Jessica's Monthly Management Memo - February 2025

Hi Reader,

I'm writing this while I've got this playing over on my second monitor to help bring some calm vibes to what feels like a very not-calm external environment globally. Those of us leading teams have what feels like an increasing load on our shoulders these days, so I'm sending this in hopes something here provides more joy and ease in your leadership this month.

Let's get to your Monthly Management Memo - as always with something bold, something new, something borrowed, and something to pursue.

🔥Something Bold - Stop asking for cover letters when hiring​
​I think they can be avoided in almost all cases. See here in the comments for what I recommend you do instead, which gets you even more helpful information than a cover letter would.

🆕 Something New - File naming advice​
​​One of my client teams that I've led workshops for recently followed up to see if I had any advice for them on file naming conventions. I thought I'd share my response to them with all of you, too.

I think lots of different naming conventions can work - often, teams like to start with dates at the front of the file name to help folks know when a document was created, so that’s a popular approach. I think, in general, the advice to “be as specific as you can” is a helpful rule of thumb - the more specific, the more likely someone can easily find the document they’re looking for.

I think the more significant hurdle is in the backlog - folks likely have hundreds (thousands?) of old documents that aren’t following any naming conventions, and updating those can feel impossible. So I’d suggest a convention, get some input from a small but diverse group of folks, and then ask folks to start using that convention moving forward. This generally needs to go hand-in-hand with a simple and not overly complex folder system that everyone could easily use (in other words, it doesn’t have too many levels of folders, and if I asked a group of folks where X document should go, everyone would have the same answer). Remind folks that search is powerful, so having some folders with dozens or hundreds of documents might be okay. Unless there’s a good reason to separate into subfolders for a particular area, don’t spend too much time getting incredibly specific.

To help deal with the backlog of file naming and organizing, here are two suggestions:

• Feel OK with creating some folders like “All Development Documents Before 2023” and just dragging big chunks of rarely-used documents into there. Renaming these from years ago is probably not a good use of anyone’s time.
• For more recent documents, set a timer in a team meeting and have everyone spend 10 minutes renaming and organizing docs. Then, at the next meeting, do 10 more minutes. The little chunks of time will make meaningful progress AND help everyone learn the new system.

🤝🏼 Something Borrowed - Hard conversations are the tax you pay for deep relationships.​
A piece I enjoyed in a newsletter from Sahil Bloom recently: "When you avoid a hard conversation, you're taking on a debt that has to be repaid (with interest) at a date in the future. Time doesn't heal anything when it comes to relationships. Make the minor repairs along the way, and you'll avoid the major repairs later on.Your success in building deep, loving bonds is proportional to the number of hard conversations you're willing to have."

🏃🏾‍♀️ Something to Pursue - If you need focused work time​
I just looked, and I've now been to 112 Flown focus sessions - it's essentially a co-working platform with live sessions where you come into a Zoom room for 1 or 2 hours (facilitated by kind folks, my faves are Viki and Ant), name what you're focused on during that work block, and then get to work using the science-backed approach of being in the space with other folks who are also focused. It is working to provide a little joy in my day and help me get past procrastination or just quiet the general overwhelm of inputs from 5 different places all at once. I feel like managers with our meeting-heavy schedules often need this kind of focused space. The 30-day trial period gives you time to experience it and see if it helps. I asked them for a discount for my community, so if you use my link to sign up for your 30-day free trial and end up wanting to use it long-term, you’ll get 20% off. If you join a session where I'm in there, say hi to me in the chat!

P.S. Joyfully Managed Worklife, my program for designing a work life that is effective but avoids burnout, is likely back starting in May. If you want to help me pick the date and time for the cohort live sessions, fill out this quick form.

Bring your team, I'll bring my A-game. I love helping teams with workshops on topics of productivity, team culture, and effectiveness at work. Find out more and book a free chat to see if I can be helpful for your organization.