Helping young leaders ask a better question

by Kristin Miller | Director of Resident Development

As the Director of Resident Development, my team and I spend most of the day coaching leaders who have Gen Z working for them. We coach the coaches, so to speak. This week, a leader relayed a story of their resident asking, “What would you do?” The leader told her what she’d do, and she went and did that.

It was a disaster.

WHAT WOULD
YOU DO?
VS
WHAT WOULD YOU DO
IF YOU WERE ME?

She acted as if she were a 45-year-old veteran leader, making a decision that overstepped her role, rather than responding with the humility and discernment expected of a young leader who had only been on the team for a few months.

Always remember: giving a great answer to the wrong question might not be the best plan of action. It’s great to receive questions, but sometimes we even have to help them ask the right question.

Young leaders often seek guidance by asking, “What would you do?” On the surface, it’s a solid question, one that taps into the wisdom of those with more experience. Yet, there’s a better question that takes the conversation deeper and yields more personalized, actionable advice: “What would you do if you were me?” This subtle shift creates a bridge between raw advice and real-world application. Let’s explore why this reframing matters and how it can transform leadership development and decision-making.

At its core, “What would you do?” assumes the leader being asked can simply transfer their strategy or decision to someone else’s situation. But contexts differ: their unique skills, life experiences, and pressures shape their choices. For instance, a seasoned leader with years of ministry experience may answer based on resources, networks, and confidence built over time—elements a young leader might not yet possess.

Kristin Miller/Director of Resident Development

By asking, “What would you do if you were me?” young leaders reframe the discussion to consider their specific circumstances, abilities, and limitations. This approach invites coaching that aligns with who they are today while still aspiring to who they can become. The coach might instead consider the residents’ limited budget, smaller network, or early-stage confidence in their abilities. The response becomes a step-by-step plan that meets them where they are.

Leadership development is as much about context as it is about strategy. At Leadership Pathway, we emphasize the importance of tailored guidance. As described in our coaching frameworks, developmental conversations should account for a leader’s challenges and growth stage. This means equipping them with answers and the ability to discern and adapt those answers in their unique context.

Here’s why this personalization matters:

1. Empathy in Leadership: When a coach answers, “If I were you…” they are stepping into the leader’s shoes, considering their skill set, level of experience, and immediate challenges. This builds trust and empathy in the relationship.

2. Tailored Growth: Generic advice often misses the mark. Specific, contextual advice helps leaders take the next step in their growth journey while staying aligned with their current capacity and resources.

3. Critical Thinking: This reframing encourages the resident to weigh how a mentor’s advice fits into their reality, fostering better decision-making skills. Always remember, the younger the leader the more prescriptive our coaching must be. “You do and I’ll watch.”

For coaches and residents, asking better questions starts with a mindset shift:

COACHES: Be willing to pause and imagine the mentee’s reality. Avoid offering cookie-cutter advice and instead ask clarifying questions: “What’s your current challenge? What’s your capacity right now?”

RESIDENTS: Don’t hesitate to share your limitations and context when seeking guidance. For example, instead of saying, “How would you lead this meeting?” try, “Given my experience and the dynamics of this group, how would you lead this meeting if you were in my role?”

So, if you’re the one being asked for advice, don’t just fire off what worked for you. Take a second. Ask yourself, “What’s their reality?” Do they have the same resources? The same experience? If not, adjust your response. Instead of saying, “Here’s what I’d do,” say, “If I were in your shoes, here’s how I’d approach it.”

The goal of great coaching is to bridge the gap between where the resident is now and where they want to be. And let’s be real—coaching isn’t about creating clones of yourself. It’s about helping someone become the best version of themselves.

Do you want to learn how to coach the next Generation? Join us at our next Masterclass. It’s a two day intensive on this topic.