Most leaders I work with are proud of their “no drama” cultures. Meetings run on time. People nod. Decisions get made without much friction. Disagreements get resolved offline, if at all. We tend to interpret that as success. I’d argue it’s often the opposite. When people stop speaking up, it’s rarely because they’re fully on […]
A senior director sits across from her boss in a development conversation. She has been told, again, that she needs to “work on her executive presence” if she wants to be considered for the next role. She nods, takes notes, and walks out with no clearer sense of what to do tomorrow than she had […]
A few weeks ago I sat in on a strategy session where a senior leader pulled up a polished AI-generated analysis of his competitive landscape. It was thorough. The frameworks were sound. The data points were current. Around the table, heads nodded. The conversation moved quickly toward implementation. Nobody asked whether the analysis had framed […]
A chief transformation officer had what she called her “cascade problem.” Every major transformation update followed the same path: she briefed the executive committee, the executive committee briefed their direct reports, the direct reports held team meetings, and by the time the message reached the people actually doing the work, it bore almost no resemblance […]
A division president last year described her situation with unusual clarity. “The board wants bold. My people want stable. And I’m supposed to deliver both without acknowledging the contradiction.” She wasn’t exaggerating. Her board had approved an aggressive digital transformation roadmap tied to a three-year value creation thesis. Meanwhile, her organization had just been through […]
A Fortune 500 company I worked with spent $4.2 million on leadership development in a single year. Custom programs. Top-tier facilitators. Off-site retreats with all the right frameworks. Eighteen months later, their employee engagement scores hadn’t moved. Exit interviews still cited the same complaints: unclear expectations, inconsistent feedback, leaders who avoided difficult conversations. The programs […]
A chief operating officer at a midmarket industrial company told me recently that her organization had deployed over forty AI-powered tools across the enterprise in the past eighteen months. Productivity dashboards, predictive maintenance models, automated customer service agents, AI-assisted procurement workflows. The technology worked. The results were promising. And yet, three separate business units had […]
A Fortune 500 company was eighteen months into a sweeping operating model transformation when the executive sponsor departed. The incoming leader, a well-regarded external hire with a strong transformation track record, did what every leadership playbook tells you to do: she made her mark fast. Within sixty days, the initiative had a new name, a […]
Jesse Jacoby
