Preparing to Lead Your 2026 Strategy Session

It’s that time of year: fiscal year closing, annual planning, and 2026 leadership strategy sessions. A lot of the leaders I work with are preparing for their strategy sessions, and they’re in charge of leading them. As they think about the different personalities in the room, the agenda, and the outcomes they aim to achieve, they often realize that preparing for and guiding these meetings is actually way harder than it looks.

I wanted to write this practical guide for you (or the person leading the session) to help your team prepare for a session that delivers alignment, clarity, and actionable outcomes.

When these strategy sessions are designed well, they can become powerful opportunities for collaboration, realignment and clarity on what’s next. But when they’re not...(dum dum dummm - cue dramatic sound effect) they can be extremely draining. The kind of meetings where you go around in circles and have the same conversation over and over again.

My goal is to help you prepare for a productive meeting that’s both energizing and result-driven!

1. Set expectations early

Your meeting will only be as successful as your prep. Of course there are always things you can’t plan for, but there are plenty you can.

As you prepare for your meeting or retreat, the following things need to be clear beforehand:

• What outcomes do you want to achieve?

• What should participants prepare or review?

• What do you expect from them and how should they engage during the session?

Once you have these inputs, you can start shaping your agenda. Share it with the team in advance and ask for their feedback. This is an easy way to create ownership and make sure everyone walks in prepared and aligned. Ownership and clarity prevent assumptions from becoming silent killers.

2. Know what matters most

What matters most to your team right now? This goes beyond the strategy planning. Think about doing a pulse check, how are individuals doing right now? How is the team feeling about working together? Are there any significant events or developments in their personal lives that could also impact their work? 

These things might not come up in boardrooms, but they shape how people show up. Many parents are helping their kids prepare for college; this is vital information! Someone might be moving, renovating, or caring for aging parents. Others are becoming grandparents or are dealing with personal health challenges.

These life moments, exciting or stressful, are extremely important and can have a big impact, which can all affect focus and energy.

And beyond the personal side, look at what’s been happening inside your organization. Are there tensions, leadership shifts, layoffs, team expansions, or challenges that could surface during the session?

As you think about this, consider these questions:

• What’s the purpose of the session beyond strategy planning? Alignment, conflict resolution, team development, or key updates?

• How does the team feel about working together?

• What challenges can derail the conversation, and how can you address them?

3. Design for all voices

While preparing for my last retreat, a colleague reviewing my agenda gave me some helpful feedback:

“Make sure you design for all voices.” 

Some people are more introverted (like my colleague is), and some are more extroverted (like I am). It’s easy to forget to design for people who are the opposite of you. 

When designing your meeting, think about who’s showing up. What personalities will there be in the room and what are those dynamics like? 

Based on that, you can include a mix of reflections, discussions, brainstorming, group conversations, 1:1s or triads, and silent reflections.  

Some people naturally dominate conversations, while others hold back their thoughts until it feels safe to share (which sometimes never happens). You can intentionally design for inclusivity by using tools like timers, sharing rounds and designated speaking turns to create equal participation and balanced conversations. Here’s an example of how that might look in real life.

Sharing rounds: 

1. How it works: Everyone gets a moment to share. Allow silent reflection first so people can gather their thoughts.

2. When to use: Early in a session to warm up and hear all perspectives, after a brainstorming session or emotional discussion to capture reflections, or when you want to hear different points of view without it turning into a debate.

3. How to structure it:

1. Go in a set order (clockwise, by function, alphabetically, pick a number) or at random (“popcorn style”).

2. Give clear boundaries: “Everyone gets up to 2 minutes to share on [topic].” or “Let’s do a quick round of sharing, your biggest insight or takeaway so far and let’s stick to one per person.” 

Facilitating while being part of the leadership team can be tricky. It’s essential to be clear about the role you play. Impartiality is key to success and often your biggest challenge. You can’t guide the conversation and fully participate at the same time. There may be moments when you need to step in or out of the facilitator seat; just make sure you’re upfront about this.   

4. Create the right environment 

The space you’re meeting in, as well as the energy and flow of the day, matter more than most leaders realize. How and where you meet can set the tone for how people show up. 

If you’re meeting in your usual office space, where people are walking in and out or interrupting to ask questions, it can completely derail the focus.

When you choose a space, keep distractions to a minimum. Look for good natural lighting, comfortable seating and clear rules around phone use (phones off and stowed away in a basket, yes you read that right!).

Plan your breaks strategically, alternate between short toilet and coffee breaks (10 minutes) and lunch breaks (around an hour). Don’t underestimate mental fatigue; if you notice people dozing off or yawning uncontrollably, take a quick break, do an energizer or step outside for some fresh air. 

If your meeting includes travel or an overnight stay, consider accommodations that support rest and connection. A good night’s sleep, shared meals, and meaningful moments outside the meeting room help your team connect and recharge. These fun activities (cooking classes, shared dinners or team outings) are just as important as the work itself. They create space to unwind, strengthen relationships and build the trust that makes collaboration flow more easily once you’re back in the room.

5. Participate or facilitate, you can’t do both...well

Leaders often underestimate the role of a facilitator. If you’re leading a conversation while trying to contribute in a meaningful way, it can get messy fast. 

You’ll find yourself half-listening, half-sharing, and half-thinking about what comes next. Facilitation requires you to stay impartial and manage the process in a way that benefits the whole team, all while reading the room. Participating requires you to share your own opinions, ideas, and reactions. Trying to do both at once usually means you’re not doing either well. 

While you’re designing the agenda, you need to decide if you’re facilitating, participating or doing a bit of both. When will you step out of the facilitator role to join the conversation? Who can help you hold the space when you’re participating? 

Even in leadership teams, you need someone who guides the process so everyone can focus on thinking and contributing without having to manage the flow. 

And sometimes (more often than not) it’s more beneficial to have an outside facilitator guide the process for you. That way, they can work their magic while your team works theirs. 

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Leadership strategy sessions are high-stakes moments that shape your company’s direction and drive organizational growth. Intentional preparation makes all the difference.

I’m at capacity until January 2026, but here’s how I can help you right now:

• Design & prep your session: I’ll help you map your agenda, anticipate challenges and make sure that everyone’s working toward the same goals.

• Introduce you to experienced leadership facilitators: People in my network who can help guide your offsite.

In 2026, I’ll also start hosting leadership retreats on Curaçao (you heard it here first!). If you want your next strategy session to be unforgettable, let’s connect!

Feel free to send me an email at renate@twenty6consultancy.com or drop me a line on LinkedIn if you have any questions!