Better Questions. Better Leadership.

“Hey Ryan, how’s it going this week?”

“How is everything today?”

“Have you sent the proposal yet?”

“How did it go?”

“How is everyone doing this morning?”

“Do you need anything else from me?”

Managers have to ask a lot of questions. There are projects to track, work to monitor, and employees to connect with. Most of these questions have to do with staying informed. As a new manager once told me, “I have so much to keep track of, and so few answers.”

These questions serve a critical purpose in the role of a manager, but they don’t necessarily help employees solve problems, take ownership, or think differently. When we ask stronger questions, we create opportunities for better thinking, development, and performance.

Allow me to present the distinction in this manner:

• Transactional questions help us gather information, check status, and move work forward.
• Transformational questions help people think differently, build capability, and take ownership.

Transactional questions help you, the manager, understand what’s happening. Transformational questions help the employee understand what to do next.

Let’s be clear, managers need both types of questions. The trick is not getting so caught up in status checks that we do not leave room for coaching and teaching.

With that in mind, let’s take a look at the transformational questions that can supercharge your next 1:1 or team meeting.

Coaching Questions

Most managers are promoted into leadership because of their technical knowledge, and as a result they tend to be more comfortable solving problems rather than coaching. Solving problems yourself can be powerful in the short run, but it’s a fast track to burnout and overwhelm if it becomes your default approach. (Remember Supermanager?) 

The next time you find yourself tempted to offer advice or instruction, try these:

• “What have you tried so far?”
• “What options have you considered?”
• “Which options excite you? Which make you nervous?”
• “What do you think the problem is?”
• “If you could do anything, what would you do?”

In these circumstances, transactional leadership feels helpful and supportive. Transformational questions, however, build capability and confidence over the long run. Don’t rob someone of a problem they could learn to solve.

Development Questions

This category might be my absolute favorite to explore with leadership teams. These are critical conversations that don’t take place nearly often enough. In my experience, these discussions get relegated to performance reviews or skipped entirely because leaders are afraid their direct reports will start looking for a new job. My take - If they’re not developing, do you really want them on your team? And if they’re looking for a new job, wouldn’t you prefer to know?

These questions can help you learn more about your employees’ goals, interests, and aspirations:

• “Which part of your role do you most enjoy?”
• “What do you want to get better at?”
• “What’s something you would like to do more of?”
• “Is there anything you want to try, but haven’t had the opportunity?”

Use these conversations to uncover potential stretch assignments, mentoring opportunities, and new responsibilities that serve both the employee’s development and the team’s needs.

At a past stop, one of my coworkers shared his love for video production. When the firm needed to ramp up marketing activities, he was tapped to lead creative marketing efforts, and he blossomed in the role. That capability would have remained unknown and untapped without development questions like these.

Today’s development conversations can offer answers to tomorrow’s questions.

Stay Interviews

Stay interviews are the proactive counterpart to exit interviews. While an exit interview asks a departing employee why they are leaving, a stay interview asks a current employee what keeps them engaged (and what might eventually cause them to leave).

Use these questions to determine what’s going well, and flag any issues that could create problems later on:

• “What do you enjoy most about working here?”
• “What keeps you in this role?”
• “What would make you consider leaving for another opportunity?”
• “What could I do differently as your manager to make your position even better?”
• “Is there anything you would like to do more or less of?”

These questions make for great discussions in 1:1 meetings, and while you don’t necessarily need to schedule a formal stay interview every quarter, I advise sharing a question or two with your employees ahead of the conversation.

Your best employees want to be supported, challenged, and developed. But that means different things to different people. These questions help you engage your A players and keep them growing in ways that they value most.

The Most Important Question

So far, this list has focused on questions you can ask others. Even more important, though, is a critical question you can ask yourself:

“What do they need from me right now?”

Great leadership is contextual. The best leaders don’t use the same approach with every employee or every situation. They evaluate what’s happening and determine what each person and situation needs.

Perhaps this employee is lost and needs direction. Maybe they need specific instructions to help them overcome a unique challenge. Or, they might just need someone to hear them out for a few minutes before they choose a course of action. This question helps us evaluate a situation, consider the employee’s perspective, and look for the right approach.

Ultimately, the goal isn’t to ask more questions. It’s to ask questions that help your people think, grow, and take ownership. Better questions will strengthen your relationships AND improve the outcomes of your leadership.