Belonging-Driven Strategy: Blueprint for Planning Sessions That Unlock Real Alignment
Today’s best strategies don’t just come from smart people—they come from trusted teams. We know a good strategy goes only as far as the connections that carry it. This guide provides practical steps to transform executive planning meetings into shared alignment, true ownership, and lasting results.
At Flying Horse Resort & Club, we see firsthand how planning around belonging makes teams stronger. Let’s help you create your next breakthrough.
Table of Contents:
Why Belonging Matters in Executive Teams
Five Ways to Run Strategy Sessions that Create Ownership
Exercises and Habits that Encourage Honest Conversation
Tips to Turn Decisions into Real Action
Ready-to-Use Agenda: How to Lead an Aligned Executive Session
Tools: Conversation Starters and Simple Checklists
About Flying Horse and Getting Started
1. Why Belonging Matters for Successful Teams
People don’t always remember what we say or do, but they remember how we make them feel. For teams, feeling included and safe is key. When leaders trust each other, they bring their best ideas and are more likely to support group decisions.
A few facts:
● Teams who feel safe and included do better work and keep people longer (Google’s research backs this up)
● If people feel left out, they hold back ideas or tune out
● Strong teams don’t just say “yes” they feel responsible for the next steps together
The bottom line: For an executive plan to be effective, people must feel they belong. That’s when strategy sticks.
2. Five Keys to Sessions that Build Ownership
Start with Shared Purpose Make sure everyone is clear on why the meeting matters. Try opening with, “Together, we’re deciding not just what we’ll do next, but who we are as a team.”
Include All Voices Use small groups or take turns leading parts of the meeting, so everyone weighs in, not just the loudest people.
Set the Stage for Honesty Set simple ground rules: every idea is okay, and people can challenge ideas respectfully.
Show Decisions in Real Time Write down choices on a whiteboard or shared screen so everyone sees what’s being decided and where there’s disagreement.
Make Commitments Clear in every meeting with one round where each leader says exactly what they’ll do next. Write it down and follow up.
3. Exercises and Habits for Honest Conversation
Quick Check-In start by asking everyone, “What’s one thing you want to see happen today?” or “How are you feeling about this meeting?”
Write Before You Speak Ask a question, let people write their thoughts quietly, then share out. This gets better answers from the group.
Look Ahead to Problems Ask, “If this plan goes wrong, what likely caused it?” That way you can fix issues before they start.
Thumbs Up, Down, or Sideways. When making big decisions, let people show with thumbs if they’re fully on board, unsure, or not convinced yet. Talk about any hesitations.
You’ll find more of these simple facilitation ideas in the resources at the end of this guide.
4. Tips to Make Decisions Stick
A lot of meetings create good plans, but then nothing happens. Here’s how to make sure your group follows through:
Assign someone to check on actions two weeks after the session
Ask, “What will be different for us three months from now if this works?” and plan towards that future
Email everyone’s commitments and decide together when you’ll check progress
5. Ready-to-Use Executive Session Agenda
Here’s a template you can use or adjust for your team:
09:00 - 09:30 | Arrive and coffee, group check-in
09:30 - 10:15 | State the meeting purpose, agree on the rules
10:15 - 11:15 | Quiet writing, then group share-out on important questions
11:15 - 11:45 | Small group discussions to surface more views
11:45 - 12:15 | Decisions written up where everyone can see
12:15 - 12:30 | Short check-in: feeling good about where we are?
12:30 - 01:00 | Lunch and informal talk
01:00 - 01:45 | Look ahead for potential problems
01:45 - 02:30 | Final round of commitments and action steps
02:30 - 02:50 | Wrap up: what stood out, and what action will you take?
6. Tools and Conversation Starters
Questions to Try:
“When have we pulled together, even when the going was tough?”
“Is there a concern you have that hasn’t been raised yet?”
Quick Checklists for Meetings:
Does everyone know the plan and why we’re meeting?
Who’s running the meeting, who’s keeping notes, and who will check follow-ups?
Did we finish by making sure every action has one person responsible?
Did everyone get to share a last thought or concern at the end?
7. About Flying Horse and Getting Started
At Flying Horse Resort & Club, we host and support executive retreats that turn planning into real progress. Whether you need a creative spot, skilled facilitators, or team assessments, our goal is to help your team turn ideas into results.
Want to learn more?
Schedule a free chat or check out our planning resources and retreat options here.