How to plan and run a leadership offsite (and actually make it worth the time)

A format for quarterly and annual strategic offsites with your leadership team

There’s a version of leadership team alignment that feels real but isn’t. Everyone’s in the weekly meeting, nodding along, hitting their updates. It wraps, and everyone gets back to the day-to-day, in-the-weeds work.

But when was the last time you all actually stopped and asked the hard question: are we actually going in the right direction?

Here’s what I see happening, especially with younger companies and first-time CEOs.

The CEO builds an annual plan and hands it to the leadership team. Maybe the CFO was involved, maybe not. The CEO basically says, “Here’s the plan, go execute.” The leaders had little to no input. The plan is handed down rather than built collaboratively.

The result? You lose the buy-in that comes from people co-authoring the plan. Instead, you’re just telling them what to do.

Another mistake: they build a plan at the start of the year and spend the next 12 months executing against it, as if they don’t need to adapt or change anything. They put on blinders and just keep marching forward. They don’t stop to ask: are these initiatives actually attainable? Are we trying to do too many things at once? Have we thought through all the interdependencies?

They say most companies don’t die of starvation – it’s indigestion. Too many different things at once. — Amish Jani

Amish Jani told me that on our podcast interview, and I couldn’t agree more. Everyone’s eyes are bigger than their stomachs, and we all try to do too many things at once. You need to zoom out. You need to reassess the plan.

That’s what quarterly and annual leadership offsites are for.

You need to meet in person and dedicate time entirely to working on the business instead of in it. No customers, no fires, and no Slack. Just the leadership team, a clear agenda, and enough space to have the conversations that don’t happen in your weekly leadership meetings (if you’re even doing those).

I’ve used this format dozens of times with my companies and the teams I advise, and the results are always the same. They walk out with real alignment on where the company is, where it’s going, and who’s doing what to get there. That clarity is gold.

Here’s how to plan and run an executive team offsite.

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Key takeaways

• Run a leadership offsite once per quarter, plus an extended annual session for next year planning. In-person attendance is non-negotiable.

• Bring in a third-party moderator so you can participate as a contributor instead.

• Set clear ground rules before you start: confidentiality, full participation, and the CEO makes the final decision.

• Use the offsite to set no more than three specific, measurable objectives for the next quarter or year.

• Each leader builds their own initiatives that ladder up to the company objectives, stack-ranked by priority.

• The “what we won’t do” exercise is just as important as the planning itself.

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Table of contents

• How and when to set up a leadership offsite

• The logistics

• Ground rules

• The executive offsite agenda that works

• What you walk away with

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How and when to set up a leadership offsite

You need to do these four times a year, every quarter. Plus, an extended annual session in October or November for next-year planning. Quarterly offsites should run at least a full day, maybe a day and a half, and annual leadership offsites should be two to three days.

In-person is non-negotiable. The dynamic is different, the focus is different, and the team-building simply doesn’t happen on Zoom. If you’re doing these remotely, you’re not really doing them.

You need every functional leader to attend. Title doesn’t matter, just like it doesn’t matter in your weekly leadership team meetings. If someone is leading a major part of the business, they belong there. If they’re not there, you’re missing part of the picture. As you get bigger, this will become a true executive leadership offsite, and you will likely have only C-level execs attend.

Bring in a third-party moderator. Don’t try to run this yourself. When the CEO runs the session, they can’t fully participate because they’re managing the room instead of contributing to the conversation. A third party changes the dynamic. Everyone, including the CEO, becomes a contributor.

Alex Estevez encouraged me to do a leadership offsite in the early days of BetterCloud, and he ended up attending as our moderator. Alex had been a Venture Partner at Accel and the CFO of Atlassian and BigFix before recently starting Vidian Partners. He understands building a company. That’s the type of person you need as a moderator, because, even if they’re not an expert in your industry, they’ve seen enough patterns and know the questions to ask.

A good moderator also helps with the prep work, keeps everything on time, calls on people to ensure everyone participates, and asks the hard questions. That frees you up to just be in the room like everyone else.

Who should the moderator be? Ask one of your advisors to join you at the offsite as a third-party moderator. It should be someone outside your organization who understands your business. They should work closely with you and the person planning the offsite to ensure it goes smoothly.

The logistics

Have your EA, head of people, or Chief of Staff plan this. Get three quarterly offsites on the calendar at the beginning of the year, plus the annual leadership offsite. This is a key part of your operating rhythm, so you need to be proactive about it and plan it well.

If you wait to schedule these, you’ll be competing with people’s vacations, conferences, customer meetings, and everything else that will come up. Booking them ahead of time makes it a priority for everyone and ensures your team can plan for them.

As for location, get out of the office. Find somewhere with good AV and enough space, you’ll be in the room for a long time. For the annual offsite, fly or drive 90-120 minutes away. A real change of scenery matters. If the budget allows, go somewhere with some activities or nice restaurants nearby so the team can bond outside of the planning sessions.

Order breakfast and lunch to the offsite location. Going out takes too much time and breaks the momentum. But schedule dinner somewhere fun after the first day. It’s going to be a packed day, but it’s important to get out, share a meal and drinks, and bond with the team outside of business conversations.

Most of the prep work falls on the CEO and CFO to gather numbers and determine priorities. Everyone else just needs to show up and be prepared to participate. As the company scales, your leaders will have more to bring to the table. But if they’re great leaders, they’ll already know what’s happening in their orgs, what the priorities are, and where they need support from the rest of the team.

The first time you do a leadership offsite, it might be a little awkward, especially if your leaders are also new to the experience. That’s okay. You’re building muscle, and the more you do it, the more comfortable and prepared you and your team will feel. Eventually, you’ll all look forward to these offsites.

Ground rules

Everyone attending needs to be on the same page here. Set these expectations ahead of time and again on the first day of the offsite.

• Everything discussed stays confidential, within this group only: You’ll share the output with the company, but it needs to be thoughtfully packaged first. You also need to be able to talk about anything, and not everything is meant for the whole company.

• Phones and laptops down: Have everyone set an out-of-office on email and Slack so the rest of the company and customers know they’re at an offsite. That said, you need to build in enough time so people can check in. You don’t want anyone half-present because they’re stressed about what’s piling up in the inbox.

• Every person participates in every topic: No one gets to coast. Be very clear about this. Everyone on your leadership team should know what everyone else is doing and should have opinions.

• Expect friction, and welcome it: You’re there to push and challenge each other, and that’s a good thing. Most leadership teams are too nice to each other. This is the time to have it out, challenge each other, and talk about the things that have been bothering people. You want those conversations happening in the room, not behind closed doors after the fact.

• If you don’t ask a question, we assume you agree and understand: This one matters most. I say it at every offsite, and every time I say it, hands go up.

• The CEO is the final decision-maker: This is collaborative, but if we reach a point where a decision needs to be made, it’s the CEO’s call.

With the ground rules set, you’re ready to get to work. Here’s the agenda I use every time.

The executive offsite agenda that works

Every offsite I run follows the same structure. Here’s how it works.

1. Why we’re here (5-10 minutes)

Frame the day before you dive in. We’re here to do four things: build the team, align on the current state of the business, set goals for the next quarter (or year if it’s annual planning), and confirm we’re still pointed at the same long-term destination. That’s the focus, and everyone needs to be locked in.

This is also where you share the ground rules with them as a reminder.

2. Team building (60 minutes)

There are various ways of “breaking the ice”, but here’s what I do.

Ask everyone to submit three things ahead of time (using a Google form or something similar) that literally no one could know about them. Not something you can find on LinkedIn or elsewhere. The moderator should collect these responses.

Then, have the moderator read them one at a time without naming the person. The team then guesses who it is, and once they get it right, the person tells the backstory.

I did this once, and someone said they were a junior Olympic powerlifter. Everyone thought it was this huge Eastern European dude, but it was this tiny little woman. The purpose of this part is to boost energy and enable people to learn more about their colleagues.

Another option is a superpower exercise, where everyone writes each other’s superpower on a big sheet of paper, votes on the top one, and reads it to the group. It makes people feel seen. I’ve seen people take those sheets home to show their families.

If you have time, and especially if there are a lot of new people on the team, I recommend the LifeLine exercise. Everyone plots a timeline of their life, starting at birth, and they mark the important moments as positive or negative. Each person presents their timeline to the group, walking everyone through the highs and lows. It’s amazing how well everyone gets to know each other when you do this.

The user manual exercise: If you haven’t done this with your leadership team yet, this is a great place to run it. Read the guide here.

3. Strengths and weaknesses (75-90 minutes)

Now you dive into the business. Have everyone write down what they think the company’s top strengths are. Then go around the table and put them all on the whiteboard. Everyone gets three votes. You’ll see some start to cluster – those are your real strengths.

Then do the same for weaknesses. This always takes longer than strengths. But great leadership teams don’t let themselves off the hook easily. The point is to surface those things out loud.

This is usually where friction starts. Someone’s department is going to come up as a weakness, and that’s okay. Some people will disagree that it’s a weakness. That’s also okay. These are the moments that you and your leadership team need to work through and come out aligned on a path forward.

Review the top 3 strengths and weaknesses before you move on. And keep the top weaknesses in mind throughout the offsite. You and the entire leadership team should be thinking, “If these are our weaknesses, what initiatives can we prioritize to address them?”

4. State of the business and market (60-90 minutes)

This is where the CEO and CFO begin presenting the numbers. Revenue, new logos, gross retention, cash burn, or profitability. Give everyone the full picture, including wins, challenges, competitive landscape, market dynamics, and lessons learned. Don’t sugarcoat this. Be really honest about where the company stands and how you feel about it.

Then open it up for questions and use this rule: If you don’t ask a question, we assume you agree and understand everything that was shared.

Hands will go up. Discuss any concerns and clarify things, then move on only once no one has any more questions. If the room is quiet, start calling on people. Go around the room, and ask each person how they’re feeling about what you just shared.

5. Paint the big picture (10-20 minutes)

Now you paint the three-year picture. How many employees will we have in three years? How many customers? What’s our revenue? What have we built? What haven’t we built yet? How much will we have raised? What is the market saying about us?

Make it as vivid as possible. This is a gut check to assess if everyone sees the same general destination. You’re effectively asking, “Do we all see where we’re going?”

This is where you need to inspire the team to get them on the same trajectory. For example, some companies prioritize growth. Others focus on efficiency, profitability, new markets, or new products. The point here is to ensure everyone understands the company’s current direction.

At annual planning, this section might have a lot of meat. You might be changing your focus from the previous year. For quarterly planning, this section is primarily about reconfirming and restating the big picture, with minor changes as needed.

6. Next quarter strategic objectives (60 minutes)

I recommend focusing on three objectives. This forces you to truly prioritize. Usually it’s growth, something about new customers, retention, product adoption, new products, team, hiring, or culture. These need to be specific and measurable. Not themes, actual targets.

Some examples:

• Land 100 new ICP customers by the end of the year

• Expand product usage for existing customers to an average of 3 core modules

• Improve efficiency across the company to achieve cash flow and become profitable by the end of the year

Those are big goals that touch every function in the company. The first goal alone might mean you’ll need to hire more salespeople, ramp up marketing efforts, and reprioritize the product roadmap. These are company-wide objectives, not just departmental goals.

You need to explain the “why” behind each one and then open the floor for questions.

7. Individual initiative planning (60 minutes)

Now, each person should split off and build out their own initiatives that ladder up to the company objectives. I like to have a primary, secondary, and tertiary objective per initiative. The initiatives might impact one or multiple objectives.

They should be written as SMART goals, with a clear note of who on the leadership team they’re depending on to get there. Have them rank them by priority and limit it to 10 max. The reality is, they probably won’t achieve all ten. Three to five is more realistic, but that’s okay.

One important note: don’t list the things that are just keeping the lights on. Engineering fixing bugs, sales doing calls, and hiring… those are table stakes, not strategic objectives. The exception is when something routine becomes a major shift or requires a significant investment.

Before presenting to the full group, have people pair up with whoever they work closest with (sales and marketing, product and engineering) and review each other’s initiatives first.

8. Leader presentations (30 minutes per leader)

Once everyone has reviewed their initiatives with their peers, have them present their top 10 to the full group in stack-ranked order. Have them lay out all 10 before anyone asks questions.

Debates will happen, and that’s okay. That’s the goal. This is the time to challenge each other. If sales has a big initiative that depends on marketing, but sales ranks it first, and marketing ranks it last, that’s a problem. And you want to catch that now, not later.

Adjust the ranking in real time. The CEO is the final decision-maker, but the group should work through it together first.

The hard part is drawing the line. If you’re planning for a quarter, you can probably only realistically execute the top three things. Decide that in the room and say it out loud. What you land on isn’t set in stone. It will get refined over the next few days or weeks. But the goal is to walk out with a draft everyone can live with.

9. What we won’t do (60 minutes)

It’s easy to think about all the things you’d like to do. But it’s equally important to be intentional about what you won’t do. I usually like this one to happen on the second day.

Give everyone 15 minutes to write down the things they explicitly won’t be doing this quarter. These should be things they want the group to know about and have documented. Then go around the room, and have each person explain one item. If anyone pushes back, have the discussion.

Do this three times to make sure you’ve surfaced everyone’s top “won’t do” items.

10. Review (60 minutes)

From there, do a final review of the full list of initiatives and go around the room to confirm everyone agrees. Figure out what you’re telling the rest of the company, when you’re telling them, and who owns each piece of communication.

Start with a consolidated spreadsheet of all initiatives (three to six per leader). Do a sanity check. Does the full picture make sense? Is 90% of it dependent on an already overwhelmed engineering team? Are these roofshots that are attainable, or moonshots? Unless you’re the best company in the world, the mix should probably be 90% roofshots and 10% moonshots.

11. Reflection (20 minutes)

And finally, I like to close every offsite by going around the room and having everyone reflect on the process and the time spent together. I like to ask the group for two sentences about how they feel. Encourage them to be open and honest.

Then, you share how you feel about the experience, priorities, future, and the team. There will probably be ups and downs, and that’s normal. But always wrap it up on a positive note.

What you walk away with

When you do this well, you leave with a few very specific things.

• Real alignment on where the business is (and where it’s headed)

• Quarterly or annual objectives that everyone on the leadership team has agreed to do and is ready to be accountable for

• Individual initiative plans with cross-functional dependencies on the table

• An explicit list of things you’re not going to do

Have a plan for communicating with the broader company: When all your leaders disappear for a day or two, the rest of the company notices. Have a plan for what you’re going to communicate, and when. The next all-hands is often the best opportunity to communicate this more broadly.

The leadership offsite is where the operating rhythm starts

The offsite feeds directly into everything else in your operating rhythm: your leadership team meetings, your board meetings, and your company all-hands. Those meetings only work if everyone is pointed at the same destination. The offsite is where you set that destination.

The companies that do this consistently are the ones that don’t drift. They catch misalignment before it becomes a real issue. They make hard decisions in the room rather than two months later, when the damage is done.

In my experience, this is one of the highest-leverage days a leadership team spends together all year, because it influences everything that happens next. The planning matters, but so does the trust that’s built between the team during that time.

FAQs

How often should you run a leadership offsite?

Once per quarter. The annual offsite in October or November should be for planning the next year.

Who should attend a leadership offsite?

Every functional leader, regardless of title. As the company scales, this usually narrows to your C-level executives.

Should the CEO run the leadership offsite?

No. Bring in a third-party moderator. When the CEO runs the session, they’re managing the room instead of participating in the conversation. The CEO and maybe the CFO will present the state of the business, but everyone should be participating in the group sessions.

What’s the difference between a quarterly and annual leadership offsite?

Quarterly offsites are shorter, usually one day, and focused on course correcting against the existing annual plan. Annual offsites run two to three days and set the strategic direction for the year ahead.

What should be on a leadership offsite agenda?

A typical agenda includes team building, reviewing strengths and weaknesses, a state-of-the-business presentation, setting strategic objectives, and a “what we won’t do” exercise.