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Ben Files

The Importance Of “Why?”

August 22, 2025 by Ben Files

By Ben Files ’25 (DCI Fellow)

Time of day is a fleeting thing in the digital age. Whether it be on social media, or even in person, the end goal of political discussions increasingly seems to be finding ways to one up or outsmart the person you disagree with, rather than trying to understand their perspective and find middle ground.

This trend manifests itself well in the rise of pop-up debates or tables, pioneered by internet stars Steven Crowder and Charlie Kirk. In theory, these pop-up debates are brilliant: they are framed as spaces for anyone to come and discuss any political topic with someone, including Crowder and Kirk themselves, who are incredibly knowledgeable on most political subjects. While these pop-up debates do produce some productive, thoughtful, deliberation, Crowder and Kirk are incentivized to share on social media the exact opposite.

In practice, the most famous clips from Crowder or Kirk are when they “punk” people whose views differ from them. In turn, this incentivizes hosts such as Crowder and Kirk to seek out less real deliberation, and more opportunity to defeat the person who takes the stand to talk to them. In some instances, these hosts will make a point of not answering certain questions to ensure that their position remains superior. This process is only beneficial for the hosts and their staff.

The brave participants who take the stand at these pop-ups often do not have a healthy deliberation. This result can discourage many participants from engaging in similarly framed events, which may indeed involve meaningful discourse across party lines. Further, the viewers gain little from these clips – sure, they may pick up some new talking points, but overall they learn that the point of political discussions is to win, because winning is fun.

But, deliberation isn’t about winning. For my deliberation project with the DCI, in which I collaborated with DCI Fellows Liam Mann and Jane McNeill, I wanted to implement on campus a pop-up deliberation table similar to those created by Crowder and Kirk. Crucially, though, I wanted to ensure that all participants felt comfortable being, in a way, vulnerable around complete strangers, able to talk about their political opinions without fear of being “punked.”

To do so, I decided to take an approach that was the opposite of the common practice of Crowder and Kirk. Instead of asking hard hitting follow-up questions, I would reply to participants’ responses with a simple “why?” This simple follow up is not rudely interrogative and does not attempt to steer the conversation off-course or throw off a participant’s train of thought. Rather, it is almost like an alley-oop, a way to extract more information in a non-hostile and respectful manner.

The use of “why?” was surprisingly effective in our conversations. Our pop-up discussion table featured 27 questions covering a wide range of topics, from politics to philosophy to pop culture. These questions were printed on note cards and folded, allowing participants to choose a question at random. Then, participants would answer the question on the card they had selected, and if their original answer was not sufficient, we would ask the famous “why” question.

Following conversations with approximately 35 participants, I have drawn two key takeaways regarding thoughtful deliberation and the use of a “why?” question. The first, broader trend I noticed was that participants were far more apprehensive and concise when answering political questions. Often, we needed to follow up with a “why?” question here, to better understand participants’ views on term limits or abortions, for example.

Second, I noticed that any apprehension around answering was compounded when participants approached us in groups, whether it be friends or other students. Again, the use of “why?” helped here, as participants were encouraged to explain their position more, which in turn (I think) put them more at ease. Across the board, our “why?” question gave participants the time and place to explain why they believe the things they do, an opportunity that is often not afforded to people in political discussions.

A simple “why?” is crucial for improving deliberation and political discourse because, quite simply, it gives people the time of day. When people feel comfortable expressing how they truly feel, real personal and societal growth is possible. It may not get the most internet clicks, but true understanding of our political differences is crucial to creating a better tomorrow.

Filed Under: Fellow Posts

When Can We Change our Mind? The “Flip-Flopping” Phenomenon

December 4, 2024 by Ben Files

The American political arena is full of questions post election of Donald Trump. What will Trump’s second term look like? How will American foreign policy shift? How could pollsters be so wrong – can we trust them anymore? Why did the Democrats, and Kamala Harris, come up short?  

A majority of the recent political buzz pertains to the last question: how did the Democrats fail so miserably? There is a lot of finger pointing going on, in attempts to explain the Democrats’ failure. Was it the inability to capture the Latino male vote, or the lack of open primaries, or even the lack of time Kamala had to prepare and properly campaign? Democratic voters may have been disillusioned by the dramatic shift in positions – also known as flip-flopping – that the party took this election cycle. Harris, keen to win over battleground states, walked back on several issues such as fracking and immigration in hopes of gaining support from moderate Republicans. This may have undermined her support among her base while not being sufficiently persuasive to swing voters. But critiques of flip-flopping are ubiquitous across the political spectrum. During Harris’ campaign, Trump lambasted her indecisiveness, which some might view as hypocritical considering Trump and his running mate J.D. Vance also changed their positions on particular issues as well.  

The left’s frustration (many young democrats feel their opinions were disregarded by the Harris campaign) with some of Kamala’s new policies is understandable. A shift towards matching any “flip-flopping” with hostility, though, is not positive for America or its democracy.  

Things have not always been this way, though. In a 2016 journal article titled, “The Flipside of Flip-Flopping: Leader Inconsistency, Citizen Preferences, and the War in Iraq” by Sarah E. Croco, a professor of Government and Politics at the University of Maryland, we gain crucial insights into why some “flips” are reacted to so negatively. Essentially, voters succumb to confirmation bias when deciding to support a flip or not. Croco states, “Citizens are rarely put off by a leader’s change of heart provided the politician’s switch moves him closer to their preferred policy” (253). In our case, if Kamala started with positions leaning center-right, and shifted her stances to be left-leaning, she would have seen an increase in support from Democrats, and they would therefore disregard her flip-flopping.  

Further, Croco claims that in the 2004 presidential election between George Bush and John Kerry, and the 2012 election between Mitt Romney and Barack Obama, there were high levels of flip-flopping among the candidates (referencing Kerry and Romney), but this had little effect on election day. In Kerry’s case, although he flip-flopped his position on US involvement in the War in Iraq, anti-war voters still would have preferred him to Bush (253). Additionally, Kerry only flip-flopped on one issue. Serial flip-floppers may fare even worse, as they are perceived as less credible when they flip on multiple positions. Further, serial flippers are even more prone to criticism than a politician who flips on just one issue (Croco, 255). In Kamala’s case, this “serial flip-flopping” may have been key to her demise.  

Croco’s article points out the stigma against flip-flopping, but does not provide any way to combat it. The DCI provides the foundation for combating anti-flip-flopping mindsets from the ground up. Through D Teams or forum events, the DCI makes a space for respectful, open minded conversation across partisan lines. One purpose of these discussions is for people to broaden their perspective on a certain issue, like DEI or campus protests (both of which were D Team topics for this semester), and maybe even change their opinions on an issue as a result of hearing another perspective.  

Should we not extend this sentiment to politicians? Politically-motivated serial flip-floppers may receive less sympathy from the public eye, but thoughtful single issue flippers should certainly be given more leeway. Just like us, they too can change their mind. The onus is on we the people, and our political leaders, to not propagate indiscriminate anti-flipping rhetoric, as anyone can – and should be allowed to – change their mind.   

Citations

Croco, Sarah. 2016. “The Flipside of Flip-Flopping: Leader Inconsistency, Citizen Preferences, and the War in Iraq.” Foreign Policy Analysis 12 (3). 

Filed Under: Blog Posts, Fellow Posts

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