Madison’s Question to Matthew: Being in leadership means taking risks. What risks have completely failed? How did you reconcile that? How may have it created new opportunities? Where did you see the growth from that experience?

As someone who has led at various levels and in numerous capacities, the idea of risk is something that is almost always energizing for me. I love the idea of moving into new territory, trying to do new things or trying to do existing things in new ways. It is fun to think something through the best that you can, knowing that you will never have all of the information necessary, and then to step forward – I liken it to building a bridge as you are walking on it, building just far enough ahead for the next step.

All that being said, the idea of failure in the midst of leading still makes my heart skip a beat. There are times when, in the midst of leading a new initiative, you can’t see far enough ahead and you are not sure of the next step. Or the previous step you took just didn’t work out as you thought and you have this sense of free falling without any means of stopping – it is out of control. As I thought about this question, I realized that there have been several ways that I have seen or experienced failure.

1) Overconfidence in my abilities – When leading out, I can typically see the entire conclusion of the initiative in my mind, completely finished and operating smoothly – not all the steps to get there, just the finished product. I then embark on the journey of making it a reality only to realize sometimes, part way through, that my skillset is not adequate enough to make it all happen and that I don’t have the right people around me to fill in my gaps. This causes sleepless nights.

2) Overconfidence in others – I can recall situations where I have embarked on an initiative with someone that I believed could deliver their part of a new project. However, in reality, they didn’t have the skills that I thought they had, or they didn’t have the grit to follow through. (At times, looking back, I should have seen it, but I convinced myself that they could pull through.) These are always difficult circumstances as they may have believed that they can do their piece and were not personally aware of their gaps. At times they have been friends and this has led to awkward conversations.

3) People’s overconfidence with me – this one is strange to think about yet their have been times when someone has believed in me so much that I “drank the kool aid” and believed in their belief in me and didn’t pause long enough to determine if this truly was my area of strength. These have caused much stress as I didn’t want to let them down yet I knew part way in that this was not going to be easy.

4) Overconfidence in my vision of the future – I can at times become so convinced in what the future could look like that I become blind to the many aspects that would cause it to fail. This will most often occur after a number of successes that has increased my confidence in my thinking. Perhaps it is pride that has set in, a belief that I am in the zone and nothing can get in the way of my perceived clarity of thinking.

All that being said, I prefer to see every failure as a way to learn and grow. And often, this is the case. However, angst for me arises when those around me during these times of failure do not want to allow learning to happen. There are always some people who seem to be looking to say “I told you so” and believe that it is their purpose in life to take you down (this is my perception at times, although in reality I don’t believe it is typically true, at least I choose to believe it is not the case.) At my core, I really don’t want to disappoint anyone and knowing that a leadership decision I made frustrated someone or caused them to lose confidence in me is disheartening.

To lead is to risk, and to risk is to choose to fail. Not all risks will lead to success. Sometimes you’ll achieve partial success, sometimes none at all. To lead is to accept that you will be misunderstood when things don’t go as you declared at the start. If you are not willing to accept this reality, then you shouldn’t take on positions of leadership. You can manage, you can administrate, you can guide – you just shouldn’t lead.

So what have I learned through the failures that I have encountered?

First, I have learned what I am good at, what I am adequate at, and what I am very poor at. Reflecting on past failures has caused me to “stick to my knitting” more and more.

Second, I have come to appreciate the unique skills that others bring that will allow my leading to have a greater chance of success. I have become much more willing to listen to the other voices and their perspectives – this often saves me anxiety as things are implemented. I especially am willing to listen to those people who have been with me through various leadership risks as we have come to respect each other over the years.

Third, there is a big difference between seeing and creating a vision for the future, and leading people into that future. I have enjoyed conversations with many visionary people, those who can see the beauty of what could be. Yet I have also seen many of those same people be unable to take people to that future because of an inability to lead well. I believe that holistic leadership is both vision of a better future as well as an ability to influence others to go there with you and use their abilities in the process.

Writing this blog has caused a fair amount of reflection on my leadership going back to High School. It has been an interesting journey – one the I know has not yet ended. More failure still to come.

For the Kingdom.