The Post Covid19 CoS, Pt. 2: Knowing What’s Really Going On When You’re Not Colocated

June 6, 2020 (Adapted from my newsletter, The Briefing. Originally published May 26, 2020.)


Our March 25 issue of The Briefing covered resources that might help in managing through crisis or chaotic times. Check it out if you missed it.


Ready or not, the distributed or remote, digital-first CoS is on the rise, increasingly replacing her primarily co-located peers. What will this new normal look like?

This is the second part in a series on how the CoS role is changing under our feet, and what it will look like in the not-too-distant future. This series won’t be exhaustive, because a lot of this change is still unfolding around us, but I think you will appreciate the insights here, because they will enable you to make adjustments and bring along your exec, leadership team, and organization with you if that’s required in your context.

With everyone suddenly distributed, we needed a way to virtually “stop by someone’s desk,” because sometimes an ad-hoc conversation can provide clarity to an ambiguity, or because serendipitous conversations can sometimes spark creativity. – Ari Schapiro, CoS at Auth0


Part 2: “Knowing What’s Really Going On in The Organization”
A chief of staff (CoS) I spoke to this week wondered if she was the only one struggling to keep pace with the shift to a suddenly-distributed workforce, because so much of her CoS role was based on colocation and physical face time:

I used to have so much more time with my boss. My boss and I were unusual in that we actually carpooled together, which offered a lot of depth of back-and-forth conversation, alignment, and shared context. But even at the office, we would meet (even briefly) before an LT meeting to make sure we were aligned first or anticipate questions that could come up. My boss and I were literally co-located in the center of our office. I could run down the hall and give so-and-so a heads up that they’ll need to prepare for a coming change that my exec had just mentioned. Now we’re suddenly disconnected.

She’s not alone. What she’s experiencing is really two sides of the same coin, plus what I’ll call the outer edge of that coin. First, the two sides. Chiefs of staff play at least two important roles for their execs:

  • managing information flow into the principal exec’s office, leadership team, or board
  • reaching out to get information that is useful for those stakeholders

You could think of one as a “push” model and one as a “pull” model. Both are ways to ensure that your exec, leadership team, board, and others know what’s really going on in the organization so that they can make and execute great decisions.

Traditionally, CoS have used informal, as well as formal (but almost all in-person) channels and touch points with others for all this communication. These are your water cooler conversations and sneaker diplomacy. These also include being located in close physical proximity to your exec’s office so you can “run interference” on people stopping impromptu at your exec’s office. A lot of CoS swear the role wouldn’t work without those informal, in-person touch points and interactions. Yet, here we are, with an increasingly remote chief of staff presence, many of whom are seemingly doing just fine without those physical touch points. So, the questions become:

  • Are we losing the touch points and they don’t really matter?
  • Or, the touch points matter, but not as much as we think they do?
  • Or, have the touch points simply shifted to a different venue of virtual meetings and team communication tools like Slack and Teams, via the forcing function of Covid-19?

The answer to all three questions, to varying degrees, is yes. In-person touch points might be best, but what is good enough, and how can we prevent “best” being the enemy of “good enough,” if we assume that organizations are shifting to more distributed models, even if they’re hybrid models and not exclusively distributed?

It would be easy, and perhaps tempting, to conflate the mode (a CoS has to be good at sneaker diplomacy or has to have physical touchpoints) with the desired outcomes (the goal is not sneaker diplomacy, it’s gathering information that supports decisions or execution). Yet, like many things we’ll examine in this series, the modes quickly date themselves, even if the functions and outcomes don’t, or don’t as often.

With a distributed org, you need to minimize the number of times that urgent-in-the-moment needs arise… While occasionally unavoidable, we view these scenarios as a planning failure rather than a normal mode of execution. – Stephen Levin, CoS at Zapier

A lot of people I talk to are familiar with Scott Berkun’s The Art of Project Management: How To Make Stuff Happen, in which Berkun highlights the need for relentless follow up and savvy. “If email doesn’t work, switch to phone,” he writes. “If phone doesn’t work, then drop by their office.” In a distributed model you can switch modes, but you can’t “drop by their office.” So how do you manage the push and pull of info in a distributed model so you know what’s going on in the organization and can get stuff done?

For Richard McLean, a home-based CoS in Cambridgeshire, UK, the solution is a relatively simple matter: “Keep an eye on different Slack channels,” he says.

Ari Schapiro, CoS as Auth0, points to some other workarounds.  “Pre-COIVD 19, we had 55% of our workforce (at least half of our leadership team) remote. With everyone suddenly distributed, we needed a way to virtually “stop by someone’s desk,” because sometimes an ad-hoc conversation can provide clarity to an ambiguity, or because serendipitous conversations can sometimes spark creativity.  In a distributed model you have to more proactively look for and create moments like that by doubling 1:1s or by enabling ad-hoc encounters through apps like Donut, basically shifting information flow to virtual settings.”

At Zapier, CoS Stephen Levin adds, “With a distributed org, you need to minimize the number of times that urgent-in-the-moment needs arise. Any time you’re requiring a response in less than 2-4 hours, you’re probably breaking someone’s flow, or they might just be in meetings and not see it. While occasionally unavoidable, we view these scenarios as a planning failure rather than a normal mode of execution.” He also stresses that how you handle situations like the office-drop-by depend on your team’s cultural norms. In their (publicly available) Slack etiquette guide (see Further Reading, later in this article), Zapier works hard to set the expectations and prepare people for the norms of distributed work. Without these norms and preparing employees for how to engage one another, distributed work would be a challenge. Examples he mentions:

A healthy distributed culture has to be responsive to Slack, calendar invites or phone messages. The number 1 company value is default to action, so if I don’t get what I need from others, I’m empowered –even expected—to take action myself or escalate around them. We spend a lot of time teaching effective writing and remind people to assume positive intent.

For Levin and Zapier, a savvy “escalation” path in the distributed world might look more like:

  1. Public Slack message.
  2. A) Slack direct message with a link to the public thread. B) Repeat Slack DM in a few hours is it’s urgent, or the next day if it’s not.
  3. Calendar invite dropped onto your and their calendar.
  4. A phone call or text probably indicates an emergency and would be answered accordingly.

Levin says he’s used #4 only once.

Of course, each virtual workaround for collocated modes of interaction comes with tradeoffs:

  • Starting with Levin and the Zapier model, with so much depending on the preparation and norms, not every organization finds themselves with those norms in place today. Getting them in place will require a (perhaps rapid) shift in culture and norms. If those are missing (even if you’re currently working on them), you’ll be left with a “messy middle” at best, and a challenging environment at worst.
  • Schapiro reminds me that while you can use some of the previously-mentioned apps to recreate those casual, serendipitous conversations, in a distributed model you have to more proactively look for and create moments like that. It takes more work and intentionality at a time when many leaders and employees (including CoS) are already prioritizing their most important priorities and making difficult tradeoffs in how they spend their time. Further, he says, “Lots of screen time = fatigue/burnout, at least for many people.”
  • Microsoft CEO Satya Nadella recently expressed similar concerns for an all-virtual workforce, even as Microsoft were among the first large companies to encourage employees to work from home. “What I miss is when you walk into a physical meeting, you are talking to the person that is next to you, you’re able to connect with them for the two minutes before and after.” He also worries about burnout, mental health, and isolation from an all-remote workforce, and hints that perhaps hybrid models will work best in the future.*

None of the tradeoffs mean that “remote doesn’t work” or that you should stop trying (more) virtual work, but each is a risk that you, your exec, your leadership team, board, and the organization at-large need to articulate, come to terms with, communicate about, and work through as you go.

Perhaps a starting place is to think about your current networks, and move toward your ideal state from there:

  • How do I manage inflow of information today? What works/doesn’t with those mechanisms?
  • How do I manage outreach for information today? What works/doesn’t with those mechanisms?
  • Given the as-is state, what do ideal and acceptable to-be states look like, and what challenges can I anticipate in the “messy middle?”
  • What are the supports I need from my exec, my leadership team, my peers, to make the shifts I need to make?

For further reading:



Chief of Staff Mastermind Cohort 2 – Registration Open Through Midnight June 12’s Chief of Staff Mastermind Cohort 2 is a year-long learning experience with 12-20 chiefs of staff from Fortune 50, startups, nonprofits, and academics that combines the power of peer advisory, CoS-specific training, and group and 1:1 coaching. For some of you, the timing is not now, with everything going on – for others, this is precisely the time to get the support you need in this challenging role and these challenging times.

Given the current context, we revamped Cohort 2 as a more virtual offering that lessens the time commitment from already-busy chiefs of staff and offers more flexible pricing than our previous workshop and cohort offerings. Here’s a video I made that highlights what you’ll get out of the cohort.

Learn more or register now.

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