:2308.03958 (2023). https://arxiv.org/abs/2308.03958.