Generosity of Learning

Leadership coach Crane Wood Stookey offers these two practices to help train you in the attitudes of generous leadership. 

We usually accept that teaching others can be a generous thing to do. Being willing to learn from others can also be generous.

What do your people know that you don’t? Have you made an effort to find out? Have you created a culture in which people expect to learn from each other up and across the organizational chart as well as down?

It may feel a bit unsettling to encourage people under you to show that they know more than you do, but people are always going to know things you don’t know. None of us are omniscient. An excellent way to engage people is to ask them to teach something, and then make the effort to actually learn it and make use of it.

Curiosity practice

If you are not naturally inclined to seek out what you can learn from your team members, you can start with safe territory. For instance, if your child is doing a history project, ask people when they’re settling down to a meeting whether anyone knows about that historical period. Ask them a question your child is addressing, and let everyone hear the answer. Share the answer with your child, and report back what they say. Or if you’ve heard that one of your team members speaks another language, ask them to teach you some phrases. Actually learn the phrases, accept coaching on pronunciation, and greet that person with those phrases when you see them. The possibilities for learning are many. You can be as creative as you like.

The point is not to make conversation or single out people with little “relationship” tricks. The point is to train yourself in the habit of learning from your team. It helps to ask about things you have some genuine interest in, but you can also find ways of being genuinely interested in what each person can offer. You might be surprised at what you can learn, and from whom. Everyone has something to teach, though it may be submerged. You can create conditions for them to discover it and offer it. That’s what makes this a practice of generosity.

Putting-to-use practice

The more immediately practical kind of learning is the kind that directly benefits the team’s efforts. Do you have lunch and learn sessions where people can present or report to their colleagues on relevant topics in which they have particular expertise? If you do, set the example of asking questions, being careful not to sound as if you’re testing them. Is there something in the tactical plan you’re not clear on? Who can explain it? Let them explain it to you when others can hear too. In any situation, try to notice opportunities for people to show what they know in a useful way, and then help their teaching to emerge.

When someone is being a showoff or undermining the contribution of their colleagues, you can speak to them more directly about the culture of teaching and learning that you want to create. Or you might be able to find a way to let the situation do the work, by looking for things the showoff really needs to learn and for ways their colleagues can teach them, publicly, without humiliation. Ideally this would be about something truly useful to the person in question, that they can feel the immediate benefit of.

When some people are hesitant to offer what they know, you may need to more actively create opportunities for them and provide some protection for their first steps.

Then, when challenges arise and you’re not sure of the best course of action, you will have trained your people, and yourself, to engage the full spectrum of your abilities, together.

For more about Crane Stookey, read Learning the Ropes by Barry Boyce, here on

Crane Wood Stookey is a Tall Ship officer and leadership coach who specializes in workforce engagement. This article is excerpted from his new book, Keep Your People in the Boat—Workforce Engagement Lessons From the Sea, published by ALIA Press. 

The crews of the H.M.S Heda & Griper cutting into Winter Harbour, 1819.

Photo © Public Library Special Publications