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The Power of Asking

In 2016 I landed my “dream job.” As the head principal of a building with 200 staff and 1,600 kids, I was asked to lead one of the largest high schools in Iowa.

At 34 years of age, I was the youngest-ever principal in this building. When I began, I heard words like “I’ve been teaching longer than you’ve been alive” and “I’m old enough to be your mom” from several employees.

Hearing this feedback made me feel good about my professional accomplishments. However, I also wanted to prove to staff that getting the job was no fluke.

To demonstrate my competence, I immediately made changes to our Building Leadership Team (BLT). Without asking for feedback, I told our teacher leaders we were making changes: who was on the team, the frequency of meetings, the topics of conversation, and our methods for communication.

“We did this in my previous school and it worked really well,” I explained to the BLT via email.

While I didn’t think these changes were a big deal, I quickly realized our leaders weren’t ready. Almost immediately, I heard grumblings that BLT members were unhappy.

When I asked my secretary what she thought the issues were, she provided some harsh feedback: “They don’t like that you didn't ask their opinion,” she shared. “You’re just telling them what to do.”

“Ask their opinion?” I rebutted. “I shouldn’t need to 'ask their opinion!' I know what I’m doing.”

This standoff between myself and the BLT lasted months. Despite the fact that I was creating tension with key building leaders, my pride couldn’t handle being wrong. “If I give in now, they won’t respect me in the future,” I worried.

While our team eventually accepted my ideas, the damage was already done. I senselessly created adversarial relationships with individuals – relationships that took months to recover.

In turns out I made this common rookie mistake: I was telling instead of asking.


“The best leaders are great listeners,” said James Kouzes and Barry Posner in The Leadership Challenge. “They listen carefully to what other people have to say and how they feel. They ask good questions, are open to ideas other than their own, and even lose arguments in support of the common good.”

It took more than ten years in administration to finally comprehend the importance of listening. But when I did, I noticed three significant changes.

First, I learned that listening improved employee engagement. When I started asking employees to share their opinions, they felt more valued. Not only did employees feel more committed to the work, asking questions created a feeling of mutual respect led to deeper relationships between myself and those individuals.

Don't forget food service employees when it comes to asking for input.

Second, I learned that listening helped my decision making. My younger self didn’t think it was necessary to ask employees for advice. Once I realized the shortsightedness of my thinking, I discovered that employees had a lot of great ideas. By asking staff to give feedback on a decision, they were more likely to support the outcome – whether they agreed with the decision or not.

Third, I learned that listening made my job easier. Early in my career, when staff came to me with concerns I immediately felt compelled to give them answers. However – once I started asking questions instead of giving answers – I noticed that employees were fully capable of solving answers on their own. This prevented me from assuming the burden of employee issues.

“But shouldn’t leaders assume the burden of employee issues?” you may be thinking. “Isn’t that ‘servant’ leadership?”

While getting involved in every employee issue sounds noble, in reality bosses simply do not have the bandwidth to assume this responsibility. Administrators who stubbornly insist that every employee issue runs through their office create a massive organizational bottleneck where employees wait days (if not weeks) to be told what to do.

Instead, administrators should help employees work though problems by asking questions and trusting employees to make their own decisions.


One of the most important parts of being a great listener is knowing which questions to ask. Below are five questions that not only generate productive conversations, but also strengthen relationships. While these questions are primarily used for 1:1 meetings with direct reports, they can be easily adapted to any employee conversation:

“What’s going on in your world?” While there are several ways to start a conversation, this prompt is effective for a couple reasons. First, this question ensures that the conversation is focused squarely on the employee. Second, the open-endedness of the inquiry gives subordinates complete control over where the conversation goes next.

“What’s keeping you up at night?” Did you know that nearly half of American employees lose sleep at night as a result of worrying about work? Not only does this question resonate with employees, it helps skip over surface level issues while focusing squarely on the topics that matter most to employees.

“What barriers are you experiencing?” Whether it be a personality conflict with a coworker, the need for additional training, a lack of financial resources, or a need for clearer expectations, asking employees to name specific barriers gives administrators the best opportunity to understand that individual's current reality.

“What are your next steps?” Administrators are notorious for jumping in and giving advice as opposed to asking questions for the purpose of earning trust and building capacity in employees to sort through their own issues. Oftentimes employees have solutions to their problems … they simply need to be trusted.

“What do you need from me?” While some leaders may be fearful that this question will result in an unreasonable request ... most employees are good about respecting their supervisor's time and will decline an offer for assistance. The beauty of this question is that both sides are clear about the leader's next steps.


Steve Jobs famously said, “It doesn’t make sense to hire smart people an tell them what to do; we hire smart people so they can tell us what to do.”

Don’t make my same rookie mistake:

Stop telling employees what to do.

Start asking employees what to do.


If you liked this article, you'll love my books Learning Curve and Turning Points.



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