The Post Covid19 CoS, Pt. 3: Water Coolers and Whiteboards

3 March, 2021 (Adapted from my newsletter, The Briefing. Originally published 8 Oct., 2020.)


This is the third part in that series on the rise and establishment of the digital-first CoS, 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.

“Over time the question of how to do this virtually will be less and less frequent, and we might even see its opposite: ‘How do you transform practices with an “in person” environment?’ Or ‘How to deal with physical meetings?’” – Ari Schapiro, CoS at Auth0


Part 3: Water Coolers and Whiteboards?
In the previous installment of this series, I explored how traditionally, CoS have used informal, as well as formal (but almost all in-person) channels and touch points with others for achieving their desired outcomes. 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. I explored the resulting questions:

  • Did those in-person touch points really matter at all?
  • Or, the touch points mattered, but not as much as we thought?
  • Or, have touch points simply shifted to a different venue through virtual meetings and team communication tools like Slack and Teams, and they replicate the in-person touch points “good enough?”

This installment, then, is a deeper dive into those touchpoints and how we can get more of them than we think in virtual meetings, starting with sidebars and whiteboards.

Several dozen CoS I’ve spoken to over the summer have expressed a sentiment like, “Yeah, we’re making the all-virtual thing work, but we used to have those informal sidebar conversations before the meeting, or after the meeting. We’ve lost that now.” So, what about sidebars? Did they go away? Certainly, in many situations they did.  But did they have to, or are there some things we can do to bring them back in a virtual world? Some suggested starting points:

  • Open meeting tools early – this can seem counter-intuitive. Some of us have always been the time keepers and prided ourselves on starting right on time, or a lot of us seem to be running from back-to-back meetings to more back-to-back meetings. Yet, with most team video conference solutions, there’s nothing stopping you from opening the meeting early and kicking around some informal banter while you’re waiting for everyone to show up. There’s also nothing stopping you from letting people know you’re in there early if they want to hop on, too. If you haven’t been doing this, it might take a couple meetings to get folks to catch on, but signal it ahead and let them know what you’re doing. Empower them to talk while you’re waiting for the principals to trickle in. CoS for the productivity and morale win!
  • Start meetings late. Now, I can see the springs popping out of some people’s heads already, but hear me out. This follows in the context of my previous point about opening the meeting tools early. If the Zoom call is open early, and people are having meaningful sidebars, and especially if your principals or critical attendees are still trickling in, don’t be so rigid about the schedule that you shut that great conversation down. In the current environment, these opportunities might be few and far between. Your team will appreciate that time. It can add value.  Flex the kickoff of your formal agenda to start 5 minutes late. Remember, this is one tool in your box. You don’t have to use it. But it’s nice to know you can.
  • Use chat. What is chat in a Zoom or Teams call, if not a sidebar mechanism? It was made for this. Chat can easily become a distraction, with people are paying more attention to the sidebars than the main discussion. And some people seem better able to shift in and out of this while continuing to catch salient points of the main discussion, so it puts some onus on you to gauge who’s paying attention on the main stage and who’s not. Especially if you’ve asked people not to multitask during the meeting.
  • Use parking lots. Participants in our Chief of Staff Mastermind cohort will tell you I always have a parking lot for sidebars that come up, which might be important conversations to have but often can wait until later or don’t help us meet the objectives for this meeting.
  • Use breakout rooms (and your meeting time) wisely. If you’re using Zoom, you’ve got breakout room capability. Build in breakout time at the end of your formal meeting time and let everyone know that’s what you’re doing. At the end of your formal agenda, you (or someone) has likely recapped the discussion and action items. That’s a great time to ask if anyone would like to continue a conversation that came up. Because this one happens at the end, it hinges on your ability to finish other agenda items on time or early. And with some savvy use of Kanban boards and time breakdown charts, you should be able to get better and better at that over time, especially for regular meetings.


In many situations, perhaps especially design thinking, Agile, and LEAN meetings, you facilitate conversations that lead to divergent thinking (post-its on a wall or window, etc.) before bringing that discussion back to convergent thinking (organizing the post-its that group members have posted, by priority or by category, affinity diagrams, using additional stickies to vote 1st, 2nd, 3rd preferences and other qualitative work, etc.). Or maybe you and your exec are talking about a problem or approach, and one or both of you jump up to white board it. Tools like and Mural exist, but do they scale?

According to Richard McLean, a home-based CoS in Cambridgeshire, UK, “It is a combination of digital tools, like Miro, plus good virtual facilitation skills.”

By all accounts, the tools are very effective for doing what we do in person. I shifted our CoS Mastermind Cohorts to a virtual-first offering in May, using Zoom as my platform and Mural as my whiteboard of choice.

For video conferencing, Zoom’s secret sauce is the breakout rooms. If you need breakout capabilities, it’s hard to beat. A lot of people like Teams’s interoperability with Office 365 products they already use for a seamless experience. Figure out the criteria that are most important to your team, prioritize those, and make your selections accordingly.

For whiteboarding/collaboration, consider tools that enable multiple users to markup a virtual space in real time, or that control access and turn taking, whatever you need. Some have templates you can use for different kinds of conversations, others let you “green field” it every time. Like video conferencing, criteria first, then selection, but be intentional.

As for scalable, it’s not often that you’ll facilitate a truly interactive discussion with large groups (versus, say, using a Webinar or gathering feedback in advance).

Facilitating Virtually
So, what do virtual facilitation skills look like? Most of you know I’m a big proponent of the CoS as facilitative leader (primer here). And, in most ways, that doesn’t change in function, only form.

You still manage content and process. You still (or help your exec) set expectations and define the desired outcomes for the leadership team ahead of time, define ground rules, and enforce them during the meeting. You still contribute substantive opinions on the issues.

The ground rules are an area ripe for change. They will likely to change to reflect the tools and reality your people are in.

  • Consider having more small group meetings where interactive conversation are encouraged and easier than large groups.
  • Set expectations that some work will be done in advance of the meeting. So-called silent meetings give people time to read during the meeting, but even then, you’re using that time for reading, instead of maximizing the team’s interaction, debate, problem-solving (the real value creation) while in the room together.
  • Decide how and to what extent you want participants to minimize distractions (or just be okay if they are checking phones, chatting, etc.)
  • Decide whether to have video enabled by default. It helps you check nonverbals, but comes with bandwidth issues for some people working from home.
  • Decide if everyone should remain on mute by default. For your kids’ school or scouts, probably best; for adults, not most likely to drive engagement.
  • Intentionally call on all participants for their perspective at some point in the call.

Funny enough, many of these considerations will help make your in-person meetings better, too.

Need more examples? Consider how the Hudson Institute of Coaching, my coach training alma mater, shifted from very intimate, in-person learning experiences to virtual experiences that maintained the value people derived from those in-person meetings:

Still, not everyone likes the tradeoffs in shifting to an all-virtual world or thinks the benefits outweigh what you lose. There has been some research on “Zoom fatigue,” a commonly-cited phenomenon among CoS I’ve spoken to this spring and summer.  Some commentators have suggested a hybrid workforce (versus all-remote) is the most likely scenario in the future, for a variety of reasons.  And, one of our very own Chief of Staff Mastermind Cohorts voted to wait and graduate the cohort in person versus doing it virtually.

Whether we end up in all-remote workforces or hybrid ones, it remains clear that the old world will not return, and like with all change, we have a choice to hold on to what is useful from the old ways, let go of what didn’t work so well, and find new opportunities that weren’t present before.



Chief of Staff Mastermind Cohort 3
In the white water of 2020, all of us got thrown from our rafts. For chiefs of staff in 2021, now, between the rapids, is the time to take stock, plan, and up-level for what’s next/ Your best chance of success is not going alone. Come join up to 40 of your CoS peers for Chief of Staff Mastermind Cohort 3 to achieve your best results. Let me be your guide, and let your CoS peers be your raft mates.

Global Chief of Staff Mixer Series
Don’t miss our next mixer on Being a Chief of Staff During a Pandemic, March 25, 9am Pacific/Noon Eastern, 5pm GMT. We’ll explore ways to facilitate strategic planning or other key meetings remotely, and we’ll have some fun doing it – the Feb 23 group created what I think is the world’s first CoS Playlist on Spotify (hint: another way you can connect your teams – have them create a playlist on the spot!) and one CoS stayed behind to say, “Thank you – that was the best virtual meeting I’ve ever attended!”

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