Ten Tips for Conducting a Successful Strategic Planning Session

Written by

Shane Capper

The art of strategic planning can be thought of as a delicate mix of science and creativity, designed to harness opportunities and leapfrog our competitors. Sounds good in theory, but when it comes to running strategic planning sessions, outputs often fall short of expectations. The truth is, we often miss the collaboration necessary to design truly visionary plans.

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To overcome this, our team use a structured workshop approach based on a proven methodology rooted in capability-based planning. Regardless of your chosen methodology for strategic planning, our extensive experience conducting strategic planning sessions has taught us these ten keys to success.

  1. Don’t teach the methodology

    Despite your eagerness to demonstrate your prowess in strategic planning, resist the urge to upskill audience members. The goal is not to teach strategic planning, although an overview of your intended approach will help settle participants.
  2. Don’t be afraid to use a straw-man or two

    You’ve probably heard the expression "it’s easier to critique than create", and in this case, it still rings true. Have a go at defining challenges and objectives, creating capability maps and even prototype a rough roadmap. Even if it's wildly wrong, it will help inspire further thought and increase participation. The audience will get a kick out of correcting your work. A word of warning, though: this requires a fair amount of humility - try and avoid setting up a defensive stance!
  3. Mix it up

    A whole raft of sessions with the same collaboration techniques will be unlikely to produce the desired results. Search for exciting design thinking techniques; the audience will thank you for making it somewhat fun and engaging. The same goes for the methodology itself; combining various steps in the same exercise can be fruitful. Watch the audience closely and pivot your approach as needed. Some of the best sessions I've run were stitched together mid-workshop.
  4. Worked examples

    Take the time to develop fully worked examples. Stakeholders are more likely to engage once they understand the desired outcomes. Walking participants through an example will allow them to create their own based on real-life insights.
  5. Don’t debate what capabilities are and are not

    A mistake most of us make at some point is trying to defend what capabilities are and are not. You're not going to win friends by getting into heated discussions with architects and business managers about what constitutes a capability. Capture what stakeholders are saying and transform it offline. Diving into rabbit holes debating definitions is the easiest way to derail the workshop.
  6. Use business sponsors

    Engage sponsors (or their delegates) beforehand and seek their endorsement for the workshop approach. Ask them to introduce critical workshops and set expectations, even if it's only a cameo appearance. You'll want to avoid defending the merits of the overall approach and workshop design.
  7. Reinforce the iterative approach

    The best strategic roadmaps are built incrementally, but this makes participants uneasy at the best of times. Take the time to emphasize the iterative nature, reinforcing the idea that outputs from other stages are revisited and uplifted as new insights are discovered.
  8. Set expectations at the start of each session
    This is more of a general workshop tip but a crucial one. Ensure the group are aware of workshop goals, expectations and etiquette. More importantly, take the time to capture the group's session expectations, revisiting them often. A mid-session mutiny is never comfortable; trust me on this one, I've had to recover from a couple with some very senior people in the room!
  9. Know when to use a digital approach and when to use a whiteboard

    Engaging an audience with a laptop and screen is more complicated than it looks. It may seem like a good idea to capture the ideas on the fly, but expect a level of lethargy from stakeholders as they discover they can tune out undetected. Whiteboards, stickies, and an active audience placing their thoughts onto the board are worth their weight in gold.
  10. Use a war-room (digital or physical)

    Chances are, you're not going to elicit all the insights you need during active workshops. Less confident or shy individuals will often stay quiet for fear of "getting it wrong". Either way, using a semi-permanent war-room will help those contribute in a way that feels safe to them. Ensure all outputs are highly visible and invite stakeholders to participate offline. If you're working remotely, use cutting-edge platforms like Miro or Mural to run workshops online; it takes a bit of practice, but it's worth it!

Once you conduct your first few sessions, your abilities will mature, and strategic stakeholders will feel the confidence necessary to be successful. The secret sauce for all of this is to start with creating an inspiring future vision, which is luckily one of the easier workshops to run. Such a vision will then kickstart the workshop series and hopefully enable the creation of a beautiful strategic plan.

Our strategic planning methodology

Our team have run many strategic planning workshops following Jibility's six-step methodology. With its roots in capability-based planning, Jibility helps your organization gain consensus on where the capability gaps are, and what needs to change in order for the strategic vision to be executed. Try Jibility for free!