Make the Most of Your Annual Planning Offsite

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Annual Planning Offsite

If there is one thing we've learned from working with strategy and operations leaders across hundreds of growth stage companies, it's that strategic planning is an ongoing, ever-evolving process. Gone are the days where companies spend hours in an annual team planning session, only to walk out with a plan for the coming year that they never revisit. Welcome to the age of dynamic, real-time strategic planning. 

At Elate, we have the opportunity to work with some of the leading companies in the world as they set out to build their strategic plan, and guide them on their journey to reaching their company's long term vision. Yet, for every company we work with, we advocate taking the time to refocus and center your leadership team on the long term vision for the company. And for most companies this comes in the form of an annual planning offsite. 

Whether your company operates on quarterly OKRs, EOS annual goals, or another of the popular operating frameworks that exist today, the opportunity to disconnect from the day-to-day grind of the business and focus on the long term strategy is invaluable to the success of the business. 

Today, we'd like to share how we are working with companies in four common areas of the annual planning offsite: 

- Establishing an offsite meeting purpose for your team

- Creative ideas for offsite meetings

- Building a leadership offsite agenda

- Strategic Planning Software to help implement your plan

Whether you are looking to set a virtual offsite agenda or an in-person offsite meeting agenda, there are a number of offsite meeting ideas that can help set you and your leadership team up for success as you head into the new year. 

Offsite Meeting Purpose

Let's begin by addressing the actual offsite meeting purpose. It likely goes without saying, but this process should be one of the most productive days your company has every year. For some leaders, this statement might come with an eye-roll or a chuckle, because often an annual planning offsite ends up being the opposite. 

What a strategy offsite can often fall into the trap of is a lot of leaders voicing the struggles they are currently facing in their department, because they are unable to disconnect from the short-term pain they’re experiencing in order to think of the long term health of the business. 

Or maybe you've experienced a team offsite where a lot of great ideas are brought up, but nothing ever comes to fruition. Ideas are easy to come by, execution is hard. 

The simple fact is that whether you are doing a one day, two day, or full week strategy offsite you are pulling together some of the smartest, most experienced, and likely highest-paid individuals across your company to think about the future of your business. 

And that's the key part: the future of your business

It's important heading into the meeting that any offsite meeting agenda is focused on what the future looks like. Setting a one, three, five, even ten year outlook should be the starting point. Figuring out what big bets will be made, what type of investments are needed, and how to best structure the organization for success are all important. However, you have to start broad to go narrow. 

When setting an offsite meeting checklist, don't build it in a way that's focused on the problems of today. Instead, set an expectation up front that this is a safe space for dreaming big. Thinking about the future. 

This is where the vision for the company should be reaffirmed and the priorities of the company can be aligned around that long term direction.

Creative Ideas for Offsite Meetings 

Another challenge often overlooked in building a structure for an annual planning offsite is the overall venue, agenda, and format. So often we get bogged down in the logistics of coordinating the event (try coordinating 5+ executive schedules), that we lose sight of how to maximize the team offsite. 

So whether you are looking for creative ideas for virtual offsite meetings or the perfect venue for your in-person team offsite, here is an offsite meeting checklist to help get the juices flowing: 

  1.  Do you want members to spend time together in one spot or have the opportunity to escape home? We use the word 'escape' a bit loosely in this context, but it's seriously something to consider. Often we find that if you are planning a two-day offsite, one of the best ways to get team member's minds off of the day-to-day grind is to simply take them out of their regular environment. Obviously, this might be easier said than done when it comes to scheduling, but the reality is that if you want folks to truly immerse themselves in the long term vision of the company and connect in a healthy way, think about scheduling the event somewhere that allows people to disconnect and focus on the purpose of the meeting. 
  1. Start with team offsite questions that open people up to something bigger. This isn't just about the long term vision for the company, it can also be about the career hopes and aspirations of team members. What do they love about their job? What do they wish they had more of? What is it that helps them feel fulfilled in their work? Better understanding the person behind the job title and building empathy across team members will immediately open up channels of communication. 
  1. For virtual offsite ideas, don't make it all about an agenda. Is there an opportunity to have a family meet and greet, a wine and apps trivia session, or even a virtual whiteboarding session? There are plenty of platforms available that can make this a reality. 

After speaking to the purpose of the offsite and some creative ideas for setting your team up for success, now we can get into some of the details of setting your leadership offsite agenda. 

Leadership Offsite Agenda

The leadership offsite agenda is one of the most important parts of the offsite, because it helps set the tone and direction for the session. However, don’t be fooled: it doesn’t have to go seamlessly down to the exact minute. 

The agenda is meant as a guide, and while you need to be pretty direct at staying close to the guide, keep in mind that certain sessions may end up going a bit longer, while others may go shorter. Good conversation can often have this effect on leadership meetings. Just make sure it’s focused on the right priorities and outcomes your team agreed to heading into the day. 

So now, let’s get into some of the details of setting your leadership offsite agenda. 

First, the off-site meeting agenda template should have one owner. This owner can be the Chief of Staff, COO, or another member of the leadership team, but it should likely be someone that can bring an unbiased view to the conversation and work with every team member to ensure everyone is in alignment on expectations. You don't want too many cooks in the kitchen. One owner will help a seamless flow that's been thought out, rather than a haphazard approach that just throws everything anyone wants to talk about into an agenda. Bonus tip: for those companies that are looking for a bit more direction, bringing in a consultant can do wonders to help drive conversation and keep every team member engaged. Also, quick plug for Elate and our services team for any that might be interested! 

Next, start broad to go narrow. This isn't the first time we've said this, and it won't be the last. You can't be focused on the day-to-day challenges your team is facing. Start with the company's vision. Where are you aiming to be in 10 years? What are the rocks, objectives, or milestones that define success in 10 years? Whether it is revenue, customers, users, units sold, or any other variation of your key metrics, you need to have a definition of your vision with quantifiable goals that can be measured. 

Additionally, no offsite agenda template would be complete without talking through the ideas for how you unlock this 10 year vision. The ideation portion of the offsite meeting can be broken down into priorities that can still be aggressive, but start to be viewed in one, three, five, or ten year timeframes. Having the collective voice of every member of leadership will help add context to how feasible these ideas are from different parts of the business. 

Finally, what does the coming year need to look like for you to continue on your path to long term success. Often the visionary CEO is setting the vision for the company, but the annual offsite meeting can help set the stage for the annual goals or OKRs your team needs to hit in order to take the next step in reaching the vision. This part of the process also needs to have an element of ruthlessness to it. You can't do everything, and often you shouldn't be taking on more than three to five company themes for the year. Be critical of the ideas your team has come up with, and be able to defend the importance of the objective being proposed and how you achieve it in the coming year. 

In addition to what we cover here today, there are also a number of other templates for an offsite planning agenda that are very prescriptive. From outlines such as an annual OKR template or an EOS quarterly meeting agenda pdf. However, this section is meant to provide a high-level structure of main areas that can be tailored towards your business. 

Strategic Planning Software

As you head into your company's strategy offsite this year, keep in mind that this isn't where the process ends. It’s only the beginning. The offsite meeting is designed to set the stage for the coming year and center your leaders on the vision and direction of the company. However, for the best strategy and operations leaders, this serves as a springboard to how you evaluate growth opportunities for your business over the coming 12 months. 

For any high growth company, priorities may shift, markets will change, and competitors can throw curveballs your way. That’s why it's important to understand your plan needs to be flexible and dynamic. 

With that in mind, ask yourself whether you are building the foundation of your strategic plan and company strategy offsite in a way that matches this mindset. 

Too often we see companies take a standard offsite planning template, and fill it out in excel or in a powerpoint presentation to be shared with the rest of the company. Whether you use OKRs, V2MOM, or EOS strategic planning, the reality is that you should be building your plan in a solution that allows for this long term scalability and flexibility. 

Elate is the leading Strategic Planning software built to help SaaS companies communicate their vision, create alignment, and track performance all in one place. It was built out of the frustration of leaders trying to make goal-setting acronyms work for teams. Purpose-built for growth, Elate gives your team a realistic framework for strategic planning.

From the leadership offsite meeting to the quarterly goals being set and every weekly leadership team meeting in between, you should have a solution that drives your business forward. 

If you're interested in learning how we are working with other strategy and operations leaders, reach out to our team today!

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