Dear Friend,

By the time you read this, the office will be yours. 

Somewhere in a drawer, you’ll find the transition memo I’ve been writing for you. It contains passwords, institutional history, names of donors and all the practical things that never make it into annual reports.

This isn’t that memo.

This is the one I almost didn’t write. It’s the one about leadership.

Seven years isn’t a lifetime, but it’s long enough to learn a few things the hard way. Most of what follows comes from mistakes, not successes.

Don’t lead alone.

One of the biggest misconceptions about executive leadership is that your job is to make difficult decisions. It isn’t. Your job is to create a process through which difficult decisions become shared decisions.

Invite people into consequential conversations before you’ve reached your conclusion. Let trustees help shape strategy. Let university partners know what you’re wrestling with. Ask your senior staff what they’re seeing before you’ve decided what you’re seeing. People become invested in decisions they help create. You’ll also discover that life is much easier when you aren’t standing alone out on a limb after making every consequential decision by yourself.

If you remember only one thing from this letter, let it be this: steward your top donors.

This is the place where I was least disciplined.

I always enjoyed fundraising. I loved introducing people to remarkable students and inviting them into the story of Brown RISD Hillel. But I was never as methodical about stewardship as I should have been.

If I had another seven years, I would know exactly who my top 50 donors were, and every one of them would hear from me regularly. Not because I needed something, but because stewardship is the work.

One board member used to tell me, “Money follows leadership.” At first, I thought he meant that charismatic leaders raise money. Now I think he meant something much deeper: people invest in leaders they trust. Long before they write a check, they’re deciding whether they believe in your judgment, your steadiness and your capacity to lead an institution they care about.

Protect your staff more than I did.

I came to believe this late, and I wish I had understood it earlier.

Your staff’s attention belongs with students. Their emotional energy belongs with students. As much as possible, insulate them from board dynamics and competing centers of authority. 

Staff should never wonder who they’re actually accountable to. Clarity is a gift.

Take them out for coffee. Celebrate them in front of one another. Practice hakarat hatov (gratitude) constantly.

People often talk about transparency as though it’s primarily an informational challenge. I think it’s mostly relational. People work harder for leaders they admire.

Build your board before you need your board.

I see now that the nominating committee is one of the most consequential committees in any Jewish organization. Its work isn’t finding enough people to fill seats; it’s asking who should help shape the culture of this institution over the next decade.

Recruit all year. Think all year. Cultivate all year. 

By spring, the slate should almost feel inevitable because the conversations have already happened.

Become known for calling early.

Don’t let people be surprised unnecessarily. One of the great gifts you can offer an institution is becoming its early warning system. Trust is often built by timing.

Whether it means reaching out to your board chair, your university president, your chaplain or your largest donors, become the person who shares difficult news before someone else does.

Write more than feels necessary.

One thing that consistently served me well was direct communication with trustees, alumni, parents and supporters.

Develop a recognizable voice, writing regularly enough that people begin to recognize not just your opinions but your temperament.

(Interestingly, I found that this translated much less effectively to students. Executive directors don’t build trust with students primarily through emails. Instead, they build trust through presence, through relationships and through the culture they help create.)

Speaking of culture…

I came to believe there’s an important difference between student leadership and student governance.

Student leaders build culture. Student governance governs culture. Healthy Hillels need both.

But if I had to choose where to spend my energy, I’d spend it cultivating builders.

The future of Jewish life depends more on the students creating community than the students debating policy.

A word about pluralism.

You’ll inherit disagreements. That’s part of the blessing and the burden of leading a pluralistic Jewish institution. Whenever our community found itself divided, I tried to remind people of two truths. 

The first is that Judaism has always been multivocal. Argument has never been a bug in the Jewish tradition; it’s one of its great features.

The second is that we are still one people. Our shared history matters. Our shared future matters.

Pluralism without peoplehood eventually fragments. Peoplehood without pluralism eventually hardens. Hold on to both.

One last confession

Over the years, I sometimes found myself speaking with more sharpness than wisdom. I don’t regret saying difficult things, but I do regret some of the ways I said them.

I’ve become convinced that anger is usually a poor leadership strategy (even when you’re right — no, especially when you’re right).

If I had another seven years, I think I would spend more energy cultivating gentleness without sacrificing conviction.

Now make it your own.

Finally, remember that you’ll occasionally wake up wondering whom it’s politically necessary to disappoint that day. I’m not being cynical. But I am being honest.

Don’t measure your leadership by whether everyone approves of your decisions. Measure it by whether people continue to trust your integrity after they’ve disagreed with you.

Seven years from now, you’ll probably write a letter like this to the person who succeeds you. I hope that when you do, you’ll have different reflections to share.

That will mean you’ve become not the steward of my Hillel, but the steward of yours.

With gratitude,

Josh

Rabbi Josh Bolton is the senior fellow at Brown RISD Hillel, where he served as executive director from 2019 to 2026.