A few weeks ago I had an incredible conversation with Nick Gray (🎧 Ep68) on how to host a successful cocktail party. He literally wrote the book on building big relationships through small gatherings. I’m so used to hosting/attending dinner parties, but they’re so time-consuming, complicated, and stressful. I didn't realize cocktail parties are perfect for the life optimizer (80% of the benefits and 20% of the work). This blog post highlights the important aspects of Nick’s party operating system. Use them and you can organize and execute successful events.
After talking to Nick, I’m sold on how much a two-hour high-energy experience can help you live a richer life, so I’m going to try and adapt his plan to host an event in San Francisco for All the Hacks listeners and readers (ie: you!). So if you’ll be in SF on 11/30, please RSVP here and I hope to see you there!
🍸 Hosting Memorable Cocktail Parties
If the idea of hosting an event seems stressful, then the plan I learned from Nick Gray, that I’ll lay out below, should make things so much easier. Also, keep in mind this isn’t a dinner party that can require lots of cooking, last forever and have a lot of dishes to clean up. It’s a cocktail party that if done right, should be easy to plan/host. In fact, my favorite takeaway from Nick is that if you can get in the routine of hosting a cocktail party every few months, it can serve as the perfect way to reconnect with new people you meet. For example, instead of scheduling a follow up meeting/lunch with a new professional connection or play date with a family you meet at the park, you could just say “it was great meeting you, I’m hosting a cocktail party next month and would love to invite you to join.” So if that sounds good to you, or even if you just want tips for an event you’re already hosting, here’s everything you need to know:
The Pre-Party Stage
⌚ Scheduling
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Choose a non-competitive time. The best nights are Monday, Tuesday, and Wednesday because they don’t compete with social schedules. Also consider a time that accommodates parents' needs. Make your party easy to say yes to by hosting it on a less-trafficked evening.
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Give yourself a short lead time. Aim for a date that is 3-4 weeks away, so you’ll have enough time to prepare, without procrastinating. There is no perfect time, so don’t wait for it.
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Set an end time. Communicate that the party has an end time, so guests will show up on time. Your party should last two hours, which means there will still be plenty of energy and conversation right up to the end. Having your party end on a high note will ingrain in the people's minds that they had a good time, and they will want to come back again.
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Consider planning for childcare. If kids are invited, think about how you could make it as easy as possible for you and your guests. You could hire a babysitter and/or create a separate area for a “kids party.”
🧑🤝🧑 Start with your core group
It's crucial to get the first five commitments before you do any deep planning. Let your closest friends, neighbors, or colleagues that you will be hosting a cocktail party on (certain) date, and ask if they will join you. Using this method, you can test the date and time you selected to see if it’s viable. This approach saves you time preparing invitations (if the time ends up not working) and signals to the rest of the invitees that a party is happening. Here is what Nick suggested, “I am thinking of hosting a cocktail party on Tuesday 6:00pm-8:00pm. Would that work for you?” Simple, straightforward.
When the five commitments have been secured, create an online RSVP page and request those first few people RSVP online. This will help you get an accurate headcount. More importantly, it signals social proof that people are already attending, and entices others to come as well. RSVP pages are an effective way to create a social contract. After the five have RSVP’d “yes”, invite everyone else. Nick recommends Mixily and Partiful since they are both free, but Paperless Post has a bit more customization. See Nick’s platform suggestions here.
👭 15 to 20 attendees is ideal
As host, you don't actually want to play the role of “host” the whole time, so don’t have your event be too big. That can be exhausting, because you are always on and your goal should be to step back and serve as facilitator, since after all, cocktail parties are intended to bring people together. So it’s your job to bring them together.
But don’t go too small, having more than a few guests actually makes hosting easier (Nick mentioned Priya Parker's book The Art of Gathering). Conversations naturally split into two when you have more than 6-8 people. That's why Nick recommends 15-20 people. There are enough connections to be made with this many people, and the limit of two hours means your guests probably won't have a chance to talk to everyone. This will leave guests with a sense of curiosity about the next event.
😰 Take steps to reduce stress
Your goal to be should have an easy, simple, lightweight event that eliminates the stress associated with planning. So here are some tips:
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No food. If you include food, serve simple snacks like chips/dip, pretzels and/or veggies. More food means more stress. This is not a dinner party!
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Cocktails only (wine is OK, but no beer). Setting up a self-service bar would be ideal. Have a few different bottles of alcohol, mixers, and ice. Avoid serving beer, since everyone has different preferences. Nick’s hosted hundreds of parties without beer and said it always works (he also calls the extra bottles, cans, and space it takes up "party shrapnel”). Wine is fine, but stick to limited options. Two bottles of red, two of white, and maybe some rose, if it's summer.
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Be sure to offer non-alcoholic options. Perhaps some juice, water, or seltzer.
🙋 Set clear expectations
The simple addition of structure and expectations can make your cocktail party so much better. Hands down, Nick says this is one of the primary indicators of hosting a successful event. Here is a simple way to articulate these expectations:
“Hey, I’m getting friends together for cocktails and icebreakers. Because I am terrible at remembering names, we’ll have name tags. You don’t have to bring anything, we’ll have mixers, drinks, alcohol and seltzer. Hopefully you’ll meet some new friends.”
More on the name tags and icebreakers below, but Nick includes some sample event pages and copy you can use on his website here, or in his book.
📣 Send a few reminders leading up to the party
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One week before. This reminder is pretty standard. You want to send a brief note that highlights the date and time, but also points to upcoming details: “Hey everyone! We are looking forward to seeing you guys next Wednesday at 6 PM. More details to follow.”
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Three days before. This reminder is unique. Again, repeat the date and time, but this time include some guest bios. It is a helpful way to ease anxiety for some guests and gives people an idea of who is attending and who they might want to meet. An example of a bio could be: “Nick Gray - recently moved to Austin, Texas. He lived in New York for 13 years. Ask him about green tea.” This process should not take you longer than an hour.
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The morning of the party. One last message! You can use the same email that you sent three days before just to give a last reminder. You’ll send all of these messages to keep your party top of mind and ensure a great attendance.
The Party Starts
📛 Use name tags
It’s an easy way to make an introduction and an easier way to remember someone's name. It’s a simple but effective strategy. Nick says this is a hill that he will die on and even for a casual social gathering of friends and neighbors, name tags are a must.
🧊 Use icebreakers
I can see a few of you rolling your eyes, but hear me out. Icebreakers, when done right, let people share a bit of their personality and help spark new conversations. You could introduce them saying “I do icebreakers, so we can all meet somebody new. I hope you'll say hello to a few new faces.”
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Set the rules for sharing. Before each icebreaker, tell guests how to include their names, their work (or something they're excited about), and the answer to the icebreaker question. Repeat this format each time you do an icebreaker.
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Provide clear instructions. Instructions reduce surprises. The host should lead first, then ask permission for the person on their right or left to proceed next, and then indicate the direction the group should go.
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It should take five minutes to complete. The trick is to have everyone standing. Sitting down leads to follow-up questions.
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Lead yourself. There is nothing more frustrating than someone taking forever with an introduction, so go first and set a good example yourself. Also, don’t be afraid to stop people that are talking too long (or even have your spouse or close friend go second and intentionally take a long time so you can politely follow up with a reminder to be quick).
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Do three rounds throughout the party. Icebreakers serve as natural conversation starters and endings. The first icebreaker should be done in the first 10-20 minutes of the party, before everyone has arrived. It is an awkward time, when energy levels aren't high, but an early icebreaker will help release that energy. Then you can do it again 20 minutes later when everyone is present and another 30 minutes later.
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Get started with something simple. Make sure your icebreaker is easy to answer, will move quickly, and the answers won’t elicit judgment from others. Ask questions like “what’s one of your favorite things to eat for breakfast?” because breakfast is light, human, and taps into your personality. Stay away from “what’s your favorite book ever?” Books are subjective, definitive, and can elicit judgment from others. The icebreakers can get deeper as the party progresses, but ease your way into that (e.g., “what is one of your favorite purchases that made you life better the past year?” or “what is one of your favorite pieces of media that you have consumed over the last couple of months?”)
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As the host, be quiet. As soon as everyone has had a turn, the host shouldn’t say anything. Let the natural awkwardness turn into liveliness. Turn up the music volume again and continue.
🎵 Put on background music
Don’t stress about a playlist, just use a curated playlist that someone else curated. The music should be upbeat, positive, easy/happy, and not too loud. (Or you can use Nick's playlist)
👋 When it’s over, kick people out (respectively, of course)
Time flies when you are having fun, but stick to the end time. The proper way to handle this is to communicate it during the party. Make a last call announcement 15 minutes before the party ends.
“Thank you all for coming! You all made it very special. It's 7:45. I said the party would last until 8:00. Since this is a school night, I want to make sure everyone gets home early. Grab a last drink, say hi to somebody you haven't met yet, and we will wrap it up in about 15 minutes.” (then turn the music back on)
After 15 minutes, turn the lights up and the music down. Thank everyone again for coming and take a group selfie (it'll be helpful, trust me). The goal with this is to clearly demonstrate the party's finality.
Post-Party
✉️ Send a thank you note with the group selfie
In the morning, send a short message thanking everyone for attending. Include the group photo (as more social proof) and ask them if they'd like to be invited again. It's an easy "yes" and is a way to start your guest list for your next cocktail party.
It may be obvious, but as the host, you want it to feel like an awesome and easy experience. If you felt more energized than you were before the party, it’s an indicator that you are doing something right. I am sure if you followed all of these tips, you gave people the structure and opportunity to feel comfortable and meet many other people.
🤔 Now what?
If you loved this and want more, I know you will enjoy my conversations with Nick: Check out the full episode on cocktail parties and museum hacks (🎧 Ep68) and our follow up on maximizing points, travel destinations and jet lag (🎧 Ep69).
And definitely check out Nick’s awesome book (The 2-Hour Cocktail Party: How to Build Big Relationships with Small Gatherings) and the website to share so much more content on party planning.
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