The other day on Twitter a CEO asked who they should emulate as an interviewer for their new podcast.  There are so many different styles.

But these days, everyone is doing more content marketing, more podcasts, more digital events, and more.

We’ve done quite a few at SaaStr :).  7+ years of events.  10+ mega digitial events since 2020.  Almost 500 episodes of our podcast.

Personally, I don’t think I’m a great interviewer.  But — we do have the data, and my interviews are generally some of the most popular and downloaded.  So let me share what we and I’ve learned.  13 steps to making your interview, your podcast, etc. … at least better.  And probably even interesting:

1/ Interview your heroes.

This is the #1 hack.  If you interview folks you truly look up to, it’s so much easier.  When I do the SaaStr podcast myself, I try to just interview folks I’m generally deeply interested in.  Either the CEO or the startup.

2/ Do an hour of research

Folks just don’t do enough research for an interview.  I see this again and again in our digital events when top-tier speakers bring a moderator that just … doesn’t prepare enough.  Google is your friend here.  Spend an hour learning about 5 things about the speaker you personally find super interesting.  That’s a great start.

3/ Write out 5 great questions + 5 back-up questions

Now, take the top 5 things you learned from research and make 5 great questions to ask.  5 is plenty if you listen.  5 will consume a full 30 minutes, or even more.  I like to add 5 back-up questions too in case things go differently than expected.

4/ Listen, and ask +1 follow-up question on the great responses

Too many folks just doesn’t listen enough.  Go where it takes you.  Ask your team if you listen enough.  Listen more.

5/ Share questions ahead of time. Most will read them, some will add good ideas.

Here’s an example of the questions I used with the CEO of Klaviyo.  Some folks will add comments.  Some will add questions and things they want to talk about.  Some will just briefly review.  But every CEO I’ve send questions to has at least read them ahead of time.  It makes everything better.

6/ Make it super easy on the guest. Do it when it works for them.  Make it effortless.

I can’t tell you how many podcasts I’ve tentatively agreed to join as a guest, when the moderator then dumps me on an agency or EA that won’t schedule something at an easy time that works for me.  These ones in the end never happen.

Respect the speaker’s time and find a way that it always is convenient for them.  More than that — Make it Effortless for Your Interviewees.

7/ Make the ask yourself, as a superfan. Much higher chance they agree.

If you are having trouble getting top speakers to join your events, podcast, etc. — ask yourself.  Ask as a super fan.  Ask as an SDR.  Write literally the best email ever.  Everyone reads a great email.

8/ Some guests don’t care you don’t have 100k downloads. It’s OK.

Don’t worry that you aren’t a Top 10 podcast.  Some guests don’t care, especially if you have a new channel or a fresh voice.

9/ If not IRL: everyone knows how to use Zoom

There are a lot of great tools out there for podcasts, videos, events and more.  But here’s the thing.  They are all harder to use than Zoom. Default to Zoom.  It makes it effortless again for your interviewee.  It just works.

10/ For guests everyone has heard before — there are always stories and insights from them that folks haven’t. Find those stories.

Some of the worst content out there is from A+ speakers … that we’ve all heard 1000 times before.  Listen to a few sessions they’ve done — and avoid all those questions.  Find some fascinating veins others haven’t mined.

11/ Great audio is the most important. Great video helps, but is secondary. You can’t reuse content w/o great audio.

Everyone is excited about 1080p+ video these days and great backgrounds.  They are nice.  But what really matters is audio.  If you have amazing audio on both sides, you can reuse the content again and again.  If the audio is crummy, the content is hard to reuse.  And no one really wants to listen.

12/ Founders are 10x-20x more interesting than non-founder CEOs and execs. Non-founder CEOs are always just on message.

A lesson learned over the years.  Founders are just better to talk to.  They hide less, and are far more open and vulnerable.  They are never afraid to admit their mistakes.  A non-founder CEO can be OK, but they are a lot harder to make interesting.

13/ VCs want to interview their portfolio company CEOs. But portfolio co CEOs usually don’t want that — at all.

Don’t force guests to be interviewed by folks they don’t want to be interviewed by.  Especially their VCs!  Founders often enjoy reconnecting with their first VCs and top angels.  But they really don’t love being interviewed by later-stage investors.

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