The Process Behind Our Annual Offsite Planning Session

How to plan your yearly offsite, what to review with your leadership team, and how they can help you hit your goals.

Kyle Racki
Jun 13 · 11 min read

One thing is universally true about founding a SaaS company. At some point in the journey, the founder has to get their head out of every department and start running the company as a whole.

For me, that stage came when Proposify had grown to the point where I didn’t really know how best to manage my time and lead effectively as CEO and co-founder.

We were growing quickly and I had to put faith in my leadership team and let them run their departments. Business coaching was invaluable in that transition.

In the early days of a startup, you’re constantly grinding. Your focus is solely on building a product people care about, getting market fit for that product, and finding the cash to keep it all going. Every day is a fight to survive till tomorrow.

It’s a daunting shift going from day-to-day survival mode to planning the future of the company one, three, even ten years down the line. Yet, daunting as it may be, this shift is necessary if you want to scale your business to the heights it’s capable of reaching.

The inflection point, the curve of the hockey stick — call it whatever you want— at some point, your business is ready to scale and you’ve got to make the jump. And when you do, you need a plan.

EOS and the annual planning session

About eighteen months ago, my business coach, Dan Martell, turned me on to the EOS system.

The Entrepreneurial Operating System, or EOS, is a framework for structuring a rapidly growing business outlined by Gino Wickman in his book Traction.

We rolled this system out at Proposify after Dan introduced me to the benefits. One of the central components of the EOS system is a yearly planning session with the core leadership team.

This session is a time to sit down with your decision-makers and outline the big vision for your company. It’s a chance to lay out the long-term road map; all your goals, metrics, and milestones are put forth, discussed, debated, refined, and documented.

We’ve had two of these sessions at Proposify. The first, in 2018, was the hardest. We were at ground zero. We’d hit our inflection point and it was time to implement a more systematic approach so we could continue scaling and growing revenue.

We didn’t have a three-year strategy or a scorecard. We didn’t have our mission ironed out or our company values articulated. The first annual meeting was our first chance to think about and document who we were as a company.

Our second planning session, in January 2019, was far more productive. We’d already established a baseline, a foundation to build off. We weren’t building a vision from scratch, which gave us the opportunity to refine and better articulate who we are, what we’re all about, where we’re going.

This is how we did it.

The importance of going offsite

I’m sure you’ve noticed the office gets rather distracting from time to time.

Hell, if you’re a SaaS founder and your workspace isn’t buzzing, what are you doing?

It’s near impossible to escape the emails, the Slack notifications, the different team members popping in when there’s a new fire going — don’t get me wrong; things that make the office a vibrant and dynamic place to work, but not necessarily conducive to an in-depth planning session.

Going offsite lets you get a different perspective. Away from the office, away from the distractions. This year, we actually did our annual planning session on the weekend, in a turn-of-the-century house on the edge of a frozen harbour an hour out of the city, with a roaring fireplace, guitars, and a pool table, and a yard coated with knee-deep midwinter snow.

In other words, about as far from the boardroom as you can possibly imagine.

Pictured: Me thinking about our 2019 goals.

Beyond the distractions of the midweek office, doing it on the weekend brought a different dynamic to the session. As well as being a super productive session which helped us define a clearer company direction, it was a great way to come together as a leadership team.

That’s one of the benefits that often gets overlooked. You spend a third of your adult life at work, and if you’re a founder of a tech company, work can easily become your entire life. You’re asking people to come together to solve really complicated problems. It’s so important you enjoy the company of your colleagues.

Making these bonds stronger has undoubtedly helped us be a more effective leadership team.

The Proposify yearly offsite planning session agenda

Before you plan where you want to go, you have to know where you’ve been.

Much of the first day was spent discussing the previous year. We went over how we did financially, metrics we hit and ones we didn’t, the big problems we ran into and whether we solved them; generally what went well and what didn’t.

These sessions are never passive, and it’s important to kick it off with some involvement from everyone present. (To give you some context and an idea of the size of the session, there were seven people on Proposify’s leadership team plus my co-founder, Kevin Springer and me present.)

We kicked it off with everyone going around the room talking about their accomplishments for the year, things they’re proud of their department or the company as a whole for getting done, and what they hope to get out of the next two days.

That serves the deeper purpose of allowing you as the founder and the person running the session shape the content and discussion to align with people’s goals and expectations.

Day one: Implementing EOS tools

The EOS toolkit is extremely robust, many of them designed to help structure high-level planning sessions such as an annual planning session. Here are a few we use and what it looks like when we put them into practice.

The Organizational Checkup

Part of the retrospective analysis, this is a survey the leadership team completes prior to the two-day session. It consists of 20–30 questions designed to assess the health of the company and the clarity of our vision and the direction we want to take.

The results of this survey give us a clear idea of our strengths and weaknesses and the biggest challenges we’re up against.

It’s a great way to get some data on where we’re at without relying on pure gut instinct. The objectives that come out of that survey guide the rest of the yearly planning session and beyond and helps us keep tabs of how successfully we’re executing the company vision.

The Vision/Traction Organizer (V/TO)

Shared among the leadership team and the rest of the company, this concise doc outlines the high-level goals of Proposify. It’s a place for the vision of the company to exist on paper and not just an abstract concept or a series of loose definitions of where the company’s headed shared by only a select few.

It works on a higher level too because it forces you as the founder to lay out the vision for the company in a clear, concise, and shareable format. It contains all the elements you need to iron out during the first major planning session of the company:

  • What are your core values?
  • Describe your niche: what’s the core focus of your company?
  • A specific, goal-oriented one-year plan.
  • A three-year picture.
  • A 10-year target.
  • High-level marketing strategy: who are you selling to?
  • Three unique differentiators that set you apart.
  • What are the major projects?
  • What are the biggest issues?

Outlining the core values of a company is essential, and an entire process in itself. But it’s imperative to a company’s survival. Proposify’s core values define everything we set out to achieve as a company. They make the basis for hiring and firing decisions, inform the work we do and resonate in every aspect of the product.

We asked these questions at our first annual session and refined them in the next. The process of answering them was a challenge, but it was also good fun. There was a lot of healthy debate and passionate argument and great ideas as a result.

If you’re running the session, make sure you have a whiteboard or a flip chart and capture those ideas. Later, that gets condensed into the V/TO document and kept in a place everyone can access it.

The Issues List

Every company has a list of issues longer than they care to admit. But, great companies have a defined process to tackle those issues systematically.

The issues list is pretty self-explanatory; it’s a list of the biggest challenges within the company. This list, by necessity, isn’t much fun to write or look at. But denial ain’t just a river in Egypt; if you want to get anything done, you need to take a hard look at the big ugly things holding you back.

A condensed, concise version of this list goes into the V/TO document. At Proposify, we review and discuss this list as a leadership team at quarterly planning sessions and weekly sync meetings. Each issue gets ranked in order of importance, assigned to a department, and eventually solved.

Once an issue’s solved, it goes into another category in the doc as a solved issue. This lets the whole team reflect on what we’ve accomplished and how we did it.

The yearly planning session isn’t the time to solve every issue your company is up against. But it is the time to put a plan in place to solve issues one by one.

Wrap it up

All that will take up day one. You want to make sure these sessions are productive and you need to make sure they remain that way. You don’t want your leadership team dreading next year’s session.

Break bread together. Cook a nice meal. Have a beer or two; these sessions are as much about making great memories with your team as they are about planning.

Day two: setting goals and looking to the future

You’ve laid the foundation, reflected on the year that was, and identified the big challenges. Now it’s time to formulate a plan to solve them.

10-year goals

Start big, right? The 10-year goals are all about aiming as high as you can. These are the BAHGs (Big Hairy Audacious Goals): Curing cancer, making transport available to everyone in the world, solving global warming — make them as big and crazy as you like.

These goals aren’t financial, they’re ideological. They exist to inspire the people in your company striving to achieve them. They’re designed to coax the kind of bold, confident thinking needed to change the game.

Three-year picture

Still a long way down the track, but much more tangible. It’s likely there are people on your team now, painting this picture, who will be with you in three years to see it realized.

The three-year picture is more tactical, based on metrics like expected ARR, number of employees, and a concrete date by which to accomplish these things. This picture hits closer to home and creates a sense of urgency; after all, what you achieve in one year is one-third of the way to the three-year picture.

One-year plan

The one-year plan is all about detailed specifics. An exact revenue number. A certain profit percentage if sales are your primary revenue generator. If you’re venture-backed, specific growth metrics or CAC payback period.

What are your key performance indicators? For SaaS businesses, these are things like net MRR churn, average contract value (ACV), or your net promoter score (NPS). You need your key metrics to be at a certain point to generate your goal revenue. The annual planning meeting is the time to determine what those metrics are and how you’re going to achieve them over the next four quarters.

Budgets, rocks, and pebbles

The annual planning session is the time to iron out departmental budgets. Each department head needs to walk away with an exact figure that determines how much they can spend and how many people they can hire.

You also need to define your Q1 rocks. The rocks are the big tasks, a handful of which need to be prioritized and set every quarter for each department. The pebbles are smaller tasks, often assigned to individual team members, that contribute to achieving the rocks. The sand is everything else: Putting out fires and addressing small issues, but nothing of great import and nothing that will move the needle in the long run.

Much like with an actual jar, if you put the sand in first it will fill up and there won’t be any room for the rocks. But if you put the rocks in first (ie: keep priorities straight) the sand and pebbles will fill in the gaps around the rocks, as they should.

We review the status of these projects at our weekly sync meetings. Usually, completing these projects will coincide with hitting our key metrics.

Each quarter we plan new rocks. There’s no point in trying to plan projects a year out, enough will change in three months that you’ll need to reevaluate priorities, and new challenges or opportunities will emerge that necessitate new projects.

I like to think of it in terms of Outcome, Strategy, Actions.

  • Outcome: Where we need to be in a year (planned a year out)
  • Strategy: How we’re going to get there (assessed every quarter). Involves big-rock planning, issue solving, and setting new quarterly targets.
  • Actions: The exact steps we are taking to execute the strategy (assessed every week). Involves reviewing the weekly scorecard, and communicating progress on big rocks.

You want to strike a balance between shiny-ball syndrome — getting distracted and pulled in multiple directions — and being rigidly committed to the plan so much that you won’t adapt to new data or learnings.

If you take the above approach, it will help you stay focused on the goal and see it through, while also staying nimble and adaptable in terms of how you get there.

The importance of holding annual planning sessions

The biggest surprise at our most recent annual session was that there were no surprises.

The entire leadership team was in sync. There was little contention or debate, and not for lack of holding back. I attribute this year’s smooth sailing to the foundation we laid at our previous annual planning session.

It’s a testament to the clarity of the strategy we outlined in that first meeting. Everyone on the leadership understood how their department fits into the broader company mission.

These planning sessions are an outlet for open discussion and debate; a chance for everyone to communicate honestly about where the company is going and how it will get there. I encourage you to give it a try. It’s a commitment and it will fundamentally change how you run your business, but rolling it out at Proposify has definitely been for the better.

It’s an opportunity to hold your ideas about your business and your mission up to the light and reveal all the flaws. But it will also let you clarify your values and separate game-changing ideas from the chaff.

Take the strategies born of these sessions and document them, share them with the rest of the company in an all-hands meeting, and put them into action. And, when you do, let me know what comes of it in the comments.


Enjoyed this article? I’d appreciate you giving it some claps. Also if you’re an entrepreneur, check out my book, Free Trials (& Tribulations): How To Build A Business While Getting Punched In The Mouth available on Amazon.

Kyle Racki

Written by

CEO of Proposify, Author, Speaker, Investor

Welcome to a place where words matter. On Medium, smart voices and original ideas take center stage - with no ads in sight. Watch
Follow all the topics you care about, and we’ll deliver the best stories for you to your homepage and inbox. Explore
Get unlimited access to the best stories on Medium — and support writers while you’re at it. Just $5/month. Upgrade