What I learned about socially responsible leadership during my year with LeadBoston

November 16, 2017

Last fall, an email from ChickTech landed in my inbox. It included a mention of a program called “LeadBoston.” I hadn’t heard of it, but I was on the lookout for leadership development opportunities, so I clicked the link.

That click has led to quite the year.

If you haven’t heard of it either, LeadBoston is an 11-month executive leadership development program, facilitated by YW Boston. The goal is to grow a group of executives into a cross-sector network of socially responsible leaders, and the emphasis is on experiential learning.

During the dozen times this year when I set my out-of-office notice for LeadBoston program days, I was learning about the city while taking a walking tour in Roxbury, visiting a middle school in Dorchester, meeting in a South Boston healthcare center, studying class and poverty in a basement room at Catholic Charities, looking at affordable housing in Chinatown, and hearing from an inmate at Suffolk County House of Corrections about his plans to complete his sentence – and never come back.

I learned from my classmates – lawyers, police officers, nonprofit leaders, entrepreneurs, human resources executives, medical professionals and others. And I also got to learn about how Boston works from many of the people who help run it, from the police commissioner to the head of the teachers’ union to advocates for vulnerable communities. 

Measuring “professional development with a purpose”

If there were ever a year to get pushed out of your lane and learn more about the systems that built the community around you, 2017 was it. A lot of the themes that dominated our LeadBoston conversations this year – including racism, class and privilege – were ones I spent far more time thinking about after November 8, 2016 than I did before. And because of that, I spent much of this year learning by listening.

My classmates, I think, would say I have been quiet. I would say that many of them had far deeper experience as change agents, and I wanted to soak up what they knew.

But there were also LeadBoston program days when I had to remind myself why I was there, how my participation could affect my professional path in the private sector, and how it would benefit my employer, who sponsored my attendance and was gracious about the amount of work I missed this year to complete the program.

So, I’ve been going back through my LeadBoston notes to review what I did with this time.

On my application, I wrote:

I have spent my career looking for the place where Doing Good intersects with Doing Well. I have been lucky enough to seek that intersection as a journalist, as a teacher and as a marketer. Today, I have a position that calls on the experiences I’ve gained in all those roles; I create content high-tech businesses use to connect with, educate and influence their audiences. I work for a company I believe in, which also believes in me... I know I am capable of doing more as a leader in my organization and in my community. This is my personal and professional focus for 2017.

Did I maintain that focus? Am I a stronger leader than I was at this time last year?  

Leadership lessons that will linger

As a cohort, my LeadBoston class agreed that what we said within the group would stay private, but that what we learned would leave with us. Below are some of my takeaways that adhere to those ground rules, and which I will revisit often to remind myself of the value of this experience for me as a private sector professional working in a small business, and hopefully for those teammates, clients and partners with whom I’ll work in the years ahead.

  1. Have difficult conversations, respectfully. We started every conversation with reminders about dialogue best practices: Share the air. Be willing to listen. We don’t need to agree. Step up and step back. They’re good reminders for participating in any potentially challenging discussion.

  2. Don’t stick to “your story.” This was a subhead in a Harvard Business Review article we read in January called “The Authenticity Paradox.” As the author argues, “we tend to latch onto authenticity as an excuse for sticking with what’s comfortable,” and that is in direct conflict with the transitions often required of leaders.

  3. Remember that knowledge is a worthy goal. Early in the year, the facilitators asked if we were used to attending meetings where we’d ultimately solve whatever problem or challenge we faced. (Me: YES!) That is not what LeadBoston was about, and we didn’t land on quick fixes for the issues we examined. Our program days focused on expanding knowledge and building on it for the long game.

  4. Put a pebble in the water. Another way I heard this discussed throughout the year was “do what you can, with what you have, where you are.” It’s a refreshing reminder for anyone working inside the fail-fast-boil-the-ocean-play-hard-or-go-home culture of the tech ecosystem. When the lense is on creating more equitable workplaces and communities, the pebble-sized changes slowly add up – including in how those actions change the person who takes them.

  5. Show up differently. Peter Bregman talks about the trouble with most leadership programs in his article, “Why so many leadership programs ultimately fail.” A quote from that piece, shared early in the program, stuck with me all year. It encompasses much of what I’ll take away. Bregman writes: 

What makes leadership hard isn’t the theoretical, it’s the practical. It’s not about knowing what to say or do. It’s about whether you’re willing to experience the discomfort, risk, and uncertainty of saying or doing it.

In other words, the critical challenge of leadership is, mostly, the challenge of emotional courage.

Maintaining momentum for change-making

The kickoff for the LeadBoston year was an “advance” – because we do not retreat. The finale is a leadership commitment – because the end is also a beginning.

Each member of the group identified a project to begin or build on. For my part, I’m partnering with LeadBoston colleagues from Bunker Hill Community College and the Council on American-Islamic Relations (CAIR) Massachusetts to plan “soft skills” field trips into Boston companies. Students will get the chance to tour a business, eat lunch with employees and learn about their professional experiences. And the companies will get the chance to expand their networks, demonstrate corporate social responsibility and differentiate their corporate culture for the two-thirds of the millennial workforce who weigh a company’s social commitments before deciding to join its team.

If you’re interested in hosting one of these visits, reach out to me on LinkedIn.

And if you’re interested in getting a spot in the LeadBoston class of 2018, get moving.

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