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

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.

We thought it was about time Hossain shared what she knows. After 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 often 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 often 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 after 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 often 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 often 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." After 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 after 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 lofty 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. After 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 after 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 after 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. Often, 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 soften 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.