12 Common Mistakes When Organising a Strategy Planning Session or Workshop:

Scene of meeting going terribly, with a man pretending to hang himself by his tie
We all make mistakes. Don't let your next strategic planning session be one of them. Follow these 12 tips (and a bonus) to make yours a success.

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Sometimes it feels like organising a strategy planning session is harder than creating the actual strategy. After facilitating 100+ strategy session with boards, C-suite, managers and teams, here are some tips that may help you avoid the most common mistakes.

  1. Lack of clear objectives: If you’re booking your strategy day, then thinking about whose coming, then thinking about the agenda, you’re doing it all backwards. Failing to establish clear and specific objectives for the strategy session can lead to a lack of focus and direction. It’s essential to define the purpose of the session first, and let that drive the attendees and the agenda. Useful prompt to consider: 12-months from now, what do we wish we all understood and decided now?
  2. Overloading the agenda: Trying to cover too many topics or cramming too many activities can be overwhelming and counterproductive. If you do only what’s important and do it properly, you’ll have happier participants and better outcomes.
  3. Ignoring participant diversity: Strategy sessions often involve people from various departments , ages, technical expertise and backgrounds. Not considering the diversity of participants can hinder engagement and limit the range of perspectives presented. When in doubt, provide plenty of space and mechanisms to elicit response from all who are attending.
  4. Neglecting pre-session preparation: CANNOT STRESS ENOUGH!! Without providing participants with relevant materials or pre-session assignments, you’re going to waste big chunks of time in one of the most important meetings for the year. A good rule of thumb is 1 hour of prep for each hour of a participant (e.g. 8 people for 8 hours requires 64 hours of prep). It sounds like a lot. Until you start getting awesome results from having excellently prepared session.
  5. Lack of facilitation skills: A well-facilitated strategy session can make a significant difference in its effectiveness. A facilitator be part-coach, part-referee, helping everyone to perform on the day, whilst keeping the rules and structure. The less ‘in the organisation’ they are, the more they can truly wear the facilitator hat.
  6. Dominating personalities: If certain participants dominate the discussions, it can stifle input from others and prevent a balanced exchange of ideas. A good facilitator (particularly an external) helps to level the playing field without embarrassing the shy or shutting down the boisterous.
  7. Inadequate breaks and downtime: Back-to-back sessions without sufficient breaks can lead to burnout and reduced productivity. Encourage participants to get outside, use fresh air, and avoid devices.
  8. Not writing down the key actions and decisions: This is a decision-making and direction setting forum, not an all-day chat. Failing to document important ideas, decisions, and action items during the session is an easy way to undo a great session.
  9. Neglecting team-building elements: A strategy session is an excellent opportunity for team-building and strengthening relationships among participants. There’s no point in having ‘the perfect strategy/plan’ if everyone hates each other at the end.
  10. Disregarding follow-up plans: You should really start with this in mind, as the strategy session should be the thing you need to break the deadlock with what your future plan should look like. After the strategy session, it’s crucial to have a plan for implementing the decisions and strategies discussed. Neglecting follow-up can render the entire session less effective.
  11. Inflexibility: While it’s essential to have a structured agenda, being too rigid and unwilling to adapt to unexpected situations or changing dynamics leads to the question: are you driving the agenda, or is it driving you?
  12. Keeping boring: I’m not saying this to be cute. It’s hard to be engaged, ambitious, empathetic and discerning when you’re in an all day meeting that’s dryer than a cat’s tongue in the dessert. Monitor the energy in the room, and have some tricks up your sleeve to brighten the energy if you’ve been down in the weeds too long.

There’s a lot of art and science that goes into a great strategic planning session. Whether running a 1-hour strategy session or a multi-day strategy workshop, the above list still applies. Like most things, the above list isn’t going to guarantee success, but it is going to go a long way to help you with the most common, and avoidable, failures.

If you’ve still got questions, reach out to us at Guided Strategy, and we can run sense check your current approach, discuss strategy tools to help you achieve your goals, and discuss options for facilitation.

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BONUS TIP: Venue: It’s hard for big ideas and bold conversations to happen in a stuffy room with no windows, next to a freeway, with no outdoor space or a projector. A good venue will never write a good strategy. But a bad venue will be a constant distraction that impedes a day that’s got a lot riding on it. Always visit it before the day, and write a checklist of what’s important to your team to get the most out of it.

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