On the slow, deliberate work of raising up the leaders who come after you

There is an old hand who used to work the lumber yards near where I grew up, a man who had taught maybe a hundred younger men the trade over forty years. I asked him once how he chose who to invest in. He said, “I did not choose. I just paid attention to who was paying attention.” Then he added, “And I made sure I taught while I was working, not after. If you wait until the work is done to teach, you will never teach. The work is never done.”

I have thought about that conversation more times than I can count. It contains, in two sentences, what most leaders get wrong about developing the people who come after them. We tell ourselves we will invest in our team when things settle down. We tell ourselves we will start mentoring next year, after this initiative wraps. We tell ourselves the development will happen later, in dedicated time, when the calendar opens up. The calendar does not open up. The work is never done. And the people we said we would develop, eventually, leave or stagnate or are quietly passed over for the next opportunity, because the development we promised them was always going to happen later, and later turned into never.

“The leaders you are developing are the ones you are developing right now, in the work you are already doing. The rest is intention without action.”

Why we postpone what we know we should do

If developing people is so clearly the work of leadership, why do so many leaders postpone it? I have come to believe the reason is rarely a shortage of time. It is something more honest, and harder to admit. Investing in another person’s growth is slow, expensive, and often invisible in any current quarter. The return shows up years later, sometimes after we are no longer in the role, sometimes in the success of someone who will not remember to credit us. None of those outcomes scratches the itches that drive most of us in our seasons of greatest output. The work of developing others has to be done for its own sake, or it does not get done at all.

Scripture is direct about this. Paul, writing to Timothy from prison, gives a charge that has shaped my own thinking about leadership development for many years. “And the things that thou hast heard of me among many witnesses, the same commit thou to faithful men, who shall be able to teach others also” (2 Timothy 2:2, KJV). Notice the chain. Paul to Timothy. Timothy to faithful men. Faithful men to others also. Four generations in one verse. Paul is not telling Timothy to build a platform. He is telling Timothy to build a chain that will outlast both of them. That is what leadership development is. It is the work of building a chain that does not break when one link steps out of the role.

The deception of generic investment

Most leaders, asked whether they invest in their people, will say yes. They believe it. They genuinely care. They go to the team functions. They say encouraging things in performance reviews. They mean well, and the people around them know they mean well. But generic care is not the same thing as deliberate development, and the difference shows up in the lives that get changed.

If I asked you, right now, to write down the names of the two or three people you are deliberately developing this quarter — with a specific stretch you are putting them through, a specific conversation you owe them, a specific experience you are engineering for them in the next ninety days — could you do it? If you could not, you are doing what most leaders do, which is generic care that feels like investment but does not produce leaders. There is no shame in this. It is the default. But the leaders who actually build chains are the ones who refuse to settle for the default, and who pay the price of being specific.

Jesus, who could have built any organization he wanted, chose twelve. Out of the twelve, he poured deeper investment into three. Out of the three, he had a particular friendship with one. The pattern is striking, and it is not accidental. The leader who tries to develop everyone equally develops no one well. The leader who develops a few well changes the trajectory of an organization for a generation.

“You cannot disciple a crowd. You can only disciple people, one at a time, with their names written somewhere only you see.”

Three disciplines of the leader who actually develops people

Name them, specifically and privately

Pick two or three. Not because the others do not matter — they do, and they will receive your general care and competence as a leader. But your deliberate development can only be deliberate if it is specific. Write the names down on a piece of paper, or in a journal, or in some place that only you see. Then, for each name, write three things. What stretch do they need this quarter that they cannot give themselves? What conversation do I owe them that I have been postponing? What experience can I engineer for them in the next ninety days that will grow capacity faster than another year of doing what they already do well?

If the answers come quickly, you are already doing the work. If they come slowly, or vaguely, that is information. The development is not happening. The intention is. The two are not the same.

Give them work that is genuinely uncomfortable

People do not develop by doing what they are already good at. They develop by being put one step beyond their current capacity, in conditions where the stakes are real but recoverable, with a leader nearby who will not rescue them from the discomfort. The discomfort is the development. The stumble is the development. The look of bewilderment when they realize they are responsible for something that is harder than what they expected — that is the development.

The hardest part of this, for most leaders, is not finding the stretch work. It is resisting the urge to step in and take it back the moment the person struggles. We tell ourselves we are helping. We are usually protecting our own discomfort with watching them struggle, and we are stunting their growth in the process. The proverb captures it. “Iron sharpeneth iron; so a man sharpeneth the countenance of his friend” (Proverbs 27:17, KJV). Iron sharpens iron through friction, not through ease. If your developmental relationships have no productive friction in them, they may not be developmental at all.

Talk about their future, not just their performance

Performance conversations look at what someone has done in the last quarter. Development conversations look at who someone is becoming over the next several years. Most leaders have plenty of the first kind and almost none of the second. The result is teams full of people who are well-managed and underdeveloped, who know exactly what they did last week and have no idea where the relationship is taking them.

Once a quarter, sit down with each of your two or three. Set the deliverables aside. Ask, “Where do you want to be in three years? What is in your way? What am I doing that helps, and what am I doing that hinders?” Then listen, slowly. The first answer is usually rehearsed. The second answer, if you wait for it, is more honest. The third answer is sometimes the one that changes everything you thought you understood about the person you have been working with for years.

Leadership Reflection

•  If I asked you to write down, this minute, the names of the two or three people you are deliberately developing this quarter — with the specific stretch each one is in — could you do it?

•  Which person on your team has been given work in the last ninety days that genuinely stretched them, and how did you handle the moment they stumbled?

•  When was the last conversation you had with someone on your team that was entirely about their future, not their current deliverables?

•  What chain are you building? Who, on your watch, is being prepared to do for someone else what no one ever did for you?

The chain that outlasts the role

The lumber yard man I mentioned at the beginning of this essay died several years ago. I went to his funeral. The room was full of men in their fifties and sixties and seventies who had passed through that yard at some point in their early lives, and many of them got up to speak. They did not talk about lumber. They talked about a man who had taken time, in the middle of the work, to teach them how to think about it. Most of them, by then, were running their own crews. A few were running their own businesses. One was a foreman on a job site bigger than anything the old man would have been able to imagine when he first hired the kid in question.

That is what leadership development looks like, when it is real. It is not a program. It is not a quarterly initiative. It is the slow, deliberate, often invisible work of pouring into specific people, in the middle of the regular work, while there is still time. It does not pay in any current quarter. It pays for decades, in the lives of the people who learned, on your watch, how to do for others what you did for them.

Whoever the two or three are, in your world right now, write the names down today. Then, before the week is out, do one thing for each of them that you would not have done if you had not written the names. That is how the chain begins. The work is never done. So you might as well start teaching now, while you are doing it.

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A note from Lee: If any of this lands where you are right now, and you would value an unhurried conversation with someone whose job is to help you see clearly, the door is open. connect.msgresources.com/leadership-advisory