The Art of Facilitation

Aka Unleashing Knowledge, Insights, and Goodness from your Community

Sep 2, 2016 · 9 min read

This post is based on a talk I delivered at the #ValueAddVC Summit on August 24, 2016, hosted at Union Square Ventures in New York City, to 40+ community directors at leading venture funds throughout the country.

In thinking through what I wanted to discuss today — I thought to myself: what is the one thing every single one of us does at least once a quarter, if not every month, every week or even every day?

And that is: the Art of Facilitation.

Now I imagine all of you here today are already kick-ass facilitators. You host tons of events and dinners and so forth, so you are all very, very good at this.

But for us at Work-Bench, facilitation is especially important for two fold reasons:

The first is that our mission and vision for community at Work-Bench is both very simple and very hard:

Get THE very best and brightest in enterprise tech together.

We are lucky to do this with our venture fund, but also with the center of gravity and home and hub for enterprise tech in NYC we have been building:

With our 32,000 sq ft workspace just down the street, home to 15 of NYC’s top enterprise startups, we host more than 200 hyper-targeted enterprise events a year, everything from meetups to sales roundtable lunches to dev talks to dinners, to conferences, and more (all of which is only possible thanks to Stephanie and the incredible event machine she runs).

So the “easy” part is getting people in a room together (and as you all know, easier said than done).

But the 2nd part is what I call structured serendipity:

You’ve now got the smartest, most brilliant, and passionate people in enterprise technology in a room together.

Or you may have some of the country’s top CEOs in one place. You know who they are in your portfolios: they are VERY busy, their time matters, and so you better bring your A-game.

How do you — as a community leader — extract and unleash all this incredible knowledge and insights and experiences and expertise from their heads?

I’ve seen this done well, but I’ve also seen it done superbly well, and I’ve seen it truly elevate the quality and caliber of the discussion.

That to me is the art of facilitation.

So what I’ve done here today is:

  1. Collated some of our best practices around facilitation and what we’ve learned over the past 3 years at Work-Bench and our 500+ events.
  2. I’ve also had the opportunity to work with a phenomenal public speaking coach who has worked with the likes of Sheryl Sandberg, Jessica Alba, Facebook, Amazon, LinkedIn and so forth, whom I cannot recommend enough.

Here’s a look at some of our top events.

2016 New York R Conference


This is our 2016 New York R Conference.

This was our 2nd sold-out year, with 250+ data scientists descending upon Work-Bench, and 2 packed days of 29 speakers across corporates, startups, and academia.

If you’re like me, you realize the night before, after weeks of cramming and prepping for the conference: “Sh*t, I need to introduce 10 speakers tomorrow.”

And these speakers are all brilliant and have Ph.d.s and more — and I’m tempted to copy and paste and read their bios.

After all, a lot of what you see with emcees feels very improvised, off-the-cuff speaking.

But what I actually learned is that it makes such a difference to put the time in to know each speaker. After all, they themselves have put so much time into their talks. It makes a tremendous difference to set up the right context, the right energy, and the right excitement level.

What made a huge difference for us was to simply find a personal fun fact about each speaker that humanized them, that made them stick in the audience’s head, and that made them stand apart from the 28 other speakers.

For example — we had a speaker who I asked his favorite drink, and he thought for a minute. He got back to me with:

“Jack Daniels…because it’s not too high brow…but it gets the job done. Just like my research.”

This made me laugh out loud for perhaps a bit too long, but also made it easy for me to connect him with the audience.

*One protip*: through my research, I learned it is incredibly effective when introducing someone…to save their name for the very end. What I mean by that is this:

This next speaker inspires me everyday. She has been training tirelessly for the NYC Marathon in November and she is doing it for an incredible cause. We are so proud of her at Work-Bench.

Please join me in welcoming…[PAUSE]…Stephanie Manning.

Who doesn’t love walking on to that?

NY Enterprise Tech Meetup & Panel on “How to Get Press Coverage for your Enterprise Tech Startup” — Jan. 2016


This is our NY Enterprise Tech Meetup that we host every month at Work-Bench.

We bring together 120 enterprise enthusiasts, across startups, corporates, and VCs for demos, panels, pizzas, and beers.

This is a photo of Mickey Graham, our amazing Communications Director at Work-Bench.

With him are 4 top tech writers here in NYC, across TechCrunch, Forbes, Fortune, and Bloomberg Technology.

Mickey is about to extract from these writers their top PR secrets for enterprise startups.

With regards to moderating, we’re actually a bit of a split camp here at Work-Bench on some of the tactical issues above.

When I moderated the Enterprise CEO Summit in May with David Politis of BetterCloud and Daniel Chait of Greenhouse, we didn’t do a prep call ahead of time — because both Dave and Dan are incredible CEOs who are very busy.

But what that means is that you as moderator need to put in 3x as much work, in both stalking and being a chemist.

Luckily I’m very good at stalking, and what I mean by that is getting to know your panelists’ kids’ names, deep-liking their tweets, and watching every video I could find of past interviews.

What this does is gives you ammo to create a discussion that feels personal and well-researched.

But more importantly, the real reason you should do this is because as moderator, you should already come in knowing 80% of what the panelist is going to say.

This enables you to take the panel to the next level as a “chemist” to “mix” the panelists accordingly. You want them to interact, react, play off one another, agree, disagree. Whatever it is, you as the moderator need to be in control of the conversation. So stalk and mix.

Enterprise Marketing Leaders Dinner — March 2016


Intimate dinners — we all host these at our venture funds and portfolios.

At Work-Bench, we host and curate dinners across a number of enterprise functions and verticals: marketing, customer success, AI, infrastructure, and more.

We just hosted an Enterprise CEO Support Group dinner a few weeks ago with 10 of NYC’s top enterprise CEOs, leading Series D to Seed companies, based off a Medium post I wrote, about how CEOs need support groups too.

If you’re lucky like us — you’ve hosted many great dinners with natural-flowing, rich discussion.

But then there will be that one dinner, when the discussion comes to a halt.

That’s when your contextual moderation comes into play: to draw out the most useful common threads, challenges, and best practices amongst your dinner guests.

We aim for every dinner to not only have great food, wine, and people — but at least one actionable insight for every attendee to take away.

We bring not only a set list of prepared “just in case” questions — but also notes on each attendee, their company, and a recent win or ask, and a general “map” of high-level points the discussion should hit.

For certain dinners, pre-submitted questions from the attendees can also help shape the conversation.

Again, every dinner should “feel” natural — but underneath it all, you as a facilitator are conducting the conversation, adding value, and connecting dots, experiences, and insights, to keep the good wine and great discussion flowing.

2015 Dreamforce Conference: Salesforce for Startups Panel

#4 Rocking Out as a Panelist

Lastly, you’re on a panel at Dreamforce. There are 5 of you as panelists.

How do you stand apart from the other panelists?

The one big take-away I learned here from my speaking coach is that, as a panelist, you often want to come in and drop all your knowledge and expertise on people.

And sure, people do come to panels to learn.

But more importantly, people want to be engaged, to interact, and to laugh.

So I like what I call “turn ‘em questions”: turn ‘em back to the audience.

Engage your audience, be a game show host, make people feel good and make them feel smart (oldest trick in the book).

One example of this is with intros we did at the start of the panel at Dreamforce. Folks usually start with: “My name is…I’m from…”

When it was my turn, I asked for a show of hands and asked:

Who here has sold into a large company before? Who has survived procurement? Who loves compliance?

How many of you jump out of bed in the morning, thinking: I can’t wait to tackle that security audit from my Fortune 500 customer?

How many of you *love* procurement?

That’s right, none of you.

Because what you should be thinking about, day in and out, is how to build the best product out there, and how to get it to as many people as possible.

That’s where Work-Bench comes in. We want to help you with the hardest part of building an enterprise startup — getting in front of corporate customers.

By turning these questions around onto the audience, my hope is that they associated me and Work-Bench as a venture fund to positively help navigate through this pain.

Embracing this approach — in both engaging the audience and having fun —has transformed how I think about panels (and a lot of life!).

And lastly…

Yes, videotaping yourself before you speak will be totally painful…but it’ll be worth it. I promise you!

Enormous thanks goes out to Michael Balaoing of Candlelion, who has transformed so much of how I approach public speaking :)

Thank you goes out to Jonathan Lehr, Mickey Graham, and Stephanie Manning for their great eyes on this post.

Jessica Lin

Written by

co-founder & VC @Work_Bench | GED educator | rethinking work

Welcome to a place where words matter. On Medium, smart voices and original ideas take center stage - with no ads in sight. Watch
Follow all the topics you care about, and we’ll deliver the best stories for you to your homepage and inbox. Explore
Get unlimited access to the best stories on Medium — and support writers while you’re at it. Just $5/month. Upgrade