Exploring New Possibilities When Stuck

Breaking through succession planning paralysis: When you're stuck, exploring 'what if' scenarios with your team can illuminate possibilities you never considered.

Entrepreneurs often feel paralyzed by the sheer number of decisions involved in succession planning. 

If this is you, you’re not alone. 

According to Harvard Business Review, a staggering 70% of businesses fail to make it to their second generation of leadership.

The complexity can be overwhelming, leaving many business owners stuck in a cycle of indecision. 

Sometimes being stuck is the best time to explore new possibilities. 

It all begins with conversations.

The Power of “What If?” Scenarios

When your succession planning stalls, one of the most effective ways to break through is to initiate conversations considering different scenarios without immediately judging them. 

These conversations often lead to options you might otherwise miss.

Some powerful “what if” conversations that can help you see your succession planning in a new light:

Scenario 1: The “Bus Factor”

What happens to your business if you’re suddenly unable to lead it? This uncomfortable but necessary question forces you to consider:

• Who would step in immediately?

• What decisions would be delayed or never made?

• How would your customers, employees, and community be affected?

This scenario often reveals gaps in your current leadership structure and can highlight the urgent need for developing a strong bench of leaders.

Scenario 2: The Timeline Shift

Consider how your approach might change based on different timelines:

• One year left: What essential knowledge must be transferred immediately?

• Three years left: What leadership development needs to be accelerated?

• Ten years left: How might you gradually transition responsibilities while maximizing your impact?

Each timeline creates distinct possibilities and priorities. By exploring all three, you might discover a hybrid approach that works better than your current plan.

Scenario 3: Different Exit Strategies

Without immediately ranking them, consider these possibilities:

• Selling to an outside buyer: What would this mean for your legacy and impact?

• Closing the business: What would a dignified wind-down look like?

• Building and selling to your team: How might this preserve your company’s values and impact?

The Criteria Question

If you’re considering selling, look beyond just the financial aspects. Ask yourself:

• Will the buyer multiply or grow your company’s impact in the community?

• How will they treat your employees?

• Will they preserve the values that made your business successful?

The Value of Outside Voices

Sometimes, the most powerful breakthroughs come from outside perspectives. In our Succession Planning for Impact masterminds, outside voices often illuminate blind spots and offer fresh solutions.

These voices might come from:

• Mentors who have successfully navigated succession

• Coaches who can ask the right questions

• Mastermind groups where peers share their experiences

• Employees who understand your business from different angles

Start with significant questions. Don’t start with the answers. Start with thought-provoking questions. Outside voices excel at asking questions you might not think to ask yourself.

The Reverse Obituary Exercise

One powerful tool is writing your own obituary. This exercise helps you clarify:

• How long do you want to have lived?

• How many more years do you have left?

• Who do you want to show a lifetime of love and devotion to?

• What big vision do you want to accomplish before you die?

• What do you want people to feel and say when you’re gone?

This exercise often reveals what truly matters to you, which can guide your succession planning decisions.

Breaking Through the Stagnation

If you’re feeling stuck in your succession planning, try these steps:

1. Explore scenarios without judgment: What if you had one year? What if you sold to your team?

2. Seek outside perspectives: Join one of our Succession Planning for Impact masterminds or engage a coach.

3. Start with conversations: Succession planning begins with strategic conversations. During these conversations, answers will begin to surface.

4. Use the Seven Steps: Follow our Succession Planning for Impact Method to guide your journey.

Remember, unanswered questions ought not paralyze you. With the right guidance and support, you will gain clarity and direction that will provide valuable insights, help identify blind spots, and offer a structured approach to the process.

Your Next Step

Ready to break through your succession planning stagnation? Email Sunshine@​cultivatingimpact.biz with “chat” in the subject line to reserve a free consultation. 

Together, we can explore the scenarios that will lead to your ideal succession plan—one that ensures your business continues to be profitable and bless your community for generations to come.

You can do this!

Harry T. Jones