• Nonprofit Learning Lab

Do Ask Big Questions

Updated: Aug 1, 2019

This is a guest blog post and is posted with permission from Interplay Coaching.


If I have learned one thing by working with people in organizations, it’s that there’s much more telling than asking going on.


Technological advancements, competition, globalization, pressure for increased productivity and chasing dollars all contribute to heavy workloads and little free time. So when asked for help, leaders tend to give a quick answer and tell employees what to do. It’s just faster and easier.


Providing a quick answer is the right response when in the midst of a crisis that requires immediate action. But giving a quick answer doesn’t work best when trying to build the capabilities of staff. Employees and leaders get into a pattern of asking and telling. And while that can be frustrating for both, breaking away from that pattern is harder than one would think.


Helping leaders slow down their interactions enough to ask a question that gets the other person to think benefits the employee, the leader and the organization overall:

When a leader interrupts the ask/tell pattern to create a new ask/ask pattern, most employees will respond to these new expectations by coming to you less to solve problems because they feel empowered to do more themselves.Building the skills, capabilities and focus of those who report to you is both rewarding and part of your job.Asking questions helps make you a more effective boss by modeling better boundaries.Asking questions cultivates employee creativity — they may come up with better ideas than your own.Your work culture becomes more inquiry-driven and accountability-focused, building a team of people encouraged to ask questions and solve problems. Better clarity reigns, and some problems are resolved before they even begin.


But the trick is how to pivot from telling to asking good questions that provoke thinking in others.


Here are some rules I use:

Listen with curiosity. Calmly follow the thread of what someone is asking or saying without preconceived notions. Turn off the voice in your head that wants to jump in or interrupt. Instead listen with the intent of understanding even if the person frustrates you. When you stop thinking about you, the questions come.

Begin questions with “what,” “when” or “how,” and then ask about specific steps. “What three steps can you take to…?” “Help me understand” and “Can you clarify” are good openers as well.

Stay away from “why” questions like “Why did you…?” “Why” questions lead people into their stories, which can waste time or make people feel forced to justify an action rather than think differently. “Why” questions aren’t great for shifting someone to a more productive place.

No “yes or no” questions allowed, save one exception: If you want to hold up a mirror for someone to see how they appear then a “yes or no” question can be helpful. For instance, “Are you aware that when you say…, it makes others…?” or “Was it your intention to…?” Otherwise “yes”/“no” questions generally yield easy outs.

No “leading the witness” questions where you basically plant the answer you want to hear in your lead up to the question.

No “lecture lead-in” questions where you come across as moralizing or parental — it just shuts people down.

From my days as a geologist, I use the expression “water finds the weakest point” when talking about unproductive behavior patterns. Water flows to the specific spot where it can seep, often wreaking havoc. Our behavior patterns follow this concept: If person A continually solves problems or does extra work for person B, then person B has found person A’s weak point. Person A needs to interrupt this pattern by not taking on “water” or the work of person B. Interrupting the pattern is when positive change begins to happen.


Planning a conversational strategy ahead of time and role-playing lends practice, skill-development and confidence in handling challenging conversations. I urge my clients to develop a confidence-building set of “hip pocket” questions: questions they memorize and use at a moment’s notice, such as “What have you already done to…?” or “What is the size of this problem?” Finally, sharing with an employee in the moment what is and isn’t working is a good leadership practice.


When leadership is able to break the ask-tell cycle with their employees, staff either rise to the occasion or update their resumes. Both results can be desirable.


If you’re in a leadership position, think about the patterns you fall into when interacting with your team. Notice how often you go into telling mode instead of asking a question that changes people’s thinking, encouraging them to solve problems for themselves. Interrupt the pattern: Do ask; don’t tell.

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