I've been doing open office hours off and on for the past few years, both in person and over Skype, but last month I decided to try something different and experiment with holding office hours over Telegram. There is clearly lots of value to doing these kinds of meetings in person or via video chat, but I thought holding the conversations over text messaging could offer a low pressure, more casual way for people to pitch me their startup, get feedback on their ideas, ask for advice on a product or career challenge, etc. I've become a big fan of Telegram over the past couple of years and have shifted a lot of my professional and personal messaging to the platform, so it seemed natural to try this there.

My hope was that by making it easier to have a conversation that those who might find jumping on a Skype call with a stranger a little intimidating would feel more comfortable reaching out. I also thought it might be an easier format for those who aren't native English speaker. It probably wouldn't hurt that because everything would be conducted over text I'd probably be able to hold multiple conversations at the same time; it'd be a simple way to scale my availability since I'd be able to chat with more people during the same amount of time.

So I posted something on Twitter and on my blog asking if anyone would be interested in trying it out and received enough responses via email and DM that I decided to carve out a couple of hours on my calendar the following week for eight 15-minute sessions, with the expectation that sessions would likely run over and so some discussions would happen concurrently. (If you're especially curious, I used Calendly for scheduling the sessions.)

Some takeaways:

It was a more efficient use of time. Some people had a very specific ask of me and only needed to chat for a few minutes. For those requests scheduling a call or an in-person meeting would probably not have been the best use of time for either of us, especially since with chat it's easier to get straight to the point. Trying to have that same conversation over email would likely have taken longer and required much more back and forth to get the same result.
I was able to be more considerate in my responses. Doing the conversations over text message meant I could take time (although not too much time!) to think about my responses. When you're speaking with someone in person or a call there is a lot of pressure to respond immediately to whatever they're saying. Chatting over Telegram gave me a little bit of a buffer to consider my responses before offering them.
Having overlapping chats worked, for the most part. Only a few people needed to chat for more than 15 minutes and I was able to handle two conversations simultaneously when I needed to. But I do need to work on being more responsive, one person told me that it was sometimes hard to tell if I was preparing to respond or waiting for them to respond. This is something that you don't have to worry about with a meeting or call and I will have to be mindful of this next time around.
There can be miscommunications/misunderstandings. One person explaining their business model to me kept writing "1.06%" when they meant "106%" and it took more than a few minutes to untangle what they meant. I suspect if we had been on the phone or in person it would have been easier to get clear up the confusion. Fortunately this was the only misunderstanding in the eight chat meetings I had that day, but having conversations entirely over text does risk some nuance being lost and it's something else I am going to keep in mind going forward.

Will I do it again? Yes, absolutely. I had a bunch of great conversations and the flexibility of the format made it easy for me to find time for it. If you're interested in signing up for a future Telegram office hours session let me know!