What Happens When AI Agrees With You Too Much
This week’s roundup: Reddit’s quiet takeover (1B people use it every single month?!), how AI sycophancy messes with your judgment, and what workplace icks really mean.
We’re back with my biweekly roundup of what I’ve been reading, listening to, and quietly obsessing over. I curate these letters because it’s fun; the content that I include here makes me think or teaches me something new and I hope it does the same for you too.
This week’s edition features articles from Vogue, WSJ, Fast Company, and NY Magazine. It also features a link to a podcast I was a guest on this week!
Total read time: <8 mins.
My Open Tabs
→ THE ARTICLES I CAN’T STOP THINKING ABOUT THIS WEEK
Open Tab #1: Did You Know That ChatGPT is Likely To Defer To Your POV? (WSJ)
Personally, I think AI sycophancy is one of the most compelling arguments against over-reliance on tools like ChatGPT, specifically for decision making at work. If you haven’t heard of this term, it’s the tendency of AI systems, particularly large language models, to excessively agree with or flatter users, even if it means sacrificing accuracy or objectivity. Yikes! There are some really great uses for AI, but this phenomenon is a major red flag for me when the use case is something like navigating workplace relationships—especially if you’re engaging with it in the heat of the moment.
I loved this episode (starts at 5:30 mark). It’s a quick 7 min listen. This is the part that stopped me in my tracks:
“It might seem like the AI is just being polite or easy to talk to, but our research shows that this can lead to real harm. Instead of challenging us or asking clarifying questions, the AI just ends up reinforcing our biases. Imagine a doctor describing a patient's symptoms and the AI just confirms the diagnosis without exploring alternatives, or a lawyer inputting potentially incorrect facts or biased facts and the AI just ends up reinforcing those in the decision making process. Because AI sounds smart, we often trust it without questioning it.”
This topic is really important to me, I will likely dedicate Monday’s newsletter to tips for navigating it and avoiding common pitfalls. I use AI too, it’s the world we live in. But when it agrees with me a little too quickly, I get suspicious 🤨
Open Tab #2: How To Listen To Opinions You Don’t Want To Hear (Fast Company)
Okay, so…maybe you’re ready for more push/pull in your conversations after learning about AI sycophancy? Well, I’ve got something useful for ya!
Look - I am strong willed, which has generally served me well. But on the flip side, it means that I am pretty bad at listening to opinions that are not aligned with my own. And on top of that, I take things personally. At least I’m self aware!
So when I stumbled upon this article, I felt mildly attacked—but I read it anyway. And honestly? It’s good. The part that is staying with me is how much confidence it takes to integrate opposing viewpoints into your own recommendations, POV, or assumptions. It covers why humans are resistant to differing opinions in general (whew, not just me!). Most importantly, it offers three concrete steps to get better at this.
Related, I saw Bad Shabbos this week and there’s a pretty funny bit about non-violent communication in it that reminded me of one of the recommendations in this piece.
Open Tab #3: Is There Anything to Be Done About “the Ick“? (Vogue)
I think about icks a lot. I personally don’t think they’re limited to dating. My hot take? They absolutely show up in the workplace too—but we mislabel them as legitimate grievances when, in reality, they’re just icks. And those shouldn’t be treated like HR-level offenses.
To be fair, they really do trigger what Vogue perfectly called a “full body ugh”. That teammate that constantly cc’s your manager (specifically the kind that does it not because they’re an op, but because that’s just how they’ve learned to operate in the workplace) or that colleague that calls you a nickname or shortens your name unauthorized. Workplace icks become risky when you start making character judgments as a result of them. If it goes unchecked, it can limit your ability to work with the “offenders” effectively. Luckily, there’s tips in the article about how to come back from the ick that I think are broadly applicable to work too.
I’m sitting on a newsletter draft about professional icks that’s not quite ready for prime time, but it’s coming. Until then, this article is a great primer.
Open Tab #4: Can Reddit Survive AI? I Think Yes. (New York Magazine)
Until fairly recently (2023ish), I hadn’t thought much about Reddit unless it was in relation to Alexis Ohanian and Serena Williams lol. So if you’re like me this may feel like a niche pick, but I found myself surprised by some of the details in this article. Reddit seems to be having quite the moment right now. I think the company’s resurgence signals how some people are reacting to AI and algorithmic content served up on social media.
According to NY Mag, in 2023, Reddit had around 60 million unique visitors a day. Not too shabby. But here’s where it gets interesting, just 2 years later they’re seeing 108 million visitors a day, 400 million a week, and well over a billion people are using it every month?! This blew me away. Those numbers mean something financially too. Reddit CEO Steven Huffman’s shares are now worth over $600 million, their employee count has grown 30x in the past 10 years, and the company is finally profitable.
I can’t believe the platform has been around for 20 years and has managed to steer clear of influencer culture. Although, they’re largely still reliant on the hard work of (unpaid) volunteer moderators (note: some have received stock options). At some point in recent years, I noticed that my google searches were returning Reddit threads and I became an occasional Reddit user myself.
That was by design.
If you care, my favorite subreddits are NYCbitcheswithtaste (lol it’s real and has 106k members), 90DayFiance (912k users!), and sexandthecity (surprisingly only 87k users). When I find myself gravitating to Reddit, it’s because I’m seeking real recommendations (that feel authentic and vetted) or I’m looking for a funny/snarky take on something I’ve watched (movies, TV, etc).
They’ve come quite a long way since the Ellen Pao drama. Wild.
My Newsletter & Podcast Features
→ IN CASE YOU MISSED IT: THIS WEEK’S NEWSLETTER
If You’re Contemplating A Career Change, Read This First
This week’s newsletter has everything: Drama! Suspense! Triumph! And of course, the insights that you all have come to know and love me for (humble brag— but not really). I’ve spent a lot of time in my career thinking about transitions. Some of my pivots were smooth—natural, even. Others? Messy, emotional, full of second-guessing. I’ve lived both. And I’ve supported countless clients, friends, and colleagues navigating the same uncertain terrain.
So if you’re contemplating a career change and it feels scary or hard, just know this: it’s not just you.
Now go on and read my post for a much needed boost.
→ IN CASE YOU MISSED IT: NEW PODCAST
My Framework for Excelling at Leadership (The Confidence Lounge)
I joined Elyse on her podcast to talk about the 3 traits top leaders have in common (+ the exact framework I use with clients) and why knowing the difference between a high-achieving leader and a rising leader actually matters.
We also got into delegation, specifically what the best delegators do differently and how the best delegators set their teams up for success without micromanaging. It’s packed with so much insight, I honestly don’t know how we covered it all in 45 mins.
And if you’re like, “Wait! I didn’t know you did podcasts!?”—surprise! I started guesting on them this year and have done about 15 so far. I love talking about leadership. If you have a podcast or are connected with someone who does, give me a shout.
That’s it from me this week. May your wins be major and your icks be minor ✌🏾
Also, if you enjoyed this newsletter, like and/or comment on this post.
—Ashley
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Omg Ellen Pao! That name took me back