What Does Winning Look Like?
Answering one of life's most haunting questions.
4/13/20262 min read


What will your organization look like one year from now? What are the revenue and expense numbers in a year? How many people are on staff? What will you be doing a year from now that will make you more successful than you are today?
Those questions make many people nervous. Some will say, “It shouldn’t be about winning. We should focus on being faithful.” But shouldn’t being faithful to your vision and work have a result? Some will avoid answering that question out of fear of failure. By keeping the end game ambiguous there is a self-induced delusion that one doesn’t have to worry about numbers, culture, sales, donations, and staffing.
What does winning look like?
You must be able to answer that question. In certain circles, winning is seen as a crime or a sin. For them, it does not honor the dignity of humankind to have a business that beats the competition. Many have grown to accept that winning is doing just enough. They’ll do just enough to make payroll, pay for health benefits, meet their tax obligations, and satisfy clients.
I’ll ask it again, what does winning look like?
I urge you to have a clear vision of what winning is for you and your team. It will usually involve an income number, delighting customers, building a strong culture, expansion to other markets, increased consumers, and employee engagement. A vision must have measurables that make clear if the organization is winning or failing.
Winning is intimidating. It scares us. We begin to hear whispers that we’re nothing more than an imposter. That can force us to step back and redefine the goal posts to ones that aren’t quite as challenging.
No one drifts into greatness. A ship doesn’t find its way to port by chance. There’s a detailed plan with maps and a trained crew. Greatness isn’t bestowed on someone simply because they tried. It is earned because you labored, overcame setbacks, pushed through doubts, and achieved the goals you had defined.
Face your insecurities and begin to consider what winning looks like. Stop sitting in the shadows hoping no one sees you’re doing the absolute minimum to exist. Start living and stop just being alive. Write the question on a piece of paper and allow it to haunt you. Start dreaming what crossing that finish line would be like.
Today is the day. Spend some time with the question. See a future that is better than the one that currently is.
What does winning look like?
Leadership Matters,
Brian