On Purpose Leadership & Strategic Planning

strategic planning retreat manual

The CEO’s Guide to Strategic Planning Retreats That Get Results: PART 1

Purposeful strategic planning is critical to the success of any organization. as a leader, the most important activity of your position it so set and achieve your organization’s annual strategic plan., this three-part series is designed to give you a step-by-step framework for planning, executing and debriefing your strategic planning retreat to ensure maximum results., part i: what to do before your annual retreat.

First, we begin by outlining the key things you need to do before your retreat, so you can get your team onboard and create a powerful strategic plan.

According to Insights 2020 research, organizations that “over-perform” in terms of revenue growth link everything that they do to a clearly defined purpose. When your team members share a powerful purpose, they become more collaborative and creative. This will help you stand out from your competitors, reach your goals and drive revenue.

One of the best opportunities to align your team around a shared purpose is during your annual strategic planning retreat. Giving your teams time to step away from their day-to-day routines allows them to focus on the big picture and how they contribute to the overall purpose and mission of the organization.

Some leaders are skeptical about the strategic planning process, considering it a waste of time or boring at the very least. It doesn’t have to be this way.

If you create a strategic planning process that centers around the unique needs of your organization and is structured so that all team members participate in the construction of the plan, it can produce exceptional results.

Here are seven things to do before your retreat to put your organization on the path to success:

1. decide if you want to create a team strategic plan.

As a leader, you have two options for creating a strategic plan:

  • Create one yourself
  • Develop one as a team

Creating a plan yourself may be appropriate during crisis or turnaround situations. However, in most cases the more powerful approach is to develop a plan with your team – harnessing their passion, input, knowledge, and power.

Developing a plan is an engaging team process. Creating a strategic plan that aligns organizational and individual purpose is extremely powerful. It gets everyone into alignment and gets them inspired about achieving shared goals.

2. Conduct market and team research

To make it to the finish line, you must know where you’re starting from. Conduct research before your strategic planning retreat to understand what’s going in your industry, with your customers, and in your company.

For example, you can:

  • Determine if your organization is on purpose or off course.
  • Collect market data on what your customers are thinking and what they want.
  • Research what external factors are impacting your market.
  • Conduct an employee audit or survey to gain an even better understanding of your organization’s culture and morale.
  • Perform financial forecasting and look at the implications of different options.
  • Identify potential growth opportunities.

3. Pick a date

The best time for a strategic planning retreat differs for every organization. Plan your retreat during a slow period, when sending your leadership team out of the office will have the least impact on your operations. Pick a date that gives your team time to ramp up for the next cycle or season. Although the summer months tend to be slower, they may not be the best time for a retreat if much of your staff is on vacation.

Many organizations try to cram their retreat into two days. While doing it in two days is better than not doing it at all, in many cases, this tight timeframe won’t always give your team room to think creatively. Try to get away for several days and incorporate some relaxing and team building activities into the agenda. This allows your team to build relationships with one another, as well as be more productive and creative during your planning sessions.

4. Determine whom to invite

Invite a cross-section of your organization – from veterans to rookies – to your strategic planning retreat. Include people from different parts of the organization, especially those who interact with customers.

For example, you can consider inviting:

  • The core people you need to execute your strategic plan
  • Senior executives
  • Board members and/or advisors
  • Key customers who can share their experiences
  • New team members, as the retreat will get them up to speed quickly and allow them to develop rapport with their colleagues
  • 1-2 potential future leaders who could gain valuable experience at the retreat

Try to limit the group to 15 people. Going beyond this number can hinder the free-flow of ideas.

5. Pick a location

It’s vital to get out of the office – and away from distractions – during your strategic planning retreat. Picking a scenic environment with unique activities will make your retreat memorable and boost team spirit. It’s also a reward for asking your team to leave their homes for an extended period.

Make sure your venue has good catering and meeting facilities. But don’t pick a venue that is too formal, as a stuffy setting will reduce collaboration and participation.

6. Plan your agenda

Create an agenda and share it with your team at least one week in advance. This gives them time to pull together information before the retreat and prepare for the various activities. Your agenda should be somewhat flexible in terms of topics and timelines. Don’t try to cram in too many topics, as you likely won’t get through everything.

Here are some key topics that will help you build an on-purpose strategic plan:

  • WHY: Develop or reaffirm your core philosophy, or “why” you exist. What is your mission? What are your core values?
  • WHAT: Discuss “what” your organization’s goals are for the coming year.
  • HOW: Plan “how” you will executive your strategic plan. What are your timelines? Who will be responsible for what?

7. Hire a facilitator

It’s always best to to engage a third-party facilitator for your strategic planning retreat. An internal team member will always have biases that impact your planning. And when the leader tries to moderate a planning session, they often unintentionally shut down their team. After all, no one wants to argue with the boss!

Your team will feel more comfortable contributing with the help of a neutral third-party facilitator. The more they open up, the more insights you will gain about how you can improve your organization and drive results.

Find a facilitator you trust – one with the right amount of experience to guide your team through this complex maze. Look for someone who inspires your team but is modest enough to step back and let you and your team take the credit. Your facilitator should also be prepared to challenge your leader and team to be their best … but not in a threatening or overpowering manner.

What you do before your strategic planning retreat has a huge impact on your results. It’s vital to get your team excited about the planning process, as this will align everyone around a shared vision and help you achieve your goals.

Stay tuned for the next article in this series, where we will share strategies for running your planning retreat and how to follow up after the retreat to ensure your ongoing success.

Related posts:.

  • 5 Keys to Building a Strategic Plan That Fuels Growth
  • The CEO’s Guide to Strategic Planning Retreats That Get Results: PART 3
  • The CEO’s Guide to Strategic Planning Retreats That Get Results: PART 2
  • The #1 Mistake That’s Ruining Your Strategic Plan

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strategic planning retreat manual

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How to Lead a Strategic Planning Retreat

How to Lead a Strategic Planning Retreat

There is no substitute for getting your team (and your whole organization) working toward the same goals. A strategic planning retreat can pull everyone’s heads out of the office, so you can look at the bigger picture together.

We have learned some important lessons that make the difference between success and failure in strategic planning efforts. If you’ve already decided that you want to lead your own retreat (instead of bringing in an expert facilitator), you can increase your odds of success by paying attention to these keys.

#1: Measure your Mountain

When I lived in Africa, a massive and beautiful plateau rose 3,500 feet above us just a few miles from our home. Since I was in fairly good shape from running and riding my bike, I didn’t really need any preparation to hike up to the top. But when a friend challenged me to climb Mt. Kilimanjaro with him (19,341 feet!), I knew it would take a lot of work to get ready.

Before your strategic planning retreat, you need to measure your mountain to understand what you are trying to accomplish. Do you want to come out with a full 3-5 year Strategic Plan? A more limited Annual Plan? Or just a review and refresh of a plan you already have? Once you decide, make sure to set expectations by letting your team know exactly what you want to get done on the retreat.

Keep in mind: the bigger your mountain, the more work you need to do in advance.

#2: Assemble the right questions

A common pitfall in strategic planning is not digging deep enough to uncover the real issues. If you ask superficial questions, you will end up producing a plan that looks remarkably like what you are already doing but with bigger numbers. If you want to get past that, you’ve got to ask the right questions.

The right questions are not only difficult to answer, they can be difficult to think of. Here are a few to get you started:

#3: Share responsibility for preparation with your team

Sharing responsibility is not just good leadership, it’s also smart. Let people choose areas of ownership (or make assignments). They will accomplish more preparation than you could alone, and they will be more invested in the process. That’s two big wins for you.

What areas does your team need to prepare in advance?

  • Logistics. This includes arranging the venue, meals and snacks, materials on site (projector, easel charts or whiteboards, and markers), calendar invitations, and reminders.
  • Research . Someone needs to collect relevant information like recent financial reports, any available market information, and the last set of written plans or goals that you have.
  • Employee survey results. Don’t take the risk of having your wonderful new plan blown off by your employees because you didn’t consult them. A simple survey can give you a feel for what employees are seeing and raise issues for discussion at the strategic planning retreat.
  • Agenda and schedule. You need an agenda to follow that will guide your discussion at the retreat. A schedule and a dedicated timekeeper help you stay on task and make progress. If your team knows what is on the agenda, they can prepare to discuss items in their own areas.

#4: Stay in your role

Since you have chosen to facilitate the retreat, your team needs you to stay in that role. Here is what happens when you don’t have good facilitation:

  • The group gets sidetracked and chases rabbits
  • Discussions go long and do not conclude with specific actions or decisions
  • Quiet people watch and don’t give their input
  • Loud people talk too much and dominate

Committing to the facilitator role is difficult for most CEOs or owners/presidents. You can facilitate, or you can participate, but you can’t do both at the same time. The facilitator doesn’t answer questions—he or she asks them and follows up with more questions to get the team to really think.

Once you start championing an idea, you have become a participant, and it’s hard (or impossible) to facilitate discussion of the alternatives. If you switch roles mid-retreat, your team may get confused or disengage.

“You can facilitate, or you can participate, but you can’t do both.”

A strategic planning retreat could be just what your team needs to create alignment and break through obstacles.

Have questions?     Reach out and talk to us about how you can plan and lead a successful strategic planning retreat for your team.

Like us on Twitter , LinkedIn , or Facebook to get thoughtful articles on the bridges leaders must build and cross to inspire greater performance.

Written by Phillip Shero

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How to organise a strategic planning retreat

strategic planning retreat manual

Companies thrive when they’re guided by clear, mutually agreed-upon strategies. From experience, we know it can be difficult to fit high-level strategic planning around day-to-day activities. Enter, strategic planning retreats.

Strategic planning retreats bring company leaders and employees together to discuss core company themes, identify opportunities and develop a clear roadmap for the future. They allow employees from all levels to take a step back and think about the bigger picture - regaining purpose, clarity and structure to their workflow.

What is a strategic planning retreat?

strategic planning retreat manual

A strategic planning retreat is an off-site event that gives decision-makers a chance to build new strategies and formulate plans for the future. It's a chance to bring together key members of the organisation and have comprehensive discussions on how to drive company growth and success.

Importantly, strategic planning retreats also aim to strengthen team dynamics while meeting a set of desired outcomes. This way, you’ll have a cohesive team equipped with the right tactics to benefit the organisation long-term.

How can a strategic planning retreat benefit your team?

1. it's an opportunity to evaluate success and direction.

During a strategic planning retreat, team members can take a break from their daily grind and redirect their focus toward the overall performance and direction of the team or company. They can evaluate how well they’re functioning as a unit, determine which areas they’re excelling, and identify areas for improvement.

It’s also a great opportunity to make sure everyone is aligned toward accomplishing individual and administrative goals.

2. Fostering team cohesion

Strategic retreats allow your team to get together in a relaxed and open environment to reconnect and ground themselves. It’s a chance for team members to loosen up and get to know each other beyond their Slack emojis.

Spending time together on a team offsite and engaging in unique, thoughtful team-building activities will undoubtedly strengthen bonds within the team - increasing mutual trust and ability to communicate openly.

3. Develop leadership skills

Strategic retreats are not just for improving team cohesion, they're designed to help team members become people leaders .

Through specific activities and training, individuals can improve their decision-making capabilities and develop their leadership skills - in an environment without consequences.

Things to consider when planning a strategic planning retreat

  • Objective(s): Aside from fostering team cohesion and developing leadership skills, think of some team-specific objectives to get the most out of your retreat. This could include organisational matters, such as developing a new strategic plan and reviewing current company performance.
  • Facilitator: Assign a facilitator to ensure that the retreat agenda is met and that all attendees can participate comfortably.
  • Distance: An ideal distance for your retreat should be no longer than two hours away. Try to avoid tiring out team members on the journey before the retreat has even begun. More on this to follow.
  • Accommodation: The accommodation for your offsite must enable a seamless offsite. We're talking about faultless wifi, lots of breakout areas and outdoor space for connecting organically with coworkers.
  • Catering: Keeping it healthy and light is best to stop people feeling sluggish. Make sure veggie/vegan options are available, as well as the ability to cater for any allergies and intolerances.
  • Team-bonding activities: ditch your escape rooms and engage in unique team-bonding activities such as foraging, cooking classes or intuitive painting.
  • Mindful moments:
  • Adding breathwork or meditation exercises can work wonders to focus the team before any major discussions.

Best practices for a strategic planning retreat

Pick a location that aligns with your goals.

Location, location, location. To make the most out of a strategic planning retreat, not just any venue will do — it must align with your aims and objectives for the offsite.

Wherever you decide to go, Basejam is a big believer in the value of nature-based retreats. The benefits of being outside are infinite, not least in helping gain mental clarity and shaking off the stresses of city life.

This doesn't mean a four-day, unplugged camping trip - but we know that prioritising connection to nature will pay off both personally and professionally on your retreat.

When searching for your site, start with baseline requirements like your headcount and required facilities. Then think about the kind of vibe you want to curate, and the features that will entail. Such as:

  • Proximity to nature
  • Unique activities
  • Catering options

With Basejam you have access to a curated list of retreat-ready venues along with key, unique information about each one. You can filter your search results based on location, accommodation style, amenities, number of people, and even reason for retreat. This way you’re able to discover an ideal venue for your specific needs.

strategic planning retreat manual

Wellbeing retreat, nature reserve and regenerative farm stay in rural Somerset →

Establish clear goals.

What do you want to achieve by the end of your strategic planning retreat? Be specific—a clear goal (or multiple) will give your team and offsite direction and purpose.

Be extremely clear about the goals you have for the occasion. Consider the ideal result and the criteria you will use to evaluate its success. When you have a clear objective in mind, work backwards to create a strategy that will get you there.

Identify who should participate

After defining the objectives and scope for your strategic planning retreat, it's time to identify who should attend the meeting and their roles throughout the event.

Include those who will lead and implement the strategy. Active engagement before, during, and after the meeting increases the likelihood of a successful retreat.

Employee participation is essential at every stage of the planning process, but strategic planning retreats often involve leadership and key decision-makers.

Set an agenda

Make an agenda that addresses all the critical problems identified in your pre-retreat evaluation. Make sure the agenda is open to unexpected debates or new topics. Consider holding break-out seminars to address departmental challenges.

The schedule should also include adequate time to discuss the tasks that emerged from the retreat. Set aside time to create a follow-up strategy to guarantee that the plans discussed during the retreat are effectively implemented.

If you need a helping hand, use this handy agenda-setting template to get started.

Design a structured process

Once you have a clear grasp of the objectives, scope and participants for your strategic planning retreat, it's time to develop a structured process. Plan with specific goals in mind, and decide who will lead each discussion.

While you may be eager to see results, keep in mind that hearing from all voices is critical. Aim for genuine participation from all those involved, and create a safe environment in which team members feel comfortable sharing their ideas. It's important to make sure no individual dominates the discourse.

Move from the macro to the micro (and then back to the purpose)

Begin your retreat by talking about the broad picture—external forces and your organisation's mission. After that, address your objectives and challenges.

Use cue cards to have a private talk about the challenges to increase participation. Solve these problems together.

Review goals and actions to ensure they are in line with the mission of your organisation. This method results in a productive and aligned retreat.

Use data-driven insights

When making strategic planning decisions, rely on facts and relevant insights.

To ensure a strong SWOT analysis (strengths, weaknesses, opportunities and threats), conduct interviews and surveys wherever possible. This analysis will give the necessary context for strategic decisions.

strategic planning retreat manual

Create and use pre-work templates after gathering enough feedback to ensure that all meeting participants begin with an idea of the present situation, difficulties, implications, and objectives. This baseline allows everyone to get started on the same page.

Encourage diverse perspectives

In both small and big group conversations, encourage everyone to speak up. When the loudest voice dominates the discourse, valuable viewpoints might be lost, resulting in bruised feelings and at worst, isolation and disengagement.

Allowing everyone to contribute allows you to realise your team's full potential. It results in a strategy plan that is not only visually appealing but also effective in attaining your objectives.

Prioritise actionable items

Make a targeted strategy plan by identifying essential initiatives and ranking them in terms of impact and feasibility. Keep objectives manageable to avoid being overwhelmed. To turn goals into actionable tasks, create a detailed action plan with specific phases, responsibilities, and dates.

Document everything

Keep complete notes of all retreat conversations, decisions, and action plans. These records will be useful references in the future. By documenting everything, you can quickly track progress, revisit ideas, and verify that the retreat's conclusions are applied properly over time.

Feeling ready for your strategic planning retreat?

By taking a break from your daily work routine and dedicating time to a strategic planning retreat, you can form stronger collaborations, well-defined strategies, and a clear roadmap to your business’ success.

Explore a curated list of inspiring company retreat venues with Basejam and start planning your transformational retreat.

strategic planning retreat manual

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How to Run an Effective Strategic Planning Retreat

Posted On: May 27

Business Excellence , John's Rants , Strategy

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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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!

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.

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

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.

i really enjoyed your little article and they have been so helpful to me in making it easier for me to run my retreat effetively. God bless you so much.

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?

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.

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

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.

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.

c1 , future , Leadership , planning , planning retreats , retreats , strategic planning , strategic Planning Retreats , Strategy , team building

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Strategic planning retreats (4 mins).

How to Facilitate a Strategic Planning Retreat

A strategic planning retreat can be a very effective way to set or reset the general direction of your organization, but only if it’s run correctly. Learn how to conduct a retreat that produces results from Erica Olsen, Co-Founder of OnStrategy.

For more resources on building your strategic plan, view the  Essentials Guide to Strategic Planning.

Video Transcript

“Hi, my name is Erica Olsen. Today’s whiteboard session is how to hold an effective strategic planning retreat or a strategy offsite. So what is the purpose of a strategic planning retreat? The number one thing we want to get out of any retreat is setting the strategic or corporate direction as well as identifying priorities for the next year about how we go from where we are today to where we’re trying to go and specifically next year, what are the priorities we need to have in place in order to keep moving forward?

Get the Free Guide to Create a One Page Plan to Communicate Your Strategy

Normally, it’s done on an annual basis, that may or may not be something you want to adopt in your organization, but most retreats are done annually over a several day period; some organizations break them up, but for the most part, done annually. A couple of considerations to take into note as you’re thinking about when to hold your retreat annually, ideally it’s done in advance of your budget process. So we don’t always have the luxury to do that, but ideally the strategic planning priority should actually inform the budget process. It should also align your performance review or performance evaluation so you’re establishing individual goals based on corporate goals, and one big thing is no big changes are going to be occurring in the short term right after the retreat. This happens oftentimes, maybe there’s a big consolidation, a move, a big announcement about someone moving jobs; don’t hold your retreat if that’s in the foreseeable future, just wait, otherwise you’ll torpedo the whole thing.

Ok, so whether you’re doing it yourself or you’re hiring a facilitator, a couple more considerations to take into note in addition to when but who and what’s on the agenda. So, who should be involved? Well, most of the time, of course, the executives are always involved in the off sites. Perhaps you’re holding an offsite with your department and that information’s rolling up, that’s great. You know, we can’t have everybody at the table, so if you’re not holding department off sites, make sure to do employee surveys so you get their ideas into the strategic planning session, so as I say they’re at the table, at least with their ideas there if not in person. And make sure that you have a different set of thinking styles. So sometimes we’ll recommend the clients to bring in some external experts, maybe some different people in the organization who might not be executives but have different types of thinking, different perspectives so you’re making sure that you’re getting a well-rounded perspective of the organization and the competitive environment.

Really quickly looking at the agenda, this is very basic, it’s a great way to break down off site agenda because a lot of people can relate with kind of the thinking around the structure, which is “where are we now?” So looking at our strategic position, strengths, weaknesses, opportunities and threats, “where are we going, what’s that vision in the future?” So looking at re-calibrating where we’re trying to go as an organization, and how are we going to get there? So those are really your goals and actions, maybe you’re setting longer-term goals, but at a minimum, next year’s goals for priority setting for everybody in the organization. The most important thing though that you need to do is to think about what you’re going to do after the retreat before the retreat happens because we always have a problem of going from having a great couple day session to actually getting into implementation, so whatever you do, don’t forget to make sure you have a plan in place for what do we do after the retreat. Good luck.”

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3 Steps to Facilitate a Strategic Planning Retreat

by Sara Gropp | Feb 15, 2019

Strategic Planning , Project Management

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Whether you are leading a planning retreat or participating in one, what makes an effective planning retreat? The facilitator can ensure the group has a plan and accomplishes their goals. A participant can help keep the conversation on topic, as it is common for a group to want to jump into the solutions of a plan before determining the focus areas.

Earlier this year, we discussed the 4 Steps of Strategic Planning . Step three is to “facilitate consensus”, which usually occurs at a planning retreat. The main purpose of this step is for the planning team to start to reach consensus about the future direction for the organization, including goals and strategies. We follow three key steps to lead an effective planning retreat.

1. Provide Summarized Materials

First, create a pre-read packet of summarized materials from the first two steps of the strategic planning process. This helps equip the planning team with rich feedback from the key stakeholders (step 1: collaborate) and understand the context (step 2: assess). You also want to give your planning team enough time to review and process the information before the day-of retreat. This allows the group to make thoughtful recommendations. There are several ways to present a pre-read packet: a narrative report, a PowerPoint presentation or an interactive online file.

During a project with the Wabash County Early Childhood Education Committee, we created a Tableau Public file titled the “Impact of Early Childhood Education in Wabash County”. This included five tabs summarizing key community demographic data, program information and stakeholder feedback from employers and parents. The titles for visuals were worded as a question to help the audience pull out key messages from the information. During the planning retreat, we reviewed this information but they had already seen it and digested the information. This allowed us to start having some meaningful conversations.

2. Identify “What” You Want to Accomplish

After leading the team through a review of the information, the majority of time is spent to make meaning with the data and identify goals and strategies for the future. Having some great discussion questions is helpful to focus the conversation with participants and help them use the information presented.

Many participants at planning retreats want to jump right into strategies or solutions. We work hard to help steer the conversation to reaching agreement first on the “what” we want to accomplish with the strategic plan. Help the group to narrow their ideas to 3-5 key focus areas or goals to help carry the strategic plan forward. By bringing the team together, they will have consensus. As we have mentioned earlier, buy-in from the team is crucial to keep momentum going for the strategic plan.

This discussion time can be done as a full team, split into small groups or partners depending on the size of the planning team. If you do break into small groups make sure you come back together as a large group and collectively reach consensus about the goals/ focus areas. We like to use stickers to help participants “vote” or prioritize their top choices.

3. Determine “How” You Will Accomplish It

Finally, after the “what” is determined, transition the team to discuss the development of key strategies and solutions that address the focus areas. This is the “how” we will accomplish the goals of the strategic plan. Similar to the previous step, discussion can be as a group or broken up into teams.


Once you have your top goals and strategies identified, then you can “workshop” them into a more detailed operations or implementation plan that explains the who, what, and when in much more detail. This is what sets apart a strategic plan from sitting on the shelf and not being implemented to a strategic plan that truly moves the organization or community forward.

There are different tools and activities that can be used during the facilitation step of the strategic planning process. Depending on what works best, the main thing to remember is to engage, focus and prioritize.

Now that you have hosted an effective planning retreat you are ready for the final step of the strategic planning process – create. If you need assistance with facilitating an effective planning retreat, or with any step of the planning process, Transform Consulting Group is here to help. Contact us today!

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Making the Most of Your Planning Retreat

For some, the word “retreat” is a dirty word. It too often means a day (or more) spent in a windowless room engaged in conversations and discussions that rarely seem to do much to advance the organization. Even the word “retreat” suggests going backward instead of forward. Should it surprise us then that nonprofit board members recoil at the very mention of a “planning retreat?”

When it comes to strategic planning, however, a retreat can be an invaluable tool that can actually speed the planning process. Think about it this way: a good strategic planning process should engage the board (and often the staff) in grappling with some important and/or thorny issues. The board needs time to explore these issues and discuss them fully, and it is unlikely your regularly scheduled board meetings provide the time needed for this.

So, rather than have these important discussions in piecemeal over several meetings, or leave them to committees, consider carving out some time—unhurried and unencumbered by the regular business of the board—to “retreat” into a planning mode. Structured right, and well-facilitated, you just might find that the board retreat is where the board is at its most productive.

In our work with our clients, there is sure to be a retreat (or an “extended planning meeting”) at some point along the way. Our experience informs the recommendations that follow:

  • Many boards maintain the practice of having an “annual retreat.” As the date approaches they struggle to figure out what to do with the time. If you have to figure out why you are having the retreat, don’t have it. Don’t waste your board members’ time.
  • Plan the agenda carefully to maximize the time. Before you schedule the retreat, determine what it is that you really need to accomplish. If you could do the same thing in a regularly scheduled meeting or by sending it to the board in writing, don’t do it. Use the time to deal with BIG issues—with strategic questions—that truly need time and careful thought.
  • Don’t underestimate the value of this opportunity for board members to get to know each other in a different setting. I’m not suggesting you spend lots of time on icebreaker exercises, however. I’m suggesting you find ways to help board members get to know each other at a deeper level and, ideally, advance the agenda too.
  • While our experience suggests a 5-6 hour block of uninterrupted time works well for most retreats, we’ve also worked with organizations where the retreat was chopped-up into separate sessions on different days. In a few cases, we’ve had groups that have met on two successive evenings for 3-4 hours each. In another case, we worked with a group that separated their sessions by a few weeks, purposefully, so they could take ideas from the first session, explore them further, and then pick-up the work at the second meeting. These approaches aren’t ideal in maintaining continuity and cohesiveness, but they can work.
  • It’s hard to facilitate and manage a meeting and also actively participate in it. Consider the potential value of paying a professional facilitator to help you develop your agenda and manage a meeting that helps you achieve your desired outcomes. A good facilitator can help to manage the time, ask (and ask again) the tough questions, and ensure participation by all the participants.
  • Keep in mind that while a retreat is often a part of a strategic planning process, it should not be the process. We see a lot of “annual planning retreats” as just that—a once a year occasion to create the annual work-plan. These sessions are helpful but rarely strategic. You should anticipate that a planning retreat will be an aspect of almost any strategic planning process, but it will be just one part of a multi-step process.

In our experience, it is not unusual to find that board members can’t remember what happened at the last board meeting, but they can often recall quite distinctly what happened at the retreat that took place many months ago. The retreat offers an opportunity for some truly meaningful discussion and for important decisions that can shape the direction of the organization. Board members appreciate these opportunities.

Plan your retreat well, maximize the time together, and focus on the BIG issues, and you’ll find that retreats can be essential tools to advancing the work of your board and your organization.

You’ll find more strategic planning advice, like this post written by Starboard’s Jeff Wahlstrom, on our website: www.starboardleadership.com . If you would like to talk with a member of our consulting team about your strategic planning process or facilitating your upcoming retreat, use our contact form to begin the conversation.

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