Mastermind Dinners

Mastermind Dinners: Build Lifelong Relationships by Connecting Experts, Influencers and Linchpins

By: Jayson Gaignard (2015)

[Pigeonhole] A Practical Rule Book

[Premise] A “Mastermind Dinner” is one person’s effort to connect individuals with a similar commonalities through a curated dinner experience of 4-8 people. Conducting these dinners will deepen the organizer’s relationships with the attendees and build a stronger network for all that are involved.

  1. Background and Mindset (p 11-43)
  2. Build the guest list (p 44 – 75)
  3. Prep the location (p 76 – 77)
  4. Conduct the dinner (p 77 – 95)

[Key Points]

  • Relationship building (or networking) is a mindset that stems from a deep caring for others
  • I would rather have a closed Facebook community of 500 members for my podcast than an email list of 5,000
  • Mastermind dinners are great for:
    • Reconnecting with old ties
    • Introducing people who can benefit from knowing each other
    • Connecting with people who I’ve been meaning to connect with for quite some time
  • “Local” Dinners are hosted in your home area, “Location” dinners are hosted when traveling
  • Tip: Hold a dinner for speakers. Event producers rarely do anything for their speakers
  • Be sure there is at least one commonality amongst your guests
    • Don’t select people at both extremes of the unifying commonality
    • Don’t invite anyone with a conflicting interest (competitors)
  • Group of 3 is a little too small, 4 is a good natural set up.  At 5 you begin to act as the facilitator. At 6 you should consider a round table and at 8 consider a private dining room.
  • Run a couple of smaller dinners with less “known” names to get comfortable
  • Be clear on your “Why”.  Why are you putting on dinners? Why do you want certain individuals?
  • Avoid reaching out to potential guests “cold”. Try to leverage direct connections or social media connections.
  • You do not need to have a commonality with your guests, they must have an commonality.  Commonalities include:
    • an Organization
    • a Platform
    • an Event
  • Build a guest list by inviting the most likely ‘yes’ first, then the second and so on (this is called the ‘Food Chain’ approach) – Or – Get a ‘big fish’ first and you will find getting other yeses will be easier (this is called the ‘Anchor Tenant’ approach)
  • A good salesman knows that his first real sale is himself
    • Sample sales video:
  • Trying to land a big name?
    • “What works in the military works in marketing, and that’s the unexpected”
    • Why are you reaching out to this particular person? What is the desired outcome? Be very clear.
    • Are there alternative people who could help me reach the same desired outcome?
    • The most important question: What’s in it for them?
  • It’s imperative that you know who you’re reaching out to, inside and out.
  • To reach someone, try to use the least ‘noisy’ medium for them
  • The success of the outreach is often in direct proportion to the amount of effort you put into it. Getting them emotionally hooked and eliciting a response is more difficult than just getting a message in front of them.
  • For emails use open-ended subject lines and try to include something specific to them
    • Keep the email short and prompt a response that invites a second email
  • Send personal videos to the attendees 6 months after the event
  • Tool for no response: Yesware
    • Try to restructure your email and provide a little more information
    • Simply resend the original email
  • Responding to a “No”: try “under what circumstances would you say yes?”
  • Tools: | | LinkedIn search
  • Facebook post when traveling: “Traveling to San Diego, do you have anybody you think I should connect with while I’m in town?”
  • For Local Dinners, set up one or two ‘go to’ locations
  • Two approaches to guests:
    • Don’t do any research so that the conversation is open and natural
    • Know as much as possible about each individual so that you can facilitate good conversation and find ‘uncommon commonalities’ (recommended)
  • Send a calendar invite for the event, but do not share the guest list
    • Send a quick reminder email the night before
    • Send a text the day of so that they have your phone number readily available
  • Recommended that the host pay for the meal
    • If it’s a ‘user pay’ dinner, invite the guests to a ‘dutch treat’ dinner and set up an Eventbrite page to collect money in advance
    • Or, can play payment games such as credit card roulette or phone stacking
  • With 6 or more guests, consider assigned seating
    • ‘Table Searing’ is sitting the most interesting and outgoing person at the center of the table
    • Switch seats at some point in the dinner to mix up the conversation
    • Host should sit in the center to be the ‘conversation cop’
  • Arrive 25 – 60 minutes early to make sure you have the right table and that no guests are left waiting
  • Kick off the dinner by explaining your relationship with each person, why everyone is there and the ground rules
    • Everything shared in the room stays in the room
    • Order wine by the glass, not the bottle
    • No cell phones
    • Order first and get that out of the way
    • Set the end time (you can always go to the bar after)
  • Start off the formal introductions yourself
    • Top professional or business achievement
    • Top personal achievement
    • a Bold Goal
    • “Thorns and Roses” (something going well, something with potential (a bud) and something that is a pain
    • Any other ice breakers
  • Conversation should kick off after intros – be a facilitator
    • Be conscious of people’s body language at the table
    • make sure that everyone shares stories and experiences and enjoys themselves
  • Take a picture of the group to share on social media, or to be part of a follow up email
  • Connect people after the event with a group email or Facebook message
    • Thank them for investing their time
    • Include one or two points from the dinner
    • Include a resource list of items that the conversations covered
  • Carry a small notebook to record important points and resources from the dinner
  • If a guests asks you how they can “deliver value to you” after the meal, ask them to connect you to an interesting person
  • Email the group a year later to say “Happy Anniversary”
  • use #Mdinners to enter into a monthly $100 drawing
  • Contact the author at