The Steepest Curve: Growing into Leadership

“The first year’s the hardest.  It’s going to get easier,” my supervisor said, in a soft, kind voice.  I was sitting in his office, trying not to let the tears spill down my cheeks.  It was two weeks into my first project coordinator role, something I’d been thrilled to throw my full self into.  I was so sure I was going to be a natural!  My brand new two-person team disagreed.  I’d miscommunicated a task in a way that felt demeaning and they were furious with me.  They weren’t wrong, I’d made a mistake, and I had no idea how to fix it.  I’d always been highly competent at my work and feeling a sense of immediate failure shook me to my core.  My goal was to build an impactful program and be a supportive, effective supervisor.  Neither were anywhere as easy as I’d thought, both required a host of new skills, and I was suddenly plagued with doubts about my abilities.  These are not the ideal building blocks for a new manager and a new program, but I know my story is not uncommon.

Every time I’ve taken on a new role, my old friend ‘self doubt’ reappears, though the lessons I learned that very first year are touchstones that I revisit often.  This work is hard and important.  We work in high stress, low resource environments with services impacting vulnerable populations.  No one should take that responsibility lightly.  But how do we approach this challenge strategically and proactively to achieve success? 

Shaky Foundations

Taking on a new team is a time of great vulnerability for the leader, the staff and the program.  How this process unfolds can set up a legacy that supports the work long term, or be a stumbling block that takes time and effort to overcome (if it can be).  Because the demands of our work are so immediate, we often short change this process which can stymie program effectiveness, reduce morale, and lead to costly turnover.  Most of us got to these roles because we demonstrated commitment to the work itself, not because we had management acumen.  These skills are developed over time, with our newest leaders often starting out in their roles under-resourced and under-trained, yet immediately held to what can feel like excruciatingly high expectations.  I’ve seen too many wonderful potential leaders not make it through that first year. 

Like a Boss

“I want to be a good boss,” is the goal of most new leaders.  We want our staff to feel the support we didn’t always feel, get the training we wish we had, and be able to do the work effectively without causing any inadvertent harm.  This typically is much harder than new managers assume.  New managers often first present as the ‘manager they wish they had’, which can quickly backfire when a team has different needs.  Nearly all of us have gone through the moment of pain when our good intentions and best efforts fell flat.  This can be a tremendous blow to the confidence of a new leader, and hard to depersonalize.  Leadership is a process, and can require a lot of uncomfortable self-reflection to do well. 

Behind the Curtain

There is often a line between direct service staff and the organizational hierarchy.  Font line staff often have little understanding of all the details and complexities that go into running a program, nor should they be burdened in ways that take them away from their primary commitment, the service itself.  New managers are often getting their first glimpse ‘behind the curtain’ into the glamorous world of complicated reporting, expense tracking, and negotiating organizational conflict.  This stretches us in new ways and taps skills that are often underdeveloped in the nonprofit world (like math!) Navigating that process can knock a new leader on their heels, feeling exposed when they come up short against expectations they hadn’t realized were part and parcel of the new job. Depending on the new leader’s personality, they can react to this feeling of vulnerability in frustration and anger, or internalize feelings of defeat and self-doubt. Neither end well if nothing is done to remedy the situation.

This feeling often returns with each major career advancement.  I didn’t understand what a director really did from my manager position, and I didn’t understand executive leadership until I was sitting in that chair.  Each new position entails navigating a tremendous learning curve while also trying to assure a new team of your leadership abilities. Finding a balance between necessary tasks, staff support, and organizational leadership is a near daily dance, and one we rarely examine or build intentional processes around. 

It’s Lonely at the Top

One of the things many love about nonprofit work is the close social ties we form in these places.  Nonprofits get by on love and passion, and we tend to be a highly supportive bunch to our colleagues.  However, new leaders often feel lonely and isolated in their roles.  Their base of colleagues to lean on has reduced as their pressure to preform has increased.  It is patently inappropriate for leadership to burden their staff with their insecurities, and often hard to engage with our own supervisors about our challenges.  We want to be thought of well, and prove we were the right hire, which can lead to a reluctance to engage around our toughest challenges and fears.   

I remember even after years of leading, it would still sting when my team would go out for lunch together in a big, happy, raucous group, in which I was not included.  Rationally, I knew this was healthy.  My team needed to have their own group process, their own systems of informal support, and some distance from the person with so much power over their day to day lives.  I WANTED them to have that.  But it also didn’t feel great to eat a sandwich alone in front of my computer slogging through yet another report.  We absolutely should have a warm, friendly relationship with our teams.  But being a ‘buddy’ over a boss is a losing strategy, but one fairly common in our sphere that relies so heavily on team support to survive.

Where Do you Turn?

The most vulnerable transition points in our career are often where we have the least tangible support.  When leaders take on a new team or a new role, the stakes are high.  We need to present as competent leaders to our new teams, even when we might not feel that way at our core.  We want to show our supervisors that we are worthy of our new demands, and it can be difficult to explore all the facets and complex aspects that challenge our growth.  I was very fortunate that I’d had someone who I felt solidly believed in me when I faced my first painful supervisory hurdle.  They were someone I could cry in front of, without feeling like they’d doubt I had what it took for the job.  And still, I was reluctant to dive into the harder details, and I didn’t want to take their precious time to explore my own feelings of inadequacy. 

When a host of managers were promoted at the same time, that organization did something brilliant, it provided us with a supportive outlet in the way of private group consultation.  Every other week those in my parallel position across the agency would gather with an extraordinary facilitator to explore all aspects of the work, staff support, skill development, internal conflict and doubt.  It was a place of learning and growth, and also a place of mutual support from those who were going through the exact issues I was.  I wasn’t alone, I wasn’t failing, I was doing everything I could to succeed in a challenging situation, just as my colleagues were.  Years later, one of those group members is my current buisness partner.  Another has been one of my closest personal friends for over a decade, far outlasting our time in the organization.  This investment in us forged life long connections, a community of support, and empowered all of us to lead with a sound foundation of intentionality and the skills we needed to succeed. 

In a sector better known for reactive responses than proactive solutions, I still find myself impressed and grateful the organization worked so hard to give us what we needed to be successful.  While all of us have since moved on, we consider ourselves agency champions and cheer their ongoing success at every turn.  This process significantly improved our morale and skill as leaders, and as I grew more confident and effective as a supervisor, I also watched my team thrive, service engagement increase, and turnover reduce. 

The First Year is the Hardest         

That first year of being a supervisor was humbling.  My supervisor was right when he said it would get easier, it did.  In busy, fast-paced nonprofits, you’ll see a lot in a year, and as you practice and work through all the idiosyncrasies of your program, it will become more natural.  You’ll find the rhythm to the year, and not make silly mistakes like planning a major event during the close of the fiscal year.  I remind myself of this with every new position I take, the first year is the hardest. 

As with almost all things in life, the passage of time itself helps. But for emerging leaders who are tasked with managing programs relied upon by some of our most vulnerable constituents, and who occupy a key role in supporting the health of an organization’s staff morale, we should ideally not trust to time alone. Coaching, training, and personalized action plans can help ensure a successful transition for these promising staff and their valued teams.  Investing in targeted supports for emerging leaders, at such a vulnerable and complicated time, allows our organizations to do good, better. 

Rachel Del Rossi


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