Steve Moore’s list included a good indicator of early leadership that’s worth commenting on: individuals who are willing to take on a challenge others won’t. The ones who show initiative to take advantage of opportunity. The ones whose resistance to risk is overtaken by a compulsion that someone has to do something.

Leaders sometimes appear to come out of nowhere with a sudden success. I suspect I know what Malcomb Gladwell would say: that there are no overnight successes, and the individual has put in a lot of hours beforehand that led to such “instance success.” I agree. I think it’s easier to spot failure than to spot competence, and individuals like these have likely shown signs of potential along the way. What gets them noticed is the turnaround situation where they made something out of nothing.

There’s a well-worn piece of advice that seems relevant: Fools rush in where angels fear to tread. Remember that line from Amazing Grace, where a 24-year-old William Pitt first proposes to William Wilberforce that he thinks he can make a run at prime minister?

Wilberforce: No one of our age has ever taken power.
Pitt: Which is why we’re too young to realize certain things are impossible. Which is why we will do them anyway.

Some watch that movie and get inspired by Wilberforce; I get inspired by Pitt. Wilberforce succeeded through persistence and endurance; Pitt succeeded by sheer audacity. Perhaps he was a fool, but maybe that’s the point. In Moore’s recent book, While You Were Micro-Sleeping, he makes the point that experts and elitists “can’t ask the dumb questions that often trigger new ideas.” Most innovations come from fools.

Certainly, the pessimism born from experience becomes a block to innovation, but I think there’s another factor at work than just being too young to show caution. I think it’s a matter of conviction and motivation — that sometimes a situation is so dire, with no one willing to take it on, that a young person decides the worst they can do is fail. They have less to lose. Or that a frustrated young leader who never gets opportunity sees in a challenge a chance to go all in. With great risk comes great reward. We can probably all think of young leaders who took on big challenges and came out of nowhere to lead a new era. These are the kinds of stories we love.

But what about the other side? The stories of those who try and fail — or who never try — don’t get told. The younger generations have been long characterized as having an unhealthy fear of failure. Pessimism and skepticism is just as rampant among the young as it is among the old. I’ve had conversations with three young leaders in the past month who have recently faced choices: one relatively safe and one with greater risk. In all three cases, the young leader has opted for safety. There are good reasons for their decisions. No one would question their logic. But I’m disappointed.

Here’s the thing. Organizations need young leaders to step up. Hierarchical organizations need young leaders who master relational influence over positional authority. High-process organizations need young leaders who push back on bureaucracy and ask uncomfortable questions. Monocultural organizations need trailblazers who easily bridge cultures. And older, established organizations need age diversity.

What it comes down to is that the world doesn’t need an older you. The world needs young leaders who are willing to step up and take on the unique challenges we’re facing… today.

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As I was walking into the office a couple of weeks ago, I noticed that a young leader was wearing a blazer… again. In a pretty casual department his attire stood out. Turns out he’s been dressing up consistently since the new year. When I asked about it, the response was that he’s trying to take himself more seriously.

Taking yourself seriously is a quality worth adding to our list of early seeds of leadership. There are a number of indicators that a person is preparing himself for future roles. At the earliest stage, this might include dressing up. It might also include a desire to spend time with senior leaders. Let’s look at a few examples.

When I was visiting with another organization recently, one of the senior leaders pointed out what first stood out to him about their youngest vice president: he had never been intimidated by leaders at the highest levels, instead choosing to interact with them… and ask lots of questions. I’ve seen this kind of thing myself when the board or senior leadership team gathers. A few young, rising leaders inevitably show up at break times.

A fortysomething leader came to me one day and told me he was considering throwing his hat in the ring to be considered for a promotion. He asked me what I thought. Among other things, I asked him if he considered people at that next level to be colleagues. How comfortable was he with walking into their office to have a conversation? Realizing that he was already at ease at that level was one factor in his decision to pursue a new leadership position.

What it comes down to is whether someone acts like the position they see themselves serving in.

I’m not talking about people who “sell out” to get a position. I think authenticity is extremely important in leadership. In fact, when I moved into the Offices of the President a year ago, I went to two people who knew me well and gave them permission to call me on it if they ever saw me becoming a clone of those I work around. If I ever become someone else in an attempt to get ahead, I want friends who are close enough to point out my hypocrisy.

What I’m talking about is the way David, hiding out in a cave in the wilderness, acted like the king he would become. His circumstances didn’t matter, and he didn’t let the group of misfits surrounding him bring him down to their level. He behaved in a manner suited to a king, and in so doing, laid a course for the way he would act as king.

Let me loop back and unpack one of Tim Elmore’s seeds: leadership gifting.

In my experience with the Threshing Floor, I’ve seen all kinds of potential in leaders. Leadership is seldom positional at its beginning, though I’ll grant that some didn’t know they were leaders until they were thrust into the deep end. More often, the thing to look for is an interest in, gifting for or calling to leadership. I blogged on the subject last year, focusing more on interests and abilities.

But how do you identify leadership gifting? What are its earliest seeds? Does someone who’s gifted necessarily know it? In my experience, they don’t always know it, and it takes someone alert enough to recognize the signs. To show a lot of patience with a young person who asks lots of questions. To allow failure — even encourage it — in someone who shows a lot of initiative and then take the time to debrief and stir them to try again. To spot a learner who’s unafraid of feedback or even seeks it, and then to reward it with well-thought-out, specific feedback.

I remember a few years ago I sought out the opportunity to work with a collection of individuals that was discouraged but talented. When I considered taking this position, I looked specifically at one young leader who had a huge amount of passion and an amazing ability to encourage others, but for some reason rubbed some people the wrong way. He had a reputation for success, but was sometimes too quick to make an end run if he ran into an obstacle. I think it’s safe to say that some in leadership considered him a thorn in their side. Yet when I moved on to another position, his potential won out; he ended up moving up to take some of my responsibilities.

At one point I sent him to a week-long leadership event that utilized an anonymous 360 review. I decided to be very specific in my feedback, believing that to move to the next level there were some things he needed to work on and sensing that he would approach this opportunity with a hunger to learn. In talking with him afterwards, he thanked me for the feedback and suggestions I had made. He knew exactly which comments came from me. Why? Because he knew I would always be completely honest with him, and my comments stood out among the feedback he’d received.

Now, this was an individual who knew he was a leader. I’d love to hear your stories about how you spot leadership gifting in someone who doesn’t recognize their gifts.

What should we look for in a potential leader who has not emerged yet?

Last year, Steve Murrell posted Tim Elmore’s list of traits he looks for in those he seeks to train in leadership:

  • gifted to lead
  • influential with people
  • fruitful even before they have a leadership position
  • trustworthy in small things
  • serving in some capacity already

This a a great starting point. The first one is a bit nebulous and probably becomes evident only as you look at the other bullets. The last three are certainly related. The idea is that leadership is scalable. Someone who uses relational and spiritual authority to bear fruit without the position is likely to be even more effective once they have positional authority. Jim Collins says as much in his monograph Good to Great and the Social Sectors. So look for fruit, even in the smallest things.

I’m intrigued by the sports management business. Trades, drafts and coaching hires are compelling to me, because general managers are searching for hidden gems. You’ll often see a general manager trade “too much” for a pitcher who was average in the minor leagues or who had a losing record with another team. It’s evident that they see something they can work with in the middle of failure. That’s the job of an established leader: to mine for talent among those with less experience.

When you think of potential leaders in your setting, what are the seeds you look for?