Introduction: How to Interview – What I Learned from over 20 Years of Interviewing
Interviewing is an art, but one that anyone can learn with practice. As an introvert, and someone who grew up in a culture where she constantly heard that children should be seen and not heard, I have sharpened my listening skills over the years. In this updated how-to interview guide, I will share what I have learned over a 30-year period, including how artificial intelligence has transformed the interviewing landscape in recent years.
I mentioned that as an introvert; I honed my listening skills, but I wanted to add that expert interviewing is so much more than active listening because you can be a great listener, yet a lousy interviewer. Today, with AI tools at our disposal, the art of human connection in interviews has become even more critical to distinguish authentic conversations from automated interactions.
Who is This Updated Interviewing Guide for?
This how-to interview guide does not cover the technical aspects of interviewing because many podcasters have good posts on that topic. However, all the excellent equipment and AI tools in the world will not help you if you do not know the fundamental principles covered below. I learned them over 30 years of interviewing many people and conducting focus group interviews, now enhanced by understanding how AI can both help and hinder the interview process.
- Podcasters using AI-enhanced production tools.
- Video interviewers leveraging automated transcription.
- Content creators using AI for research and preparation.
- Student radio show hosts exploring AI assistance.
- Information interviewers in the age of chatbots.
- Anyone conducting interviews while navigating AI's role.
How AI Has Changed Interviewing in the Last Decade
The Opportunities AI Brings to Interviewers:
Research and Preparation Enhancement: AI has revolutionized interview preparation. Tools like ChatGPT, Claude, and others can help you research your interviewee's background, suggest relevant questions, and even help you understand complex topics your guest might discuss. I now use AI to generate initial question frameworks, though I always customize them based on my specific goals and the interviewee's unique expertise.
Real-time Transcription and Note-taking: Services like Otter.ai, Rev, and built-in AI transcription in Zoom have transformed how we capture interviews. This means you can focus more on listening and connecting rather than frantically taking notes. However, I still recommend taking some handwritten notes for key moments and emotional nuances that transcription might miss.
Content Repurposing: AI excels at helping transform long-form interviews into multiple content pieces – social media clips, blog posts, newsletters, and more. This has made interviews more valuable as content assets.
Language Translation and Accessibility: AI translation tools have opened up possibilities for interviewing people who speak different languages, making global conversations more accessible.
The Challenges AI Presents:
The Authenticity Question: With AI becoming more sophisticated, interviewees (and audiences) are increasingly concerned about authenticity. Are the questions genuinely from you, or AI-generated? This makes establishing trust and personal connection even more crucial.
Over-reliance on AI Research: While AI can provide extensive background information, it can sometimes give you outdated or incorrect information. Always verify AI-generated research, especially for recent events or personal details about your interviewee.
The Human Touch Becomes More Valuable: As AI handles more routine tasks, the uniquely human aspects of interviewing – empathy, intuition, reading between the lines, and creating emotional connections – have become more precious and necessary than ever.
Have you read?
7 Tips on How to Conduct Great Interviews [Basis for How to Interview: What I Learned after 20 Years of Interviewing People]
How to Formulate and Ask Intelligent Questions
Updated Tips for Conducting Interviews in the AI Era
Tell the Interviewee What to Expect (Including AI Use):
At the start of every interview, tell the interviewee what to expect so there are no surprises. In today's world, this includes being transparent about any AI tools you're using. I now mention if I'm using AI transcription, and I always clarify that while I might use AI to help with research or post-interview processing, the questions and conversation are authentically mine.
For example: “I'll be recording our conversation and using AI transcription to help me focus on our discussion rather than note-taking. I may have used AI to research your background, but all my questions come from genuine curiosity about your work.”
Listen More and Talk Less (Even More Critical Now):
When I ask a question, I listen to what the interviewee is saying to me. During the interview, the interviewee is the most important person in my life. She has my undivided attention.
In the AI era, this human attention has become even more valuable. While AI can process vast amounts of information instantly, it cannot replicate the experience of feeling truly heard and understood by another human being. This is your competitive advantage as an interviewer. 
I have always liked to listen more than I talk, but making someone feel as if she is the most important person in the world, I learned from Julia Conn Watt. Julia died from cancer of the adrenal in 2003, but every time I visited her, while I was talking, I felt special, like I was the most important person in her world, at that moment in time. This human connection is something AI cannot replicate.
Ask the Right Questions (Enhanced by AI Research):
AI can help you craft better questions by analyzing your interviewee's work, recent interviews, and expertise areas. However, the art is in knowing which AI suggestions to use and how to make them authentically yours.
I now use a hybrid approach:
- Use AI to research the person and suggest question topics
- Craft my own questions based on that research and my specific interview goals
- Always include questions that AI couldn't generate – those based on intuition, current events, or personal observations
The most powerful questions often come from connecting dots that AI might miss – linking something from their recent work to a broader trend, or asking about something they mentioned casually in a social media post.
Be Clear and Direct (While Navigating AI Misunderstandings):
Ask direct questions, and if the interviewee doesn't want to answer, move on. However, be aware that some interviewees might assume you're using AI-generated questions and respond more guardedly.
I've found that explaining my genuine interest in specific topics helps overcome this barrier. Instead of just asking “Tell me about your leadership style,” I might say, “I noticed in your recent LinkedIn post that you mentioned learning to delegate differently during remote work. I'm curious about how that evolution happened for you.”
Ask for Clarification (More Important Than Ever):
With AI-generated content everywhere, people sometimes speak in ways that sound polished but lack depth. Don't be afraid to ask for real examples, personal stories, and specific details that reveal the human behind the expertise.
“You mentioned X, could you give me a specific example from your own experience?” has become one of my most valuable questions. It cuts through any AI-influenced polish to get to authentic, personal insights.
Leverage AI for Better Follow-up Questions:
While conducting interviews, I sometimes use AI transcription not just for record-keeping, but to help me identify key themes emerging in real-time. Some advanced tools can even suggest follow-up questions based on what's been discussed, though I'm selective about which ones to pursue.
The key is using AI as a research assistant, not a replacement for your interviewing instincts.
Verify AI-Generated Information:
If you've used AI for research, be prepared to fact-check claims during the interview. AI can sometimes provide outdated or incorrect information about people's current roles, recent achievements, or personal details.
I've learned to phrase research-based questions carefully: “I read that you recently [achievement/change] – could you tell me more about that experience?” This allows them to correct any misinformation while still showing I've done my homework.
Handle AI-Enhanced Guests:
Some interviewees now use AI to help prepare for interviews, generate talking points, or even craft responses. While this isn't necessarily problematic, you can encourage more authentic conversation by:
- Asking unexpected questions that require personal reflection
- Focusing on recent experiences they haven't discussed publicly
- Asking about their feelings and personal reactions to events
- Requesting specific examples and stories
Traditional Tips That Remain Essential:
Speak Slower:
This remains as important as ever. I still have my “SPEAK SLOWER” reminder, and it's even more critical now when many interviews are recorded for multiple platforms and global audiences.
Don't Rely Solely on Technology:
Technology fails, and now we have even more technology to potentially fail! Always have backup plans for recording, transcription, and connectivity. I now maintain multiple backup systems because losing an interview is even more costly when you factor in all the AI-enhanced content you could create from it.
Honor Time Commitments:
With AI helping us generate more questions and research more thoroughly, it's tempting to cover everything. Resist this urge. Respect your interviewee's time, and use AI to help you prioritize which questions are most essential.
New AI-Specific Considerations:
Ethical AI Use in Interviews:
- Always disclose when you're using AI tools
- Don't use AI to generate fake questions or personas
- Respect privacy when using AI transcription services
- Be transparent about how AI-generated content from the interview will be used
Post-Interview AI Enhancement:
AI can help you create multiple content formats from one interview, but always maintain the authenticity and context of the original conversation. Don't let AI tools misrepresent your interviewee's words or intent.
Staying Human in an AI World:
The most successful interviewers of the next decade will be those who use AI to handle routine tasks while doubling down on uniquely human skills: curiosity, empathy, intuition, and the ability to create genuine connections.
Conclusion: How to Interview in the Age of AI
Interviewing has evolved dramatically since I first wrote this guide, but the core principles remain the same: listen more than you talk, ask thoughtful questions, and create authentic human connections. AI has given us powerful tools for research, transcription, and content creation, but it has also made genuine human interaction more valuable than ever.
The interviewers who will thrive are those who embrace AI as a powerful assistant while never losing sight of what makes interviews truly compelling: the uniquely human moments of insight, vulnerability, and connection that no algorithm can replicate.
Use AI to become more prepared, more efficient, and more able to focus on what matters most – creating a space where your interviewee feels heard, understood, and inspired to share their best insights with the world.
After 30 years of interviewing, I'm more convinced than ever that while technology will continue to evolve, the art of human conversation remains irreplaceable. AI is a powerful tool in our interviewing toolkit, but it's the human heart of the conversation that creates lasting impact.
Additional Resources for AI-Enhanced Interviewing:
- Research Tools: ChatGPT, Claude, Perplexity for background research
- Transcription: Otter.ai, Happy Scribe, Rev, Zoom's built-in transcription
- Content Repurposing: Various AI tools for creating social media content, blog posts, and summaries
- Fact-checking: Always verify AI-generated research with primary sources
Remember: AI is your research assistant, not your replacement as an interviewer. The questions may be enhanced by AI, but the curiosity, empathy, and human connection must always be authentically yours.
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