How to Run an Effective Strategic Planning Retreat

Posted On: May 27

A very close friend asked me to facilitate his organization’s upcoming strategic planning retreat, but unfortunately the days he needed were already booked for another client. The next best thing I could offer was some advice. I have probably facilitated 80 or 90 retreats in the last 20 years, from non-profits to the Fortune 50 – here is how I typically approach a planning retreat…

1. The best place to start is at the end, or as Mr. Covey says, “Begin with the end in mind.” So step one is to create a very specific description of exactly what you want as the deliverables from the event. What would a perfect outcome look like?  How will it be measured? If you can figure out specifically what you want the retreat to achieve, it is pretty easy to go backwards from the finish line and build a program to reach it successfully.

2. Use an outside facilitator, someone with superb experience in running many, many similar retreats. There are two main reasons to use a facilitator; Process and People. Any truly qualified facilitator will have a proven process they had used for years to get teams successfully to the desired outcome. It really does not make too much of a difference what process they use, so long as it is intuitive, easy and effective. The other main reason for a facilitator is people, or better said: egos.  You need someone who is NOT from the organization that can step in and take control if things get off track, someone who is not afraid of the political ramifications of telling the boss to be quiet! An outside facilitator is perfect to play the part of “process weenie” in shutting down tangents and pushing back on overbearing individuals. If someone from inside the organization tries to run the retreat, it can often be a “career ending” performance.

3. Decide whether this is a “strategic planning” retreat or a “planning” retreat. In other words, are the people there actually going to take part in setting the strategy, or are they simply there to figure out how to implement someone else’s already developed strategy? I have seen a lot of retreats go up in flames when the participants thought they were going to be able to have real impact and influence on building the strategy, only to find out it had already been set in stone and their only role was developing a work plan.

4. Is the team ready to have this kind of high-level retreat? Do they have the level of trust and professional respect necessary to have the sort of open, honest and robust discussion critical in developing a truly effective strategic plan? If people do not feel extremely comfortable sharing opposing opinions, fighting for unpopular positions and challenging the status quo – you will never be able to have the intellectually rigorous debate needed to arrive at a superior strategic plan.

5. Try to get as much done before the retreat as possible. Typically I do three key things a few weeks before the retreat.

A) I deploy an internet-based “Organizational Effectiveness Audit” to every person who will be involved in the retreat.  This is a brief, confidential survey to gauge the level of trust, openness, and respect within the team. If the scores from this audit are not high enough, I will recommend replacing the first day of the retreat with a High-Performance Teams workshop in order to get the group ready for the rest of the work.

B) I ask everyone to carefully review the current Vision/Mission (if they have one) and to come prepared with any specific comments and suggestions — ONLY if they feel very strongly that changes need to be made. Opening up the vision and mission to general discuss is usually opening up a can of worms you’ll never get shut again. The way I look at it, the vision and mission are sort of like a tattoo. They are supposed to be pretty permanent and are very painful to change, so you need to be certain you’re not happy with what you have before you undergo the effort of working on it.

C) I ask people to do a fair amount of SWOT work before they arrive. I give them a number of key questions under Internal Strengths / Internal Weaknesses and External Threats / External Opportunities and ask them to fill in the answers to the best of their ability. The key here is that the answers MUST be in the form of a statement of “fact.”  Things they either know or don’t know. No guessing, no estimating, no assumptions – we need to deal with facts. This is usually pretty hard on the teams, because they have so many “unknowns” – but at least when we discover what we “do not know” – we now know we need to go find those facts!

6. Once we get to the retreat, it should be a very brief discussion to quickly determine if the vision/mission is still relevant and on target. (If not, I try to work fast to get consensus on appropriate changes.) With everyone on board for the vision/mission, the next step is to break people into teams to do the full SWOT analysis. I like to try to keep the teams small enough so that no one can hide and not participate, four to eight people is just about right. I also want each team to have representatives from different parts of the organization, not all from the same department or managerial level – diversity is important here in order to get several different views and opinions. I will typically give them about three hours to share all of the SWOT homework they did before the session and develop lots of new SWOT issues as a team. (Again, everything must be written as a “factor,” a clear and specific statement of fact).

*** Side Note: I do not let the teams talk to each other once they start the SWOT process. I want them to work completely independently because I am interested in seeing how strongly the different teams are correlated on what they feel are the best strategies. In consulting terms this is called MECE (Mutually Exclusive – Comprehensively Exhaustive). If all of the teams come back and say pretty much the same things, then I have a high confidence level that a bunch of smart people looked at a lot of data and came to a general consensus on the appropriate course of action — and I know that it did not happen through “group think” because the teams did not cross-pollinate! If all the teams come back and present wildly different strategies, I know I have a problem. And, if the teams come back with about an 80% overlap? Well, that is where the facilitator earns their fee, by working to mesh and mold the various ideas into a single coherent and agreed-upon strategy.

7. Once I feel comfortable that we have pretty much exhausted the SWOT analysis, I will ask the teams to go back and take all of their SWOT factors and prioritize them.

– An “A” priority factor is one that requires immediate attention. It is a critical issue and demands action.

– “B” factors are important but require no action right now. They might need action in a month or two, or we might have to address some “A” factors before we can take any action on one of the “B” factors.

– The “C” Factors are important, but there is nothing we can specifically do to impact them. These might be economic, political, or regulatory factors that we need to watch carefully and possibly respond to, but there is nothing per-se that the organization can do to influence or control this particular factor.

8. When the factoring process is complete, the teams sit back and look for patterns in their factors. Where do they seem to group together? Do we have a high number of “A” and “B” factors around say… customer focus or funding, or marketing? The goal here is to look for the three or four major areas that all of the critical A & B factors seem to be falling into. These then will become your Strategic Objectives (Strategic Thrusts, Major Objectives, Key Result Areas, Strategic Priorities…whatever name your organization likes.)

*** Side Note: you notice I said three or four Strategic Objectives. Okay, maybe you could stretch it to five – but you cannot have 23 Strategic Objectives! Not even 15, 12 or 10. The key to an effective strategy is FOCUS. You must get it down to the few truly critical priorities and then most importantly… figure out what to say “NO” to.

9. In most retreats, this is about as far as you can get, with possibly a little discussion about the tactical implementation of the strategies. This leads me to two VERY important issues.  The first is that the diverse teams we created to develop the strategies are not good for deciding on tactical implementation issues. Those plans should be developed by the people who will be held responsible for actually doing the implementation. I try to let the people who do the work every day figure out the best way to do it in the future. Yes, we give them some ideas and input, but ultimately they need to decide on the best way forward for the projects that they have the most expertise on and will be held accountable for successfully completing. The other key issue is that a strategic plan is NOT complete until you have also developed a “Strategic Execution Plan.”  So at this point, I usually complete the retreat and send the project teams off to work on their specific implementation plans.

10. Perhaps several weeks later, after a number of rounds of sharing and editing the strategic, tactical, and execution plan rough drafts, the entire planning team gets back together to look at the final document. Here is where they hash out the last details and work to create a document that everyone feels good about and is willing to commit to. Often times, when I feel the entire group is pretty much there, I will have everyone stand up. I then say, “If you are very happy with this document, this vision, these key strategies and the tactical and implementation plans to support it — and you are 100% committed to executing this plan and being held accountable for what is in it… please take a seat.” For anyone left standing, we discuss their issues until one of three things happens: they change their mind and freely sit down — they convince everyone else to make a change in the plan because of their input and then sit down- or they refuse to commit to the plan, which usually means they leave the organization (this does not happen very often – but it does happen!).

At this point the plan is finally complete and here is what you have accomplished:

  • You have given everyone a say in the outcome, a chance to fully participate in crafting the key strategies to move the organization forward. This is critical for obtaining buy-in. If they helped build it – they own it.
  • You have endured a thorough and exhaustive process to ensure the best possible ideas and suggestions went into the plan – and that the plan did not get hijacked in a group-think session.
  • You have prioritized the key strategies to allow for the proper allocation of resources, people, funds, and time – by figuring out what to focus on and where you must say “no.”
  • The people who will be responsible for actually implementing the plan have played an integral part in developing the specific tactical plan for effectively executing the strategic plan.
  • You have gained consensus and commitment to accountability in a very public and powerful way.

Now comes the REALLY hard work…the 100% disciplined execution of the plan for the next ten months or so before it is time to start the process over again! (To see my article on Effective Execution click HERE)

Hope that helped a little – let me know if you have any questions or comments — John

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  1. John,

    These are all good points – very well done! I thought that I might add that, in my consulting experience with “Strategic Execution Plans,” (love that terminology) I’ve personally found documents to be a poor way to enhance execution of strategic plans – they get forgotten about, lost, or quickly become obsolete when new ideas or challenges emerge, in my experience.

    This has lead me to believe that Strategic Execution Plans must be online – with mechanisms of having people “interact” with the plan on a regular basis (at least 2 times per month). I think the plan must be structured in a way that: (1) allows people to regularly be reminded about their part in making the plan a reality – and be rewarded for doing so (2) allows for obsolete portions of the plan to quickly be “pruned” when necessary and (3) provides a quick mechanism of building solutions to problems into the plan “on the fly.”

    Hope these thought are helpful to the conversation – thanks for your good work, John!

  2. John – a wonderful summary of some true wisdom. We’ll be sure to read this before our next retreat. We’re considering our next one soon and the topic of venue came up. I wonder if you could share your perspective regarding on-site/off-site venues? Have most retreats you’ve worked on been one day affairs?

    Loved Brian’s suggestion on recording elements online as well. We use an online “whiteboard” to track strategic topics – as well as weekly operational agendas. Having a short, scheduled discussion to review the more strategic whiteboards periodically might reduce the impact of sudden shifts that might occur as part of a yearly retreat outcome.

    many thanks for your contribution.

  3. Skip — I am a 100% fan of off-site retreats. I have seen so many planning sessions get completely derailed when they are held on-site — and people keep coming in a grabbing people for emergencies and phone calls and client issues… if you are serious about getting real work done – it needs to be off-site. Next question — luxury or isolation? Some people take their team to a lodge way out in the woods to keep them focused — others have retreats at fancy hotels so they can play golf on the last day. Either can work fine — as long as the group is very disciplined and understands that they are there for a planning retreat — not a vacation! Typically most of the retreats I have done start at 10 AM on a the first day — run all afternoon up to dinner — with significant homework assigned. Then an early start at 8 AM on the second day — go until about 4 PM – then let people go home. If it is a very large company with a highly complex strategy — we might add on another day — but after that people’s brains are mush and you won’t get any more value out of having them there. Better to send them off to work for a few weeks on what you developed — then come back together for a one-day review.

    Hope that helps — let me know if you have any more questions — John

  4. Thanks for your comment regarding “The Four Most Important Things I’ve Ever Learned”.
    I have been a “lurker” for quite a while. I didn’t post comments as I was new to the blogging world. I really appreciate all that you share – very helpful.

  5. Great Article. I am planning to start a full time ‘Corporate Retreat Business’ in Asia. I have been trained in Compression Planning in the US. Any pointers from anyone what steps I need to take?


  6. John – I would be interested in knowing what some of the key questions you are asking the participants to answer re: Strengths/Weaknesses/Opportunities and Threats before they arrive for the off-site. Any suggestions??

    Many thanks for this.


    1. Mark, great question. Depending on the type of organization I add another five or six questions. Here are a few that I typically include:

      If you are the CEO what would you be focused on in the next three years?

      What do you think the staff of the organization needs to work on?

      What you think the board of the organization needs to work on?

      What is the one most important thing we need to accomplish during this planning session?

      What do you believe are the three biggest trends impacting the organization over the next 3 to 5 years?

      Again, I would talk to the CEO and key staff members to determine if there were additional questions I needed to add, but I try to keep it at 12 questions or less. I hope you found this helpful – take good care – John

  7. Thanks for putting these ideas together in one spot; your generosity is appreciated. I’ve been looking at Making Thinking Visible by Ritchhart & Church for ideas on facilitating group planning and learning sessions, and it compliments what you have suggested here. I’ve facilitated many workshops over the years, but this weekend will have the chance to work with a Search and Rescue organization as they develop their Strategic Plan. I will follow much of your advice — thanks again.

  8. Thank you John. This is a rich write-up.

    I worked with one of the big 4’s…facilitated a few strategy sessions as a consultant and currently lead the strategy unit of a growing firm. I’m truly excited with all the experience and pointers you shared because they provide better clarity on how to conduct my next strategy session.

    I also agree that buy-in is an important benefit of conducting a strategy session and this should never be confused with a simple communication, review and documentation exercise.

    Your pre-strategy primers (questionnaires) and use of SWOT also re-enforces my opinions as follows:
    – Strategy sessions need not be a confounding workshop of complicated frameworks
    – Best fit approach must be considered based on business size/maturity, practical realities, audience profile etc.
    – Understanding limits and realities (e.g. using SWOT) helps to keep a strategy practical while leaving leaving enough room for innovation

    Thanks again John – your article is indeed priceless.

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