The two crucial types of “how” to address in remote meetings

Hadassah Damien
6 min readMay 26, 2020

For many of us, the practice of “being in remote meetings” has been turned up a few notches, and not all of us are enjoying the experience. This article explores two critical elements of meetings that often get missed, but which greatly help creating better in-meeting experiences and after-meeting outcomes:

Going in: How will we conduct this meeting?

Heading out: How will we work with the output of this meeting?

Basic UX of meetings

When a meeting is productive, you leave feeling like you know what you’re supposed to do next — and what others are responsible to do. You may have more questions than before, but they’re better-informed questions. Your frustrations are minimal, perhaps your video software cut out once or an important speaker froze mid-sentence, but you all were able to recoup. You were able to get alignment, clarity, or insight from others in the meeting.

If a meeting is unproductive, it can feel like entering one of Dante’s levels of Hell: are you in Limbo where nothing is happening yet you are struck with grief? Or perhaps you’re in Greed, where people seem to push boulders at each other in a battle that never really materializes? Unluckily you might be in Hearsay, locked in a burning stone coffin, unable to get anywhere. And it should go without saying that if your meetings are Violent, rain of fire or being forced to swim in boiling blood are not ok behavior, either in or out of the workplace.

The two crucial “how” questions

You can avoid Dante-level meetings by planning, informing, engaging, and confirming with participants — or being a participant aware of the plan for the list above. Shortly after entering any meeting, if not beforehand, you should be able to answer the following basic questions:

  1. How will we conduct this meeting?
  2. How will we work with the output of this meeting?

If you’re leading meetings, you need to generate and share the answers to these questions. They will inform what you prepare, how you move the session along, and how people participate — or don’t.

Woodcut From A Venetian Edition Of The Divine Comedy, c.1520

Going in: How will we conduct this meeting?

Thinking of meetings as an engagement experience shifts our thinking to pay attention to our expectations for those who attend, and to think of ourselves as stewards of others’ experiences.

Know the basics

When you’ve got a process to build off, a quick 15-minute planning session ahead of a meeting is usually enough to define and share out:

  • Who documents or takes notes, and who facilitates?
  • What is the agenda, purpose, and intended outcome of us getting together?
  • Who talks? For how long? To the whole group or in smaller groups?
  • If we come to a decision point, who decides and how?

Organizational debt, where such processes aren’t built out, is real — and might mean your organization is still creating answers to some of these. Welcome to your opportunity to prototype and test in service of everyone having a better meeting life! Collaborate to draft out an ideal set of answers to the above, and then agree on the version you want to bring forward at your next meeting.

Leave a trail

Along the way, documentation and visual sharing matters a lot — especially in remote meetings where ideas can get lost in the Zoom/chat/backchannel shuffle. Using whiteboard collaboration tools like Mural or Miro can greatly enhance a meeting, by enabling visual and graphical learners to combine forces and sync ideas together. A well-organized shared word processing document can also do the trick. I like to use the chat function of the video software as a way to collect questions and ideas, and copy them into collaborative documents to work from.

The key is orienting people, and keeping them oriented by saying where to put comments and ideas, and if you’re in multiple documents, which document to look at when.

Heading out: How will we work with the output of this meeting?

In Never Split the Difference, professional negotiator Chris Voss warns against “getting to yes without specifying how.”

Friends: every meeting needs to end with “how” the focus of the meeting moves along.

Reference files

After a meeting, documented ideas, decisions, and reference materials are super valuable to help those both in and not in the meeting understand what happened and what to do about it.

If you have an idea of how you’ll need to work after the meeting, let that define how you collaborate to collect ideas.

Name the stakes & keep focus

Decisions are rarely neutral, and the more impact a decision might have the more important it is to ensure you know who and how a decision gets made, so that meeting participants level-set their expectations correctly. If a decision is going to mean someone has to do work, how is that person or team represented? If a decision means allocation of time, money, or supplies, who needs to say yes to that, and are they present or accounted for?

Finally, the facilitation skill of moving things along is a gift to all present and can be the key to ending up at an output. Allowing an unrelated point to go unfinished, collecting an idea for a later discussion, interrupting if needed, or closing out a conversation all can allow a meeting to center back around its purpose.

Next steps

Every meeting’s last few minutes should include a recap of learnings and decisions, and participants should be invited to self-nominate or confirm who needs to take anything back to others, be responsible for decisions, or perform follow up actions.

When next steps start to get out of control — too big, I like to organize them into Now > Next > and Later, and invite people to take on “Now” tasks, and simply identify who needs to keep track of the Next ideas and plans, no commitment needed.

Doing the work in real life

While it’s not particularly difficult to create an agenda and activity plan for a meeting, it can be very hard to re-set norms that are in place.

If you see someone struggling to get people engaged in a meeting, you can help simply by participating — or by shutting up and asking to hear from someone else if you’ve been talking a lot. If you’re creating a meeting and struggling to get people to participate in new ways, name it. Try: “We’re trying a new way today, so our meetings can be more productive. Is anyone unwilling to give it this try with me, just for this meeting?” Then — ask for feedback on what worked.

Finally — most organizations have at least a few meeting wizards: people who run beautifully efficient, clear, and productive meetings. Watch them, learn from them, and ask them what they to do make their meetings work so well.

Fun trick: if your meetings are at a workplace, guesstimate the cost of any meeting in terms of everyone’s salary for the time you’re planning and in-meeting. If you’re meeting for community or cultural work, guesstimate the total time of the meeting (including planning, listserv communications etc) and imagine that time as removed from socializing, self-care and rest. Either assessment should lead you to ask: was this meeting worth it?

Making the work experiences we want

As we build groups, organizations, and new ventures in these changing times, the question we have to contend with is: which experiences do you want the people around you to have?

In this time of transition, with huge problems to solve and opportunity spaces opening, replicating old work styles that create broken teams is irresponsible.

Designing for remote is a specific opportunity for you to build towards ever-better work. Ask yourself: What am I noticing about the culture of meetings I’m in? What would need to change for all my meetings to be useful, efficient, fun, and productive?


Hadassah Damien is a design strategist and facilitator, economics researcher and finance educator, open source technologist, award-winning artist, and entrepreneur.

This is a segment from a book in-progress; follow me on twitter @HadassahDamien to stay tuned, or reach out to me and my colleagues at Staircase Strategy if you want remote facilitation training or coaching.



Hadassah Damien

design strategist & facilitator // economics researcher @rffearlessmoney // progressive technologist // performer