Good day, CharterFolk.
Today we are pleased to share a Contributor Column from Christina Greenberg, the Founder and CEO of Edgility Search.
Christina is the founder and CEO of Edgility Search, which leads executive searches and recruitment engagements for charter schools and nonprofits serving the K12 education space. She can be reached at cgreenberg@edgilitysearch.com or follow her on LinkedIn at linkedin.com/in/christinalgreenberg.
The Second Year Cliff
The first year of leadership for a new charter school ED or CEO often looks like success.
Successful relationships are built. There are no major fires. Staff are relieved and the board is pleased. Sometime around late winter of the first year, most boards exhale and think: We made a good hire.
And maybe they did. But here’s what I’ve seen happen next – the second year arrives and the leader stalls.
Not dramatically. There isn’t a big scandal or looming crisis. Just a quiet settling. The organization keeps humming, meetings still happen, and kids are still in classrooms. But the transformational work – the enduring strategy, the bold move, the thing that was supposed to make this hire matter – doesn’t materialize.
And the board? They’ve already moved on.
Year one has a script; year two doesn’t.
The first year has a built-in structure: listen, learn, stabilize and build trust. Most capable leaders can execute it. Year two has no such script.
By the second year, the relational groundwork is laid and the honeymoon is over. Now comes the actual job: setting direction, building strategy and making hard calls. That transition from stabilizer to transformer is harder than it looks. Without clear goals and honest feedback, many leaders default to what’s comfortable: keeping things running.
And keeping things running can look a lot like leading – right up until it doesn’t.
This isn’t just a leader problem.
This is the part boards don’t want to hear.
The second-year plateau is often a governance failure. By year two, most boards have mentally filed the leadership question under “resolved.” The intensive onboarding attention fades. Evaluations become perfunctory or disappear entirely. Goals that were vague in year one never get sharpened. And nobody – not the board chair, not the executive committee – is sitting across from the leader and asking: Are we actually moving, or are we just maintaining?
Boards often hire for transformation and then create conditions for stagnation. They set an ambitious vision in the job description, celebrate the hire, and then step back at exactly the moment the leader needs the most clarity and support. The executive is left to figure out “forward” alone, without explicit goals, without honest feedback and without anyone holding the mirror up.
That’s not oversight. That’s abdication dressed up as trust.
The drift that follows looks like stability until it doesn’t. By the time anyone names the problem, the window for easy course correction has closed and the board finds itself back where it started: wondering why things feel stuck and whether they need to make a change.
That cycle is expensive – in money, in time, and in the toll it takes on everyone who works there.
What should boards do differently at the 12-month mark?
The second-year cliff is preventable. It doesn’t require a new framework but it does require boards to stay engaged past the point where engagement feels urgent. Our team at Edgility Search has developed a tool for boards and leaders to evaluate whether they are set up for success at this crucial juncture (available here).
Some of the key principles are listed below.
Set explicit goals for year two. Not aspirations but actual direction. What does meaningful progress look like in the next 12 months? What should be measurably different by this time next year? If the board and executive can’t answer those questions with specificity, that’s the first problem to solve.
Recommit to a real evaluation process. This should not be a check-the-box review but a genuine two-way conversation about performance, support and alignment. The best evaluations aren’t just about assessing the leader; they’re about getting honest about whether you’re set up to succeed together.
Ask the question most boards never ask. At that year-two conversation, a board chair should look the executive in the eye and ask: What do you need from us that you’re not getting? The answers are usually simple. And they’re almost never asked for because leaders don’t want to seem like they’re struggling.
Who are the leaders who thrive in Year Two and beyond?
The charter school leaders who do their best transformational work in years two, three and four aren’t necessarily more talented than the ones who plateau.
Instead, I’ve found that they’re the ones whose boards stayed engaged by setting clear expectations, holding honest conversations and asking hard questions when the path forward wasn’t obvious.
Hiring well is the beginning. What happens in year two determines whether that hire actually mattered.