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Your Short Guide to Leadership Off-sites

Sometimes you can find your leadership team struggling to progress with their strategic planning. Or you seem constantly bombarded with day-to-day operational tasks that distract you from the long-term vision. The truth is, many leadership teams face similar challenges when it comes to aligning on strategy and executing against long-term goals when there are so many urgent tasks competing for attention. The good news is that there is a proven solution to these challenges: leadership off-sites.

In this short guide, we’ll provide you with everything you need to know to plan and execute a successful leadership off-site, including tips on agenda setting, facilitation, and common mistakes to avoid.

Read on to bring your leadership team together for a productive, high-impact off-site that sets your company up for long-term success.

What are leadership off-sites?​

The simplest definition of a leadership off-site is the moment when the leaders of a business get away from the office to have conversations for specific outcomes. It’s a useful exercise to develop the company’s culture and break away for fresh thinking. When used in a regular cadence, it keeps you and your team accountable for what you’ve agreed to in the previous gathering. In that sense, every leadership off-site should be intentional, planned and themed according to the business’s context.

The three types of leadership off-sites​​

Metavolve’s team has been a part of, facilitated and advised on thousands of leadership off-sites across the globe. In doing so, we’ve found that there are three types of leadership off-sites worth doing and occasionally using a hybrid approach:

  1. Strategy Setting
  2. Strategic Planning
  3. Team Building

Strategy Setting Off-sites​​

The strategy-setting leadership off-sites are a breakaway to discuss the business strategy.

During this session, your leadership team evaluates and amends the relevant strategic elements so your business can adjust to the new market or internal environment conditions. Every strategic decision you make should have a minimum time horizon of a 1-year impact.

Why this focus on the long term? Because you and your leadership team are gathering to make decisions that will curate the various strategic pillars towards the best strategy. Hence, the best strategy setting off-sites we’ve contributed to were kept at the senior leadership level. However, inviting high-potential leaders into the meetings is also likely to increase your strategic pipeline of talent who are capable of taking on strategic roles.l

Strategic Planning Off-sites​​

The strategic planning off-sites are a breakaway to discuss, identify and commit to the action plans for the priorities of this immediate next year or quarter.

The main goal of this session is to align your key leaders on an execution plan that will achieve the business strategy. Typically these are used for annual and quarterly cadences as resource allocation at the project leadership level happens here.

Strategic planning off-sites are also a useful break-away type for individual teams or functions. They can bring their improvement plans to the table, which can be approved by a senior leadership team. You can do these cycles in smaller time horizons with more focus on the details or longer time horizons and manage it in a more granular manner in between.

Team Building Off-sites​​

Anyone who’s been a part of a team knows that great teams don’t happen organically. The best leaders take a deliberate effort to develop, grow and cultivate a great team. There’s a whole host of books on the subject and activities that you can do to achieve this outcome.

In our experience, using personality assessments can be really effective in facilitating team building and development. After everyone has completed and explored their own behavioural patterns, strengths and development areas, they get together with their team to unpack its composition and grasp better ways to work collectively.

In this setting, you start to develop a common language to discuss deep topics with empathy for the people that you work with. This leads to team members becoming more effective in working together often resulting in teams operating in a complementary way.

The Hybrid Approach​​

Without realising it, many leaders choose a hybrid approach. They discuss topics across two or all of the off-site types discussed above. This format can only work if the sessions are agenda-based with time boundaries. Because these breakaways have the sole purpose to align the team with the future direction of the business, you need to be very deliberate about the outcomes you’re aiming to achieve.

For example, you can have a strategy session that focuses on changing the market positioning of your business. The first half-day can be focused on the discussion, evaluation and decisions. The second half-day can be focused on planning the implementation of the change in market positioning.

Common off-site mistakes​

Leadership off-sites are beneficial for individuals and teams to understand and contribute to the future of the business. However, they can easily turn into recreational times when not facilitated effectively. For you, Metavolve has identified below the most common off-sites mistakes so you can avoid them for your next break-away.

Inviting too many people​​

The more the merrier? It doesn’t work like that for a strategic meeting.

When you organise a Strategy Setting off-site, inviting large groups of people doesn’t make sense. Either you’ll be adding more complexity and opinions to the conversation or you’ll face a disengaged crowd. Sure, enabling some debates can spark astonishing ideas but it can make you go far beyond your agenda. Remember, blue-sky thinking can always happen outside of the meeting.

If it’s a Strategy Planning session, then adding teams from different business units can be confusing. In fact, this type of meeting is meant to discuss specific items of the business strategy. You want specialists to come up with a long-term vision for their team and can only do so with people who can actively engage with these topics.

Inviting non-strategic people​

Your leadership off-sites are designed to achieve focus and alignment with the business’s future as a team. Just like the number of people you invite, you need to be deliberate about who you invite.

Because if you start bringing non-strategic people into a strategy-setting session, no one wins. You’ll more likely face change resistance, boredom, or misunderstandings from those who have more operational roles. Not only this, but also the strategic members of the team become frustrated for continuously getting into the details or needing to explain everything about their thinking.

In short, if you want to get away from this leadership off-site with meaningful decisions, invite strategic people.

Using it as an excuse for a social bonding event​​

Most businesses believe that great relationships between co-workers are created outside the workplace. Thing is, this is not completely true.

Of course, having fun together is a cool way to develop working relationships and friendships. Team members will get to know each other and carry these playful memories with them for some time. But bonding on a personal level does not necessarily make your team members turn into a stronger and more cohesive professional team.

On the other side, while your people get to bond with one another, what are they taking away regarding the business strategy? Does everybody know what they’ll have to think about or execute the next Monday? Are they aware of what their roles would be in the next year’s project?

Remember, your strategy sessions should always be organised and facilitated with the intention of making meaningful progress towards executing your vision for the future of the business.

Trying to achieve too much​

This must be our favourite pitfall to unpack.

Entrepreneurial businesses never run out of ideas for creating new opportunities or improving the current situation. But there’s a constant issue with the way they approach it. Either they can’t evaluate the priority of each of these new projects or they overlook the allocation of appropriate resources.

So, here’s a piece of advice: before you and your team confirm a priority or project, consider how much time everyone will need to commit to this. Weigh up how much is on everyone’s plates and then make the appropriate decisions around resource allocation.

Not having set outcomes​

We can’t emphasize it more than we have throughout this article. You must plan every single one of your strategy sessions according to your desired outcomes.

Without identifying them, your agenda can be confusing for everyone involved in the meeting. You’re also leaving it up to the team to organically get to the right answers. When it happens, you and your team are overlooking how much you are missing out on to drive the business forward.

The consequences of the decisions from these sessions can genuinely make or break your business. So, take it seriously and set the outcomes that you’re wanting to achieve by the end of the session.

In summary​

In short, planning a leadership off-site can be a daunting task, and lead to frustration when the results don’t match your expectations. However, if you overlook the planning and execution of these strategic sessions, you’ll just end up wasting resources and damaging the trust and cohesion among your team.

Remember, there are three overlapping but distinctive types of leadership off-sites with their respective purpose and outcomes.

The key to creating off-sites that are memorable, effective, and deliver tangible results that you and your team can be proud of is to be deliberate about:

  • the meeting agenda,
  • the teams that are invited,
  • and the expected outcomes.

Now, use your learnings from this guide to get your off-sites right and fuel your business’s growth!

Are you ready to create a stronger, more cohesive team? Start planning your leadership offsite today with Brett Matheson and see the results firsthand.