The Strategic Summer Advantage

Shani Dowell is the founder of Possip and a recognized leader in workplace communication and equity-driven feedback systems.

How can you maximize the less structured ways of summer as a strategic advantage?

Plan for success.

Whether leading a nonprofit, heading a business, your family, or managing a community initiative, summer planning can help you reset, refocus, and build a strong foundation for the year ahead.

Here’s a roadmap to help you make the most of the season:

1) Schedule a Meeting With Yourself for Vision Setting & Reflection

Start with yourself and put a meeting for at least 1 hour with yourself. Get away from the computer and go somewhere different.

Reflect on your vision- for 5 years, 5 months, 5 days.  What do you want to see? How can you know if you are on track to what you want to see?

2) Build a Master To-Decide | To-Do | To Table List

Either with your leadership team (or just your own brain and a cup of coffee) map out a comprehensive list. Use digital tools that allow for sharing and real-time updates, like:

  • Slack
  • Google Sheets

If you’re more analog, printable to-do list templates can work just as well. The point is to create a master document where responsibilities, timelines, and statuses are visible and trackable.

3) Identify Training and Development Opportunities

With kid schedules and longer days, summer is a great time to mix up what people are doing. It’s also a great time to lean into training and development opportunities. This is a great time to encourage people to read books, listen to podcasts, take online courses, or take other steps that will help them improve in their work.

4) Make Feedback Data Your Superpower

Feedback isn’t just for course corrections- it can be a catalyst for trust and progress. Proactively seek input from key stakeholders as you plan.

Ideas to try:

  • Host virtual focus groups with clients, community members, or volunteers.
  • Ask team members to weigh in on early drafts of plans or proposals.
  • Review feedback from the past year (surveys, customer reviews, post-mortems) to identify patterns.

Collaborative planning doesn’t mean consensus on everything, but it ensures broader buy-in and fewer surprises down the road.

5. Don’t Skip Rest and Renewal

Let’s be real: burnout doesn’t take a vacation. Strategic leaders know that rest is not a reward- it’s a prerequisite for high performance.

Whether it’s a long weekend unplugged, daily walks, or afternoons off with your family, make space to restore your energy. You’ll come back with sharper focus, better judgment, and renewed creativity.

Final Thought

Summer offers you a powerful opportunity: time to breathe, plan, and lead intentionally. Use it wisely. With a mix of smart tools, shared accountability, strategic learning, and restoration, you can set yourself- and your organization- up for your strongest year yet.