The Ultimate Guide to Holding an Incredible Executive Offsite – Day One

Executive offsites should be exciting not because you are going cliff-diving between sessions but because you are shaping and directing your company for decades to come. 

The agenda you will learn in this article will give you and your team an opportunity to reflect on past successes and challenges and cast a vision for the company so powerful and enduring that it will outlast everyone in the room.

It will align your goals, fill you and your team members with passion and purpose, and create more clarity in one day than you’ve been able to develop in the collective history of your organization.

If you’re a Visionary leader, you’re going to love it. There will be stories, vision, passion, and ideas. If you are an Operator, Processor, or Synergist, you will find so much clarity and context for your decisions as together, you and the team identify the why behind all that you do together.

Even if you don’t lead or even attend an executive offsite, there is still so much here for you to learn because a great offsite will tap into many of the most timeless leadership principles that apply to our personal lives just as much as our business operations.

So here’s what the agenda for day one looks like at a glance.

1. State of the Union: a look back at the history and current circumstances of the organization
2. Team Building: unlocking the potential of a healthy, cohesive leadership team
3. Mission and Vision: establishing the foundations of the business and the direction moving forward
4. Values: Building a strong, productive culture around shared traits and behaviors
5. Goals Part 1: Setting incredible and inspiring long-term goals

Session 1: State of the Union 

Duration: 60 minutes

This is the session where you, as the leader, will speak the most. Start by setting a clear goal for the event. This will be something along the lines of, 

“When we leave here, everyone on this team will know our why, agree on our values, and have a clear picture of where we are going and our next steps to get there.”

Next, tell the story of the business. Why did you start it? Of which accomplishments are you most proud? What were the biggest mistakes you made along the way? How has the organization grown each year? What stage of the business lifecycle are you in? What are the biggest opportunities you see on the horizon? What are the biggest challenges you will face in the coming year?

Finally, open up the session to discuss the quantitative (sales, profit, production, etc.) and qualitative data (wins, failures, strengths, and challenges) of the past year. You will find that this brings clarity, precision, and groundedness, to the rest of the meeting.

Session 2: Team Building

Duration: 60 minutes

Don’t worry. No candles, kumbaya, or trust falls are needed. You don’t have to get touchy-feely. But you do have to create a team (rather than just a group of individuals). 

I recommend three quick (and painless) exercises.

1. Personality/Leadership Profiles. If you use a personality or leadership profiling system, have each attendee share their type and answer this question. What do I wish other types knew about my type? If you don’t have a system, request your free Team Leadership Styles Report today. You’ll get a full report you can take to your meeting.
2. Personal Histories (optional). Have each team member share their personal story. Where did they grow up? How many siblings did they have? What was their first job? What challenges did they face as a child? What do they love most about being on this team? 
3. Team Effectiveness Exercise (optional). Starting with the leader, have each team member answer these two questions. a. In what way does _______ best contribute to the success of the team? b. In what way does _______ most detract from the success of the team.

For more on team building, check out The Synergist by Les McKeown and The Five Dysfunctions of a Team by Patrick Lencioni.

Session 3: Mission and Vision

Duration: 90 minutes

Establishing your mission and vision can seem pie-in-the-sky, but it isn’t at all.

First, your mission and vision become a filter for every single decision you will make moving forward. For example, goals become much more apparent. They are simply the mile-markers on our way to accomplishing our mission.

Second, mission and vision give purpose to even the most mundane tasks. 

Three men were working on a building site. When asked what they were doing, the first man answered, ‘I am laying bricks.’ The second said, ‘I am making a wall,’ and the third replied, ‘I am building a cathedral.’

A recent Harvard research study showed that purpose is a more powerful motivator than passion. This is especially true for Millennials who are making up a greater and greater percentage of the workforce.

Vision Statement

The best model of a corporate vision is Simon Sinek’s “Just Cause.” According to Sinek, your vision must meet five criteria. It must be 

1. for something (rather than being against something or someone)
2. inclusive (valuing diversity of thought, experience, and contribution)
3. service oriented (and not selfish, so don’t use the word best to describe your company or product in your vision statement)
4. resilient (it is not limited to a particular time or environment), and
5. idealistic (it should big, bold, and always further out on the horizon)

During your time together ask yourselves, these three questions.

• What are we for?
• Who do we serve?
• What bold vision is so big that it will always be true but likely never be fully achieved?

Mission Statement

Now, A mission statement is a little different. It is a bit more practical and tangible than your vision statement. If vision is about inspiration, then mission is about perspiration.

The best model for a mission statement is Jim Collins’ “Hedgehog Concept.” A great mission statement will answer these three questions.

1. What are you deeply passionate about?
2. What can you be the best in the world at?
3. And what drives your economic engine?

For help crafting your mission and vision statements, check out The Infinite Game by Simon Sinek, Good to Great by Jim Collins, Mission Statement Made Simple, or The Advantage by Patrick Lencioni.

Session 4: Values

Duration: 90 minutes

Values answer the question, “How do we behave?” Along with your mission and vision, they act as a filter for your decisions and the ground rules for how you treat each other, your clients, and your vendors. Clear values will help you rule out bad hires before you hire them and help you set the right conflict norms for your team.

I recommend identifying a word and a phrase to go with it. The words will be easy to remember, and the phrases help provide more context for the meaning. For example, our values at Eight Figure Focus are

• Character: Do in secret what you would do in the spotlight
• Courage: Challenge yourself and others to change
• Clarity: Don’t stop until it’s clear

Here are a few pointers if you are defining your values for the first time.

• Please, please, please do not choose values that aren’t real. They don’t have to be cool. They don’t have to be unique. They don’t even have to be powerful. They need to be true.
• Contrast your best “fitting” employees with those who just weren’t a “fit.” Make a list of your best employees and have everyone individually write down one or two words to describe them. Then, make a list of those who struggled or left quickly or were fired and have everyone separately write down one or two words to describe them. You should see some pretty clear patterns emerge quickly.
• Give space for your values to change or expand. In this article series, I explain how values change dynamically as an organization grows. Intentionally changing values over time is likely a sign that your organization is very healthy. For you, this means you don’t have to magically conjure up the values that will be true 20 years from now. Instead, choose the values that are true today.

For help defining your values, take a look at these articles or check out Built to Last by Jim Collins and Jerry Porras.

Session 5: Goals Part 1

Duration: 90 minutes

Building on the work you’ve accomplished so far, it is time to talk about goals. I recommend using a series of goals ranging from 90 days to 10-years.

In this session, we’ll focus on the long-term goals.

First is the 10+ year goal. 

Jim Collins famously dubbed this the Big Hairy Audacious goal. It is so far out you may never reach it, but it will get everyone pointed in the same direction. You should only have one 10-year goal.

When discussing your 10-year goal, talk about it in terms of round numbers (revenue, profit, employees, locations, etc.) and qualities (people enjoying coming to work, releasing new products and services, connected to these networks).

The 10-year goal shouldn’t feel readily achievable. More often than not, it will border on or live squarely in the impossible. This is a good thing. You may also find it helpful to quickly plot how much you would need to grow each year to get there. This seems like an obvious step, but you would be shocked at the quality of the discussion it will create.

Next, we have the 3-year goals.

This typically represents the furthest milestone that we can see if we squint while looking through some high-powered binoculars. It will be slightly more practical and within reach but should in many ways be even more challenging than the 10-year goal since it is near enough to be accomplished.

Again, define the three-year goals in terms of numbers and qualities, but this time, be a little more specific like, maybe a ten-year goal is to have 29 offices in 17 states. Your three-year goals might include establishing seven offices in the southeast making $14M in revenue and $2M in profit by December 31, 2024.

I would recommend limiting yourself to between one and three three-year goals.

For each of these goals, don’t get yourself caught in the weeds or concerned with perfection. Set a hard limit of 40 minutes for the ten-year goal and 50 minutes for the three-year goals. These likely won’t be beautiful the first time you do it. The win is a vibrant discussion and building your goal-setting muscle.

Wrapping up

That is day one. It is a packed day. Despite how much you cover, you likely find the day energizing. That’s a good thing because tomorrow you are going to pick up where you left off.

You’re going to build on the foundation and framework you laid out on Day 1. It’s like adding drywall, paint, flooring, and furniture to a previously empty frame and foundation. You get to see a conceptual start to materialize into real, tangible steps you and your team can take to move forward.

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