Don’t Text Your Assistant

The challenges of (and solutions to) text-message delegation

I don’t text my assistant. 

At least, I don’t text her anymore. When we started working together, texting seemed like the most obvious way to delegate work. It was low friction and I could capture my fleeting thoughts in words, a picture, or a meandering voice note.

It was good at first. It was easy for me and seemed fine for my assistant. I’d shoot a note over and most of the time she’d get right back to me with a clarifying question or to let me know the job was done. 

But as our work ramped up, the cracks started to show. The pace of messaging picked up as I got more comfortable with delegation and familiar with what could be taken off my plate. I would send texts in quick succession at any hour / day while complexity grew with an increasing number of open requests.

This led to some real challenges:

• Anything I messaged became the top priority, not because it was urgent but because it was received most recently

• Requests would often interrupt the flow of our conversation on another matter, confusing us both

• Delegations, especially those sandwiched between others, would occasionally get lost

• I would often catch my assistant off-hours, and she felt compelled to answer right then and there

While none of these issues were individually damning, they added up. 

A one in 20 chance that a delegation could be lost created a mental tax that any task might be lost. This background noise shattered the hard earned feeling of freedom.

These challenges were only magnified for those tasks where I couldn’t directly see the action taken. I had to trust that a text sent into the ether would be appropriately logged and completed. And this blind trust just didn’t work for me. 

I would constantly follow up on the status of open tasks, not because I was concerned that they would be done incorrectly, but because I was concerned they could have been missed. These messages were frustrating to send, and even more frustrating to receive.

I ultimately had to implement solution that rebuilt trust in our partnership.

It looked like a transactional interface for me, and a project management back-end for my assistant, both sides designed for our respective needs.

On my end, I kept it as simple as possible:

• I built a command line interface on my Mac where the keyword “ea” would send whatever text that followed to a project management board (Asana).

• A bot on my phone accepted texts, photos, or voice notes and similarly sent them to Asana. 

I optimized for delegation to be as frictionless as possible. Available on any device, with any form of content, without more than a click. 

For my assistant:

• Tasks flowed neatly into a kanban-style work board, ready to be prioritized and ultimately completed.

• The workspace gave her a dedicated place to track the status of any open request and updates along the way.

She no longer had to worry about requests interrupting her work, keeping too much in memory, or dealing with my anxiety about work slipping through the cracks. As time went on, we even extended this system into a tool where we could ask questions like “what’s the status of my TSA Pre-Check Application” that would query our workspace and return updates on any task immediately. 

In navigating the challenge of text-based delegation I learned that client-EA partnerships are more often strained due to a problem in process, not people.

You can rest assured that I no longer text my assistant. Not for her benefit, but for mine.

If you work with an assistant and think you could use some help, email me at nitin.gupta2012@gmail.com. I’d be glad to chat.