The language of leaders is questions—not monologues, lectures, or the classic “quick thought” that somehow lasts 27 minutes. Asking the right questions can spark curiosity, unlock creative thinking, and create those “aha!” moments that keep conversations fresh and useful.
When conversations become a lively exchange of ideas, people stay energized and problem-solving starts to feel like a team sport—ideally one with fewer whistles, fewer bruises, and no one hiding on the bench.
By asking instead of telling, leaders work with the way people naturally process information. The result is usually more engagement, stronger ownership, and fewer blank stares that say, “I’m nodding, but I have no idea what you want me to do.”
Here are five short questions that do the job remarkably well—no leadership thesaurus required.
How so?
Whenever someone’s meaning is unclear—or they make a sweeping statement with all the detail of a weather forecast that says “conditions may vary”—use this two-word question to learn more.
Example: In a 1:1, someone says, “This project is going pretty well.” Rather than accepting “pretty well” as a fully audited performance metric, ask, “How so?” Their answer can reveal exactly what is working, why it is working, and what you can repeat in the future.
“How so?” often opens the door to a much richer conversation and a clearer understanding of what is happening, why it matters, and how the organization benefits. Not bad for two tiny words.
What's an example of this?
Leaders often find themselves discussing something that is not working. Shocking, I know. When that happens, this question helps everyone understand the problem and move toward a solution faster.
Example: An employee says, “I’m having a hard time getting cooperation from the marketing team.” Asking for a specific example moves the conversation from a foggy complaint to something you can actually examine—preferably without convening a task force.
Sometimes the example does not match the original description at all. That is useful because it lets you calibrate on the real issue before charging heroically toward the wrong solution.
How will you know you’re on the right track?
Leaders regularly help people improve in areas that are not easy to measure. “Get better at communication” is admirable, but it is about as measurable as “be more awesome.” Defining milestones in advance makes progress easier to recognize.
Example: Instead of simply asking someone to “improve communication,” help them identify a visible sign of progress: “You’ll know you’re on the right track when team members consistently meet Friday deliverables because you’ve clearly explained the expectations.” Now everyone knows what success looks like—and Friday gets a little less dramatic.
Almost anything becomes measurable when you identify the milestones in advance. Even “better communication” can graduate from a hopeful slogan to observable progress.
What’s the next step?
Some of the best learning begins with simply starting—a revolutionary concept for anyone who has ever spent three meetings planning the meeting before the kickoff meeting. This question helps people identify where to begin and what will get them moving.
Example: After an employee walks you through a complex problem, end with, “What’s the next step?” The answer clarifies what they will do, keeps the work moving, and reinforces that they own the situation—not you, your calendar, or the emergency snack drawer.
Asking someone to name the next step makes complicated work feel more manageable. Mountains are climbed one step at a time; projects are completed one sensibly assigned action at a time.
What’s one thing you’d suggest?
Leaders need feedback, yet many discover that “Do you have any feedback for me?” produces silence so complete you can hear the office printer reconsidering its life choices. Instead of asking someone to judge your past performance, ask for one suggestion that could improve the future.
Example: Employees may hesitate to answer a broad feedback question because they are busy deciding whether honesty is safe, wise, or career-enhancing. Asking for one future-focused suggestion lowers the stakes and makes a useful response much easier.
Do not ask for a sweeping verdict on the past. Ask for one practical idea that can make the future better. It is simpler, safer, and far less likely to trigger the facial expression people reserve for surprise performance reviews.
Whether you are asking for a next step, a concrete example, or one fresh suggestion, remember: progress is often just a good question away. Use these simple prompts and watch conversations become more engaging, problems become more manageable, and the path forward become clearer—with fewer speeches, fewer assumptions, and, if all goes well, fewer meetings about why there are so many meetings.
Peter Mclees, Leadership Coach, Trainer and Performance Consultant
SMART DEVELOPMENT
Take the Next Step...
Interested
in learning how to develop your organization's leadership capability,
culture, and employee engagement ? We begin with a collaborative
discovery process identifying your unique needs and business issues. To
request an interview with Peter Mclees please
contact: Email: petercmclees@gmail.com or Mobile:323-854-1713
Smart Development has an exceptional track record helping service providers, ports, sales teams, restaurants, stores, distribution centers, food production facilities, wealth management services, real estate services, nonprofits, government agencies and other businesses create a strong culture, leadership bench strength, coaching skills and the teamwork necessary for growth.Having worked with several companies throughout their growth cycle, we have valuable insights and strategies that would help any late stage startup, small or medium sized company achieve sustained growth and prosperity.
