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3 Key Elements for An Executive Offsite

Key Questions And How To Answer Them About Running An Executive Offsite

Your executive offsite can't afford to fail. Statistics show that 61% of senior executives struggle to execute their strategy, and 44% have experienced failed strategic initiatives.

This is what a doomed offsite looks like:

  • They wander from topic to topic without a clear focus

  • New ideas don’t get generated and good decisions don’t get made

  • Interpersonal conflict (or fear of conflict) cause teams to avoid tough- but necessary- conversations

  • The offsite ultimately doesn’t grow the business

Teams often organize an executive offsite for their leaders. This allows them to focus on the bigger picture and prioritize long-term strategies. It also provides an opportunity to solve large problems.

A well-structured and efficient offsite can provide clarity on core issues. It can also boost confidence in the strategies to address them. Additionally, it can set motivating targets to help the business advance.

Small teams, large teams, and everyone in between benefits by having a time and space to zoom out of the day-to-day and reset, but few teams have the expertise to organize an effective offsite. 

They miss the basics.

There are three components to a killer executive offsite and they’re easy to implement, even for a team conducting their first offsite. 

But, if you want an offsite that's highly effective, there is a key..

The key is to have one unified mission guiding all the components. This mission provides a frame for the experience and dials up the synergy between all three elements. 

Here are a few examples of a singular overarching mission:

As a shorthand, a simple offsite mission will contain a single verb and a single noun.

  • Develop a talent strategy for the upcoming year

  • Improve our leadership team’s day-to-day effectiveness and trust

  • Navigate the big change that’s happening soon

Once you’ve identified your big-picture mission, it’s time to start with the first of the three components: Offsite Structure.

  1. “How will we run this offsite?”

Offsite Structure

Part of the offsite magic is that it’s different from day-to-day work. If your leadership team stays in the same chairs, with the same schedule of meetings, with the same work output expectations, it’s hard to disentangle and zoom out.

In order for leaders to think differently, they need to work differently.

We recommend starting with thinking through Offsite Structure because it’s usually the most tangible and familiar to first-time offsite planners.

When people enter a new headspace, they can be more innovative, make new connections, talk about conflict in a new way, and change how they think and behave. As an offsite organizer, you can curate the experience to provide the room for those positive outcomes to happen.

Some simple ways to break from the day-to-day work:

  • Go to a new physical location

  • Bring the team together for a longer period of time than a typical meeting

  • Bring in a facilitator to change how the experience is managed

  • Talk about topics that aren’t often discussed

  • Remove expectations to produce work/manage work while at the offsite

These design factors help create the headspace for leaders to step into, but it also requires that leaders are equipped to step into this new headspace. Beyond the logistical elements for an offsite, there needs to be the ingredient most teams miss when making big decisions: the data.

2. “How can we be accurate throughout this offsite?”

Offsite Data

Have you ever been in a meeting where a lot of hypotheses to a problem were suggested but later discovered that there was no evidence to support any of them?

Offsites are notorious for chasing shadows.

Since leadership teams are removed from the front lines of customers and individual contributors, their natural data set of experiences are outdated or filtered by middle management. Decisions by executives are highly at risk of being myopic, based on false pretenses, and out-of-touch with the staff and customers.

Leaders who are aware of these risks equip themselves with the best facts and perspectives before making high-impact decisions:

  • Provide a report of relevant data points for participants to read before the offsite takes place

  • Invite an archetypal customer or employee to present directly to the leadership team

  • Start the offsite with a simple show-and-tell from each leader containing their division’s data that is relevant to the overarching mission

  • Plan for the offsite’s output to be reviewed by a panel of customers/employees and then amended with their feedback

The data and evidence like those listed above helps guide strategic decisions as well as justify the outcomes, generating far more buy-in from employees and customers.

While offsite design and preparedness are the first two failure points for teams running offsites, the final component to an effective offsite is usually the easiest to identify but the hardest to do well.

3. “How do we make sure this offsite ultimately works?” 

Offsite Mandate

The cost of an executive offsite is nothing to sneeze at - leadership time, travel and expenses, facilitators, etc. - but the cost of bad outcomes from an offsite can kill a business.

It’s easy to imagine an avalanche that’s caused by a leadership team that doesn’t trust each other, bases decisions on a flawed understanding of the bigger picture, plays politics for their own self-interest, and fails to produce anything useful out of an offsite.

It’s also easy to imagine the potential of a leadership team that makes the best decisions possible to catapult a business to the next level with clear calls-to-action and a unified narrative from all participants.

Researchers found that most executive strategies deliver only 63% of their potential financial performance, and more than one-third of the surveyed executives placed the figure at less than 50%.

You can’t afford for this offsite to fail and you shouldn’t accept for it to fall short.

There are two related pieces to this final critical component to executive offsites: a mindset and an outcome.

Just like how logistics need to be intentionally designed to curate space for a killer offsite, the mindset carried by participants needs to be intentionally framed as well. Without setting the mindset beforehand, participants may come in with the wrong expectations or are unwilling to commit to the decisions that need to be made.

A well-communicated mindset should be sourced from the overarching mission but humanizes and makes it relevant to the participants:


MISSION - Develop a talent strategy for the upcoming year

MINDSET - “This offsite will set a new direction for our business”


MISSION - Improve our leadership team’s day-to-day effectiveness and trust

MINDSET - “We need to better communicate and collaborate as a team”


MISSION -Navigate the big change that’s happening soon

MINDSET - “If we don’t have a plan for this upcoming problem, our business may not survive it”

If there is a CEO or designated leader for the executive team, this expectation needs to be clearly communicated and endorsed by that individual. If the top person isn’t fully on-board with what needs to happen as a leadership team, it’s unlikely the rest of the business will follow suit.

The other half of an offsite’s mandate is a clear outcome that the offsite is due to produce. It’s an answer to the question asked at any well-run meeting, “Now what?”

Target outcomes don’t always have to be a decision, but they tend to be the mirror of the initial mindset expectation:


MISSION - Develop a talent strategy for the upcoming year

MINDSET - “This offsite will set a new direction for our business”

OUTCOME - A clear and singular set of priorities to guide our business’s talent strategy


MISSION - Improve our leadership team’s day-to-day effectiveness and trust

MINDSET - “We need to better communicate and collaborate as a team”

OUTCOME - A firm break from how we communicated and collaborated as a team with clear guidelines around our potential points of conflict going forward


MISSION - Navigate the big change that’s happening soon

MINDSET - “If we don’t have a plan for this upcoming problem, our business may not survive it”

OUTCOME - A strategic and tactical plan for handling an upcoming business threat


These two halves- a transparent mindset and a target outcome- can be the X-factor that changes your benign offsite into a transformational offsite.

A Better Executive Offsite

To recap, the ingredients for a high-quality executive offsite must include:

  1. An intentional departure from day-to-day work by curating a logistical space- physical and temporal- for your offsite

  2. Equipping participants with data and evidence to make accurate decisions

  3. A clear expectation of why the team is conducting an offsite and what will happen because of it

Underneath all of that is a singular mission to guide the momentum of your well-planned and run offsite.

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