Ira Glass on Storytelling & Why It Matters To Business Leaders

If you haven't seen Ira Glass's phenomenal two minute talk on storytelling take a second and check it out. I'll wait while you watch it below.

I can't remember how many times I watched this video over the last several years, but it has to be at least 50. I turn to it when things feel like they just aren't quite working. Or when I need a reminder that even though the work I'm doing isn't where I want it to be, I need to trust the process and keep on going.I also have every business leader I work with watch it as well. 

For the sake of this bit of writing let's break a few key parts of his philosophy apart and apply them to the business world.


"Nobody tells beginners that there is a gap and the first few years when you're making stuff, the stuff you're making isn't so good."

This isn't going to be popular, but it needs to be said. Too many founders, VC's, speech coaches and accelerator networks take the approach that storytelling is something that should be natural for the founder. Who better to know and tell the story anyhow? Obviously the founder needs to be able to articulate their story, but that doesn't mean they'll know how to do a good job right off the back.

Which is where things come off the rails. Founders are just like every other storyteller, they're figuring it out as they go. A seasoned business leader who has been studying and telling stories for decades usually can shorten the gap between starting a new story and having one that is ready for primetime, but new founders need time to breathe and the understanding that it's okay if the first few hundred iterations don't work.


"Your Taste is Still Killer"

This is one of the hardest things for any storyteller and communicator that has good taste. It's maddening when what you're trying to say/do isn't reaching your taste and people around you are giving feedback. I remember the first time I got edited early in my career for a newspaper story and it felt like I'd never be able to write a sentence again. I knew what was good, but my work got ripped apart and I suddenly got doubtful. 

If you're a business leader don't overlook this. It's good to watch TED Talks, and product launches by Steve Jobs, but don't forget those folks had this same problem you do. Keep focus on your taste and keep going.


"A lot of people never get past that point. A lot of people quit."

This is hands down what separates the master storytellers from everyone else. It is also what separates CEO's that can galvanize workforces and move the business into the stratosphere. And it's easily the most hard thing to do. 

If you're a leader, give yourself the time to let this process work its way out. Know that you're most likely not going to go up on stage and knock your first pitch out of the park. Or be able to effectively communicate down the ladder in a large organization. 

This is also a great place to watch this clip a few times. In fact, bookmark it.


"Do A Lot of Work"

There is a lot more we could talk about but I'm going to leave this right here. It's the cornerstone of this whole post. The only way to get better as a storyteller is to tell a lot of stories. There is no way around it. 

There are some hacks including hiring professional coaches, but they aren't the full answer to the problem. In fact, if you do hire a coach, grill them. Don't assume just because they say they are a storyteller they really are. The fact is they might sound super smart at first because they know formulas to put your story together, but under the hood it falls apart quickly.

I'll be the first to admit I'm not always the right fit for people and that's okay. Don't think just because you hire someone you can skip the work. 


Upcoming Workshops

Want to learn more? Check out the workshop I'm doing with Pitch Lab at General Assembly on November 13. We'll be focusing on how comedy can help you be a more engaging storyteller!

* Thanks for reading. I didn't do this in the past, but it's time to just admit it-- I'm dyslexic, can hardly spell my own name at times, and miss basic grammar every once in a while. So, please forgive me if there's a typo. What I do know is how to tell a story, which luckily for me doesn't always require writing.