Lessons from a (pretty great) #2

I am a leader who can tell a good story on stage, motivate and direct large teams, and drive impact for ambitious programs. But I see myself most as a consummate #2. This insight has been the cause of heated debates amongst friends and mentors. I would point to my #2 role model of Belinda Johnson of Airbnb, the “silent superpower” of her company, and people would point out I am hardly stealthy, nor am I a lawyer. Of course what I saw in her was somewhat different. She brings her unique strengths to whatever role she tackles, and builds community and excitement wherever she goes as she gets things done. (I have never met her, but really admire her from afar. Swoon!)

Time and again, I’ve found I’m happiest when I’m working for an ambitious, empathetic, visionary #1 who needs a partner to help make those ideas as powerful as they can be, and get the team (and clients and stakeholders) engaged while crushing it on high impact delivery. Here’s some hard-earned lessons I’ve gathered over the years.

It starts with the partnership. Certainly there are areas I’m probably not suited for given my preferences, skills and experience (won’t tackle heart surgery nor would I be any good at making any kind of slasher/gory movie), but generally speaking, I’m up to learning and tackling a wide range of work. I’ve worked across industries, from consulting to technology to higher ed/fundraising and financial services. Each role, and even each pivot started with an amazing, inspiring leader. The most successful of those roles happened when I got over my hero worship, the power differential that would spark my nerves, and viewed them as a complete, imperfect person where my job was to watch out for their blind spots. There was a recent HBR IdeaCast on “How people can become more self aware.” Tasha Eurich, an organizational psychologist and executive coach, explains that few people, especially executives, are truly self-aware, and those who are don’t get there through introspection. She explains how to develop self-awareness through the feedback of loving critics. My role as a #2 is to be a loving critic, and to make sure I am also surrounded by loving critics so I don’t get too insulated. Partnership means that I build trust through authenticity and through impeccable delivery.

Invest in the team. The best way to deliver something exceptional is to have a high performance team firing on all cylinders. And the best way a #2 can get there is by building psychological safety with people. Watching Amy Edmondson give her TED Talk at a NYC session on “How to turn a group of strangers into a team” was a revelation. I intuitively knew that my connections with people at all levels mattered, but learning about her research helped me. Recently we were conducting a transformational project, asking people to stretch in their roles and lead change initiatives. Each person was nervous about the ask. I blocked a big chunk of time in my calendar and spent 1:1 time with the leaders, building trust, adjusting their training based on what they needed. Some needed a deep dive into the users/personas so they could have a strong foundation into the “why” of the project and feel anchored to a true north as things inevitably shifted over time. Others wanted help setting up sharepoints, getting processes established and feeling grounded in structure. The end result was each lead walked away able to function and help their own teams deliver. And the investment in the team shouldn’t stop there. Check in on people. Get to know them and invest in their success beyond the delivery of that critical project. Mentor people and sponsor them. Find ways to build trust and give empathy. Encourage your #1 to get to know people and understand people’s strengths and needs.

It’s not just the what, it’s the how. The great Maya Angelou said famously, “I've learned that people will forget what you said, people will forget what you did, but people will never forget how you made them feel.” I have some very cringe worthy stories from my early years of my over-zealous “driving” tendencies bulldozing over people in the name of expediency in search of results. And where I land now is that the “how” is everything. So in my role as a #2, people feeling joy and exhilaration in their work is just as much a result I strive for as on time delivery and impact. The best example of this is early in my career, when I focused solely on the “what”, and fell flat on my face. After having done a great job on a client project with my team of 8 months, I was asked by my boss, the head of project management to move to another team, a fully formed team, and “whip them into shape”, by immediately showing them who’s boss from the start. (Never mind that this assignment was wonky to begin with.) I was told they were not falling into line on ROI and I should bring some structure to the group. I came in and started to “assert my authority” as directed. I told the team how we did things on my old team and directed people to start following new processes and start using new templates. The result was the team, always polite, ended up completely ignoring me. They would hold meetings without me and made a point of shutting me out of key decisions. Ugh. I realized very quickly how much ignoring my instincts had set us back. That lesson was a painful and important one. If a senior manager gives you a directive, how you get it done is everything. Take the time to get to know people and understand and incorporate their thinking into your overall approach.

Build trust. Those strong relationships will help you in a multitude of ways. That director of project management today would get push back from me with a directive like that. I would say, I will work to achieve your ROI (or whatever impact you want), through strong trusting connections with the team. I need to earn their respect and trust as their leader.

It’s so gratifying to do incredible work, and have an amazing boss and partner to work for in pursuing these big things. It starts with building an authentic partnership, where you seek and give candor along the way. Delivery happens through a team who is engaged in innovation and continuous learning. This is intentional. It requires investment in the teams and nurturing of those connections. And finally, while we all want big impact and results, how we get there matters. Making sure you drive results while practicing empathy will create a culture your #1 will be proud of.

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