Have you ever had an experience where you were the last to learn something vital in a situation that was important to you—and did you further discover that there were people who could have clued you in, but didn’t? I’ve seen this happen to people I’ve coached more times than I can count—but was still completely gobsmacked when it happened to me.
Teach For America is a nationwide nonprofit that recruits and trains recent college graduates to teach in low‑income schools while building a movement of leaders who work for educational equity. After nearly a decade in management consulting, I was the organization’s chief learning officer, charged with helping them scale and improve the training and performance of teachers across the country. My tenure there had a regrettably rocky start.
Less than a year into the job, I received an urgent phone call. Jade, a key leader on my team, was calling to inform me that our Northwest Summer Institute—one of our five summer training sites—was facing major challenges, just a few months before it was scheduled to begin. These institutes provided our newly minted college graduates with much of the training they’d get before they were face‑to‑face with students. In other words, if we couldn’t fix things, a fifth of our teachers would not be ready to teach in the fall.
Each institute had a team in place whose full‑time job was to make sure that every detail was lined up perfectly during the twelve months before each summer institute began. These teams were responsible for securing classroom and dormitory facilities at a host university, partnering with local school systems for summer school teaching practices, and hiring and training a hundred local staff tasked with everything from instruction and coaching to serving meals to transporting our teachers to and from the various activities. And who was ultimately in charge of these teams? Me. I’d been in contact with them and their leaders consistently throughout the year and believed I had done everything possible to ensure their success.
And yet, here was Jade, calling to tell me that major elements of one entire summer institute were not in place. The classrooms at the host university were not available at the times when we were scheduled to teach in them. Local schools that had agreed to let our teachers train within their summer school program had decided at the last minute not to hold summer school, and the schools that were holding it were now using a totally different curriculum than we’d expected. Key members of the summer staff responsible for supervising and instructing our new teachers did not have the experience or skill needed to carry out the high caliber of training we required, and some of them had already quit.
My pulse raced as I hung up the phone. I stared down at the screen in my hands in stunned silence, a new reality slowly sinking in. I pictured five hundred new teachers at the Northwest Institute rising up in protest. More importantly, I pictured five hundred classrooms in the fall without the well‑trained teachers that their students deserved.
After my moment of panic, I became mystified as to why all year long, I’d remained so unaware of the problems brewing, despite the many conversations I’d had with my team all along the way. According to what Jade uncovered, things had been unraveling for months. Why was I just learning about it now, when it might be too late to turn the ship around?
Thankfully, Jade stepped up in a heroic way. She relocated across the country to the local training site and worked intensively with the team on the ground, who sprinted day and night to rectify every problem in the weeks before the program began. In the end, the Northwest Institute ran very smoothly, and thankfully, the teachers were extremely well prepared. But had Jade not been able to perform this minor miracle, redoing months of planning in a few short weeks, the program would have suffered.
How could I have been so blindsided? All along the way, I had checked in on how things were going and what help the team needed, and I consistently left with the impression that, despite some minor hiccups, things were generally on track. It turns out, the team was scrambling to fix things as best they could, but they didn’t let me in on the full extent of the challenges, nor did they request my help. Bottom line, I was unaware of what multiple people on the team knew about how bad things were but never told me. And while I’m sure I had asked a number of questions during our meetings, the approach I’d taken clearly hadn’t encouraged my colleagues to feel safe giving me “real talk” about the challenging but absolutely critical information I needed to know before the point of crisis. Up until that moment, I had believed that we had strong working relationships where we could speak openly and directly. But clearly there was something that stopped people from speaking up in a moment when it really mattered.
What’s worse, I started to wonder: If they didn’t share information this time, despite the stakes, what other thoughts, beliefs, and feelings might they, or others for that matter, be withholding?
The left hand column
Earlier in my career, I learned a name for this painful and pervasive pattern of withholding. It was during my first job out of college, at Monitor Group. As a consulting firm, Monitor’s success hinged on our ability to find information and insights that produced the best solutions for our client organizations. To develop quality recommendations, information of all kinds needed to flow continuously throughout the organization, to our clients, and from our clients back to us.
Because of this, Monitor invested heavily in understanding what might block people’s ability to learn from one another and what they could do about it. Professor Chris Argyris provided the driving intellectual leadership required to set the effort into motion. With a joint appointment to Harvard’s Business School and Graduate School of Education, Chris’s life mission was to understand and overcome the obstacles to people learning in organizations.
Chris’s work with leaders of companies all around the world often started the same way, with the two-column case. He would ask someone to draw a vertical line down the middle of a blank sheet of paper. The right‑hand column would contain lines from the actual dialogue of a recent challenging interaction, as best as the case writer could recall. In the left‑hand column, the case writer would write the unspoken thoughts and feelings they experienced throughout the interaction.
Over time, I had the opportunity to work with consultants and leaders around the world on dissecting their most challenging interactions using this format. Time and again, I saw just how much people held back sharing the very information that would have been most helpful for the other person to know. Their left hand columns were goldmines of important insight, feelings, and ideas, but the people around them never got access to this priceless information—because they had never been taught how.
This realization ultimately led me to create The Ask Approach—a 5-step, research-backed and practice-tested method for discovering what the people around you really think, feel, and know. It takes some practice to master the steps, but I’ve seen firsthand that once people learn to apply this approach, the results are powerful. Leaders I’ve worked with described the immense relief of finally breaking out of long-standing patterns, the lightbulb moment of discovering the key insight that had kept them in the dark without even realizing it. I’ve seen people experience entirely new levels of learning, growth, and connection. I’ve watched relationships shift from sources of conflict and anxiety to mutual understanding and collaboration.
The best news is that with the tools of The Ask Approach, anyone—including you—can learn to do this, too.
Excerpted and adapted with permission from Ask: Tap Into the Hidden Wisdom of People Around You for Unexpected Breakthroughs In Leadership and Life by Jeff Wetzler. Copyright © 2024. Available from Hachette Go, an imprint of Hachette Book Group, Inc.
Jeff Wetzler is co-CEO of Transcend, a nationally recognized innovation organization, and an expert in learning and human potential. He is the author of Ask: Tap Into the Wisdom of People Around You For Unexpected Breakthroughs in Leadership and Life (Hachette Go, 2024).