Ninety Episodes In: What I Have Learned About Getting People To Tell The Truth
When I started The Keep Going Podcast I thought the job was asking good questions. Ninety-plus episodes later I can tell you that is maybe a fifth of it.
The actual job is building a room where somebody is willing to say the thing they normally leave out. Everything else - the questions, the gear, the edit - is in service of that.
Here is what I have learned doing it.
Most guests arrive with a press release
Almost everybody shows up with a version of their story they have told a hundred times. It is smooth, it hits the same beats, and it is about eighty percent true. It exists because it works - it protects them and it makes a decent clip.
You are not going to break that in the first ten minutes, and you should not try. What I have learned is to let them run it. Let the polished version out of the system. It relaxes people. Then, somewhere in the second half hour, ask about a specific moment inside that story rather than the story itself.
Not what was that period like. Something like: where were you when you got the call? Specificity is what gets past the press release, because nobody has rehearsed the specifics.
Go first
If I want somebody to talk about getting cut, the fastest way there is to talk about getting cut myself. Not a long story - one honest sentence about a time it went badly for me.
People match the level of the room. If you are guarded, they will be guarded. If you offer something real, most people offer something back. This is not a technique so much as a fact about human beings, and it works on camera exactly the way it works anywhere else.
The caveat: go first, then get out of the way. The interviewer who keeps making it about himself is the worst version of this job.
The silence is the tool
The hardest skill I have had to learn is shutting up.
Somebody finishes an answer and there is a gap. Every instinct says fill it - agree, or jump to the next question. Do not. Wait three seconds. The second thing they say in that silence is almost always the real answer. The first one was the answer they had ready.
I lost a lot of good moments early because I was too eager to keep things moving.
Prepare enough to abandon your prep
I research every guest properly. Then I try to hold the questions loosely.
The worst interviews I have done are the ones where I marched through a list. The best ones are where something they said in minute twelve was clearly more interesting than anything I had written down, and I followed it instead.
Preparation is not there to give you a script. It is there so that when they say something important, you know enough to recognize it.
Ask about the middle
Everybody wants to talk about the win, and everybody has already talked about the origin. The part nobody asks about is the middle - the long stretch where it was not working and nothing was guaranteed.
That is where the actual story lives, and it is where I take almost every conversation. What was the worst month? Who did you call? What made you think about quitting, and what stopped you?
Those questions get better answers than anything about success, because most people have never been asked them, and because everybody listening is currently in a middle of their own.
The stuff that is not glamorous
A few practical things I would tell anybody starting one:
- Audio over video, every time. People will forgive a mediocre picture. They will not sit through bad sound for forty minutes.
- Show up early. The ten minutes before you record - just talking, no cameras - do more for the conversation than anything you do once it starts.
- Consistency beats production value. Nobody builds an audience with four beautiful episodes a year. Pick a rhythm you can actually hold and hold it.
- Book people for their story, not their following. Some of my best episodes are with people almost nobody had heard of. Some of the least interesting are with people everybody has.
- Send them the thing. Tell guests when it is out, give them the clips, make it easy for them to share. It costs you nothing and it is how you get the next guest.
- Do not edit out the pause. When somebody gets emotional and stops, that silence is the most honest three seconds in the episode. Leave it in.
What it costs
The thing I did not expect is how much it takes out of you to hold somebody's hard story properly. People tell you real things - about losses, about the year everything came apart - and you carry a bit of that out of the room.
That is not a complaint. It is the price of doing it right, and I would rather pay it than run a show where nobody says anything true. But if you are going to do this seriously, know that it is a real cost and build some recovery around it.
The pattern across ninety conversations
Different rooms, different industries, wildly different lives - athletes, artists, entrepreneurs, coaches, community leaders. And almost every one of them has the same shape underneath.
Nobody's path is a straight line. Every single person has a storm season they had to survive before anything you would recognize from the outside showed up. And the ones who made it through were rarely the most talented people in their field. They were the ones who could stand the longest without a result to show for it.
Ninety episodes of evidence for one idea. That is really what the show is.
Keep going.
- Rasheed 'Showtime' Bailey
Full episodes are on YouTube. If you have got a story about the middle, reach out.