“Managing up” in a digital age

After two years after COVID sent everyone running for cover, saying “I work from home” isn’t the conversation-stopper it once was. But my experience with remote work goes back further than the nightmare pandemic hellscape we still find ourselves in. I’ve been 100% remote (not counting occasional visits to the home office) since 2010, and moreover, I’ve worked 50-90% remotely in jobs going all the way back to 2000. As a result, I’ve become a telecommute evangelist, and even co-authored an ebook about it.

In all that time, I’ve developed and honed techniques to help me continue to succeed despite the distance between me and my manager. Part of that set of skills involves the weird sub-specialty of office politics known as “managing up“. It’s easy to overlook or dismiss this aspect of work even when everyone was in the same space (let alone remote work); it’s even easier to ignore for those of us working in tech because of the inherently solo nature of a lot of our work.

All of this is preamble to explain my delight when my friend and colleague Sharon Weiss-Greenberg solicited feedback on how to manage up in a digital (meaning: fully remote) workplace – because it gave me a chance to share some of those hard-won lessons.

You can read her analysis of it here.

Sharon gleaned lessons and insights from multiple contributors from around the world and across industry, and I’m grateful she found space for some of my thoughts. But (and this should come as no surprise to anyone who knows me) I had more to share. Like, a lot more. And having nowhere else to put it, I thought I’d blog a little and elaborate.

My digital “managing up” strategy includes the following main ideas and goals:

  • No surprises.
  • Multiple forms of informing.
  • And of course, a healthy dose of CYA.

CAVEAT: Nothing works as well as work

Before you read another word, I want to be clear: My not-so-humble opinion (based on decades of experience) is that neither in-office nor remote work is intrinsically better, easier, or more appropriate. Either can work well. Either can fail. The key is how engaged and invested the participants are.

With that said…

No surprises

When we’re all in the office, it’s easier for managers to get a sense (or at least THINK they’re getting a sense) of when staff is heads-down, out and about, etc. They can lean over and can ask what’s up. There’s more of an opportunity for ad-hoc “did you just hear” kinds of conversations. At the same time, the office itself becomes its own kind of echo chamber. Everyone tends to see and hear what everyone else is seeing and hearing, and it’s easy to forget to look further or dig around for other bits of information or news.

Being remote means it’s more likely I’ll notice things my boss not only doesn’t see, but doesn’t see me see. To compensate, I ramp up my level of active communication – whether that’s in a messaging system like teams or slack; or good old email; or during live sync sessions (calls, zoom, etc).

But to avoid that increased informational load becoming tiring (for both my boss and me) I used the guiding principle of “no surprises”: For any given thing I want to share “up”, I first ask myself whether it’s likely that NOT knowing would impact my boss in some negative way.

The most obvious example of this is “bad news” situations – when a project or deliverable will slip, when something is going off the rails, etc. But there’s also “neutral news” and even “good news” that could come as a surprise, and I try to mitigate those too. Basically, I try to envision a situation where someone (my boss’ boss, for example) might say “Oh, I’m surprised you didn’t know about that.” and I take steps to avoid it.

Just to sum up: Managing up as a remote employee means making sure my boss knows what I know, but only if what I know could end up surprising them in some way.

Multiple forms of informing

I’m a natural over-communicator, and I attribute my success as a long-time teleworker – in part – to that aspect of my personality. But just as not everyone speaks the same languages I do, not everyone prefers to consume information the way I am comfortable outputting it.

For that reason I share status and progress in a few ways, and continually check in with my boss as to which form is most effective FOR THEM. Some of my managers have preferred face to face (ok, Zoom to Zoom) discussions. Others want a bullet list of my “top 5 things” in email. Some have used spreadsheets, ticket systems, dedicated “daily stand up” slack channels, and even github comments sections. Still others are fine with a laundry list of everything I’m working on.

Whatever it is (or more likely “whichever they are” because inevitably I end up tracking my work in more than one place), I have learned to accept that that is what it is.

And of course, that’s all on top of the usual “hey, what’s going on with ____” type conversations that happen spontaneously across messaging platforms or team updates.

Regardless of what ELSE I’m using, there’s one technique I’ve done since my earliest days as an in-house employee who was sent out to do per-hour contract work billed down to 15 minute increments. At the beginning of each week, I start with a blank template (usually in email, but it honestly doesn’t matter):

Monday
================

Tuesday
================

Wednesday
================

To that, I add all the meetings that are scheduled each day. Then in the Monday slot, I add all the items I hope/plan/need to accomplish.

Monday
================
- weekly team kickoff
- discuss project x with so-and-so
- internal roadmap update
fix bug in myapp module 3
change links on webpage http://blahblah
write first draft of blog post

Tuesday
================
- 1:1 with boss
- record episode 3 of video series

As each day ends, I roll the un-finished tasks to the following day. At the end of the week, anything not completed rolls to a section after Friday called “OPEN TODO”. Then I email the whole shebang – at the very least it goes to myself, but most times my boss is happy to have a copy as well.

Why do I think this helps? See the next section.

A healthy dose of CYA

By communicating in multiple ways, but especially by ensuring that at least one of those methods is track-able (the weekly email), my boss has a running list of what I’ve done, what’s not done (yet), and what I’m planning to do next. They can see when new tasks hit my list and they have the opportunity to ask questions.

This circumvents uncomfortable conversations about “not working on the right things” and “had I known, I would have told you to stop”.

If you noticed that my first two major items – “no surprises” and “multiple forms of informing” both feed into my goal of CYA, that’s not by accident. In my worst work situations, these techniques have literally saved my job. But those are the outliers. Far more often, these techniques have helped stay on track; remember not only when, but HOW I solved a particular problem; and even fought impostor syndrome. Because when I’m spiraling down the hole of “I haven’t gotten anything done”, I look back at my list and realize just how many items I’ve checked off.

BONUS ROUND: GOALS AND ACCOMPLISHMENTS

The running weekly list also helps me to go back and identify major accomplishments, and track them against goals. As IT practitioners, we tend to fall into the trap of leaping from one crisis; one unsolvable mystery; one fascinating challenge to the next. So much so that we forget to note when we’ve resolved the crisis, solved the mystery, or cracked the challenge, which says nothing of the value to the business when we did it.

The list forces me to stop for just a moment and reflect on what I’ve done, realize it’s worth, and make a little note of it. I’ve even started adding a section at the bottom of the weekly list called “Great saves and unexpected assists” where I keep track of the extras that inevitably fall in my lap.

When it comes time for my job review (whether quarterly, 6 months, or yearly) I have much less of a scramble. In fact, I have all the data I need to say things like:

  • My goal was to write 10 articles, here’s proof I wrote 20
  • My goal was to spend 10% of my time paying down tech debt, here’s the data of where that time went and what it accomplished.
  • AND… on top of all those other goals, I also did these 10 extra, unexpected, unplanned, not-part-of-my-job tasks.

With that kind of information, the onus is now on my management to prove why I DON’T deserve a raise, promotion, and – perhaps most valuable of all – respect.

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