An employee says they are overwhelmed. You move a deadline, redistribute a few tasks, and get back to work. Problem solved.

Or was it?

What if the real issue was unclear expectations, constantly shifting priorities, or missing information from another department? A quick answer might ease the immediate pressure while leaving the underlying problem untouched.

That scenario anchored the Montgomery County Chamber of Commerce’s September 9th Lunch & Learn on Leadership & Team Development. In her presentation, “Ask Better, Listen Better and Lead Better,” coach and speaker Janelle Anderson challenged a familiar leadership habit: the instinct to fix things before fully understanding them.

Her invitation was simple: “Ask one more question. Don’t solve too soon.”

When helping becomes a habit of answering

Being the person with answers can feel like proof that we are doing our jobs well. People bring us problems because they trust our experience. We want to help, and the next email, meeting, or deadline is already waiting.

Janelle described this as the leadership reflex: identify a problem, offer advice, and move on.

The challenge is that speed can hide assumptions. Even a question can carry a predetermined answer. Asking someone whether they have considered your preferred solution may guide them toward your thinking without revealing theirs.

A useful self-check emerged from the discussion: Are we trying to understand the other person, or trying to make sure they understand us?

That distinction matters in conversations with employees, colleagues, and customers alike.

Three questions to bring into your next conversation

Drawing on Deb Calvert’s DISCOVER Questions framework, Janelle focused on three purposes for better questions: understanding, prioritizing, and empowering.

Understand what is happening. Ask, “Where are you getting stuck?” or “What am I missing?” A missed deadline might reflect a training gap or an obstacle the employee cannot resolve alone. The answer gives a leader something more useful than an assumption.

Identify what matters most. Ask, “What would make the biggest difference?” A customer discussing price may be seeking confidence in the outcome. An employee requesting a different schedule may value flexibility. Understanding the priority helps clarify what a useful solution needs to accomplish.

Invite ownership of the next step. Ask, “What options do you see?” or “What’s one step you could take?” These questions give people practice thinking through a challenge and contributing to its resolution.

The framework offers a starting point. Janelle emphasized that the next question should grow from what the person actually says. Sometimes that means returning to understanding because a new part of the problem has surfaced.

The room discovered how difficult listening can be

Participants practiced in pairs, taking turns as a leader and an overwhelmed team member. The exercise included one rule: no advice.

The debrief exposed how quickly familiar habits return. One participant noticed a question turning into suggested answers almost immediately. Another observed that silence created an urge to keep talking. A participant also described looping back to an earlier question after discovering another layer of the problem.

Those observations made the lesson tangible. Asking a thoughtful question is only part of the skill. Leaving enough room for an answer takes practice, too.

The discussion also surfaced a harder challenge: familiarity with a coworker can lead us to assume we already know what their concern will be. Janelle encouraged approaching that conversation with renewed curiosity rather than letting past patterns determine what we hear.

Listening still leaves room for leadership

Attendees raised practical questions: What happens when someone says, “I don’t know”? What if their proposed solution will not work?

Janelle suggested allowing time to process, offering the option to write down thoughts, or returning to the conversation later. When a proposed solution raises concerns, questions about risks and consequences can help the person examine it more fully.

She also made clear that leaders may still need to provide information, set limits, or redirect a decision. Listening does not require accepting every suggestion. It creates an opportunity for people to be heard and develop their judgment before a decision is made.

For our Chamber, that connection between learning and daily practice is the value of conversations like this. Participants brought real workplace challenges into the room and left with questions they could use in their next conversation.

Thank you to BAE Systems for the grant that made this Lunch & Learn series possible.

What question has helped you uncover the real issue—or helped someone on your team find their own next step?