Want to Be a Better Leader? Ask These 5 Questions

I’m lucky enough to get to work with business leaders and managers who want to connect with, support, and inspire everyone on their team. They understand the importance of honing how they communicate, listen, empathize, and give feedback because they know these “soft” skills improve everything morale and collaboration to productivity and retention across the whole organization.

If the idea of “brightening” your management style feels daunting, I’ve got a secret to share. You can fast-track your success by incorporating five simple questions into your regularly scheduled check-ins and conversations with the hardworking folks on your team.

Here are five questions every leader should ask—starting today.

Will you tell me more?

Showing genuine interest in what other people think or feel creates a shortcut to connection, compassion, and empathy. An inquiry-based conversation switches up the all-too-familiar dynamic of two people “talking” by simply waiting for their turn to speak. Instead of matching or one-upping what the other person shares, probe further based on what you actually hear.

Integrating “bright” listening into your conversation with coworkers doesn’t just reflect your personal or professional values. It also reflects—and cements—the company’s broader commitment to putting human beings first.

Check out this post about the three different “settings” for listening: dim, ambient, and bright. (Can you guess which one I recommend?!)

Will you help me understand?

This question is a sure-fire way to stop small conflicts or disagreements from becoming big ones. Asking it means no one has to guess why a colleague speaks or acts in a certain way. Perhaps most importantly, it stops us from making assumptions about someone else’s motivations or intentions (you know what happens when we ASS-U-ME things, right?). The more information we gather—straight from the source, of course—the more able we’re to quickly and smoothly achieve mutual understanding.

In this post, I talk about a time when asking, “Will you help me understand?” allowed me to get an important friendship back on track.

Will you …?

Okay, this is just part of a question. The callout here is to stop asking, “Can you finish the report by Friday?” and instead to ask, “Will you please finish the report by Friday?” The former often leads to “squishy” responses like, “I hope so” or “I’ll get back to you about this.” The latter approach—"Will you”—is far more likely to garner a clear, deadline-driven response and elicit a strong sense of accountability from both parties. When you’re direct about what you need to be delivered and when, you’re more likely to get a clear, no-nonsense response.

If you struggle with making direct asks, this post offers four tips to help you “put on your big-girl pants” as a leader … and it applies to putting on “big-boy pants,” too.

May I share something I’ve noticed?

It seems like every day there’s new research highlighting how regular feedback makes employees feel valued and recognized. I love this question because it’s a gentle way to start a feedback-based conversation. Whether you’re offering constructive criticism or straight-up praise, these simple words carve out space for you to speak honestly while also respecting personal and professional boundaries.

Read this post to find out why showing appreciation and gratitude is a game-changer at work—and in life.

How can I support you?

This may be the most important question a manager can ask (yet, sadly, I rarely hear it come up). Each one of us has our own preferences around communication, support, and recognition (here’s a very quiet shout-out to all the introverts out there). When business leaders take the time to ask about an employee’s values and establish shared agreements based on that information, everyone has a chance to feel seen, heard, and appreciated.

Read this post to find out why I encourage employees at every level to create an “Operations Manual” so colleagues understand what makes you tick (and what ticks you off!).

Managers and leaders, I invite you to start incorporating these five simple questions into your ongoing conversations right away. As you consider this practical advice for being a better manager, you might also keep in mind that great leadership isn’t about knowing all the answers. Asking questions shows that you value communication, collaboration, and curiosity. That, in turn, creates a very bright culture where employees across the company can grow and thrive.

Need help creating a bright company culture? Get in touch.