I heard they have a new pill for treating skepticism.
I’m not buying it…
Hey, I’m Caleb. Welcome—or welcome back—to my monthly column, Breaking Trail, where we kick things off with a dad joke. Just like this, just because.
“Question everything. Learn something. Answer nothing.”
That quote’s attributed to the ancient Greek playwright Euripides. While it’s one that I adore, it seemingly contradicts how we’re expected to act in modern life.
I’ve become immensely fascinated with the kinds of questions we’re asking these days and the types of answers we find trustworthy. As the parent of a newly verbal toddler, this is also THE prevailing part of my life. Literally everything is met with a “what, where, or why” – as it should be. As a parent I am expected to have an answer to every single one of her questions. Luckily for me, they’re all fairly simple questions… or ones I can easily answer; depending on the level of existentialism involved. Sometimes I have to remind myself to provide an answer that a 3-year-old can comprehend.
Meanwhile, when taking off my “dad hat” and reemerging into modern society, it seems everyone has a wildly different relationship with receiving both questions and answers. In particular, I think about it in the following three buckets:
And before we go any further, I want to call out the AI of it all. The tech-bro “powers that be” have dictated our world now revolve around AI; because they spent all their money building it (when none of us asked for it). It’s THE answer… no, wait… it HAS all the answers. Right? Possibly. But only if we know how to ask the right questions.
Yet, do we even trust the answers we get to the questions we ask…?
This seems to be one of the biggest points of friction in our modern society. My friends and I are known to bemoan the “death of the bar debate.” Or in other words, we nostalgically pine for an era in which we’d have conversations that required guessing the answers to things and offering our perspectives in lieu of asking Google. Now, we’ve taken away the Google search—with its pages of answers to choose from—and traded it for one neatly-packaged answer from our preferred gen AI chatbot.
“Fake it til you make it.” This adage has been repeated more times than I can count by random strangers, and trusted confidants, when responding to questions about finding your way in a new environment or a new job. The kicker? It works. If you can speak the jargon and look the part, odds are you can “make it” by “faking it.” Underlying this, is the assumption that most of us will actually learn the subject or become experts once we’ve “made it.”
Roughly 70% of people feel imposter syndrome in their professional lives. This validates a shared, albeit shunned, level of persistent insecurity. If only 30% percent of the population feels like they belong in their role, then 70% are going to be sensitive to “proving” themselves while harboring a fear of being ousted as a fake. In my non-professional opinion, this is one of the largest reasons so many of us develop an adverse reaction to being questioned. We don’t want anyone to doubt whether or not we have the answers we’re supposed to have because then we’d feel exposed.
I believe that this phenomenon is the root of why so many people have complicated relationships with being questioned. We’re experts, right? You should just trust us. Furthermore, this charts a path of “bad faith” when it comes to asking questions and getting trustworthy answers.
If we’re insecure - questions expose fear.
If we’re secure - questions expose curiosity.
I recall once speaking to a team of junior employees, after a client meeting, where they referred to the client’s closing questions as an “interrogation.” That threw me. From my perspective, the client had every right to ask questions, and all of them were to ensure they understood our thought processes and rationale (for which, they were paying us a sizable amount). The idea that fielding a string of clarifying questions might be analogous to getting tortured for accurate answers is mind-boggling to me. I mean… right? Is this just part of the larger trend of military cosplay within corporate settings?
Don’t get me started.
In my first marketing agency job, my boss gave me the two most important pieces of professional advice that I’ve ever received: (1) always be able to tie your efforts back to the money and (2) get comfortable saying “I don’t know.”
The goal for a client presentation is, in my opinion, to address everything they expect and to be able to anticipate and respond to their questions and concerns. With all of the preparation that goes into making that happen, you may still not have every answer readily available. This is fine.
Nobody expects anyone to have all of the answers.
Seriously.
Once more for the people in the back…
NOBODY EXPECTS ANYONE TO HAVE ALL THE ANSWERS.
Okay, now then. From what I’ve experienced, you’ll actually form stronger relationships with people by being honest and admitting when you don’t know a particular answer. The important thing is to look into it and get back to them. People ultimately just want to be heard and understood. We ask questions for a wide variety of reasons and only one of those reasons is to actually get a new answer. We might ask questions to ensure the group’s comprehension. Maybe we’ll ask questions to reconcile a topic that’s been left to fester for too long. A lot of questions even get asked rhetorically, but we ask anyway in the hope that someone else will say they don’t know the answer, either.
These days, our traditional question and answer choreography has changed. Generative AI is supposedly the great “answer machine.” It’s trained on the collective human knowledge available on the internet. I want to make that part extremely clear — it is trained on human knowledge. Like, everything we’ve ever put online. It cannot fathom the way a scent on the wind might alert you to the coming rain. It does not understand what it means to feel something because it cannot comprehend truly human experiences. What it does understand is limited to what we have codified and placed within the confines of the digital systems to which it has access. With that elaborate soap-box-caveat complete, we can address what gen AI really is here, with regard to asking clarifying questions and receiving trustworthy answers.
It’s a tool.
AI is a tool for providing answers and solutions to problems that are presented to it through contextualized prompts; aka structured and explicitly defined questions and requests. We ask it for output and it provides some. For many, it is essentially the next evolution of googling something. My hope for this new shiny tool is that we don’t lose sight of how important it is to ask good questions. That’s what is actually important. Additionally, we need to question the answers we’re given and dig deeper.
Think critically.
Where does trust come from?? This is the crux. Social media, AI slop, expert articles, research studies bankrolled by corporations looking for a particular answer, click-driven news, armchair experts, etc.
The modern individual’s life is fraught with stimuli that compete for attention at every waking moment. Choosing what to engage with is enough of an effort that parsing which stuff to trust and which to disregard can seem like a herculean task. This is why AI chatbots promising validated answers are so monumentally appealing. We can outsource the heavy cognitive load of forming an opinion on something—anything—by simply asking a question and blindly trusting a software platform to give us the right answer.
The massive red flag for this though, is that it’s trained on superfluous tidbits from across the internet. I remember hearing every single adult in my life say “don’t believe everything you see online”. Now those same adults won’t stop telling me about the article they saw on Facebook. This paradox of digital illiteracy is astounding to me. It feels like we all know when we shouldn’t trust something but, still, we’re ignoring that gut-feeling because we’re perpetually being sold on its trustworthiness. That’s despite the well-documented hallucinations and pre-programmed user-bias Gen AI is known to possess. It is a subscription-based service that wants to keep you as satisfied a user as possible.
None of this is inherently a bad thing, either; Gen AI isn’t the big bad wolf. But it’s also not our salvation, either. It is a tool. We just need to remember to take what it gives us with “a grain of salt.”
Human survival is built on asking and answering questions. To be curious is to be human. Be that as it may, when we fail to question the answers we’re given, we corrupt our ability to develop trust. Both in one another and in the everyday tools we use.
Get curious. Don’t take everything at face value. Dive deeper, explore more, ask follow-ups. Because you really are right to push back on that.
I don’t want my kids to stop asking “what, where, or why?”
Do you?
Cheers,
Caleb
P.S. In addition to opening this column each month with a dad joke, I’ll be closing them with a musical coda—songs and lyrics I feel touch on the theme of the essay.
What’s Up by 4 Non Blondes
Key, relevant lyrics:
“I wake in the morning and I step outside, and I take a deep breath and I get real high, and I scream from the top of my lungs ‘What's going on?’”