Be a graduate student or recently graduate PhD with high career aspirations.
Keep the free registrations for your buddies or prospective future employers; their work need not bear any relationship to the topic of workshop.
Have several papers that you wrote be rejected from the main conference.
Never finalise the program until the day of the workshop in case some important future employer shows interest at the last stage and you need to be able to allocate him 3 hours.
Don’t rely on telepresence.
Invite several preferably ageing eminent researchers to give their standard talk which need not bear any relationship with the topic of the workshop. (see also “How to dine“).
Organise a poster session, and do not check with the hotel whether you are allowed to stick posters on the wall. Only allocate 10 minutes for poster session (preferably during the ski break or coffee break).
Presume someone else will magically ensure the presence of a working data projector.
Promise to organise a special issue arising from the workshop (not necessary to actually carry through with the special issue).
Pick a topic on which there has been a workshop for the past 7 years and rely on Laplace’s rule of succession.
Don’t try and organise a workshop on a topic that is too relevant or interesting especially in the real world.
Arrange the schedule in as inconvenient a manner possible; for example start at 7:00am and have a break for 8 hours in the middle of the day and have evening technical sessions that run until midnight or later.
Organise a panel discussion and ask participants to come with a long list or pre-prepared platitudes.
Workshop proposal guidelines are exactly that: guides that only the unimaginative fall for. Do not feel constrained by them.
If your workshop proposal is rejected, simply organise an unofficial satellite workshop which is invitation only and held before the main conference. Update: If you have a personal relationship with an important steering committee member, you can get your unofficial workshop listed on the main conference web page in a manner that makes it not only look official but in fact more important than the official workshop series.
Identify a genuinely new and as yet unformalised and unpopular line of research with many challenging open problems.