A very close friend called today to ask if I could facilitate an upcoming strategic planning retreat for his company, and unfortunately, the days he needed were already booked. So, I offered to send him a quick overview of what I feel it takes to put together a successful strategic planning retreat, and this is the information I gave him.

How to Run a Successful Strategic Planning Retreat

1. Establish a Specific Deliverable. The best place to start is at the end. Therefore, the first step to presenting a successful strategic planning retreat is to create a very specific description of exactly what you want the deliverable of the event to be. 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 that will accomplish your goal successfully. So, always begin with the end in mind.

2. Bring in an Outsider. 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 have used for years to effectively get teams to their desired destination. 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 can perfectly play the part of the “velvet hammer” by shutting down tangents and pushing back on overbearing individuals.

3. Define the Purpose of the Retreat. Well before the retreat begins, decide whether this will be a “strategic planning” retreat or just a “planning” retreat. In other words, are the people in attendance 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 down in flames when the participants thought they were going to be able to impact and influence strategy only to find out that it had already been set in stone and their only role was developing a work plan. Therefore, you should decide and communicate beforehand what type of retreat you are having.
4. Evaluate the Condition of Your Team. Is the team ready to have a high-level retreat? Do you have the level of trust and professional respect necessary to have the sort of open, honest, and robust discussion that is critical for 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, then you will never be able to have the intellectually rigorous debate needed to arrive at a superior strategic plan.
5. Prepare Thoroughly. Try to get as much done before the retreat as possible. Typically, I do three key things a few weeks before the retreat.
   •  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.
   •  I ask everyone to carefully review the current vision, mission, and values of the company (if they have them) and to come prepared with any comments and suggestions, but ONLY if they feel very strongly that changes need to be made. Opening up the vision, mission and values to general discussion is usually opening up a can of worms that you’ll never get shut again. The way I look at it, the vision, mission, and values of a company are sort of like a tattoo: they are supposed to be pretty permanent and are very painful to change, so you need to be completely certain you are not happy with what you have before you undergo the effort of working on it.
   •  I ask people to do a fair amount of the SWOT work before they arrive. I send them a survey with some key questions about Internal Strengths, Internal Weaknesses, External Opportunities, and External Threats, and ask them to fill in the answers. 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, and no assumptions: we need to deal with facts. And when we come to a place where we don’t have the facts, then we now know that we need to go find them! Here is a sample of the questions I typically ask on the survey:
     • What do you see as the top three internal strengths of the organization right now?
     • What do you see as the top three internal weaknesses of the organization right now?
     • What do you see as the top three external opportunities for the organization right now?
     • What do you see as the top three external threats to the organization right now?
     • What do you think are the top three most important areas of focus over the next three years?
     • If you were the CEO, what top three things you would change or fix immediately?
     • What is your single biggest concern about the business right now?
     • What are the top three things that must be accomplished in this meeting?

I then take all of the answers from the survey and combine them into an executive overview of the most common answers so that people can get a general feel for what the entire group is thinking.

6. Answer SWOT Questions in Teams. Once we get to the retreat, it should only require a very brief discussion to determine if the vision, mission, and values are still relevant and on target. If not, I try to work fast to get a consensus on the appropriate changes. With everyone on board for the vision, mission, and values, then the next step is to break people up into groups to review the executive report on the answers to the SWOT analysis survey. I like to try to keep the teams small enough so that no one can hide and not participate: groups of four to eight people are 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 a key here. I will typically give them about two hours to work in their groups, and their task is to review the report and work together as a team to answer the exact same questions again, but this time, to get everyone to agree on what their team comes up with for their answers.
7. Determine the Most Important Issues to Address. I then ask each of the small teams to present their answers to the questions, and I work as the facilitator to combine all of the answers from the various teams into one clear overview that everyone agrees represents a solid SWOT analysis of their company. I might not be able to narrow the list of answers down to just three in each category, but if I can get it down to four or five answers that everybody in the room agrees with, then we now have something very focused from which to work.

*** 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 well the different teams are correlated on what they feel are the best strategies. If all of the teams come back and say pretty much the same things, then I am highly confident 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 they did not do so through “groupthink” because the teams did not cross-pollinate! If all the teams come back and present wildly different strategies, then I know I have a problem. And if the teams come back with about an 80% overlap? Well, then 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.

8. Prioritize the Important Issues. Once I feel comfortable that we have pretty much exhausted the SWOT analysis and created some good thoughtful answers to each of the above questions, then I will ask the teams to review the new list of agreed-upon SWOT answers and prioritize these answers into strategic objectives. What, specifically, should they do with the information they now have in front of them; what actions should they take; and how will they prioritize their actions for time and resource allocation? I usually ask them to designate the issues as such:
   • An “A” priority is one that requires immediate attention. It is a critical issue and demands action.
   • “B” issues 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” issues before we can take any action on one of the “B” issues.
   • The “C” issues are important, but there is nothing we can specifically do to impact them. These might be economic, political, or regulatory issues 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 these particular factors.

9. Select Your Main Strategic Objectives. Again, I typically give the teams about two hours to mold all of the SWOT information into a prioritized list of strategic objectives. I want them to think at a very high level here about the big picture issues: the most important things that will drive the success of the organization over the next twelve to thirty-six months. Basically, all strategy just comes down to making choices about how to allocate precious resources: time, money, and people. By looking at the SWOT analysis and figuring out what is most important, the company can understand how the strategy should take shape and what the most important things are for them to focus on in the near term in order to best prepare for the long term. The goal is to take all this information and boil it down to three or four key strategic objectives – a handful of mission critical areas for the organization to confront.

*** Side Note: you will notice that I said “three or four key strategic objectives.” Okay, I admit: maybe you could stretch it to five, maybe even six, but you cannot have twenty-three strategic objectives! Not even fifteen, twelve or ten. The key to 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.

10. Make Plans for Implementation. In most one-day 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. The tactical implementation issues 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 on which they have the most expertise. The second 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.

11. Finalize Your Strategic, Tactical, and Execution Plans. 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 to which everyone is willing to commit.

What You Can Accomplish with a Strategic Planning Retreat

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 that will move the organization forward.
• You have endured a thorough and exhaustive process to ensure that the best possible ideas and suggestions went into the plan and that the plan did not get hijacked in a groupthink 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 when 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 all over again! Good luck running your next strategic planning retreat!