Introduction
When Tim Walz was announced as Kamala Harris’ running mate, I was heartened to learn of his background as an award-winning social studies teacher and football coach, not to mention a pioneering faculty supporter for his school’s gay-straight alliance. I can attest that teaching is the best leadership training there is. While we may not all aspire to be Vice President, lessons from the classroom transcend leadership in many settings. With the back-to-school season in full swing, I’ve been reflecting on how these lessons translate to leading People teams in startups.
My Time as an Educator
First, an important disclaimer: teaching shouldn’t be approached as a stepping stone into another field. Great educators are made, not born, and it generally takes them three to five years to find their stride. In that regard, I have mixed feelings about my Teach For America experience. On one hand, my conviction about its mission and theory of change following two years in the classroom led me to recruit hundreds into the profession thereafter. It was there that I discovered a passion for all things Talent and People, which has defined my immensely fulfilling journey for the past 15+ years. But I also regret leaving the classroom after only two years, knowing there was much more to learn and contribute. At 24, I was eager to start the “next chapter” of my career. Now, at 40, I see the value in staying the course and encourage young educators to do the same.
But we cannot skirt past the very real challenges faced by the profession: declining enrollments in teacher preparation programs, low compensation (especially in underserved districts), and pervasive stress. The latter is compounded by increasing politicization in schools (e.g., “Don’t Say Gay”-type legislation), which leaves teachers feeling torn between creating welcoming and inclusive environments – much like Tim Walz did nearly three decades ago – and risking professional repercussions.
That aside, my time in the classroom laid the foundation for a few maxims about how People teams in startups can do their best work. Here are my top three:
Invest People in the Journey
As I’ve previously mentioned, eager People leaders often rush into implementing “best practices” without ensuring their leadership teams are bought in or understand how they align with a clear strategy that engenders a higher performing and more engaged team. This can lead to People teams being seen as out of touch, needlessly burdening others with work where the “juice isn’t worth the squeeze.” Similarly, educators who overwhelm students with disconnected learning objectives – as I initially did – are bound to fail.
Like educators, startup People leaders must over-communicate the company’s direction, how their initiatives support that journey, and when outcomes can be expected. This “sign posting” should be clear, concise, and reiterated consistently, as repetition is a known necessity to get others to internalize ideas.
Ruthlessly Prioritize
In many settings, Type-A individuals often try to “boil the ocean”, tackling every plausible issue that could pave the way for success. I have done this as both an educator and startup People leader, and I can attest without reservation: It does not work! In my early teaching days, I attempted perfection, spending hours on bulletproof lesson plans and beautifying my classroom. Planfulness is critical, but educators need to be nimble when things inevitably go off course.
More importantly, it’s critical to identify the rising tides that lift all boats. In my classroom, it really came down to establishing a sense of psychological safety and relevance as to how achieving ambitious academic goals would be to everyone’s benefit. Getting the basic routines and expectations down and building off them little by little, week by week would have been a far more effective strategy than trying to nail everything on day one. It was ultimately by slowing down that I was able to actually make learning fun (e.g. writing a rap that captured every 3rd grade math learning standard; I still know it by heart!) and get to better outcomes.
The same is true for startup People leaders. Think of it this way: At the end of a quarter, would you rather have eight half-baked initiatives without any observable results or three concrete achievements? A mentor once wisely encouraged me to always uphold the “say / do” ratio – that is, to do everything that was promised, and to manage expectations accordingly when that cannot happen. Aside from listening attentively (see next tip), this is probably the best way to amass credibility and bring people on the aforementioned journey towards a higher-performing team. Less is more, and besides, introducing too many changes at once will lead to organizational indigestion.
Listen & Be Yourself
I spent my first two months in the classroom doing my best impersonation of training videos from Teach For America’s summer institute, hoping that if I could parrot their highest-performing teachers my students would magically overcome the odds. Somewhere along the way, I lost myself in the process, and my perceptive students understood and responded accordingly. They might not have used the words, but this approach rang as insincere, and they felt unheard and unvalued.
The same goes for People leaders in startups. While it’s not our job to accommodate everyone’s requests, listening with empathy and responding genuinely builds credibility. Startups are frenetic by nature, and it’s easy to overlook the importance of real conversations when a long to-do list hangs in the balance. In trying to achieve so many tactical and strategic goals People leaders often give short shrift to holding space for actual conversations. Maya Angelou’s prophetic words ring true here: People will always remember how you made them feel, and perceptions of insincerity or distractedness will foil a startup People leader’s success every time.
Conclusion
Several months ago, I was going through old photos and, as I’d imagine many teachers do, started Googling a few of my former students, all of whom are now somehow in their mid-20s. I was elated to discover that one student is in her third year of teaching Special Education and pursuing a doctorate. I cannot reasonably take any credit for this, but it has given more meaning to the most challenging and worthwhile experience of my life all those years ago.
Moments like these leave me all the more grateful to bring these lessons to the work Luminary is so fortunate to do in partnership with mission-driven organizations. If this unconventional background and approach is intriguing, don’t hesitate to book your free consultation today.
