I've been on the hiring side of hundreds of conversations, which means I know which questions reveal the most about whether a job is actually good. Candidates rarely ask the questions that matter. They ask about salary and title. They should be asking about the things that determine whether they'll grow, be treated well, and still have a job in two years.

Here are the questions I'd ask before accepting any AI role.

1. "Is this a real AI role or an AI-flavored version of an old role?"

Many "AI jobs" posted today are repackaged versions of existing roles with "AI" added to the title to attract candidates and justify lower pay. Ask what percentage of the work actually involves AI tools and techniques versus the same work people were doing before. A genuine AI role will have a clear answer. A repackaged one will get vague.

2. "How does the company actually use AI, today?"

Some companies have deep, real AI integration. Others have a single ChatGPT subscription and a press release. Ask for specific examples of how AI is used in the work you'd be doing. The specificity of the answer tells you whether you'll be doing real AI work or being the person who has to invent the AI strategy from scratch (which can be great or terrible depending on your goals).

3. "Who would I learn from?"

In a fast-moving field, the people around you determine how fast you grow. Ask who you'd be working with and what their backgrounds are. A role where you're the most knowledgeable AI person and there's nobody to learn from might pay well but stall your growth. Early in your career especially, proximity to people who are ahead of you matters enormously.

4. "How does the company think about AI replacing parts of this role?"

This is the uncomfortable but essential question. Ask directly: as AI tools improve, how do you see this role evolving? A thoughtful employer will have an honest answer about how the role grows into higher-value work. An employer who hasn't thought about it, or who gets defensive, is telling you they haven't planned for the thing that will most affect your job security.

5. "What does success look like in 6 months?"

This reveals whether the company has actually thought about the role or is hiring reactively. Clear success metrics mean clear expectations and a fair shot at meeting them. Vague answers mean you'll be judged against a standard nobody defined, which rarely ends well.

6. "How is compensation structured, and how does it grow?"

Especially at startups, a lot of AI-role compensation is equity. Ask what the cash-versus-equity split is, what the equity is realistically worth, and how compensation grows with performance. AI hype has inflated some equity packages that may never be worth what the cap table implies.

7. "What happened to the last person in this role?"

One of the most revealing questions you can ask in any interview. Did they get promoted? Leave for a better opportunity? Get let go? The answer tells you about the role's trajectory and the company's treatment of people. A pattern of churn is a red flag.

The questions I love getting asked

When a candidate asks me these kinds of questions at TTGC, it tells me they think like an owner, not an employee. They're evaluating whether this is a good investment of their time and talent, which is exactly the mindset that makes someone valuable. The candidates who only ask about salary and vacation days are telling me something too.

The honest framing

A job is a two-way decision. The company is evaluating you, and you should be evaluating the company with equal rigor — especially in a field moving as fast as AI, where a wrong choice can mean two years in a role that doesn't grow your skills while the field passes you by. Ask the hard questions. The good employers will respect you for it. The ones who don't just told you something important.

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