Here are 10 fresh strategic planning ideas designed specifically for mid-market CEOs. These will strengthen leadership, improve resilience, and drive smarter business growth.

1. Shrink to Grow: The Power of Strategic Pruning

Bigger isn’t always better. Instead of constantly expanding, prune underperforming products, services, or markets. Just like a tree grows stronger when dead branches are cut, your business can refocus its energy. What’s draining resources with little return? Cut it and reallocate efforts to what truly drives growth.

2. The “Oops” Budget: Investing in Calculated Risks

Most companies allocate budgets for predictable outcomes. But what about a fund for failure and experimentation? If your team is too afraid to fail, you’ll never get breakthrough ideas. Allocate a budget for high-risk, high-reward projects. Sometimes, failure is just R&D in disguise.

3. Redefine the Game: Competing on Your Terms

If you can’t beat competitors at their game, change the rules. Reposition your brand to leverage its unique strengths. If competitors focus on price, position yourself as the premium option. If others prioritise automation, highlight human connection and service. Own your niche instead of fighting for scraps.

4. Let Them Go to Keep Them: The Talent Retention Paradox

Want to improve talent retention? Give your top performers a structured sabbatical or time to work on passion projects. It sounds counterintuitive, but when employees have flexibility, they stay longer. They return with fresh perspectives and renewed energy.

5. Hold a Pre-Mortem: Prevent Failure Before It Happens

A post-mortem analyses failure after the fact. Instead, hold a pre-mortem: assume a major initiative has failed before you launch it. Reverse-engineer the reasons why. This exercise surfaces hidden risks. It strengthens your plan before it’s too late.

6. Crisis Dress Rehearsal: Build Resilience Through Simulation

How resilient is your business really? Run a surprise crisis drill simulating a major issue, like a cyberattack or a PR disaster. Observe how your team responds. Refine your resilience strategy. Think of it as a fire drill for your business.

7. Be the Intern for a Day: Leadership from the Ground Up

One of the best ways to develop leadership? Have senior execs swap roles with junior employees for a day. Let the CEO answer customer service calls. Have the CFO work in operations. It builds empathy and creates a stronger company culture.

8. Old-School Customer Delight: Standing Out in a Digital World

In a world of AI and automation, personal touches stand out. Try something old-school: a handwritten thank-you note, a personal video message, or a surprise call just to say thank you. Small gestures create raving fans.

9. The Stop-Doing List: Free Up Resources for Growth

Strategic planning for Mid-Market CEOs isn’t just about adding new initiatives. It’s about subtracting ones that no longer serve you. Make a Stop-Doing List of meetings, reports, or projects that waste time. Less clutter = more focus.

10. Bring in a Wildcard: Break Out of the Echo Chamber

Break out of the leadership echo chamber. Invite an unexpected guest to your strategy session. A futurist, a sci-fi writer, or even your youngest team member can challenge assumptions and offer fresh perspectives.

For more insights on crafting effective business strategies, read The Essence of a Business Strategy.

 

Strategic planning – Mid-Market CEOs doesn’t have to be a dull checkbox exercise. Inject creativity. Embrace the unexpected. Challenge the status quo. You’ll energise your leadership team and set up your business for smarter, more sustainable growth.

What’s Next?

Which of these ideas will you try first? Share your thoughts in the comments! And if you want more strategic insights please have a read of our other blogs and posts.