Cut Through The Small Talk and Connect - Lessons From 130+ Dinners, Summits and Salons - First Round Review

6/15/2020 Cut Through The Small Talk and Connect — Lessons from 130+ Dinners, Summits and Salons
ners, Summits and Salons | First Round Review
People & Culture
Cut Through The Small Talk
and Connect — Lessons from
130+ Dinners, Summits and
Salons
“Sapiens.”
“Sushi Ran.”
“Headspace.”
How many of us have participated in icebreakers during which thoughtful, but surface-
level recommendations are offered up? Once Anita Hossain, who leads the
Knowledge program at First Round, heard a similar list begin to rattle off during
introductions. Then one entrepreneur, who had attended a few of her events before,
said: “Being a founder has been an emotional rollercoaster for me. I was in a dark
place for a while. In addition to a corporate coach, I recommend a therapist. It’s
entirely transformed my ability to take on different challenges.”
That’s precisely the type of inflection point that Hossain guides groups of people
toward. Each part of the way she designs conversations for depth — a curated list of
attendees, steady moderation, thoughtful prompts and menu of topics, safe
environment and more — is geared to get people past small talk and into a meaningful
exchange. In just two years, Hossain has done this hundreds of times through 130+
events — all designed for startup professionals to learn from each other at a deeper
level. While the vehicle for these conversations varies — from summits to
unconferences to masterclasses and more — her intent remains the same: to provide
founders and operators resources to stay motivated and accelerate their businesses.
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6/15/2020 Cut Through The Small Talk and Connect — Lessons from 130+ Dinners, Summits and Salons | First Round Review
We thought it was about time Hossain shared what she knows. A er all, she's been
doing this at every stop in her career — first at Deutsche Bank, where the women's
group she helped create stemmed female attrition, and again at Wharton where she
co-led a storytelling series that convinced dozens of hard-nosed MBAs to open up
and get real. Everywhere she goes, she makes in-person experiences transformative —
and most recently as a professional coach.
But making this type of impact isn't easy. We hear from all kinds of organizations that
they want to throw events that will make their brand memorable and serve their
audience. But still so many fall flat because they lack what Hossain has come to regard
as the winning combination: intention, structure, vulnerability and utility.
In this exclusive article, Hossain describes in detail how to design and execute events
that actually make a difference. Focusing on the moderated Salon format, she walks
through who to invite, what to say, exercises to run, and how to measure your success.
If you want your audience to walk away feeling uniquely understood, capable, and
equipped to win, keep reading. They'll remember you fondly forever.
GOOD EVENTS SERVE PRECISE GOALS
To develop the best event, start with a narrowly-defined goal, says Hossain. At First
Round, every Salon aims to serve startup entrepreneurs. But she’s far more specific:
she wants everyone to walk away with at least two concrete tactics to try out, and
at least one new person they can rely on. She arrived at that objective by asking
founders what they want to change about their work and lives. What they said applies
to many different groups throughout the tech industry:
They're lonely and crave connection with peers.
Building a company is a time-consuming, emotionally-intense roller coaster. They can't
share their fears and anxieties with their employees and o en their co-founders
because they have to inspire confidence and don't want to disappoint. They can't
vent to their families because it'll stress them out too. Events provide a forum where
founders finally feel comfortable sharing with people who can empathize and won't
judge.
"Having a cohort with similar experiences, who can give each other unvarnished
opinions and unconditional support is really invaluable," says Hossain. "I heard from
one founder recently that he spotted another Salon attendee at a coffee shop, they
shared a knowing glance, and he said even that was comforting."
Because the Salon format allows people to get to know each other's goals and
challenges quite well — especially when the same people are brought together
repeatedly — unique bonds form. Several CEOs Hossain has hosted now meet on a
monthly basis for breakfast, and consider each other trusted advisors. There are a
number of stories like this.
They need proven knowledge from people they trust.
Founders don't just want advice. They want to know that something will work,
because they don't have time for it not to. The best source for this is other
entrepreneurs who’ve already overcome the problems they face. Salons are designed
for attendees to describe their most important challenges and crowdsource solutions
that have already worked for others like them.
"All the time, people say they've incorporated ideas they heard at Salons into their
companies to great effect," says Hossain. "One borrowed the idea of a gratitude
channel on Slack, where people would opportunistically post things they were
thankful for — it completely changed their culture. Another learned how to structure
an offsite to generate a far clearer roadmap. One participant recommended writing
down all the reasons your company will die and assigning one person to each reason
— several people took note to try out that tactic. I personally liked the tip of hosting a
dinner for board members the night before a board meeting, on the condition those
attending don’t discuss the company, but rather relate to each other outside their
formal roles. All to say, we try to surface specific, recommended actions as much as
possible."
In tech, there's an endless parade of conferences and cocktail parties, but few answer
these founder desires so exactly. For events to make an impression, figure out what
your audience lacks but badly needs. Engineer the conversations you host to fill
those gaps, and make that your core focus.
THE COMPONENTS OF CATALYTIC EVENTS
Salons tend to achieve goals efficiently because they have the following ingredients:
A curated guest list, ensuring that people have important commonalities
A moderator to direct the conversation and keep it flowing
Prompts that get people to open up, be vulnerable, and share stories
Content that's targeted to attendees' specific challenges
A forum to ask questions they don't normally get to ask
Preparation beforehand that clues attendees into each other's credibility and
skills
Below, Hossain will walk through each of these puzzle pieces so you can assemble
them into an effective whole.
Invite the Right People
Always find a couple common threads that will unite attendees. "What works best for
us is bringing together people who either work in the same functional areas or who
are at companies in the same stage of growth," says Hossain. "We'll host Salons for
all CEOs, or CTOs, or data scientists. But we'll o en get more granular than that,
curating lists of all early-stage CEOs, all mid-stage CEOs, all late-stage CEOs, etc."
These shared attributes in particular allow people to readily empathize with each other
and offer advice that will be relevant to everyone in the room. But you also want a
secondary dynamic. For every group, you want there to be one to two people who
are six-months to a year more experienced than everyone else. Hossain calls these
invitees "teachers," because they're able to share really relevant wisdom with the
benefit of hindsight. They'll have recently slayed the challenges the others, “learners,”
are confronting right now, which makes their advice incredibly rare and valuable.
"At first, I felt guilty inviting people who would mostly dispense advice without
necessarily getting a lot back," she says. "But I was wrong. People love paying forward
the help they’ve gotten in the past, they almost always end up learning something
new anyway, and it gives them a chance to help more people at once. So many
experts find themselves giving the same pointers over coffee a er coffee. But coffee
meetings don't scale like events do."
Generally, if attendees have their functional area or company stage in common, it
won't matter if they're coming from different sectors or industries. They'll still have a lot
to discuss — particularly about management. In Hossain's experience, everyone is
either struggling with it or aspiring to. Once a month, she hosts a breakfast crew of
senior women who come from dramatically different backgrounds, but they always go
overtime dissecting and sharing each other's management tactics.
Outside of these few commonalities, you want to maximize for diversity as much
as you can. Hossain has seen firsthand how having different backgrounds and
identities in the room strengthens the experience. These groups generate more
original insights and have livelier, deeper conversations. For all these reasons, she's
firing on all cylinders to bring diverse groups together in an industry that o en gives
up too easily. Here's what's worked for her:
Set a clear goals for yourself: Quotas aren’t a panacea, but they can be
motivating. She always has the option to exceed them, but simply setting the
bar gives her team the drive to invite 50-50 men and women and over 20%
underrepresented minorities if possible.
Be patient and push ahead: The lack of diversity at tech events is not a
pipeline problem, she says. It's that people don't take the time to go deep
enough into their networks, they fail to discover amazing people that don't
happen to pop up on their first page of LinkedIn results.
Lead a source-a-thon: Rally your broader team, then provide them with the
criteria for invitees and a spreadsheet to capture names, LinkedIn pages,
email addresses if they have them, and whether they feel comfortable
reaching out. Carve out specific time to sit in a room together, mine your
networks, and fill in the rows. Be explicit that you'd like to invite a diverse
cohort. If people can serve as warm connections, have them reach out with
an invite. If you're still struggling, meet with your teammates one-on-one to
scour their networks alongside them.
Call in referrals: "Women refer other women to events three times as o en
as men do," says Hossain. "Same is true of underrepresented minorities.
Don't be shy about asking your extended community (including past event
attendees) to recommend future invites; tell them you'd love their help
increasing diversity at your events. "Being so outward about it used to make
me nervous, but it's effective and people like to help with this." A er every
event she hosts, her team sends out a survey (more on this later), and one of
the questions uses this language to ask for referrals — it's resulted in a steady
influx of incredible people.
Assign Pre-Work that Generates Targeted Content
Before every Salon, Hossain and her team send out emails to every attendee
requesting 1-3 questions they'd like to see tackled during the event. They're
encouraged to ask about specific challenges they're facing right now.
Here are just 10 past examples that hint at the range of topics on leaders’ minds:
How do you structure your weekly exec meetings to get the most out of the
session?
What are your best practices for All Hands?
When and how did you decide to introduce hierarchy? How do you define
titles or tiers?
Internal transparency - what do you share?
How do you deal with founder anxiety?
What KPIs do you focus on, in order of priority? How do you monitor them?
How do you maintain culture while scaling? Will and should it change?
What tactics have you found to be most cost-effective for recruiting lead-gen?
How do you know when to spend time hiring great/exceptional people
rather than just executing with good people that you have?
When evaluating executive candidates, what’s the best way to evaluate one’s
ability to scale both down and up?
These questions drive the content of the program, making it timely and tailored to
everyone's experiences.
"Where would they love insight into what their peers are doing or thinking? We never
promise that their questions will be addressed, but we see this have huge benefits
anyway. They feel more bought in to participating, more listened to, more
understood. They show up because they might get answers they need,” says Hossain.
“Asking for questions is also important because it forces attendees to reflect on things
they might not otherwise. Their work is so fast-paced that they seldom pause to think,
'Oh yeah... what are my most pressing problems that I'd like to see solved? What
can't I really ask others about?' Even taking this moment will make them better
contributors.”
To make Salon content even more relevant, she's instituted a voting system during
cocktail hour before everyone sits down to dinner. She prints the submitted questions
on individual pieces of paper and posts them on the wall. Attendees get three stickers
they can place next to the topics of their choice. At the end, Hossain stack ranks them
by vote — and structures the conversation to go a er the most popular questions first.
Prime People to Be Vulnerable
Hardly anyone feels comfortable getting personal with strangers right away — which
includes divulging weaknesses, admitting what they don't know, confessing struggles
or problems. In order to have constructive conversations where people learn and
bond, you need them to feel safe and start trusting quickly. The most transformative
moments at any events come when people open up and let themselves be vulnerable.
Hossain has found that the earlier someone talks in a conversation, the more
deeply they’ll participate over the rest of the session. So, she’s become an expert at
priming people to contribute faster. Here are the key actions she recommends:
Put a lo y question up on the big screen during cocktails and mingling.
Her favorites include: “In the future, which one of these things do you think
we’ll look back on and think was the most barbaric?” Options might include:
manual driving, labeling based on gender, governing with a two-party
system, poor health care, factory-style education, destroying the
environment, war and eating meat. “With a future-looking, open-ended
question like this, there’s no right or wrong answer, so each person is
‘released’ to offer an opinion,” says Hossain. “People will organically bring it
up in their casual conversations, as I hop between clusters of people. It eases
the group into talking about things that transcend small talk.”
Seed someone in advance who's willing to get vulnerable. Ideally, find a
senior attendee who the others look up to. Pull them aside during mingling
and ask if they'd feel comfortable telling a story about a recent difficulty or
failure early in the discussion. You can also do this as a moderator, but it's
more effective if people hear it from a peer. They follow suit fast.
Set the stage for deeper sharing. A er cocktails, everyone takes a seat, and
Hossain welcomes them with crucial talking points: "Right away, I tell them
that this is an off-the-record, small-talk-free conversation — there's no
tweeting or recording — where they can be open and honest. Unlike at many
other events, they don't need to maintain a facade that they're 'crushing it.'
In fact, the best events I host are those where people don't hold back on
what's going wrong or where they need help. Be yourself and don't be afraid
to say 'this is hard' or 'I'm worried I can't do this.'" In her experience, this
quick monologue elicits a collective sigh of relief.
Use intros to open people up. Emphasize brevity here, but also ask people
to quickly answer a question in addition to providing their name, title and
company as you go around the room for intros. Something like: "What's one
thing that's going really well? What's one thing that's not?" As the facilitator,
this will give you clues about who’s willing to be vulnerable and who might
need some time.
Reinforce openness as a good behavior. Don't just set the tone at the
beginning — keep it top of mind throughout. Whenever anyone shares
something candid, follow up with: "I really appreciated that vulnerability,
thanks so much for that." Call it out. Be grateful. Before you know it, others
will be doing the same.
Run These Exercises to Deepen Connections
Hossain is a fan of quick social and psychological icebreakers that help people
understand themselves and each other fast. She recommends running one of the
following exercises for 10 minutes following intros to foster even greater empathy,
openness and willingness to share. They range from the five-minute personality test to
reframing the “36 Questions That Lead to Love” (which is very helpful for co-founders).
Some of them might sound silly, and it’s easy to be skeptical. She knows this, but a er
experimenting with dozens, swears by their power to energize and unify. Here are her
three go-to exercises:
I Am Circle: Use this when you want people establish their commonalities. Have
everyone stand in a circle with one person in the middle. That person says something
that's true about themselves. If it's true of anyone else, they quickly have to switch
places (like musical chairs).
Whoever doesn't find a spot goes in the middle, and it repeats. "It generally starts off
light, like 'I'm the youngest,' or 'I have two kids,' and then gets deeper and deeper
until people are saying things like, 'I have impostor syndrome,' or 'I grew up poor and
have always felt less than.' The movement is kinetic, and it generates a lot of empathy
right off the bat between people who probably never met before."
Tell Your Story Redux (h/t to Innerspace): Use this to break people out of stale
narratives about their jobs and career arcs. Have people turn to their neighbor and
spend 2 minutes each recounting their life stories to each other. Then apologize,
because you're going to make them do it again. This time, ask them each to tell it in a
way that's totally different from the way they normally would.
"Usually, the first go at this is almost all about work. It's an automatic script. People tell
each other where they went to college and their paths through various jobs that got
them to this moment. When forced to do something different, they immediately start
sharing things they usually never would in a professional setting — and they get really
into it. They'll talk about their childhood or why they actually transitioned jobs — they
give the other person a peek behind the scenes of what happened. When we
reconvene as a big group, we have a few people share what their partner changed
about their narrative and why they found that interesting. It helps people feel like they
got to know at least one person beneath the surface level."
Empathy Exercise (h/t to Reboot): Use this when you want people to share
something very vulnerable, and realize they aren't alone. During the cocktail hour,
have everyone write anonymously on index cards one thing that worries them about
their work or that causes them anxiety — something they feel like they can't share with
many people. Shuffle them thoroughly and place a card at each seat at the table.
Ideally everyone receives someone else's card, and can see that everyone else has
fears and vulnerabilities just like them. It generates a ton of empathy and good will at
the start of the conversation, and opens up candid sharing much earlier.
"We ran this exercise at our recent Founder Summit in New York, and we couldn't
believe how deep people went on these cards," says Hossain. "One wrote, 'I feel like
I'm everyone else's cheerleader, but no one is mine.' Another said, 'I'm thinking of
giving up,' and another said, 'Every time I pitch poorly, I feel like I'm letting my entire
team down.' We had folks read out the card they received, so they could see around
the room how many people clearly agreed or felt the same way. It was really
powerful."
In all of these exercises, the goal is to help people authentically connect and realize
others share their experience, that they can let go and tell it like it is. "When we're all
saying that things are awesome, we're not getting to the core of what's difficult or
finding the help we need. It just creates more distance. The best events shrink that
gap."
Laser In On High-Utility Insights
Cultivating vulnerability and empathy is vital, but only sets the scene. Now you can
turn to the work of surfacing the lessons, tactics and actions that will help the people
in the room overcome their challenges and succeed.
At the start of this phase, Hossain once again frames how to proceed. She says: "Be as
specific in giving advice as possible. This conversation will only be beneficial if
everyone walks away with actions you can implement at your companies. As an
example, don’t just say 'Hire A-players,' instead, tell us about the process you use to
hire great people, the questions you ask in interviews, where you source them." She
also reminds them that they're the ones driving the conversation, and she'd love their
help co-moderating by digging into the most interesting subjects, asking for the
specifics around 'how' to do things, and providing a lot of examples.
In her experience, the best advice is four layers deep, and you have to drill
through each to get there:
1. Initial responses to questions are usually pretty high level and general. Someone
might say, "I'd start instrumenting all the events in that onboarding flow" for instance.
That's a fine place to start. But you have to dig more.
2. Ask a second-order questions based on what you want to learn: How would they
do that? What tools might they use? What actions would they take? I.e. "What events
would you instrument and what analytics backend might you use for that? Who on the
team should look at this stuff? What kind of decisions should they use it to make?"
3. Ask for an example of the advice operating in practice. I.e. "How did that work for
you at Looker?" As a response, the person would ideally walk you through what
events they instrumented in onboarding and how they managed the data.
Anecdotes are extremely useful tools in this context. You want to encourage
storytelling as much as you can, and reinforce people when they share things like,
"Well at Fundera, we ran into that during annual planning..." or "I faced something
similar when we were running Facebook campaigns, we noticed that..." These stories
of struggle and resolution — or failure — might not be perfectly applicable, but they
demonstrate how advice is being applied in ways others can easily pick up and use.
It's critical that moderators consistently model all of these behaviors and actions.
When Hossain facilitates, she shares multiple stories she's heard at past events that
might be instructive or connect to the topic at hand, and she constantly digs into
second and third-layer questions when others in the group don't.
Other rules she's learned for high-utility facilitation:
Keep track of who’s speaking and who’s not - You want people to get
equal airtime, so if you see body language suggesting someone wants to
share, call on them. This goes a long way toward making people feel safe and
supported to chime in.
Interrupt the long-winded - This can be extremely hard, but you have to do
it. Make it easier by warning people at the start that you might do it, so they
shouldn't take it personally. One smooth transition is to jump in a er a point
and say, "Hey, sorry to cut you off, but I thought that was really interesting and
wondered if anyone else felt that way." You'll see a show of hands, and can
easily transition to someone else who may not have said much yet.
Give people the floor to disagree - Not everything people share should be
taken as gospel. If someone makes a contentious point or bold claim, ask if
people agree or not. It helps mix things up and draw more people in. O en,
people will sit on the sidelines rather than contradict unless prompted. You
want to give everyone a voice. This is also how you can identify and surface
contrarian insights that end up being really interesting for everyone.
Move on from conflicts - Constructive debate is good if many people are
jumping in, but if it boils down to a dispute between two, the moderator
should step in and encourage them to take it offline if they want to continue.
Time is always fleeting at events, so to so en the blow, just remind the group
that you want to get to more of their questions.
Measure Your Success to Keep Improving
Most organizations don't measure the success or utility of their events in a way that
actually helps them get better over time. Hossain and her team have made this an
imperative for First Round by sending out surveys immediately following events, and
using them to track NPS scores. As soon as surveys are submitted, the results are
pushed to a Slack channel for easy viewing and discussion. This also allows the team
to jump on low scores to diagnose what happened right away.
Here are the questions they ask every time:
1. How likely would you be to recommend a First Round Salon to a friend or coworker in
a similar role?
2. Overall, how satisfied were you with the Salon?
•Very satisfied
•Somewhat satisfied
•Neither satisfied nor dissatisfied
•Somewhat dissatisfied
•Very dissatisfied
3.What did you like most about the Salon?
4. Are there any ways we could have improved the Salon?
5. Were you able to take any advice from the Salon that you can implement at your
company?
•Yes, will implement this week
•Yes, will implement this month
•Yes, will implement this year
•No
6. If you answered yes above, what's one thing that you learned that you'll implement
at your company?
7. Are there any other outstanding people that you think should be involved in these
events?
"I know NPS isn't a perfect metric, but it's pretty helpful for events. Combined with
customer satisfaction, It lets you know whether it resonated with an attendee enough
to come back or recommend a friend. That's pretty telling," Hossain says. "Most
importantly, it helps me benchmark against myself. I'm not competing against other
VCs or companies — my eye is on the prize of doing what we do well even better."
On the qualitative side, the survey asks a few key free-response questions. The team
compiles all of the constructive and positive feedback they receive, and reviews it
once a week to decide what they want to double down on, tweak or try next. Many of
the changes they’ve made to the format came out of these surveys.
"For example, when I first started doing this, I was a very light-touch moderator — I
didn't want to get in people's way. But the feedback convinced me I needed to take a
stronger tack and provide more direction," she says. "Some people want to cover
more, some wish to go deeper on less. We try to find a happy medium, but it's all a
real-time balancing act."
Bringing It All Together
If events are part of your strategy, don't run to the default. There are plenty of basic
gatherings out there that don't move people or companies forward. Instead, consider
trying out facilitated conversations with the people who matter to you the most,
whether they are customers, colleagues, investors, or even friends. When you do, run
the following playbook:
Set a clear goal: One that serves attendee needs that aren't getting met
elsewhere.
Curate the right people: Organize around a couple common threads, but
otherwise diversify to the max.
Rely on a user-generated agenda: Ask people what they want to learn
ahead of time, and use that to structure the conversation.
Prime vulnerability: Try out the exercises described above to make people
more comfortable with opening up and sharing their struggles early in the
conversation. That's the only way you'll get to solutions.
Focus on utility: Ask deeper questions to get to the 'how' and specific
advice/actions. Encourage people to tell stories and offer examples of their
advice in practice.
Never stop measuring: Set up a system to capture and regularly review
quantitative and qualitative evaluations from attendees so you can make
smart decisions about what’s next.
Photography by Bonnie Rae Mills.

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6/15/2020 Cut Through The Small Talk and Connect — Lessons from 130+ Dinners, Summits and Salons

ners, Summits and Salons | First Round Review

People & Culture

Cut Through The Small Talk

and Connect — Lessons from

130+ Dinners, Summits and

place for a while. In addition to a corporate coach, I recommend a therapist. It’s

entirely transformed my ability to take on diﬀerent challenges.”

attendees, steady moderation, thoughtful prompts and menu of topics, safe

co-led a storytelling series that convinced dozens of hard-nosed MBAs to open up

and most recently as a professional coach.

as the winning combination: intention, structure, vulnerability and utility.

equipped to win, keep reading. They'll remember you fondly forever.

GOOD EVENTS SERVE PRECISE GOALS

to many diﬀerent groups throughout the tech industry:

They're lonely and crave connection with peers.

Building a company is a time-consuming, emotionally-intense roller coaster. They can't

shared a knowing glance, and he said even that was comforting."

number of stories like this.

They need proven knowledge from people they trust.

that have already worked for others like them.

an oﬀsite to generate a far clearer roadmap. One participant recommended writing

those gaps, and make that your core focus.

THE COMPONENTS OF CATALYTIC EVENTS

A curated guest list, ensuring that people have important commonalities

A moderator to direct the conversation and keep it ﬂowing

Content that's targeted to attendees' speciﬁc challenges

A forum to ask questions they don't normally get to ask

them into an eﬀective whole.

Invite the Right People

meetings don't scale like events do."

Generally, if attendees have their functional area or company stage in common, it

to discuss — particularly about management. In Hossain's experience, everyone is

overtime dissecting and sharing each other's management tactics.

up too easily. Here's what's worked for her:

underrepresented minorities if possible.

happen to pop up on their ﬁrst page of LinkedIn results.

criteria for invitees and a spreadsheet to capture names, LinkedIn pages,

an invite. If you're still struggling, meet with your teammates one-on-one to

scour their networks alongside them.

Call in referrals: "Women refer other women to events three times as o en

as men do," says Hossain. "Same is true of underrepresented minorities.

increasing diversity at your events. "Being so outward about it used to make

inﬂux of incredible people.

Assign Pre-Work that Generates Targeted Content

encouraged to ask about speciﬁc challenges they're facing right now.

What are your best practices for All Hands?

Internal transparency - what do you share?

How do you deal with founder anxiety?

How do you know when to spend time hiring great/exceptional people

ability to scale both down and up?

Prime People to Be Vulnerable

or problems. In order to have constructive conversations where people learn and

Put a lo y question up on the big screen during cocktails and mingling.

manual driving, labeling based on gender, governing with a two-party

system, poor health care, factory-style education, destroying the

environment, war and eating meat. “With a future-looking, open-ended

question like this, there’s no right or wrong answer, so each person is

‘released’ to oﬀer an opinion,” says Hossain. “People will organically bring it

up in their casual conversations, as I hop between clusters of people. It eases

Seed someone in advance who's willing to get vulnerable. Ideally, ﬁnd a

that this is an oﬀ-the-record, small-talk-free conversation — there's no