043: 🖼 Dashboard Envy

043: 🖼 Dashboard Envy


🧠 Oprah’s Interview Master Class + 👉 Wavelength - a social guessing game

What’s the good word?

This is the 43rd edition of Making Connections, where we take a random (illustrated) walk down tech, fitness, product thinking, org design, nerd culture, persuasion, and behavior change.

Quick shoutout: My wife’s art, which celebrates Women in STEM, was featured on @instagram and @design and I’m so proud!

Like what you see? Why not bring someone to the party?

🖼 Dashboard Envy

I think this comic illustrates something that many modern knowledge workers struggle with. When you don’t know what’s going on with your project / operations / company, you want to know everything. But really only a few things matter. Getting to those handful of critical metrics can a be a long journey.

🧠 Oprah’s Interview Master Class

An average of 17.1 million viewers watched the two-hour telecast from 8 to 10 p.m. on both coasts, according to Nielsen. The figure is well in the range of the network’s expectations. CBS paid roughly $8 million for the rights to the program and sold 30-second commercials at a rate of $325,000.

Oprah beat Dian Sawyer’s exclusive with Caitlyn Jenner coming out as transgender in 2015 (16.9M) but nothing will touch her interview with Michael Jackson in 1993 which drew a whopping 63 million people, which translates to 56% of all households (the literal definition of mass media).

Appointment viewing outside of sporting events has nearly become a relic in recent years, to the point where younger viewers of Winfrey’s show commented on social media about having to sit through commercials.

Kinda funny how much things have changed. TV used to have mandatory commercials before Netflix. (And you couldn’t binge the whole series in a weekend! Harumph.) Also a reminder that all free media monetizes via ads. Including Oprah interviews!

In the 21st century, Oprah Winfrey has become the latest in a very specific line of American TV personalities: the interviewer celebrities go to when they have some Shit to Say …Tom Cruise hopped on Oprah’s couch (to prove he was likable!) in 2005. Whitney Houston told her everything in 2009. Lance Armstrong came clean to her in 2013. And she arguably gave Barack Obama a huge boost in the 2008 Democratic primary, after she interviewed him on her talk show in 2006 and endorsed him before he even announced his candidacy … The draw of the Meghan and Harry interview was the royals, for sure, but Oprah’s presence added both legitimacy and the sense that something big would happen.

There are so many ways to carve a niche out for yourself and its interesting to see how Oprah has amassed a singular position for herself as a trusted, authoritative, and yet empathetic interviewer for leading figures.

“She asks the questions that you as a viewer really want, and she does it in a way that’s so disarming, and it feels like you’re on the journey with her,” said Pat Fili-Krushel, the former ABC network president and NBCUniversal News Group chairwoman. “Journalists aren’t supposed to show how they’re feeling — and she’s not really a journalist, though she definitely is one of the best interviewers. … And because of that, she can emote.”

It’s interesting to note how Oprah uses warmth and empathy both to put her interviewers at ease but also to persistently get to the questions she knows her audience wants answers to.

Oprah excels at creating a friendly, warm atmosphere in which famous people feel as though they can share their innermost thoughts. It’s not clear how much the Meghan and Harry interview happened roughly as presented on television, or if it was edited to create a more coherent progression of its subjects’ thoughts. (Obviously, all interviews are edited to remove filler and false starts.) But Oprah’s genius lies less in the overall scope of an interview (though she’s also good at that) and more in the micromanagement of individual moments. An interview subject can say something shocking, and Oprah is skilled at guiding the exchange so that it plays out to its fullest effect, while giving the subject space to process their thoughts and decide whether they want to share more.

The tweet below shows the moment they’re talking about - drawing out the story of the Royal Family’s concerns of Meghan’s son’s complexion. When you’ve been a talk show host for 25 years, you’ve had A LOT of practice.

Plus, Fili-Krushel said, viewers are so accustomed to seeing her on TV from her years on her talk show that even if they don’t realize it, there is an added level of relatability that automatically makes the interview more intriguing.

“When someone is on TV in your living room five days a week, you think you really know this person,” she said. “You can’t underestimate how accessible that makes her.”

I like the idea of Oprah being the original creator / influencer / streamer. Her show puts her in your home everyday. A decent segment of the country has a parasocial relationship with Oprah.

I don’t know that I would want Oprah pressing President Joe Biden on his policy proposals, but she’s the right choice for a moment when a very famous person has a very tricky story to tell. And more importantly, her status, her skill, and her long history of being great on television made her maybe the only person in the world who could have risen to Meghan and Harry’s challenge.

The only drawback for Oprah is maybe her willingness to trust her interviewee’s answers. Though I’m sure after the James Frey debacle, her team did more vetting on key facts surrounding anyone she talks to.

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👉 Wavelength - a social guessing game

Looking for a new casual game you can play IRL or online with friends? I’ve been enjoying Wavelength. Your friends pick a spot on a spectrum (underrated actor vs overrated actor) based on a clue you give them (“Heath Ledger”).

Officially, it exists only as a physical board game. Unofficially, it has been rendered as a web app that supports 2 person free play, 2 person cooperative, and teams (4+ people). I’ve played it with coworkers, friends, and my wife and it’s a great way to see where our opinions align and where they differ, while challenging yourself to be creative.

Welp, that’s it for this week. Hope you got to enjoy some good weather if you’re in NYC (where I am) because it’s about to get cold again soon. At least we get Daylight Savings time back!


👨🏻‍💻 About Me

Jason Shen is an entrepreneur and business leader passionate about technology and human resilience. His past startups have reimagined transportation, recruiting, and gaming; backed by notable investors at Y Combinator, Techstars, and Amazon. As an operator, he’s built products and led teams at companies like Facebook, Etsy, and the Smithsonian.

Jason has written about productivity, resilience as well as the future of work in publications like Fast Company, VOX, TechCrunch and has spoken at events at TED, Google and The White House where his ideas have reached millions. He lives in Brooklyn with his wife, two kettlebells, and many piles of books.