6 lessons from going live with Oprah

6 lessons from going live with Oprah

I was sitting at my computer willing the words to come.

I’m creating a workbook/guide for independent professionals and the last 10% of it has proved by far the hardest. 

Midway through my mid-distance stare into nothing in particular, my phone rang.

It was someone I’d spoken to only once before, and was one of those serendipitous moments that maybe only ever happens in New York City.

A spare ticket to see Oprah Winfrey’s new show.

In Times Square.


In just under two hours.

Did I want to come along?

To use Derek Sivers’ parlance – this one had to be a ‘Hell Yeah’.

An hour and forty later and I’m outside the Playstation Theater; cameras flashing, breakdancers breaking, protest groups protesting. Just a regular Tuesday afternoon in Manhattan.

I have to admit, the last time I watched a full episode of Oprah’s was nearly 20 years ago, on a slow midweek afternoon the summer before I went to university.

But despite being out of the loop, I knew that she still occupied a place very few do. Those with a truly one name personal brand. 

Madonna, Kanye, Trump, Lebron. Howard.


Here’s what I learned from an afternoon with Oprah and a series of interviews for her Super Soul Conversations series.

Welcome to Oprah Land
Entrance to the Playstation Theater

Stay unrehearsed, trust in the edit

The celebrity guests were a lot less polished than I expected.

There were some long pauses, mangled and rephrased answers, various ‘ums’ and ‘errs’ (Just like real people!)

The show didn’t feel overly rehearsed but I felt there was an implicit trust in the editing process – not to audio airbrush every finest detail, but that the multiple angles would easily enable the conversation to flow in a natural but still polished way.

Give credit to the edit, and keep the conversation natural with a gentle sheen of polish.

Don’t kill the vibe

On a similar note, even when a guest stumbled or something didn’t quite feel right, there was never a call to pause recording. And the chances of hearing the words ‘don’t worry, we’ll cut that part’ felt slim to zero.

Why? It kills the vibe, it ends the magic, we need to suspend our disbelief, and the show must go on.

This is especially true for a live studio audience, but holding the vibe still matters if it’s just two of you in a pokey podcasting room. Get it right and wonderful things can happen. Lose it and the conversation falls flat.

Interruptions are ok

As a counter to vibe killing, there are interruptions. Oprah will happily talk right over the top of a guest if need be.

This takes confidence, skill and also restraint. It’s easy to either fawn over a guest, step off and let them meander, or to go the other way and trample over their narrative.

A well-placed interjection or challenge can be hugely valuable in a conversation, and you can even change vibe – just don’t kill it.

Know the rules of the game

Oprah’s place feels like a club. 

While we’re all made to feel part of the experience, like a lot of other clubs this one still has a hierarchy. You know who’s running things.

This club is built on a sense of aspiration – we can all become better versions of ourselves. 

There’s also the dichotomy of her staying ‘real’ while also regularly making it clear who she now is in the world, the wealth she has, and the power she holds. Sometimes the tongue in cheek feeling comes through, other times the masks slips. 

Oprah doesn’t fawn over guests, but she will stick very close to the narrative and stay right on brand – even if that means some pretty obvious inconsistencies in how different guests are treated.

But whatever you think – it’s her club, her rules. If you don’t like it, go somewhere else.

Batch it

If you’re putting on a near full-day show in Times Square and people are paying upwards of $200 a pop, it needs to be legit. And being legit costs.

The only sensible way to make it work is to batch it and get as much value as possible from the experience. 5 guests, not 1. 45-minute interviews, not 15. Concession stand open throughout.

But even if you’re not Oprah (whaddya mean you’re not?!) – this still makes sense.

Editing podcasts one at a time is laborious. Getting studio space is time-consuming. If you’re going live, make it an event.

Don’t under estimate the by-products

Pre-show the OWN General Manager appeared on stage to tell us about all the channels the content would be appearing on. Not just the whole show, but various elements within it. I lost count halfway through. 

Whether or not you’ve got a sizeable audience and distribution channels, the takeaway here is to re-use, re-purpose, remix.

Discover the by-products you can create, then rinse and repeat.

The body of work keeps building, and the web of reference points keep growing.

We’re in a multi-channel world – batches and by-products are the way to go.

Those are 6 lessons from me spending a couple of hours onboard the Oprah express. 

There’s no doubt plenty more to learn, and a gargantuan body of her work to explore, but hopefully you grabbed a few insights into how to hold conversations, hold space, build your tribe, and batch it.

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