How hard is it to have a conversation on Twitter? So hard even the CEO can’t do it.

By Kurt Wagner

Twitter CEO Jack Dorsey
Drew Angerer/Getty Images

Twitter wants to be the place for the most important public conversations online. It still has some serious work to do.

Twitter CEO Jack Dorsey and Recode co-founder Kara Swisher agreed to conduct an interview Tuesday on Twitter, and it had all the makings of a great read: The CEO of one of the most influential and controversial tech platforms in the world taking questions from one of the industry’s most ferocious reporters.

The only problem? No one could follow along.

Despite the public interview, and a dedicated hashtag (#karajack) for the event, it didn’t take long before the dozens of tweets between the two started to get confusing. They were listed out of order, other users started chiming in, and there was no way to properly follow the conversation thread.

Swisher’s questions about Twitter’s complex abuse policies, and Dorsey’s subsequent responses, were floating around my timeline along with the regular tech news and opinions I always look at. If you wanted to find a permanent thread of the chat, you had to visit one of either Kara or Jack’s pages and continually refresh. It made for a difficult and confusing experience.

Dorsey even admitted so himself.

“I am going to start a NEW thread to make it easy for people to follow (@waltmossberg just texted me that it is a “chaotic hellpit”),” Swisher tweeted, referencing Recode’s other co-founder, the now-retired Walt Mossberg.

“Ok. Definitely not easy to follow the conversation,” Dorsey replied. “Exactly why we are doing this. Fixing stuff like this will help I believe.”

(Recode chronologically compiled the full interview in two Twitter Moments. Check it out here.)

That wasn’t the only problem. Swisher pressed Dorsey on what the service’s greatest problems are, how Twitter plans to take responsibility for them, and the ways that Twitter is trying to better police its service. “Please give me three concrete things you have done to fix this,” she tweeted multiple times.

If you could find that whole exchange, you ran into another problem: Twitter’s 280 characters just don’t leave enough room for a nuanced conversation.

To that last tweet, for example, Dorsey replied with a list of four items, including things like “We have evolved our polices,” and, “We have prioritized proactive enforcement to remove burden from victims.”

Swisher’s responses: “WHICH?” and “HOW?”

There simply wasn’t enough room to have the kind of nuanced conversation the subject requires. It was symbolic of Twitter’s broader problem: It’s almost impossible to have a smart, healthy argument on Twitter because no one has the space needed to share their thoughts.

The consensus that this interview was too hard to follow — and it was a wildly popular opinion — overshadowed what could have been a great conversation. Kudos to Dorsey for taking the time to field tough questions — though many of his answers weren’t very satisfying. He even left his comms team at the office, apparently!

Tuesday’s event was a chance for Twitter to show off what makes its service so incredible — that you can watch two industry titans share ideas back and forth in real time, in public. Maybe Twitter should build some kind of live chat feature for these high-profile interviews? Maybe Twitter is already building some kind of live chat feature for these high profile interviews?

“This thread was hard. But we got to learn a ton to fix it,” Dorsey tweeted after the interview wrapped up. “Need to make this feel a lot more cohesive and easier to follow. Was extremely challenging. Thank you for trying it with me. Know it wasn’t easy. Will consider different formats!”

We know that Twitter is trying to improve its conversations feature. Maybe when it does, we’ll get round No. 2.