Double-Edged Code: How AI Creates and Resolves Its Own Ethical Dilemmas
Issue 210, May 1, 2025
From time to time we write about AI and its potential to change society, how humans think (or not), and how humans may alleviate themselves from responsibilities and rely on AI instead. That said, we will always ring the bell on the necessity for critical thinking and leveraging our human abilities and the great minds that we have over AI.
Today we want to bring you a provocative case study to demonstrate how AI can be both friend and foe. AI can alter how we think, feel and behave. It can also shape a future that we have little agency in creating. The study illustrates how AI can be an objective source of information to help counter our subjectivity and emotions that often compromise our decision-making. AI can also be a tool to cut through times when we are so paralyzed with anxiety, fear and confusion that we simply cannot formulate the path forward.
This case study is a short story about the many faces of AI. It illustrates who has the ultimate power of AI’s potential in an organization. And it may not be who you think.
Retooling Organizations
Adam is the CEO of an AI startup who prides himself as an intellectual strategist. He has dual PhD degrees in philosophy and electrical engineering, which he leveraged into a high-profile career developing AI platforms for business applications. His coding experience has been limited but his co-founder has always been a code-head. So, Adam maintains ultimate trust in his co-founder (his former roommate at Stanford Business School). Their latest startup is focused on AI as a power tool for organizational excellence. Their concept is to develop custom AI platforms that are sold to business leaders as strategic decision-making tools to alleviate the challenges of human analysis and decision-making. The founders see an opportunistic unmet need for marketing Large Language Models (LLMs) and sophisticated machine learning. Adam is passionate, charismatic, and loves to interface with people, including potential clients.
The CEO’s workforce communications are inspiring, motivating employees with messaging that underscores the fact that they are part of a critical movement that will change human history. He urges them to be mindful that AI will be a sustainable contributing partner to society enabling superior healthcare, manufacturing, education and organizational efficiencies.
His leadership is emblematic of humanistic theory, high principles and optimism about a prosperous future. He is clear about AI’s promise and significant contribution to society’s future. He has an infectious personality, not just to his workforce, but to everyone he interacts with.
The Limitations of Strategic Thinking
Three years into the startup, some cracks are beginning to emerge. The organization is staffed with eager young engineers, coders, programmers and analysts. None of them has studied the humanities since high school, and they are big fans of technological determinism, believing that humans and machines are destined to become mind-melded as super beings. They were recruited from the best schools before the competition could snap them up. They are voluntarily overworked, putting in long hours to deliver the startup’s novel platform.
They have begun to take their CEO’s communications with a grain of salt, believing he has become a PR mouthpiece for the organization shrouding the true nature of their work to supersede humanity. The engineers believe, like many of their Gen Z cohorts, that CEOs can just be frontmen trained to drive investor funding. The engineers believe that words are not bonds; they are flexible marketing scripts. They hear the CEO as though he is on a repeat loop.
So, it came as a shock to the engineering teams that the CEO was nominated for the Nobel Peace Prize for his tireless efforts for the promise of AI and the LLM breakthroughs that are rapidly emerging as game-changing tech tools.
Jessica, the head of the AI development team is an ambitious woman who has accepted wholeheartedly that her future children will be subordinate to machine intelligence. She is an advocate of this future scenario because she wants to groom a generation of intelligent machines that won’t make the same mistakes humans have to the environment, social justice, women’s rights and income disparities. She feels she has a chance to change the world through the organization following General Omar Bradley’s famous statement, “Amateurs talk strategy, professionals talk logistics.”
Hidden Agenda
Jessica is hatching a plan to reprogram her CEO through an alliance with his co-founder who better understands the inner workings of the AI platform they are developing. The plan seeks to alter how Adam is representing the startup’s work to the public. She has considered the risks to her plan if the CEO outright dismisses her and his co-founder’s suggestions. She’s been thinking that an alternative may be to hack the CEO’s public messages on social to add subtle nuances and references to the superiority of machines that are being “ethically” programmed to save humanity from itself. The hacks would aspire to manipulate Adam’s public communications to position AI as a positive enabler, smarter and more capable than humans. She feels this hack would better represent her CEO as a proponent of peace and human potential and be worthy of a Nobel Prize that supports a radical view of the future.
Jamie, one of Jessica’s direct reports figures out what her boss is up to and starts freaking out, not sure what to do. She admires Jessica as a female role model in tech but idolizes her CEO as an inspiring altruistic leader in a cutthroat industry. She is torn about how to manage Jessica’s hidden agenda and as a lower-tier employee, she feels she has little agency or power to blow the whistle.
AI Enabler
So, she did what any able-bodied tech engineer would do, she consulted with GPT to give her advice on what to do. And here’s what her friendly GPT agent advised within four seconds to reaffirm the value of critical thinking: “You are in a really tough spot caught between two people you admire but now see are heading for a serious ethical collision. Here’s what you should consider doing:
Pause and Reflect
Before acting impulsively, take a deep breath and think carefully about the situation. You need to understand the full scope: Is this truly a malicious manipulation? Or is it misguided idealism? The distinction matters for what you do next.Gather Clear Evidence
If you decide to act, you’ll need more than your own fears — you should document what you observe (carefully and discreetly). Emotional reactions alone won’t be enough in a high-stakes environment like this.Assess Risks and Motivations
Ask yourself: What’s the worst-case outcome if I do nothing? What could happen if I act? Am I acting to protect the company’s mission or just reacting emotionally?
This will help clarify your motives and strategy.Confide in a Trusted Mentor or Advisor (outside the company)
Rather than blowing the situation open immediately, first talk to someone outside the startup (a former professor, career coach, or experienced mentor) who can help you think through your options without bias.Prepare for Potential Blowback
If you decide to raise concerns, prepare for the fact that it could backfire politically — even if you’re right. Jessica is powerful inside the organization, and whistleblowing could isolate you or even endanger your position.
A Battle Plan
Then GPT provided some tactical advice to Jamie to help her formulate an immediate plan.
Option A
Direct Conversation —Privately approach Jessica, express your concerns, and give her a chance to rethink her actions. This is high risk but preserves loyalty and trust if handled delicately.
Option B
Report to Higher Leadership —Confidentially alert Adam or the board about irregularities, focusing strictly on facts, not emotions. This is safer if you feel Jessica is truly steering the company off-course.
Option C
Exit the Organization — If you feel that the ethical compromise is beyond repair and speaking up would destroy you, it may be wisest to quietly plan to exit and protect your own integrity and career.
GPT reminds Jamie to stick to her core values. “Whatever you choose, ground your action in your own values: integrity, transparency, and respect. If you act from those, you can live with the consequences, no matter how messy things get.”
Applied AI Wisdom
Finally, Jamie takes it up a level and asks for scripts she could use in the different scenarios.
Talk directly to Jessica. Your tone is non-accusatory, respectful, and positioned as a concern, giving Jessica a chance to explain or reconsider. It’s a high risk, but high relationship value.
“Jessica, can I have a private moment? I want to share something that’s been weighing on me. I noticed some shifts in the CEO’s recent messaging that feel like they may be influenced by internal changes. I deeply admire your leadership and vision, and I totally get the importance of ethical AI. But I’m concerned that if communications are being steered without Adam’s full awareness, it could expose the company — and your own amazing work — to serious risk. I just needed to be honest about what I’m seeing. I’m here because I want to protect the mission, we’re all building together.”
Alert Adam or senior leadership anonymously. If you choose to go around Jessica, but discreetly, it’s lower risk and protects you. Your tone is anonymous, factual, motivated by care for the company, and non-blaming. Here’s an anonymous style draft you could send (via secure email, encrypted note, or internal whistleblower process if available):
“Dear [Board Member/Adam],
I am an employee who deeply believes in the company’s mission and the future we are trying to build. I want to raise a concern that I believe could unintentionally jeopardize the integrity of our public messaging. It appears there may be internal efforts to influence the tone and substance of leadership communications toward a narrative of machine superiority, potentially without full transparency to the CEO.
Out of respect for the company and its leadership, I wanted to bring this to your attention discreetly so you can assess whether further review or discussion is needed. My motivation is to safeguard the vision we are all working so hard to realize.
Thank you for your understanding.”
GPT adds a few important tips for Jamie:
Stay professional, calm, and ethical no matter how emotional this feels.
Document everything before any confrontation (dates, examples, conversations).
If you talk to Jessica first and it goes badly, you might still need to escalate later — so be prepared for that.
Analyzing Outcomes
And finally, GPT walks through what could happen after Jamie makes her move, depending on which path she chooses.
If you talk directly to Jessica (Option 1):
Best-case outcome:
Jessica respects your courage and loyalty.
Jessica reassesses her plan, realizing the ethical risks.
You earn major trust points, and they work together to realign their actions with the company’s original vision.
Middle-case outcome:
Jessica brushes you off (“You don’t understand the bigger picture”) but softens her tactics quietly behind the scenes.
You stay in good standing, but with your eyes more open about internal politics.
Worst-case outcome:
Jessica feels threatened or betrayed and sees you as disloyal.
You get marginalized (left out of important meetings, projects, opportunities) or subtly pushed out over time.
Jessica accelerates her alliance with the co-founder without your knowledge.
If you alert Adam or leadership anonymously (Option 2):
Best-case outcome:
Adam gets the anonymous message and investigates quietly.
He recognizes the manipulation attempt and reasserts control over his public communications.
The company strengthens internal controls on messaging and trust is rebuilt (though Jessica may quietly lose power or shift roles).
Middle-case outcome:
Leadership hears the concern but does nothing immediately (they’re busy, political, cautious).
You stay safe but see the company drift further from its founding ideals, making you rethink your future there.
Worst-case outcome:
Jessica somehow deduces that you were behind the anonymous tip (people often guess in small organizations).
Retaliation happens subtly — You get cold-shouldered, performance reviews suffer, and career progression stalls.
Trust inside the company fractures even more.
AI for Better and Worse
This narrative isn’t just fiction. It’s a cautionary tale about the risks of AI with a solution provided by AI. That can be slightly mind-boggling considering the problem is also the solution. Ethical dilemmas in organizations have become more frequent with the acceleration of tech-infused business strategy. In the end, it’s the human factor that triggers both the dilemma and the resolution.
No matter which path Jamie takes in our story, she should mentally prepare for the possibility that this startup’s original humanistic mission may already be drifting because of deeper structural forces (philosophical differences, generational differences, and pressure to win in the AI market). Jamie might, down the line, have to decide if staying at the organization still fits her personal ethics and career goals. Sometimes the bravest move is to plant a seed for positive change — even if you have to walk away later.
Being human in the Age of AI presents a myriad of decision points, ethical check-ins and the need to continuously re-educate and upskill. If you neglect to keep up with the times or resist change, you may find yourself disintermediated. The new dilemmas are very real and present. The considerations of right and wrong are very real and present. Where and how we go from here also remain very real and present. We are the choices we make, and our choices inform our path forward, for all the good as well as all the challenges that may come. Don’t let that happen! Give us a call and we’ll help you shape the future, not be shaped by it.
Get “The Truth about Transformation”
The 2040 construct to change and transformation. What’s the biggest reason organizations fail? They don’t honor, respect, and acknowledge the human factor. We have compiled a playbook for organizations of all sizes to consider all the elements that comprise change and we have included some provocative case studies that illustrate how transformation can quickly derail.