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How long is the ideal strategic planning retreat?

“Francis”, clients sometimes ask, “Why do you recommend a two-day strategy retreat?” Usually, they want to get the most from their workshop, but also don’t wish to waste a moment. After all, top executive time is quite expensive.

Assuming that your company has agreed to such a workshop, what’s the difference between one, two, or more days?

Decision-Making vs. Decision-Announcing

Sometimes, companies just want to announce decisions which have already been made…”Town Hall” style. In these settings, you intend to inform an audience at scale about something important. But you’re happy to answer a few questions and gain some initial support. Expectations are low. Participants don’t expect an open-ended dialogue on all aspects of the business.

We recommend that these short announcement-style meetings be held separately from “decision retreats”.

By contrast, the latter are designed to foster the most powerful, breakthrough conversations possible. The stakes are deliberately boosted so that extensive, game-changing resolutions can be made.

Jim Collins and Jerry Porras, authors of Built to Last, call them BHAGs – Big, Hairy Audacious Goals.

To facilitate these discussions, attendance needs to be limited to 18 people. In this way, your team can have all the necessary talks to come to consensus. Before leaving, you should ask for a clear show of support.

This is especially true for a strategic plan, hence the need for participants representing a wide range of disciplines. But there’s more.

Discomfort Thinking About the Future

In daily corporate life, only the CEO has the benefit of spending much of her time contemplating the future. After all, it’s her job. By contrast, other senior managers are more concerned about fixing everyday problems and meeting short-term targets.

Consequently, when she sits with her team at the retreat, she has a considerable head-start. Her thinking is far advanced. As such, in my role as a facilitator, I sometimes ask her to hold back, especially if she’s an extrovert. She has the knowledge and smarts to dominate the conversation from the first few minutes, but shouldn’t. Why?

Due to the nature of this unique gathering, it takes more time for her direct reports to shift gears from short-term to long. Also, they are more likely to be introverted, which means they need a chance to think quietly. Sometimes, they may be silent for the entire first day.

Unfortunately, in a single-day retreat, the event is over before they have even left the blocks. They literally drive home thinking about all the statements they wish they had made and questions they intended to ask.

The solution is to have a second day which can maximise the team’s overall commitment. Their emotional and social involvement in the process is the key to effective implementation.

Additionally, their most valuable insights are often not revealed until the second day. This impacts the quality of the strategic plan, which begs the inclusion of their ideas.

Only a multi-day retreat gives them at least one night to think. Here’s the best way to bring different thoughts together.

Start from a Blank Canvas – Together

Successful retreats with maximum buy-in all start the same way: they pull each attendees up to speed by crafting a common base of knowledge. This ensures that no-one has an “insider advantage.” Instead, subsequent ideas are based on a shared but informed “blank canvas”.

This is a far cry from meetings where the leader announces the end-result from the start. By so doing, he unwittingly reduces participants to foot-soldiers. Following his cue, they withhold their participation, wasting time and effort.

This doesn’t work, as they all need to play a part in crafting each decision, giving their all and their full attention. It’s the only way to tap into their functional knowledge and experience required by a sound strategic plan.

When these fundamentals are in place, there is no need for more than two days. Instead, you can plan for intense discussions from start to finish, which maintain momentum once it’s established.

Before the 2008 recession, clients used to expect three-day retreats as the norm, with relaxing and fun activities sprinkled throughout. That changed when budgets tightened.

But it was actually a benefit. Now, retreats are focused affairs intended to move the needle in the right direction in the shortest time possible. They require more than ever from all concerned, but the results are equally robust.

Finally, our study underway of 50 retreats producing 15-30-year strategic plans shows that two days are ideal. Given all the conflicting needs, it weaves the path and gives the company the greatest opportunity to have an effect in a single, concentrated effort.

Francis Wade is the author of Perfect Time-Based Productivity, a keynote speaker and a management consultant. To search his prior columns on productivity, strategy, engagement and business processes, send email to columns@fwconsulting.com.

You don’t normally think for long about the lasting impact your actions have on unknown business colleagues. This is particularly true if they haven’t even been born. But is there a reason to consider far-future generations of leadership in your company?

Antonio Guterres, who heads up the U.N., recently wrote a letter to his unborn great-great-granddaughter…for delivery in 2100. He titled it a “Climate-Change Apology” and began with the following question: “Will you open this letter in a spirit of happiness and gratitude—or with disappointment and anger at my generation?”

He further admits that humanity is “losing the fight of our lives: the battle against climate upheaval that threatens our planet.” But why is he unsure about her reaction? Simple: today, he sees two paths ahead and doesn’t know which one we will take.

The first leads to a trail of destruction. The other trends to planetary salvation. Given the information, tools and technology at our disposal in 2023, both are possible.

At the end, he imagines her wondering quietly: “What did you do to save our planet when you had the chance?”

His commitment is familiar to all creators of interwoven short/long-term strategic plans. As facilitators, we help clients convert game-changing commitments into immediate actions. Here are three steps I employ.

1. Use Today’s Gripes

In a typical retreat, I ask, “What are some of the complaints you have about your organisation that should have been resolved some time ago?”

This question opens a floodgate of woes. Sometimes, they stretch all the way back to the inception of the company. In fact, older heads admit that the matters being raised were mentioned in previous meetings just like this one, but never addressed.

Then we ask: “What decisions did prior executives fail to make 10 years ago that would have prevented or resolved these issues? 20 years ago? More?”

This also unleashes a torrent of suggestions. In fact, it pays to pause before proceeding.

2. Visit the Future

We then have the team envision a strategic planning retreat like this one, but 15-years down the line. “What are some of the complaints future leaders may have regarding tough decisions you failed to make today?”

Unfortunately, this query is frequently met with horrified silence.

After a few moments of reflection, the answers come out, slowly but surely. But this is a new question for most. Managers spend their days tackling immediate issues, and don’t often take a break to consider the distant future in a structured manner.

On occasion, they may speculate over lunch or drinks, and bemoan their organisation’s collective lack of foresight. But the next day, they are back in busy-mode. “We don’t have time to do interwoven short/long-term planning!”

3. Point Out a Young Person

Finally, if there is a colleague in their twenties in attendance, I point them out by name. “Bob is likely to be in that future retreat.”

I add, “His colleagues will ask: ‘What happened at that planning meeting in 2023? Couldn’t they see what was happening?’”

Just like Guterres, Bob could have two contrasting stories to tell.

One could be a tale of courage. “Amazing experience! The executive team put itself at risk, set aside its fears, and made some difficult decisions. Today, we benefit from their wisdom.” Everyone applauds.

The alternate story could be one of cowardice and selfishness. “They realised there was a problem looming, but they decided to focus only on the short-term issues that affected them.”

Why such a contrast?

Some strategic planning teams fail to address the most salient challenges openly. Instead, they point fingers at the “Big Man”, board, government, customers, etc.

Other teams just don’t care. Attendees are coasting into the second-halves of their careers, and just want to make it into retirement with a pension. They place self before service. So their “strategic” plans don’t look past three to five years of tactics: the outer limit of their comfort zones.

You may think these are bad people, but nothing could be further from the truth. Instead, they are simply caught in a trap whose mechanics they cannot clearly see. Consequently, they do their best, but it’s not good enough.

In the end, regardless of their motivation, the result is the same. Disaster.

Jamaican companies, like many worldwide, are currently rife with short-termism. Blame COVID. Or inflation. Or the war, etc. As such, our leaders are becoming cynical.

Don’t yield. Challenge them to leave future managers of your organisation with more than a basket to carry water. Instead, ask them to create a legacy of kindness, not in the form of cash, but in the strategic decisions only they can make.

Francis Wade is the author of Perfect Time-Based Productivity, a keynote speaker and a management consultant. To search his prior columns on productivity, strategy, engagement and business processes, send email to columns@fwconsulting.com.

You finally have time to look back at outputs from prior strategic planning retreats. A quick glance reveals an approach they used which includes “pillars”. If so, be aware: there are some drawbacks to this technique that could lead to a weak plan.

But you must make a decision about what to use going forward. You need to craft an approach, but why should you be wary? To understand why, let’s go back to the process typically followed.

It usually begins with a review of the company’s vision and mission statements. Then, a SWOT and PESTEL analysis of the environment are also done. Next, the team brainstorms projects which are necessary for the organization to achieve the vision. Finally, these projects are grouped into three to five pillars based on common themes.

The final product is often diagrammed as a building with the vision and mission statements in the roof, supported by the pillars. However, its simplicity belies the fact that there are some good reasons to use a different approach.

1. Pillars are merely semi-random lists

A review of the contents of each pillar shows that the link between its items is tenuous. They are simply a list of activities which are nice to do, grouped together using some common attribute. Why is this a problem?

As Peter Compo says in his groundbreaking new book, “The Emergent Approach to Strategy”, anything that resembles a to-do list is not a strategic plan.

Instead, he reasons that, at the heart of an overall framework, should be a triad: an aspiration, a bottleneck and a strategy. What is the role of each element?

• The aspiration defines the overall goal or outcome desired.
• The bottleneck represents the primary obstacle which stands in the way of achieving your accomplishment.
• The strategy defines the way in which the bottleneck will be “beaten” or loosened so that the aspiration is easy to achieve.

Together, these three elements form a hypothesis. It represents the most important changes the organization needs to make. Plus, it evolves as further information and experiences are gathered.

Unfortunately, the pillars approach masks this important nuance. Instead, it assumes that all you need to do is mobilize staff to execute disconnected projects. If this were so, executing strategic plans would be easy.

Instead, in the real world, planning teams need to adjust their hypotheses on the fly as technology advances, government regulations change, competitors take action, and customer tastes change. Together, these shifts force changes in the original hypothesis, a fact of life the pillars approach ignores.

2. Pillars hide relationships

Pillars also over-simplify reality. A mere list of activities hides the fact that projects are always interconnected. But more importantly, they only produce outcomes after the correct chain of causal relationships is followed.

For example, if you are a retailer, you may believe that an Easter Sale will bring in added revenue. However, to achieve the final result, a number of other actions need to take place.

You must become effective at reaching your audience with a promotion. Also, the sale should be launched on the right day of the month to hit paydays. Finally, the season has to be ideal for shopping, as some folks restrain their “retail therapy” during Lent.

The point is that the strategy relies on a number of variables which need to work together, but are imperfectly understood. As such, success is far from assured. The pillar approach obscures this reality and over-simplifies the challenge.

The truth is that strategy is an art in which your actions (causes) are separated from the results (the effects) in time and space. Sometimes the gap can be decades long, or thousands of miles apart.

Fortunately, there are better tools to use, like strategy maps, invented by Drs. Kaplan and Norton. These diagrams preserve the connection between key activities. Furthermore, they are easy to understand and explain to other employees.

3. Pillars emphasize short-term thinking

None of the pillar-approach strategic plans I have seen take into account long-term strategies and results. Instead, they tend to be so simple that they only work for plans which are five years or less in duration.

As such, the lists of projects in each pillar don’t tell a long-term narrative or story which builds a timeline.

Without it, complex undertakings lasting several decades aren’t possible. Think of the planning it takes to build a cathedral over a span of more than 200 years, for example.

Consequently, the list of projects found in a pillar only works for short-term tactical assignments in which the sequence doesn’t matter. This is a major drawback. The technique can’t be used to produce an inspiring, monumental accomplishment.

To craft an alternate approach, read my Gleaner article from March 19th 2023, as an example.

Francis Wade is the author of Perfect Time-Based Productivity, a keynote speaker and a management consultant. To search his prior columns on productivity, strategy, engagement and business processes, send email to columns@fwconsulting.com.