Generational Dinner #1

Back in January, I set in motion the idea to organize monthly dinners to bring together different generations to share their wisdom over an intimate meal. Here’s a detailed breakdown on why, what I’ve learned from organizing the first event, and what things might look like moving forward.

Overview of contents:

• The Motivation/Objective
• Theme
• Venue + Event Design
  • Space
  • Design
  • Agenda/Flow
• Financials
• Reflections

The Motivation/Objective

Business:

In 2020, with COVID, then following the birth of Geralt in 2022, I decided to defer my plan to facilitate mastermind groups till 2024. I thought it might be meaningful to get back into organizing at least 1 meeting a month this year to build momentum leading to it.

• Not familiar with mastermind groups? Give this post a read “The Good, Bad, and Ugly of Mastermind Groups“
• This would allow me to polish up my skills as a facilitator.
• To start to build awareness around my ability to bring together great people and give them great experiences.
• This wouldn’t be a lead generation/marketing activity (free workshop/events would be).
• Nor would this be the main offering. The financial breakdown further down in this post will clearly show that it’s a loss leader.
• But it could be a potential “middle of funnel” activity that would help surface those who are willing to invest (both more time + money) in continual learning from those who aren’t.

Personal:

Besides business, this was honestly just as important to me personally. I had severely withdrawn myself from attending public community and networking events. Both because I wanted to minimize exposure with 2 kids in the house, but also because public events were generally really time consuming (~2-hrs round trip transit to get to Vancouver + generally 2-3 hours more for the event itself) and I didn’t want to burden my wife with putting both the kids to bed alone too many evenings.

• As a consequence, I had greatly neglected cultivating and maintaining my network.
• Even though I’m an introvert and generally find networking events exhausting. I was sorely craving companionship outside my immediate circle – immigrant parents can probably relate (without my parents/in-laws around, raising 2 children takes up all your time. I only see 2 other friends and even so, maybe only once every 1-2 months).
• I personally valued not only facilitating, but participating in mastermind groups. It helped keep me growing, learning, and motivated.

Theme

To maintain focus and maximize learning, each event was designed to have a topic for discussion. This month’s topic was Negotiating a Promotion/Raise. You can read about the lessons on this topic in this separate blog post here.

There’s no perfect formula to selecting a theme, but here are some reflections specific to my choice:

• It seemed like an interesting and popular topic that would apply to a lot of people.
• Given current conditions of the job market and many people re-evaluating their careers, timing felt appropriate.

In hindsight:

Gosh was it difficult to fill this event with the right people!

• Being a paid event, ZERO organic registrations (no surprise).
• I very quickly realized that my network wasn’t a good match:
  1. I don’t believe I’m intentionally racist/ageist/sexist, but quickly realized that my network is mostly people who look like me (male, Asian, millennial). I was able to eventually fill the room with a good mix of people but it did take a lot of heavy lifting.
  2. Most of my network are entrepreneurs/freelancers – and the topic obviously doesn’t appeal to them.

I probably ended up reaching out to close to 200 people to land at 12 people expressing interest. With a bug/COVID(?) going around, there were some last minute cancellations as well and we ended up with a room of 7 people. Smaller than I’d hope, but still a healthy enough number for meaningful discussions and connection.

Venue + Event Design

I believe I put great through into the design and flow of my events. Here’s a peek under the hood if it’ll help you understand what to think about when planning yours.

For this event, the objective was to encourage discussions, create a safe and welcoming space, minimize my financial risks,

Space

For any in-person event, this is the biggest factor. It’s not only important to have a space that can hold the # of guests you’re anticipating, you’ll also want to consider layout, ambiance, and flow through the space to facilitate the best experience possible for your attendees.

My Considerations:

• Acoustics – From previous events, I’ve learned that bad acoustics can ruin everything. Can’t network if you can’t hear the other person or need to shout to get your point across.
• Privacy – A private dining room was the choice both for reduced ambient noise but also to ensure that guests felt comfortable discussing the topic without outside judgement.
• Lighting + Music – Doesn’t need to be amazing, but they help set the ambiance to facilitate networking.
• Nametags – obvious, but they always help reduce social anxiety, the stress of remembering names, and when people address other’s by their name, it helps form quicker and stronger bonds.
• Price + Quality – Not a pizza dinner, but also not too extravagant as an expensive venue would mean more financial risk for me and make it harder to sell more expensive tickets.

We ended up doing it at the private Growler Room at Romer’s Burger Bar in Kitsilano. Side note, the booking experience + actual event was great, definitely recommend for hosting private dinners for groups of under 25.

Design

• Menu – To maximize a 2-hr event, I wanted to reduce distractions. Menu options were provided in advance so attendees need not deliberate during the event and could focus on their discussions.
• Seating – Was also planned out ahead of time to ensure that people would be placed with others that they might learn the most from. Also helps with serving.
• Guest Speaker – Booked a salary negotiation coach but unfortunately due to an emergency he had to pull out. Thankfully Leslie Barrow who was just as qualified pulled through 🙂 Having a guest speaker adds credibility (as I’m obviously not an expert on the topic), helps secure registrations, and also helps spark discussions on the topic by planting some initial talking points.
• Diversity – I did my best to select for diversity amongst those invited. We ended up with a good mix of 7 people, of which:
  • Gender: 2 female
  • Generations: 1 Gen-Z, 3 Millennials, 3 Gen-X
  • Race: 4 Asian, 1 Middle Eastern, 2 Caucasian
  • Experience: 3 founders, 3 management or higher, 1 junior
• Payment – I was worried (albeit unnecessarily) that we’d end up with a room full of millennials if I did not moderate registrations. Because of this, registration on the event page did not require payment nor guarantee attendance. Some (not all) last minute cancellations might have been because those who registered did not feel as committed without putting down payment. From past experience, free events tend to have a 50% registration to attendance ratio. Paid events close to 90%+.
• Exceeding expectations – Something I try to consciously apply to the design process of any of my offerings/events as this is core to your client/attendees perception of a positive/negative experience. I was hesitant to include drinks in pricing as I was uncertain about number of attendees to begin with and didn’t want to make promises I would hesitate to keep. But since we had a smaller group and fell short of the minimum spend for the room booking, instead of seeing this as a negative and trying to recoup the loss by encouraging guests to purchase their own drinks out of pocket; since I’d probably have to cover any shortage anyways, I decided to offer open bar on the house for those that attended.

Agenda/Flow

• Arrived at approximately 5:10pm myself to set up and get myself in the right mindset for the evening.
• My introduction checklist:
  • Reiterate reason for gathering – primes everyone to be in the right space mentally for the evening.
  • Land acknowledgement – gratitude.
  • Agenda – set expectations on flow for the evening.
  • Code of conduct – to set the tone for the space so that guests can share authentically and respectfully without fear of judgement.

Financials

Original intention: $75 (tax and tip inclusive, excluding drinks). Breaking it down:

• $44 dinner
• $8 gratuity (18% required for the booking)
• $23 for event coordination

Expenses:

• 7 dinners = $308
• Drinks = $77.4
• Taxes = $26.79
• Tip = $69.37
• Total = $481.56

Revenue:

• Myself + Speaker excluded. 5 x $75 = $375
• Net loss/out of pocket expenditure = $106.56

Total time spent (yes I track my time for all my activities by category/projects) = 16hrs

Reflections

• Not a profit driver – even with higher attendance, margin wouldn’t be justifiable, more so considering the required time investment to organize. But that’s OK, it wasn’t the intention to begin with.
• Overall sentiment was positive. Despite the smaller crowd, everyone, and more importantly myself, had a good experience and learned a lot.
• Will I continue to host these monthly dinners? Yes, though not in May/June/July as I will be back in Asia for some work + time with family.
• Exploring the possibility of partnering with another friend who hosts separate but similar monthly discussion-oriented dinners.
• Planning on dropping the generational theme due to the added layer of complexity that I currently lack the network to leverage. That said, will still actively curate a diverse group because a cognitively diverse group makes for the best discussions.
• Open to restaurant suggestions – would like to maintain some level of private/semi-private dining area + ability to order ahead of time. I believe these were the 2 key elements that made it an amazing experience. A more central location (i.e. Burnaby) would be fairer for everyone to reduce commute time.
• May need to revisit pricing/payment timing – another option is to make these free to attend, buy-your-own-food/drink. But I’m hesitant as it introduces distractions from the discussion and affects venue choices. Unfortunately I may have to compromise depending on demand + effort involved in planning these events. Exact decision TBD.