Here is a behind-the-scenes look at Jeffrey Scott Consulting and how we conduct our own strategic planning.
As we enter Q3, it is time for every company to start planning the next 12–18 months before year-end sneaks up on you.
We held our annual roadmap session a few weeks ago in New Orleans.
As you can imagine, a productive retreat requires more than a good agenda. It takes preparation, team chemistry, and enough time for honest conversations.
Here is how we did it.
Build the Team Before Building the Plan
We began with a half-day of social activities.
This is especially important for a remote company like ours, but every leadership team benefits from leaving the office and spending relaxed, personal time together.
We took a two-hour historical walking tour of the French Quarter, followed by live music and a few cold drinks at a little-known European jazz club near Bourbon Street. From there, we walked to dinner and broke bread together.
This helped us reconnect as people and sparked all kinds of valuable sidebar conversations.
People, Products and Processes
We opened Day One with an icebreaker: a personality assessment exploring each other’s strengths and blind spots.
It was instructive to hear how teammates experienced one another’s strengths and blind spots. This open discussion set the tone for the rest of the retreat.
The remainder of Day One focused on:
- Past results
- Key systems needing improvement
- Our core products and how to strengthen them
- Sales and marketing updates
- Our organizational chart and future capacity
We ended the day at one of New Orleans’ most iconic restaurants, Commander’s Palace. Totally worth it!
Turning Discussion Into Action
Day Two was shorter and more focused.
We discussed our upcoming Summer Growth Summit and then spent most of the day reviewing future goals and revising our company’s Objectives and Key Results (OKRs) for the coming year.
We also used Plaud to record and summarize our discussions, making it easier to capture decisions, action items, and even the sidebar ideas.
At the end of the retreat, we evaluated what worked well, what could have been stronger, and what we would do differently next time.
My Three Biggest Takeaways
1. Preparation Determines the Quality of the Session
Preparation by both the leader and participants makes all the difference. We completed considerable work beforehand, yet agreed that even more preparation would improve our next session.
Don’t bring your team in cold. Share information, questions, and assignments ahead of time so everyone arrives ready to contribute.
2. Relationships Improve the Discussion
The social time and personality assessment created the foundation for deeper conversations.
When people feel connected and understood, they are more willing to be vulnerable, challenge ideas, admit concerns, and offer honest input.
3. Different Tools Uncover Different Insights
Using different exercises and discussion formats helped us draw ideas from everyone—not just the loudest voices.
The variety of topics also encouraged balanced participation across the team.
Your Challenge
Make time to strengthen both your strategy and your team.
My single biggest takeaway was how strongly our team wanted to support our vision and help shape the company’s future.
Don’t assume strategic planning is something you have to carry alone or that your goals must remain “reasonable.” Share your biggest dreams and your greatest needs, then ask your team to help. Just be ready to accept their input.
We were able to facilitate our own annual roadmap because we had a room full of experienced coaches.
Most leadership teams benefit from an outside facilitator who can ask the difficult questions, ensure every voice is heard, and ultimately help build a productive roadmap.
A final aha: Your budget follows your strategy.
Don’t let budgeting season shortchange your strategy. Decide where you’re going first, then build the budget to support that plan.
Regards,
Jeffrey Scott
P.S. If you’d like help creating your own annual roadmap, drop me a line!
