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“I hated my company Christmas dinners because they felt like a chore. What’s the point of events that are just an excuse for food and drinks? Is it for people to get smashed? To have an obligatory holiday routine that people need to go through? If you want your budget to be well-spent and to not miss out on opportunities to deeply connect, you have to be intentional,” says Siddhi Mittal, founder of Yhangry, a marketplace that connects people with private chefs.
Here are Siddhi’s top tips for planning a holiday event properly.
Start with a clear purpose
Ask yourself: what is the purpose of this event? For example, if it’s a year-end celebration like a Christmas dinner, the goal could be threefold:
- Reflect on the past year — acknowledge the good times and challenges.
- Strengthen team bonds.
- Look ahead to the new year.
You may also use the end of the year as a clear ritual to wind down work for holiday hibernation — it gives people permission to shut off for some time and come back with renewed energy and focus.
Once you have the goals in mind, you can design an event that goes beyond a routine dinner — and becomes an experience.
Think about your senior team differently
When organising events for leadership teams (C-Suite or similar), the stakes are higher. These individuals drive the company’s vision and energy. Their gatherings should focus on aligning the mission and fostering deep connections, ensuring they’re inspired to lead their teams effectively. Your goal is to make them feel extra special and valued.
Have a clear budget
The type of event you plan will naturally depend on your budget. A per-person budget for dinner should reflect the value you’re placing on this event. A great event doesn’t have to be expensive, but it does need to feel intentional and high quality. The higher your budget, the more options you have. For your C-suite, you should be pulling out the stops.
- £15-20 per person: opt for a casual restaurant or something simple.
- £50-75 per person: aim for a higher-quality experience, like a better restaurant or a simple catering option.
- £100+: consider private dining with a bespoke menu — you can access well-known chefs at this price point — to make it truly special.
Encourage attendees to dress up
This levels the playing field and sets the tone for a special evening.
Have a seating arrangement
It plays a significant role in creating connections. Avoid seating people with their close friends or usual colleagues — this isn’t a reunion for cliques. Instead, encourage new bonds. Identify individuals who might benefit from deeper conversations with others in the company, such as those who don’t often interact. Or, bring together leads from different functions who could do with having a deeper connection.
Be inclusive with drinks
Lots of people choose not to drink alcohol these days for several reasons, and providing appealing alternatives ensures everyone feels included. People can still have a great time without drinking, especially if you curate a great dinner experience.
Create conversation starters
To create a memorable experience, you need to guide the conversation with intentional prompts. Otherwise, people often get stuck in terrible interactions where one or two people dominate. It’s awful. Start with questions that get everyone around the room to say something. It’s nice to do one with each course.
- A good starters question to warm people up should be light but meaningful. For example, ‘What’s one favourite memory or challenge you overcame this year?’ Then watch the magic happen. People reflect, share and connect.
- The main course question can dive deeper as people are warmed up and maybe a drink in. They’ve also already shared a bit so their guards are lower. Example questions could be, ‘How have you personally grown this year through the struggles at the company? What’s one way you’re different now?’ It’s a deep question but vulnerability builds connections.
- The dessert question should be lighter and a bit more fun. It could be something like, ‘If you had to summarise your goals for next year in one word, what would it be?’
Think about adding special touches
What can you do that elevates the experience? Entertainment, music or gifting. You could also hire a facilitator for guided visualisations — it transforms the atmosphere.
On the subject of…Christmas parties
1. The Christmas party season is well and truly here — but how do you ensure everyone feels included?
3. Conversation starters. Here are some questions you can add to conversation cards to leave on the dinner table. If you’ve got a better one, drop us a reply to this email.
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