v5 Why ELT Offsites Are Worth It: Hacks I Wish I Knew 10 Years Ago

Ten years ago, I walked into my first ELT Offsite as a young E-commerce leader at a Fortune 500 company, not knowing what to expect. By the end, I was completely blown away. It wasn’t the strategic plans or business goals that left a mark—it was how trust, connection, and culture transformed our team.

But let’s be honest: not everyone feels this way about ELT Offsites. For some, they’re seen as an expensive, time-consuming exercise with questionable ROI. Why leave the office for days? Why not just have a one-day meeting and call it done?

An ELT offsite, I’ve learned, is a lot like tuning an orchestra before a big performance. Each team member may be focused on their own part, but unless everyone comes together to harmonize, the result can sound disjointed. Offsites are where teams align, find their rhythm, and ensure they’re playing in sync.

Since that first experience, my role at ELT Offsites has evolved. I went from being a participant, wide-eyed and unsure of what to expect, to actively shaping agendas as an ELT member. Today, as a Chief of Staff at a Series A Start-up, I design, run, and facilitate our ELT Offsites—a responsibility I’ve come to value deeply.

Through these experiences—across Fortune 500s, mid-sized organizations, and startups—I’ve seen what makes a ELT Offsite successful and what doesn’t. In this newsletter, I’m sharing the key lessons I’ve learned: what to do, what to avoid, and why ELT Offsites, when done right, are a game-changer.

How My First ELT Offsite Shaped My Perspective

At that first ELT Offsite, our Head of Business Unit young VP faced a daunting challenge: leading a cross-functional team grappling with friction. Instead of pushing for immediate business results, he focused on reshaping team culture.

To guide us, he brought in an external facilitator who introduced two powerful tools: the DiSC Profile and Five Dysfunctions of a Team. These frameworks helped us understand each other’s working styles and the underlying dynamics between Product, Channel, Sales, Engineering, Packaging, Logistics, and Finance.

That Offsite was a turning point. I saw how trust and connection at the leadership level cascaded through the organization, creating a more collaborative and effective culture. It's no surprising, the years after under the same VP's leadership, the BU achieved unparalleled success in the history of the company. It was a lesson I carried with me as I moved into new roles at mid-sized organizations, late-stage Start-ups, and now a Series A Start-up.

Key Factors for a Successful ELT Offsite

Reflecting on that first experience—and many others since—here’s what I’ve learned about what makes an ELT Offsite truly impactful:

1. Pre-read Materials

• The Amazon Example: Amazon starts meetings by having everyone read through key materials together, ensuring alignment and eliminating wasted time. This practice is even more impactful for Offsites, where context is critical for productive discussions.
• Preparing for the Offsite: Distribute pre-read materials in advance—whether it’s updates, strategy proposals, or performance data—and set clear expectations for everyone to review them beforehand. This primes the team for deeper, more focused conversations.
• The Impact: Pre-read materials transform discussions from surface-level updates to meaningful dialogue. Instead of spending time catching up, the team can dive into strategic problem-solving and alignment from the start.

Takeaway: Pre-read Materials lay the foundation for a productive Offsite. By ensuring everyone is prepared and aligned, you unlock the team’s full potential for in-depth and impactful discussions.

2. The Power of Facilitating

• With a Facilitator: My first Offsite showed me how an external perspective can uncover hidden team dynamics and foster deeper trust. Facilitators bring neutrality, frameworks, and the ability to navigate tough conversations.
• Without a Facilitator: Most Offsites I’ve attended didn’t have facilitators, and while progress was made, they often lacked the depth and cohesion a skilled facilitator could bring.
• Stepping Into the Role: At my current Series A Start-up, I’ve taken on the role of facilitator myself as the Chief of Staff —developing the agenda, aligning with the ELT team, and guiding discussions. While it’s challenging, it’s also incredibly rewarding to see the team come together.

Takeaway: A skilled facilitator can transform an Offsite. If you don’t have one, prepare rigorously—and don’t be afraid to give yourself credit for stepping into that role.

3. Location: HQ vs. Offsite

• What Matters Most: The environment sets the tone. A neutral location—whether it’s in the HQ city or a different one—can help the team break free from day-to-day distractions.
• Budget-Friendly Tips: If resources are tight, find a bright, open space with natural light and refreshments in your HQ city.
• The Benefits of Travel: For those with flexibility, traveling to a new city creates shared experiences and deeper bonds. Without personal obligations pulling them away, team members spend more time together outside the meeting room.
• The Challenge of Staying Local: In the HQ city, it’s easier for personal commitments to creep in, reducing the offsite’s impact.

Takeaway: It’s less about where you meet and more about creating an environment that encourages focus, creativity, and connection.

4. Agenda Development

• What Worked at My Recent Offsites: I crafted an agenda that balanced trust-building and alignment. We started with icebreakers, articulated what success looked like, and used that as our guide.
• What Works Best Now: An ideal agenda is developed by someone who understands the leader’s vision and team dynamics, then aligned with the ELT. Flexibility is key—reading the room and adjusting based on energy or tension is just as important as time management.
• Key Components:
  1. Start with an icebreaker to set the tone.
  2. Align on what success looks like at the start and revisit it at the end.
  3. Adjust as needed but stay on track with goals.

Takeaway: A great agenda is more than a schedule—it’s a roadmap to connection and results.

5. Ideal Length of the Offsite

• Why Two Days is Essential: My years of ELT Offsite experience taught me the value of letting conversations breathe. Day one often surfaces tensions or unresolved issues, and having a night to reflect creates space for clarity. Day two is where real alignment happens.
• Adding a Third Day: For teams with the time, a third day is ideal for team-building activities, recapping decisions, and cementing action items.
• No Day Three?: Ensure the team dedicates time to recapping and assigning clear next steps before wrapping up.

Takeaway: Two days are a minimum to achieve meaningful outcomes. Use additional time for deeper team bonding and alignment.

Closing Reflection

What I’ve learned is this: ELT Offsites are about more than strategy—they’re about people. Building trust, creating space for connection, and aligning on shared goals doesn’t just impact the ELT; it transforms the entire organization. Whether you’re leading a Fortune 500 team or a Series A Start-up, ELT Offsites are where ELT teams come together to dream, bond, and solve. And when done right, the ripple effects are extraordinary!