Enhance offsite planning guidelines (#14263)

Added guidelines for organizing effective offsites, including attendee considerations and location choices.

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## Article checklist

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Author: pauldambra

contents/handbook/company/offsites.md

@@ -56,9 +56,12 @@ Each team member is still responsible for booking their own flights.
 Some guidelines:
 
 - Quarterly planning is a great focal point for team offsites – it's worth scheduling your meetup for the week of planning.
-- Outside of your small team, you should only invite people who actually need to attend to make the offsite a success - if it would be 'nice to have' them attend, they shouldn't be going. 
+- Outside of your small team, you should only invite people who actually need to attend to make the offsite a success - if it would be 'nice to have' them attend, they shouldn't be going.
+- It can be useful to combine offsites but beware if you add too many people everything gets harder to arrange. There's no hard and fast rule here but the more people that are attending the more concrete you need to be on who is organising and why people are attending. It will be more work and you should be purposeful about it.
+- If the number of attendees is >10 actively consider if Kendal should be attending so there is a person attending whose only focus is making sure it goes well and everyone else can focus on the work of the offsite.
 - Specify offsite start and end times down to the hour, for clarity and efficient use of everyone's time.
 - These offsites don't happen very often and involve a lot of travel, so make sure you make the most out of it by having an agenda and an idea of what you want to achieve _before_ the start of the trip. Also, it's a good idea to have an expectation-setting session (can be async in a Figjam) to ensure everyone is on the same page about what the outcome/output of the offsite should be.
+- Choose a location that minimises layovers for attendees.
 - Make it very clear who is participating in each session. Sessions / activities require full participation from attendees, especially for the likes of a hackathon given it runs over multiple days. Ideally one person should be responsible for the agenda and run a kick-off at the start of the hackathon.
 - You should do a [360 degree feedback session](/handbook/people/feedback#ground-rules). It can feel uncomfortable doing these, but almost everyone who's done one at PostHog has come out feeling better and with a whole host of things they can improve. These are best in person.
     - This can work better over a shared cooked meal or takeaway in the accommodation rather than a noisy restaurant, particularly for people who might be anxious about the format or the feedback.