Are You Asking Your Employees the Right Questions?

Last week’s blog post began an important discussion around the topic of communication. To me, it’s important to bring up the subject of communication from time to time because it’s one of the easiest leadership attributes to underestimate. However, it is without a doubt one of the most important aspects of leadership – if not the most important aspect.

I always come back to the idea of listening as a crucial communication skill because it’s the one leaders seem to have the most trouble with. Savvy leaders who understand the importance of communication are always looking for tips on how to be more effective communicators, or how to improve the way they convey information. But they don’t always seek guidance for enhancing their listening skills.

One way I’ve found to help leaders focus more on listening is to flip the script for a moment. It’s all about empathy – when leaders consider the person they are engaging with and are able to put themselves in their shoes, their ability to engage in active listening improves dramatically. And one of the best ways to empathize with another person is to ask good questions.

Are You Communicating on Autopilot?

One of the problems I encounter most often when working with leaders is a tendency to become robotic while engaged in communication. For some reason, people sometimes lose their humanness and sense of self when they are engaging in conversations with their people. Essentially, they dehumanize themselves, which also dehumanizes the people with whom they are interacting. Words are spoken and exchanged, and information is passed from one party to another and yet no real connection has been made, and no one comes away from the conversation with any feelings of purpose and meaning.

This tendency to go on autopilot hurts leaders and causes engagement levels to plummet. People begin to dread interactions with their managers and other leaders instead of relishing the opportunity to express themselves. And when leaders become conversational automatons, they deny themselves the chance to learn what their people really think and how they truly feel.

Asking questions and soliciting feedback from your people is also critically important. However, when you fail to bring your human kindness and empathy into the conversation, it creates distance where there should be a connection. This impersonal nature of communication only serves to create barriers between leaders and their people, making it highly unlikely that employees will speak up, share their ideas and express themselves with courageous vulnerability.

So, before you make any attempts to improve the quality of the questions you ask your employees, I think it’s important to first work on your ability to be present, open and human in your interactions. I encourage you to let your guard down and connect on a person-to-person level. Then, when you ask questions, you can be sure you’re getting authentic responses and feedback.

Five Ways to Improve Your Ability to Ask Questions

If you are willing to have real, vulnerable conversations with your people, you will notice that they will be much more willing to share honest feedback with you. The key is to remain human and retain your empathy while still inhabiting your role as a leader within your organization and for some this can be a challenging balance.

To help you get into the ideal conversational groove here are five tips to help you ensure that you are always asking the right questions of your people.

#1 – Ask What People Need (And Give it To Them)

Most people want to excel in their respective roles, and they want their leaders to support them in doing so. One of the best ways to ensure this type of engagement is to ask your people what they need to do their jobs. Do they have the right tools? Are they getting the proper support from you as their leader? What environmental or cultural factors may be standing in the way? Asking these types of questions shows your people that you are there for them and that you are invested in their success. Just make sure that when you ask people about what they need, you are willing and able to give it to them (or have valid explanations for why you cannot).

#2 – Always Seek Clarity

Employees perform more productively and enthusiastically when they are confident in their roles. But sometimes leaders and their people have different ideas about what those roles should be. As you engage with your people, be sure to ask them about how they view their roles within the organization. What do they find meaningful about their work? How does the work fit within their larger worldview? The answers you hear will reveal that your people are either in tune with your organization’s values, or they may reveal areas where work needs to be done in terms of how people approach their jobs. Don’t work off assumptions; rather, ask people for clarity.

#3 – Follow Up

When a member of your team speaks up with an issue in a meeting or otherwise expresses concern, it’s important to address them directly, and in the moment. It is even more important to follow up with them after the fact. Do they feel that their concern was addressed appropriately? Do they feel like they were heard? Remember that it takes real vulnerability to speak up, so thank your people for expressing themselves, then honor those perspectives by following up with good questions.

#4 – Winning Isn’t the Only Thing…

...But it’s a lot of fun to talk about! One of the most effective ways to encourage employees to open up is to ask them about their wins. What are they feeling most proud of and why? What challenges have they overcome? What skills did they improve? What problems did they solve? Ask your people about their wins and you’re sure to hear some inspiring responses that can enlighten you about them and your organization.

#5 – Lighten the Load

The best leaders have a knack for releasing the pressure of work when it threatens to harm productivity or engagement. Sometimes the best questions to ask are those that have nothing to do with work or the organization’s mission. This goes back to my original advice above – remember to be human as you interact with your employees. Ask them about life outside the office. Inquire about family life, hobbies or any shared interests you have. Sometimes work causes us to lose perspective on the reasons why we get up and do it every day. Ultimately, going to work is about fulfilling a deeper purpose and goals. Show your people that you understand them as human beings first. Have fun. Show curiosity. Lighten their load by shifting the perspective, and if only for a moment doing this can drive engagement considerably.

Any Questions?

Asking the right questions – in the right way – is a great way for leaders to learn more about their people, enhance engagement and build high-quality organizational culture. Unfortunately, leaders don’t always know how to flip the conversational switch if they have become accustomed to operating in a more traditional, “command-and-control” model. Or they may simply not know how to open up and ask the appropriate questions of their people.

Do you have questions on what it takes to improve the flow of communication within your organization? Do you wonder what you can do to improve your ability to engage with your people? Are you unsure as to how you can improve your listening skills?

I’d love to hear from you, so please leave a comment below or email me directly at Let’s keep this conversation going!

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