The Essentials: Asking Purposeful Questions

This episode marks the end of a show that’s meant so much to us. Amy Bernstein and Amy Gallo say goodbye, answer two last Ask the Amys questions, and reminisce with founding producer Amanda Kersey. HBR’s Maureen Hoch, who came up with the original idea for the podcast, joins to share how it all began.

What if your boss turns against you the minute you ask for a promotion? Or you struggle with strategic thinking and keep getting feedback that you’re “too in the weeds”? Or the person dragging down your team is doing just enough to stay out of trouble? The Amys give advice for dealing with sabotage, shifting how you're seen, and setting expectations with difficult colleagues.

Many of us have internal beliefs—I need it done now, I know I’m right, I need to be involved—that feel like truth but actually hold us back as leaders. Executive coach Muriel Wilkins calls these counterproductive beliefs “hidden blockers,” and she talks the Amys through the process of identifying theirs and then reframing them. They also look at how blockers show up in team and organizational behavior, like when lack of trust results in too many meetings, and discuss how leaders can shift culture by first examining and adjusting their own assumptions.

Have you ever realized, mid-project, that you and your boss weren’t aligned on what success looked like or how to get there? Executive coach Melody Wilding explains why getting clear on goals and understanding each other’s working styles is essential, even when you’re already in a leadership role. They share advice on how to start these conversations in a way that feels natural and constructive, break down common style mismatches, and offer guidance for adapting without losing your authenticity.

When our colleague Kevin Evers wrote There’s Nothing Like This: The Strategic Genius of Taylor Swift, we knew we had to talk about it. For so many women, she’s a role model—personally and professionally. Four HBR Swifties who read the book highlight how her instincts and decisions offer lessons in leadership, strategy, and staying power.

Self-disclosure at work can build trust and connection, but it also comes with risks. In one of our earliest episodes, the late Columbia professor Katherine Phillips explained how sharing personal experiences helps diverse teams connect. We revisit that 2018 conversation and talk with her longtime collaborators, Tracy Dumas and Nancy Rothbard, who explain how expectations around self-disclosure have shifted, especially with the rise of remote work, social media, and political polarization. Plus, the Amys reflect on what they’ve learned about when, why, and how to open up at work.

Young women are entering the workforce full of potential but without some of the interpersonal skills they need to succeed and advance. That’s not just their problem; it’s ours too. In this live conversation from SXSW EDU, Amy Gallo talks with Neda Norouzi, an architecture professor at the University of Texas at San Antonio, and Aimee Laun, director of the Career Connections Center at Texas Woman’s University, about the gap between what colleges teach and what workplaces expect—and the critical role mentors, managers, professors, and parents can play in bridging it.

Imagine having a direct report who sobs every time you give them feedback. Or leading a team of people who’ve told your boss they don’t trust you. Or managing people for the first time—43 of them—with no training or guidance. The Amys offer advice for getting through these real situations from listeners–ot just advice, but actual language for asserting your needs, earning trust, setting boundaries, and holding your ground even when emotions run high.

Purposeful questions do more than clarify details—they reveal how you think and demonstrate leadership potential. Amy Gallo talks with a program manager looking to strengthen her executive presence and question-asking skills. Harvard Business School professor Alison Wood Brooks joins them to offer research-backed guidance on eliciting useful responses, building credibility through questions, and adapting to different conversational settings.

What do you do when a formerly supportive boss turns against you? Amy G advises a project manager who still believes in her team, just not the person leading it. Learn tactics for managing up, protecting your reputation, and preserving your sanity.