C12 Southwest Florida | Leadership Insights

Knowing When You Need Another Perspective

Why strong leaders recognize the edge of their own experience and seek wise counsel before a problem grows.

Leadership Insights Jamie Shedden September 2026

One of the things I appreciate most about sitting with business owners every month is being reminded that none of us knows everything. A leader can have decades of experience, understand an industry exceptionally well, and still encounter a situation they have never faced before.

That is not a weakness in leadership. It is simply reality.

Businesses involve people, contracts, partnerships, customers, property, employees, money, and relationships. Eventually something will happen that falls outside an owner's normal area of expertise, and the important question becomes whether we recognize that early enough to ask for help.

I have seen the value of this around our C12 table. A member may bring in what appears to be a people problem, an operational problem, or a disagreement with a customer or business partner. As the group begins asking questions, the situation often becomes clearer. Sometimes another member has dealt with something similar and can share what they learned. Other times, the most valuable outcome of the conversation is realizing that the issue has reached a point where professional expertise is needed.

Its purpose is to help leaders think more clearly, recognize what they may be missing, and know when they have reached the edge of their own experience.

01

Problems Can Grow With Time

Some issues become harder to solve when unclear expectations and uncomfortable conversations are left alone too long.

02

Experience Sees What Is Hidden

Wise counsel can help leaders recognize risks and consequences before they become visible inside the business.

03

Counsel Is Stewardship

Seeking the right perspective helps leaders make clearer decisions for the people and organization entrusted to them.

01

Some Problems Become More Complicated With Time

Many significant business disputes probably did not begin as significant disputes. They may have started with an agreement that everyone believed they understood, expectations that were never discussed clearly, a relationship that gradually became strained, or a situation that everyone hoped would simply work itself out.

There are certainly times when patience is appropriate, and not every disagreement needs to become a major issue. At the same time, allowing something to continue simply because addressing it is uncomfortable can create a much larger problem later.

This is an area where I think good leaders have to remain humble. Business owners are problem solvers by nature, and that ability is usually one of the reasons they have been successful. The challenge is recognizing when experience and instinct are enough and when the situation calls for someone who sees these issues every day.

Those are leadership questions long before they become legal questions.

02

The Value of Someone Who Has Seen It Before

Over the years, I have benefited from conversations with experienced business attorneys who regularly work with companies facing commercial, construction, real estate, and other business disputes.

What I value is not simply their knowledge of the law. The best counsel brings together knowledge, wisdom, and integrity when approaching people and difficult situations. Those qualities matter when the decisions involved can affect a business, its employees, important relationships, and sometimes years of work.

I am not an attorney, and I would not try to tell another owner what an attorney would advise in a particular situation. That is precisely why the perspective is valuable. Someone who has spent years seeing what happens when expectations break down, disagreements become disputes, and seemingly small decisions carry much larger consequences can often recognize risks that are not yet visible to the owner.

That makes me interested in what experienced counsel has learned from being on that side of the table. What do attorneys wish business owners recognized sooner? Where do good companies unintentionally create unnecessary risk? What situations tend to become more difficult because leaders waited too long to ask for advice? How can an owner protect the business while still treating people and relationships with integrity?

Those are questions I believe are worth exploring.

03

Wise Counsel Is Part of Stewardship

For Christian business owners, I also think there is a stewardship issue here. We are responsible for more than simply getting through the immediate problem. Decisions can affect employees, families, partners, customers, and the long-term health of the organization God has entrusted to us.

Seeking counsel does not remove the leader's responsibility to make the decision. It simply helps us make that decision with greater clarity.

That is one of the things I value about C12. A healthy peer advisory group does not need to have all the answers. Sometimes its greatest value is helping a leader discover that they have been asking the wrong question, overlooking an important risk, or trying to solve something alone that requires another kind of expertise.

One Leadership Question to Consider

Perhaps the larger leadership question is not whether we will eventually face something outside our experience. We will. The question is whether we have built the relationships and developed the humility to recognize it before the problem becomes larger.

When you encounter something outside your experience, do you have people around you who can help you recognize what you do not know and point you toward the right counsel before the problem gets bigger?

Leadership Is Not Meant To Be Carried Alone

C12 Southwest Florida gives Christian business owners and CEOs a trusted peer advisory table where they can think clearly, ask better questions, and seek wisdom before a problem grows larger than it needs to be.

Jamie Shedden

Jamie Shedden

C12 Chair - Southwest Florida

Working alongside Christian business owners and CEOs to build great businesses for a greater purpose.

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