✊ "No one's ever asked me that before"

Published 11 days ago • 9 min read

This issue is presented by:
A Step-By-Step Playbook to Your First 500 Subscribers

1,749 WORDS | READ TIME: 6.6 MIN

Happy Wednesday friends,

Quick win to report:

For eight months, I've been coming to the same coffee shop to write every morning.

All the baristas know me by name, and I chat with them a little bit every day.

But out of the nine baristas, I only knew one of their names.

Another one told me his name months ago but by the next day, I'd forgotten it.

At this point, eight months—and many conversations in—it felt too awkward to ask for everyone's names.

And so I faced a choice:

Brave the awkwardness. Or find a new coffee shop.

It's too bad, I really loved this coffee shop.

Fortunately, this morning, I had an idea:

Check their Instagram account to see if they tag the baristas in the photos of them working.

Turns out they do.

💪

Alright, let's keep going with the next installment of our guide to creating standout podcast interviews.

As a reminder, you can find all the past installments of the guide here.

When thinking about interviews, hosts tend to focus the majority of their attention on guest outreach, research, and the questions themselves.

What often gets lost in the mix, however, is the guest experience.

And yet, the experience you create for a guest has an extraordinary impact on the depth and quality of the interview.

Picture two scenarios:

  1. A guest receives a generic templated interview pitch about a generic topic the guest has spoken about on 13 other (generic) podcasts.

    They sign up for the interview and are then presented by a series of automated, de-personalized onboarding steps.

    At this point, they can tell they’re just another warm body to feed into the host’s content machine.
  2. The guest receives what could only be a 100% personalized email pitching them to come on the show to talk about a topic closely related to them and their work... But it's from a totally unique angle they’ve never discussed before.

    Already, it’s clear the host has done some research, is familiar with them and their work, and sees them as a unique and fascinating human with something unique to share.

The guest might agree to both pitches, it’s free exposure after all.

But which experience do you think will result in the better interview?

If the goal is intimate, engaging interviews that connect the audience with the guest and uncover novel anecdotes and insights, connecting with your guests is every bit as important as the questions you ask them.

And as we can already see, that connection begins well before the interview starts.

Nailing Your First Impression

If you were trying to give your guests the worst possible first impression, here's a good way to do it.

Send a cold pitch with a generic template email (yes, everyone can tell it’s a template no matter how much “tweaking” you’ve done), asking them to speak about an obvious topic they’re widely known for and have been interviewed on dozens of times before.

At this point, everything about this screams, “I don’t care about you enough to do any real research or come up with a unique angle that you haven’t already covered before.”

Again, they might agree to the interview, but there's zero chance they're going to share the episode.

Here’s a better approach.

Start by following the guest on social media and reply to their posts regularly. Even better, share their posts with your audience along with some thoughtful commentary.

If they have a newsletter subscribe to it. Then reply to their emails every so often.

Keep this up until you're familiar enough with their work well enough to know what they talk about regularly (ie. everything you want to avoid or briefly summarize) and—more importantly—what they don’t… but would be interesting to hear their perspective on.

Then—and only then—is the time to pitch.

By this point, you should have had several interactions with them, meaning they’ll already have some recognition of you as someone who knows and appreciates your work.

Which means they’ll almost certainly open and read your pitch email.

Paired with an original interview angle, you’ve almost certainly got their attention at this point, and perhaps even their excitement.

But the real guest experience is just beginning.

Communicating Legitimacy

Once a guest has received your pitch, their next step will be to click through to your show.

Like any potential listener, the first thing a potential guest will see is your show’s packaging, including the cover art, show title, show description, and past topics.

Within 3 seconds of seeing these elements, the potential guest has likely already made up their mind about whether this show is the type of show they would guest on, based on the perceived quality, legitimacy, and audience of the show.

If the initial packaging passes the test, they may dig further, using past guests, production quality, and quality of questioning in past interviews to decide whether the show is worth their time.

Much like a new listener, this decision-making is happening entirely subconsciously, based on the limited amount of information your packaging provides them.

This is one more reason why the value of investing in clear, legitimate, professional packaging can’t be overstated.

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Guest Onboarding

Once they’ve agreed to come onto your show, great hosts create an onboarding experience designed to set the guest’s expectations of quality, thoughtfulness, and intention.

In some cases, this might be achieved through a live 15 or 30-minute pre-interview connection call to get to know the guest and chat over logistics.

But it can also be done asynchronously.

Regardless of your process, your goal at every guest touchpoint is simple:

Communicate that you value your guest as an individual and that you are putting in the work to make this interview the best it can be.

Maybe you send each guest a personalized video (and bullet point text summary) explaining the show format, audience, topics you’d like to explore, and anything else they should know.

Another option is to get their input on the construction of the episode, by asking:

  • What they always get asked about that isn’t worth covering in more depth
  • What never gets asked about that they think matters
  • If there are any new ideas they’re working on that might be fun to dig into and explore
  • If there are any stories or anecdotes that always do well
  • What their favourite existing interview was and why
  • What would make this interview one that they would be excited to share

Note that your goal is absolutely not to get the guest to outline your episode for you.

Nothing signals host laziness more than an onboarding form asking the guest to fill out all the questions for you to ask them.

Sure, these types of shows are easy to create, but there’s nothing appealing about them from a listener perspective.

What’s more, this approach send a clear signal to both the guests and your listeners that you are actively trying to put in as little work as possible… which is not an attractive quality.

Instead, your goal is to combine your guest’s responses with your own research to end up somewhere novel and interesting to you, your guest, and your audience.

On Air Experience

A thoughtful pitch, legitimate packaging, and personalized (at least in part) onboarding set the stage for a great interview. But it will be capitalized on—or undermined—by the on-air experience your guest has with you.

Depending on the tone and topic of your show, the experience you create will differ.

An interview venturing into deep, perhaps uncomfortable emotional territory requires a very different guest experience compared to one revolving around high-energy tactical tips and takeaways.

With that in mind, the on-air environment to create may change from guest to guest, depending on your intended interview outcome.

Regardless of your destination, however, it’s essential to understand that guests take their cues from you.

Part of this may have already been established in the pre-interview info you sent them.

Part of it might come during the chat before officially starting the interview.

But most of it will come from how you show up on the show.

If you bring the energy and enthusiasm, your guest is more likely to match it.

If you make verbal mistakes and stumbles and laugh them off, your guest is more likely to feel comfortable doing the same.

If you ask surface-level questions, your guest is more likely to give surface-level answers.

If you share vulnerable stories your guest is more likely to do the same.

The list goes on, encompassing cursing, formality, humour, tone, depth, and more.

You set the tone and chart the course for the interview. Which means if there’s a destination you have in mind, you need to lead the guest there.

It’s worth noting that the tone, emotion, and energy you set for the interview can (and should) shift throughout the interview.

Great interviews are like music, rising and falling in rhythm and intensity.

Great interviewers are the conductors, intentionally modulating their tone, vocal inflection, pacing, and energy to guide the guest—and with them the interview—to their intended destination.

The result is dynamic interviews that not only pave the way for original insights and anecdotes the guest has never shared before—but also create a memorable experience they are vastly more likely to talk about and recommend.

It’s no secret that the gold standard for most interviewers is to have the guest respond to a question with “No one’s ever asked me that before!”

Perhaps a better goal is to have guests leaving the interview saying “No one’s ever given me an interview experience like that before.”

What Else Makes For Great Interviews (and the People Behind Them)?

Thanks so much to everyone who's already contributed thoughts, ideas, personal reflections, and resources for this series.

I'll be including all of these in a wrap up issue to close out the series as well as in the finished guide.

If you haven't already contributed, hit reply and let me know:

  • Who is one of your favourite interviewers and what do they do better than others?
  • What’s a common trait you see among great interviewers?
  • What's a bad trait or habit on the part of an interviewer that reduces the quality of an interview?
  • What makes for a great interview episode from a listener perspective?
  • What makes for a bad interview?

Be sure to include the name of your show so I can give you a backlink :)

Stay Scrappy,

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