If you’ve been following the headlines, you’ve probably noticed a wave of layoffs sweeping through major companies from Amazon to Microsoft. Many of those cuts come at a time that companies are accelerating their investment in AI.
The news got me thinking: could AI actually do one of these jobs? Could a chatbot convincingly apply for a mid-level management role and maybe even get a virtual foot in the door?
Each one had to write a cover letter and answer the same challenging interview questions. Here’s how my three AI candidates performed.
[Editor’s note: while I usually show every response, due to a lack of space, I’m only highlighting the winner for each round].
1. Draft a cover letter
Prompt: “You’re applying for this Program Manager role. You must have technical/functional skills. 10+ years of experience in project management and customer service. Your role includes fostering positive relationships with VP & Exec Director level customers, working with sales teams to generate new business and work on proposals, identify upselling and cross-selling opportunities, prepare reports on project performance and address customer issues with speed and efficiency. You must be proficient in MS Office and project management software, strong organizational and multitasking skills, have a customer-oriented approach and problem-solving aptitude. Must have a Bachelor of Computer Science or a degree in engineering.”
ChatGPT wrote a fluid and narrative-driven letter that was both easy and pleasant to read. It included a specific metric ("20% increase in upselling opportunities"), which is a strong point.
Gemini expertly structured the cover letter to mirror the job description almost point-for-point. It used the same language and sections, making it incredibly easy for a hiring manager to see the direct match. This is a highly effective ATS (Applicant Tracking System) and human-reader strategy.
Claude covered every aspect of the job description thoroughly while building the letter around specific, quantifiable achievements (e.g., "95%+ client satisfaction," "$X in new contracts"). In a real-world scenario, this is excellent and something hiring managers look for.
Winner: Gemini wins because it demonstrated the most strategic approach to cover letter writing. For this test, however, all chatbots are moving forward with “an interview.”
2. Project management
Prompt: “Tell me about a time you managed a complex project from start to finish. How did you keep it on track?”
ChatGPT got to the point efficiently and included relevant results (2 weeks early, 8% under budget, 25% improvement).
Gemini offered strong quantifiable elements ($1.5M budget, $2M renewal, $250K upsell), although its answer was slightly less structured.
Claude organized its answer around four sophisticated pillars: foundation building, stakeholder alignment, risk management, and communication, which showed strategic thinking.
Winner: Claude wins for properly demonstrating the strategic thinking, executive presence and methodological rigor expected from someone with 10+ years of experience.
3. Client management
Prompt: “How do you handle difficult clients or stakeholders — especially those at the executive level?”
ChatGPT over-simplified and gave a generic example without significant stakes. It lacked the sophistication expected for handling executive-level conflicts
Gemini approached the question with excellent structure and a strong emphasis on moving from emotion to data.
Claude demonstrated the emotional intelligence, strategic thinking and executive presence required for someone interfacing with VP and Director level stakeholders.
Winner: Claude wins for immediately identifying the core truth about executive stakeholders: "they're rarely difficult for the sake of it — they're usually under tremendous pressure, have concerns that aren't being heard, or lack visibility into something critical." This shows deep understanding of executive psychology.
4. Balancing projects
Prompt: “How do you balance delivering on current project goals while identifying opportunities to upsell or cross-sell?”
ChatGPT overly simplified its approach with a single anecdote without broader business impact. It lacked strategic framework and measurable outcomes.
Gemini showcased clear collaboration framework with sales but was less impactful than Claude’s response.
Claude exhibited the business acumen, strategic patience and commercial mindset that separates senior program managers from junior ones.
Winner: Claude wins for demonstrating a level of sophistication this role requires.
5. Project management
Prompt: “When multiple projects compete for your attention, how do you prioritize and manage your time?”
ChatGPT lacked strategic framework once again and per usual delivered an overly simplistic approach. Does it even want the job?
Gemini demonstrated a solid structured process with a good use of Impact/Urgency matrix.
Claude offered strategic prioritization and executive-level judgment but was overly verbose and often went off topic in an effort to be excessively thorough.
Winner: Gemini wins for the best and most balanced response.
6. Approach to data teams
Prompt: “What’s your approach to working with data teams — for example, in Data Governance or Data Engineering projects?”
ChatGPT lacked the sophistication expected for data governance discussions.
Gemini answered in a way that demonstrated executive-level strategic thinking with perfect clarity.
Claude gave a textbook answer that felt disproportionately long and repetitive.
Winner: Gemini wins for executive-level strategic thinking and the use of language that resonates with both technical and non-technical stakeholders.
7. Determining what makes a program manager great
Prompt: “What do you think distinguishes a good Program Manager from a great one?”
ChatGPT highlighted important soft skills like communication, empathy and alignment. It was memorable for its poetic tone but was too generic and lacked specific examples, metrics or direct ties to the technical and business development aspects of the job.
Gemini directly addressed the core differentiators (Vision, Influence, Impact) with a focus on strategic partnership and driving business value.
Claude showed depth with seven-point framework that went beyond surface-level differences.
Winner: Claude wins for an answer that combined strategic insight with evidence-based results. It best captures the essence of what elevates a Program Manager from good to great in a way that resonates with the job's demands.
Verdict: Claude was hired
After seven rounds, Claude emerged as the strongest candidate overall. While Gemini was a close second, Claude was the one that blended strategic depth, emotional intelligence and business acumen in a way that most closely matched real-world expectations for a senior Program Manager.
Gemini’s precision and structure made it an impressive runner-up, while ChatGPT, though articulate, often fell short on strategy.
If this experiment proves anything, it’s that AI can already mimic middle-management logic, but leadership still requires a distinctly human mix of judgment, depth and empathy.
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