Finishing Well Step 2: Address What Could Hold You Back

After you start taking care of yourself so you can serve others (Step One), you have to deal with any issues, relationships, conflicts, or fears that could hold you back from finishing well. 

This is Step 2 of a seven-part series on finishing well.

I well remember the setting. It was a parking lot after a board meeting. What the board chair angrily said to me was sharp and personal. Getting in my car, I carried something with me that was more than frustration or the pain of his remarks. It was resentment and I carried it for years.

Who knew the space this would take up inside of my soul and how many years I would carry it. Like a needed repair on my car’s engine, this was not something I could ignore forever.

This is part of what Step 2 is about.

After you start taking care of yourself so you can serve others (Step One), you have to deal with any issues, relationships, conflicts, or fears that could hold you back from finishing well. 

What are we talking about? Sometimes it is an issue in the business that everyone knows is there but remains unaddressed. Or it could be a relationship that has become strained over time, an open conflict, or some fear. Often, it is a mixture of all these things.

Finishing well takes more than a succession plan for your business. Leaders can get deep into succession planning and suddenly realize that the real problem isn’t the structure of the deal, it’s the stuff underneath it. It can be a lack of trust between family members, tension between partners or a successor who may be capable but doesn’t really want the role. Often the founder says he wants to let go, but honestly can’t imagine who he is without the platform he’s spent years building.

Left alone, those things rarely fix themselves. 

Finishing Well Step 2: Address What Could Hold You Back

The stress of succession planning sometimes exposes a hard truth: no one else can really do what the founder does. This sometimes flatters leaders’ egos but it really is a warning sign to accept the responsibility of teaching, developing and handing off what only they have been carrying.

Is trust an issue? One family business we were involved with went far better than expected because the entire Garnett family had done the hard work of establishing trust before the handoff began. Healthy relationships don’t remove hard decisions, but they do make those decisions bearable.

Is it a fear? Be aware that in seasons of transitions, small fears can become massive fears. There are fears of losing relevance, income, or daily purpose. Are you afraid that the next generation will do something differently? Or that they won’t do it well? Or, maybe you fear that in stepping back they will do it better? 

When these fears rise up, be courageous and share them with a trusted friend. This is one reason open conversations matter so much. Transparency builds trust and helps get your team on the same page. It can prevent misunderstandings from becoming conflict. And it brings private assumptions into the light so people can move forward from the same set of facts.

You need encouragement, but you also need a few people who will ask the hard questions, challenge your blind spots, and tell you the truth before a crisis does. Legacy decisions don’t come from echo chambers.

We are not talking about becoming perfect, this is about being honest about the issues that need attention, the relationships that have gone thin, the conflict you’ve delayed dealing with or the fear shaping your decisions when nobody is looking.

Like succession planning, finishing well begins with conversations. Real ones. Not rushed. Not polished. Not just legal or financial. Human conversations. What you refuse to address today will show up in tomorrow’s transition, count on it!

So let me ask you:

What issue, relationship, conflict, or fear have you been avoiding that could keep you from finishing well?

What conversation do you need to begin before this month is over?