Some managers seem indispensable.
Whenever a problem surfaces, they step in. They rewrite the proposal, call the client, settle the argument and make sure the job gets done exactly as planned.
Moses on Mount Nebo by Robert Hawke Dowling
At first, that can look like leadership at its best. Over time, however, the cost begins to show. The organization may make very few mistakes, but it also becomes increasingly incapable of functioning without the person at the top.
Employees quickly learn that every difficult decision can be pushed one level higher. Younger managers discover that when the pressure rises, someone more experienced will eventually enter the room and take over.
The result can be an organization that is highly efficient in the short term but dangerously dependent in the long term. In trying to protect their people from failure, managers can deprive them of precisely the experiences they need in order to grow.
The opposite approach can be just as damaging.
An employee is handed a difficult assignment and told to “figure it out.” If things go well, excellent. If they fail, the experience is described as a learning opportunity.
There can be value in that approach. But without clear limits on responsibility and risk, “empowerment” can become a flattering word for abandonment.
This week’s Torah portion, Haazinu, suggests another model.
In Moses’ final song, God’s relationship with Israel is compared to an eagle stirring its nest, hovering over its young, spreading its wings and carrying them aloft.
Rabbi Isaac Arama, the 15th-century Spanish Jewish philosopher and author of Akeidat Yitzhak, reads the image as a remarkably precise description of education.
The eagle does not keep its young safely in the nest until they are somehow completely ready to fly. It unsettles the nest and forces the fledgling to begin using its own wings.
But it does not disappear.
It remains close, watching carefully and ready to prevent a fall from becoming a fatal crash.
That distinction is just as relevant to management.
The goal is not to prevent employees from ever falling. Sometimes the fall is part of the learning process. The real questions are how far they can safely fall, what the organization can afford to risk and at what point managerial responsibility requires intervention.
People do not become independent simply because their managers tell them to be independent.
You cannot teach someone to make decisions while continuing to make every important decision for them. You cannot develop a young manager if, every time a meeting becomes uncomfortable, the boss takes control.
Independence is learned by exercising independence.
There is an echo here of Aristotle’s argument in the Nicomachean Ethics: We acquire abilities and qualities by practicing them. We become builders by building and musicians by playing music. Character, too, is formed through repeated action.
We do not always become ready first and act afterward. Sometimes acting is what makes us ready.
That is easy to accept in theory and much harder for a manager to practice.
No one learns how to handle a difficult client without eventually handling a difficult client. No one learns to manage conflict if a senior executive enters every uncomfortable conversation and resolves it.
A manager who genuinely wants to develop people therefore has to accept something uncomfortable: For a while, they may perform a task less effectively than the manager would have done it personally.
That requires a different management routine.
An employee arrives with a client problem. Instead of immediately providing the answer, the manager asks for three possible courses of action and a recommendation.
A young executive must present to senior leadership. Her boss does not take the presentation away from her. He helps her identify the weak points, prepares her for difficult questions and then leaves the stage to her.
A project manager makes a decision that is not optimal, but the consequences are limited and reversible. Instead of correcting it immediately, there may be value in allowing that manager to see the consequences and adjust.
This is leadership that is willing to tolerate a small amount of imperfection in order to avoid a much larger problem: dependence.
But that is only half of the eagle metaphor.
The eagle does not merely shake the nest. It continues to hover.
In managerial terms, autonomy does not mean disappearance.
A good manager knows where the employee is, how serious the risk has become and when a mistake has stopped being educational and started becoming dangerous.
Organizations therefore need to define their acceptable margin for error.
Some decisions can be reversed the following morning. Others can damage a strategic relationship, violate regulations, endanger lives or create irreversible financial losses.
Not every arena is suitable for learning through failure.
The leadership challenge is to create spaces where people are allowed to make mistakes, correct them and try again, while drawing firm boundaries around situations in which responsibility cannot simply be delegated.
The hardest part is timing.
If the manager intervenes too quickly, the employee may never discover whether he can fly. Wait too long, and the cost of the fall may become unacceptable.
The question, then, is not simply whether to intervene. It is when.
That also demands something internally from the manager.
Jumping in immediately provides a feeling of control. At the other extreme, refusing to intervene at all can become a way of avoiding responsibility.
The much harder position is to remain close, watch someone struggle, know that you could solve the problem quickly and still give that person a little more time to work through it.
That requires patience, confidence and a willingness to surrender the need to be the person in the room who always knows best.
I know that tension well from my own experience.
Early in my career as an officer, my main measure of success was completing the mission. I wanted us to hit the target, move quickly, know the details and never disappoint.
That sense of responsibility also created a powerful desire for control.
Developing people mattered deeply to me. Giving them enough room to make mistakes, learn from them and carry real responsibility themselves was much more difficult.
Over the years, I came to understand that remaining accountable for a result even when someone else has made an imperfect decision is itself a managerial muscle.
If you want to develop people, you have to learn to loosen your grip without disappearing.
You have to accept that they will not always do things exactly as you would have done them, while still taking responsibility for the environment in which they operate.
It is a muscle I am still working on.
The fact that Haazinu is read this year on Shabbat Shuva, the Sabbath between Rosh Hashanah and Yom Kippur, gives the eagle metaphor another dimension.
The idea of teshuvah, repentance or return, does not begin with the assumption that human beings will never fall.
It begins with the opposite understanding: People make mistakes. We miss the mark. Sometimes we fail badly.
But Yom Kippur also rejects the idea that a fall has to become a permanent identity.
A person can stop, examine what happened, repair what can be repaired and choose a different direction.
There is a subtle leadership lesson in that.
If we want the people around us to develop, we have to allow them to be human.
We should not define them by one mistake. Nor should we protect them so completely that they are never given the opportunity to make one.
Our responsibility is to build a system in which a fall can become a source of learning rather than a final judgment.
That idea also connects to a new song of mine, “Roots With Wings,” which will be released soon.
The title grew out of a tension I have thought about for years: On one side are roots — identity, values and the knowledge of where we come from. On the other are wings — the freedom to grow, change and choose our own direction.
Eventually I understood that the two are not opposites.
Strong roots are not meant to tie us permanently to the ground. They give us a foundation deep enough to move away from it without losing ourselves.
And wings do not require abandoning those roots. They allow us to grow from them.
That is also one of a manager’s most important responsibilities.
Give people roots: values, standards, culture and belonging.
And give them wings: authority, independence, room to make decisions and the opportunity to build a path of their own.
The same principle becomes particularly visible during leadership transitions.
Reports this week named Microsoft vice president Ohad Yassin among the candidates to succeed Michal Braverman-Blumenstyk at the head of Microsoft’s research and development operation in Israel.
Whatever the outcome, the possibility of promoting leaders from within an organization illustrates a broader principle. One way to evaluate long-term leadership is not only by the results a manager personally achieved, but by the layer of leaders developed around and beneath that person.
A healthy organization should not reach a leadership transition and discover that all its knowledge, relationships and judgment reside with one individual.
In fact, the more successful a manager becomes, the more important decisions should be capable of being made well when that manager is not in the room.
We often measure managers by the number of problems they can solve.
Perhaps we should also measure them by the number of problems their teams no longer need them to solve.
That brings us back to Yom Kippur.
Managerial self-examination is not only about asking: Where did I make mistakes this year?
It can also mean asking: Where did I hold on too tightly? Who did I deny enough room to grow? Which problem did I solve when I should have allowed someone else to solve it?
And, in the other direction: When did I call something “independence” when it was really abandonment? When should I have been present because responsibility still belonged to me?
The eagle in Haazinu offers a model built simultaneously on trust and responsibility.
It does not keep the fledgling forever in the nest. It does not throw it into the air and disappear.
It creates the conditions for flight, stays close and understands that the ultimate goal is not to catch the young bird every time it falls.
The goal is to reach the moment when it no longer needs to be caught.
The Eagle Test
Before stepping into an employee’s problem, a manager can ask four questions.
Is this a reversible mistake from which the person can learn, or a risk the organization cannot afford?
Could this person reach the answer independently if I gave them more time or guided them with questions instead of answers?
Do I genuinely need to intervene for the organization’s sake, or am I simply uncomfortable watching someone do something differently from the way I would do it?
And finally, what should my intervention achieve beyond solving today’s problem?
If I step in now, will this person be better equipped to solve the next one without me?