by Naomi Korb Weiss and Bob Sherman

At a November 2012 intimate breakfast for executives at UJA-Federation of New York, a facilitator suggested casually that participants in the room consider ‘reverse-shadowing’ one another to gain insights into other management styles and organizations. Two such executives took this suggestion to heart; below they each share the immense insights they gained from just two days.

Hers: Naomi Korb Weiss, CEO PresenTense Group

It was a typical Thursday in the life of a CEO – debriefing a board meeting, leading a staff meeting, checking a reference on a candidate, negotiating with a couple of partners and answering a bunch of emails. Or was it?

I wasn’t in my cozy PresenTense office or meeting with my own colleagues and partners. Rather, I was observing a day in the life of another CEO – Bob Sherman of the Jewish Education Project. I was simply his sidekick for the day.

After an inspiring breakfast together at the UJA Federation of New York last November, Bob and I took a casual suggestion to heart to ‘reverse-shadow’ someone else in the room. After juggling some logistics I shadowed Bob one busy day in June and he joined our team one day at the end of August. It’s pretty amazing what we each learned in less than a full day.

Bob took the appropriate actions to both alert his team in advance that I would be joining and to share with me necessary background information I would need. We began the day chatting about his typical schedule and workflow – and how much happens out of the office. He quickly opened up with candor when sharing his own reflections on a board meeting the day before and the current challenges at play. That discussion was the first sign that there were more similarities than differences between his 100-year old central agency and my seven-year old startup.

Bob’s leadership style was apparent: his deep passion and trust in his staff is the most important part of his work, and it showed in the staff meeting of department heads. I appreciated the even, calm and authoritative manner he took when leading meetings coupled with the genuine openness to learning from others. I learned much about the importance of focusing on the executive-level concerns and entrusting programming and many day-to-day operations to his team.

Despite Bob’s spacious office and relative privacy he was regularly interrupted by staff needing to sign checks and the like. It was clear that this routine was due to Bob’s open-door policy, and I found myself figuring out how to strike the balance between exhibiting such an attitude and finding a better way to focus within our small room at PresenTense filled with three or more staff on any given day.

I spent the last 40 minutes of the day peppering Bob with questions about how his organization is structured and his current challenges. Since that day, I have reached out to Bob many times with strategic  questions about board management, fundraising, and strategic planning. When I facilitated a session for congregational educators at the Jewish Education Project in October, Bob stopped by to observe and share some thoughts. Looking back, my experience in fewer than eight hours in someone else’s office not only lent me deep insights into how a seasoned leader runs a large and impactful organization but created opportunities for potential organizational collaborations as well as a mentoring relationship that I believe will continue for years to come.

His: Bob Sherman, CEO Jewish Education Project

My first jarring perception occurred when the cab dropped me off on 86th street between Amsterdam and Columbus Avenues. There was the imposing synagogue façade smack in the middle of a residential block. My day normally begins by exiting the subway station at 35th and 8th avenues and shooting the rapids of humanity pouring down 8th avenue until I enter our office building at 520. I then take one of the elevators from the express bank up to the 15th floor, which we fully occupy. Whereas on this morning, after I entered the Jewish Center on 86th street, I stepped into the harrowingly slow elevator to the 7th floor where I wandered my through a hallway maze to the one shared office where all PresenTense staff sit.

In The Jewish Education Project offices I walk around for 10-15 minutes every morning just to say hi to everyone squirreled away in their offices and cubicles, while at Present Tense Naomi shares the same 1,000 or so square feet with the other 3 people who work with her. I loved the informality and intimacy of shared space but wondered how you manage more sensitive issues or hold certain kinds of meetings without a designated meeting space. I quickly learned that some people create mental walls to separate themselves and be able to concentrate.

Though there was little doubt that the current space was less than ideal, it was fascinating to me how a single room could be divided up without walls into desk space, formal meeting space (around a table), and informal meetings (a couple of couches). And yet it seemed that people weren’t into each other’s business in a distracting way. It also seemed that there was less random chit chat than might occur in our more generous space, perhaps because each individual worked in full view of everyone else. And there was no space hierarchy, since Naomi had the same desk space against a wall as everyone else.

At one point we left the space to sit in an unoccupied office on the same floor when Naomi initiated a phone call with her counterpart in the Israel office. The topic had much to do with board and lay leadership and it was obvious that at this level we shared some of the same challenges. Regardless of the size of the organization or its scope, we all face the challenge of finding the right board members and then engaging them in the most effective ways.

Next the group engaged in a planning meeting to arrange travel and shared calendars for the year. I was really impressed by this exercise to share and coordinate schedules. It was here that Naomi’s unobtrusive and friendly leadership style became powerfully evident. She was able to create a relaxed vibe even as she remained firm and decisive when needed.

Toward the end of the day, a representative from Paychex came to speak with employees (all two of them) about a retirement plan. Having just come off negotiating with our professional staff collective bargaining unit, it was delightful to witness these two people in their twenties wrestle with what kind of retirement plan made sense for them.

Throughout the day I was inspired by the entrepreneurial energy and the relaxed and productive atmosphere I encountered. Although I was constantly aware of the differences between our two organizations, I found myself reflecting on how much we in the much larger and older “legacy” organization might benefit from learning how to operate in a leaner more nimble way. Just as Naomi helped me to reflect on my own practice by shadowing me and then debriefing, I hoped she would benefit in return from my visit. And as a huge bonus, we could now be far more empathetic colleagues, far more likely to advocate for each other and to find opportunities for collaboration.

Early in my career I shadowed a veteran central agency director for a week. It was a great way to learn about the field I was then entering. It’s been over 20 years since then and I found this new opportunity an enormously helpful and reflective experience. If you haven’t walked in someone’s shadow lately, I encourage to find a partner and do it.

cross-posted on PresenTense blog