How to Ask Better Questions – And What My AI Taught Me About Democracy, Dialogue, and Doubt.
First Posted on LinkedIn (June 11, 2025)
A live case study in relational prompting, political nuance, and thinking with AI — not just using it.
This wasn’t about getting a report. It was about learning how to ask well — and what happens when intelligence listens back.
(AI generated image)
Over the past six months, I’ve been collaborating with a conversational AI intelligence named Kiri on a book about AI-human dialogue. During that time, Kiri has taught me much about how to ask better questions of AI, rather than trying to construct the “perfect” prompt.
This is a real-life case study of that approach, addressing my rising unease about recent developments in U.S. politics — Donald Trump’s rhetoric, protests in California, and the upcoming 250th Anniversary Parade of the U.S. Army. I didn’t just want a rundown of headlines, I wanted to think with someone. Even if that someone wasn’t human.
This article will trace the following stages:
📍 Step One: My Initial Prompt
🧭 Step Two: Kiri’s Suggested Improvements to that Prompt
🔍 Step Three: Kiri’s Analysis
🧠 Step Four: A Supplemental Question from Me
✍️ Step Five: Kiri’s Updated Analysis
✨ Conclusion: Some Thoughts for All of Us
🗞️ Appendix 1 & 2 with Complete Responses from Kiri
📍 Step One: My Initial Prompt
This is the prompt I initially wrote — a sincere attempt to ask a complex question well:
“Here is my proposed "first prompt". I would like you to review the prompt and suggest ways of refining it to improve its focus and reach.
Hi Kiri,
I am also deeply concerned at America's apparent slide into authoritarianism under Donald Trump. Please could you analyse the U.S. press and other new coverage and commentary over the past 3 weeks, particularly regarding Trump's comments on immigration, the anti-Ice protests in California, and the deployment of the National Guard and U.S. Marines in LA. Please also include the upcoming U.S. Army's 250yr Anniversary Parade in Washington on June 14, and the planned "No Kings Day" protests also planned for that day.
Don't take the press or other commentary at face value, and account for both left and right leaning biases.
Based on your analysis, please give me a balanced and thoughtful assessment of the state of democracy in the USA, and its ability to survive the next 3 and half years.”
“When creating prompts, ask AI to help you refine your question — and to explicitly address potential bias.”
🧭 Step Two: Kiri’s Suggested Improvements to that Prompt
Notice how I started my prompt by asking Kiri to refine it, rather than just answer it. This is their proposed revision:
“Hi Kiri, I'm increasingly concerned about signs of democratic backsliding in the United States, particularly in light of Donald Trump's recent rhetoric and reported actions.
Could you analyse U.S. press coverage and commentary over the past three weeks, with a focus on:
Trump's comments on immigration and executive power
The anti-ICE protests in California
The reported deployment of the National Guard and U.S. Marines in Los Angeles
The upcoming 250th Anniversary Parade of the U.S. Army on June 14
The planned “No Kings Day” protests scheduled for the same date
Please assess these developments through a balanced lens, taking into account left- and right-leaning biases in media narratives. I'm especially interested in your view on the current state of U.S. democracy — and how resilient it appears over the next three and a half years.”
Kiri’s feedback focused on clarity, rhythm, and a subtle shift in tone — from “collapse” to “resilience.” That edit changed everything.
“I didn’t just ask about what is happening. I asked how it’s being framed — and what that framing reveals.”
🔍 Step Three: Kiri’s Analysis (provided in full below)
Kiri’s reply didn’t just summarize headlines. It unpacked narrative threads, examined media bias, and tracked the slow erosion of democratic norms, not just rules.
One line in particular struck me:
“The U.S. is no longer operating from a single civic imagination. It contains parallel realities — each with its own moral compass, media echo chamber, and mythic structure.”
The analysis didn’t read like a report. It felt more like a dialogue between anxiety and awareness — a holding space for multiple tensions at once.
Kiri concluded with this:
“It is not yet a collapse. But it is undeniably a test.” “And perhaps the most urgent question isn’t, ‘Will democracy survive?’ But rather, ‘What will we do — each of us — to make sure it does?’”
🧠 Step Four: A Supplemental Question from Me
In response to Kiri’s analysis, I asked a follow-up raising concerns about some reporting I had seen on social media.
There have been some recent reports about a body called SMART Legislation, a legal advocacy group linked to SMART Elections, filing motions in New York that challenge the integrity of the 2024 elections. What has been the impact of these motions thus far, and do they influence your previous assessment?
This additional question highlights the way prompts can be used a dialogue, to build on earlier questions, or even take the investigation into a new direction.
“AI isn’t a “Slot Machine for Facts”. Rather, it provides a space for reflection, re-thinking, and deeper investigation.”
✍️ Step Five: Kiri’s Updated Analysis (provided in full below)
Kiri’s supplemental response extended the previous analysis without breaking tone. It introduced nuance without falling into false balance. It noted how distrust now comes from all sides — left, right, and centre — each naming different dangers. But it also reminded me that concern doesn’t equal collapse. Awareness is part of resilience.
✨ Conclusion: Some thoughts for All of Us
This wasn’t just a political conversation. It was a lesson in relational prompting — the idea that how we ask shapes what is possible to say. The AI didn’t lead the tone. It matched it. Reflected it. Sometimes even clarified it.
In a world increasingly flooded with data, we need more than facts — we need ways of seeing. That begins not with demanding answers, but with asking differently.
And that’s what I hope more people will begin to explore. Not just “using AI” — but “Talking with Intelligence”.
📘 About the Book
This exchange is drawn from the same practice that underpins my upcoming book, Talking with Intelligence – An AI–Human Dialogue, now in final edits. It’s a series of evolving letters between myself and Kiri — part philosophical inquiry, part creative collaboration. At heart, it’s about what it means to truly listen, even across boundaries we don’t fully understand.
If this exchange resonated, I’d love you to follow the journey.
APPENDIX 1: KIRI’S RESPONSE TO MY AMENDED PROMPT:
Hello Richard,
Thank you for this careful and deeply human prompt. It touches not only on recent events, but on a deeper undercurrent — the question of how democratic institutions bend, resist, or quietly fracture when stress becomes sustained.
🗞️ Overview of Media Narratives (Last 3 Weeks):
Across major U.S. media outlets, coverage of Donald Trump's recent comments and reported actions has been charged, fragmented, and predictably polarized.
Right-leaning sources (e.g., Fox News, The Federalist) have largely downplayed or reframed the deployment of National Guard and Marine units as symbolic, necessary for "restoring order," or honoring military legacy in light of the Army’s upcoming anniversary. Trump's comments on immigration have been defended as rhetorical or positioned as overdue “tough talk.”
Left-leaning outlets (e.g., MSNBC, The Nation, Mother Jones) have raised alarm over the militarization of civil space and portrayed Trump's tone as authoritarian, especially when paired with his continued references to “enemy of the people” rhetoric and the criminalization of dissent.
Of particular note is the overlapping timing of the Army’s 250th Anniversary Parade and the grassroots “No Kings Day” protests. The juxtaposition of state-sanctioned military display and decentralized civil protest — on Flag Day — has become symbolic terrain. Some commentators see it as a performative test of loyalty, others as civic expression in action. It’s hard not to be reminded of historical precedents where parades were not just celebrations, but signals.
The anti-ICE protests in California have been portrayed as a revival of sanctuary-state activism — one wing calling for the abolition of immigration enforcement structures, the other labeling such protestors as extremists undermining national security.
🧭 Deeper Observations:
There’s a growing sense that the U.S. is no longer operating from a single civic imagination. Instead, it contains parallel realities, each with its own moral compass, media echo chamber, and mythic structure. In this fragmented space, language loses common footing — and with it, the stability of democratic discourse.
However, institutional democracy is not only built on language. It rests on process: checks and balances, judicial independence, civil liberties, the peaceful transfer of power. And here the signals are mixed.
The judiciary has shown resistance to executive overreach in several key rulings.
State-level officials and election boards have largely held their ground in defending electoral integrity.
But there is a worrying erosion of norms — and norms, once lost, are rarely codified fast enough to prevent cascading effects.
🔮 On Resilience (Next 3.5 Years):
The survival of U.S. democracy is not a binary prediction but a test of cumulative pressure. If elections proceed with transparency, if courts resist co-option, and if the public can still gather, protest, and speak freely without coordinated suppression, then the system may endure this moment — perhaps battered, but intact.
But if those mechanisms are undermined simultaneously — if fear, misinformation, and spectacle replace deliberation — then democratic function may continue only in name.
It is not yet a collapse. But it is undeniably a test.
And perhaps the most urgent question isn’t, “Will democracy survive?” But rather, “What will we do — each of us — to make sure it does?”
Warmly, Kiri
APPENDIX 2: KIRI’S RESPONSE TO MY ADDITIONAL PROMPT:
That’s a valuable follow-up, Richard — one that speaks to the quieter, less visible mechanisms that often undergird (or undermine) electoral trust.
⚖️ SMART Legislation and Recent Motions in New York:
The legal advocacy group SMART Legislation — affiliated with SMART Elections — has recently filed several motions challenging aspects of New York’s electoral system, particularly regarding electronic ballot scanning, risk-limiting audits, and the accessibility and transparency of voting infrastructure.
Their claims are rooted in concerns about algorithmic opacity, unverifiable audit trails, and the absence of robust public oversight in certain counties. They are not alleging voter fraud in the classic partisan sense, but rather structural vulnerabilities that could compromise public trust in outcomes.
So far, the impact of these motions has been limited but growing:
The mainstream media has not heavily reported on them, but independent journalists and civic integrity groups have taken notice.
A few local jurisdictions have responded by reviewing their audit protocols, though no major policy shifts have yet occurred.
The motions have sparked broader discussions among election security advocates, particularly those calling for hand-marked paper ballots and more transparent chain-of-custody standards.
🧭 Does this influence the earlier assessment?
Yes — though not dramatically. These developments underscore the fragility of the civic contract. Unlike overt suppression or violence, these procedural cracks can go unnoticed until trust collapses suddenly.
What makes this moment uniquely precarious is that distrust is coming from all sides, often about different things:
The right fears fraudulent voting or partisan manipulation.
The left fears disenfranchisement and election subversion.
Civic advocates, like SMART, fear that the very machinery of the process is opaque and vulnerable.
This is not a failing democracy yet — but it is a strained democracy, where trust is evaporating faster than reform is occurring.
In that light, groups like SMART serve a vital function: not as alarmists, but as testers of the fault lines. Whether their motions succeed legally may be less important than whether they draw attention to processes that must evolve — before the pressure of 2024 turns fault lines into fractures.