I regularly use my Claude Cowork robot assistant to interview me on various topics across different settings. Being interviewed by the AI doesn’t change what I think. It helps me say it more clearly in my own conversational voice and surfaces aspects of a topic I hadn’t consciously addressed.
The thinking stays mine. The AI’s job is to prompt and probe, never to assert its conclusions.
Where I Got the Idea
I got the idea of using my robot assistant to interview me from Chris Bailey’s newsletter post, 10 tips for using Claude Cowork, in which he wrote:
“I use interviews to create skill files and to fish out ideas I wouldn’t have surfaced on my own for articles like this one.”
Being asked questions and responding verbally unlocks thinking. It helps us understand our own thoughts and process them.
Why Speaking Out Loud Unlocks Your Thinking
An interview simulates a human conversation. One person talks about things, and the other listens and asks appropriate questions to dig deeper and prompt additional thinking.
I’ve found that responding by speaking, rather than writing, is much more effective for me. I use the Wisper Flow app to transcribe my dictation.
Interviewing helps me think through what my positions actually are, whether they’re consistent, and whether they’re true. Sometimes the prompts and questions lead me into areas I haven’t fully thought through yet or haven’t verbalized.
We think by speaking. As clinical psychologist Jordan B. Peterson wrote in 12 Rules for Life, “The people I listen to need to talk because that’s how people think.”
The article Why Speaking Out Loud Helps You Think, states this concept well:
“Verbalization makes implicit knowledge explicit. Speaking through your reasoning process surfaces assumptions, decision criteria, and pattern recognition you’re applying unconsciously.”
In his insightful book Useful Not True, Derek Sivers suggests we refine our thoughts by talking about it with others:
“After you privately internalize a belief, talk about it with friends. Explaining it to different people helps you refine it. They might see an angle or consequence you hadn’t considered.”
The Two Interview Skills I Built
Interviewing, or being asked questions, is a single technique hiding inside a dozen of my different routines.
I have two explicit interview skills:
1. The interview skill: A podcast-style deep dive. It probes vague language and easy answers, points out possible contradictions and missing specifics. It deepens personal reflection and ends with a closing takeaway question. It never accepts the first answer. There are two output modes: either my responses for a blog post, or an ideas folder summary.
2. Journal interview skill: This skill looks at the journaling that I’ve done earlier in the day, my shutdown routine, and themes to probe further. It then summarizes my responses and adds them to the end of my journaling that day.
If you use Claude Cowork, you can easily build your own interviewing skills. Tell Claude what you want to create, what it is for, and the end result you’d like. Ask if it has any questions. It will likely take several modifications before it works the way you want.
Interviewing Hides Inside Almost Every Routine
Interviewing also appears in a number of different other skills. For instance, in my shutdown routine, it ends each day with four reflective questions:
– What did I consider my biggest win?
– Where do I see room to improve?
– Do I have anything left that needs to be dealt with?
– Did anything happen to me that I’m grateful for?
Interviewing also appears in my Weekly, Monthly, and Quarterly Review skills. They walk me through the process by asking me questions I respond to. Claude Cowork gives me the information I need for each section of a review, then asks me questions that reflect on it. (For more information about using Cowork with reviews, see my blog post, How Claude Cowork Made My Quarterly Review Better — and More Fun)
Why My Blog Posts Suddenly Sound More Like Me
I use my robot assistant interviewing skills in a number of practical areas.
My blog posts have been feeling more personal and more interesting lately, at least to me. I think the biggest change is a result of doing research briefs with Claude Cowork and then having it do interviews with me based on those briefs and my notes for the post. That’s led me to transfer many of the responses I give in interviews directly into the post text.
There’s a different process at work here than what I used before. When I’m writing or dictating directly off a mind map, I’m focused on translating an outline of thoughts into writing. That tends to come across as a little more formal.
When I’m verbally responding to questions, I speak in my own natural voice and express things the way I normally would in a conversation. My posts have subsequently become more conversational than they were before, and therefore more relatable and understandable.
Underneath the hope that readers find the post more personable and relatable is the belief that my thoughts will have greater impact and bring about more change in people’s lives if they perceive them that way.
I usually put one call to action in my closing to get readers moving in a direction I think would benefit them. My desire is to have both a natural, free-flowing voice and a carefully thought-through post. The interview helps me to deliver both.
Interviewing Myself to Think Through a Topic
I also use the interview skill to think through a topic.
I tell it a topic I want it to interview me on, some of my initial thoughts, and why I want to do an interview.
I tell it what the end result I’m looking for is: that I am either weighing options to make a decision (I don’t want AI’s advice, just prompt my thinking), or perhaps I am trying to think through what I really think about a particular topic, or maybe a statement of what I believe about a topic.
The Evening Interview That Deepens My Journal
Journaling is the third major area where I use AI interviewing.
Every evening after I complete my shutdown routine, I have an evening journaling reflective session.
The journaling interview skill reads my morning journaling entries, identifies three to five unresolved threads and what’s conspicuously absent, and asks one open-ended question at a time. It then drafts a narrative entry in my own voice.
Being prompted unlocks my thinking in my journaling. Dictation allows me to respond to prompts in a natural, free-flowing style. It’s not as edited as when I write. My journaling in response to questions seems more honest, revealing, and vulnerable than my writing.
The One Rule That Makes This Work: Keep the Thinking Yours
I don’t want my AI interviewing to think for me, but to prompt my thinking. I want my thinking to stay my thinking, not the thinking that is suggested by AI.
The interview skills work because I supply the thinking, and the assistant supplies the questions. The moment it starts generating my conclusion, the value collapses.
The interview clarifies and surfaces my thinking rather than replacing it with AI conclusions. I don’t want it to insert its own conclusions into what I say. I just want it to prompt my own thinking and probe it.
There seems to be a built-in inclination for the AI to insert its own assumptions or conclusions. A few days ago, I was journaling about finishing the mind map for a blog post, which was a priority task for the day. After finishing the mind map, I continued on to dictate the post, edit it, and publish it to WordPress and Kit.
When it summarized my journaling, the AI reported that I was “surprised” when I went beyond the mind map to finish the post. I never said that I was surprised. As a matter of fact, I’ve done this several times.
Here, the AI was inserting its own assumption or conclusion into my words. More than once, I have had to remind the AI to use my own words and not insert its own assumptions or conclusions, and to strengthen the skill to keep this from happening in the future.
One Technique, a Dozen Uses
What started as a single tip from a newsletter has worked its way into nearly everything I do — my blog posts, my decisions, my daily journaling, my weekly and quarterly reviews. It turns out that being asked good questions and answering out loud is a remarkably portable skill. Once you notice how well it works in one place, you start reaching for it everywhere.
So pick one routine you already have — your journaling, your planning, your writing — and add an interview to it this week. Let something ask you the questions you’d never think to ask yourself, and see what you say back. I think you’ll be surprised at what was already in there.
Note: I wrote this blog post myself using my own words and thoughts for the initial draft. I used AI only to suggest headlines, section headings, images and text improvements.
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