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Questions Every Leader Need to Be Asking

Jun 24, 2019Business Development, Coaching0 comments

“Everyone talks about building a relationship with your customer. I think you build one with your employee first.”  Angela Ahrendts, Senior Vice President of Apple

Leadership is seated in relationships based on inclusion, trust, and loyalty, and then grows with inspiration and vision. While most leaders can easily articulate their vision and inspire their people, they fail to accomplish their goals when they neglect to form genuine relationships with their team. 

According to Simon Sinek, the author of Start With Why, one of the greatest components of any company’s success is its employee satisfaction. But to provide what your employees actually want and need, you must encourage dialogue across your company. Rather than telling your employees their role, needs, and feelings, ask them. Here are some of the questions you need to ask to build relationships with your people and accomplish your vision:   

Create Inclusion

The best leaders know they don’t need to provide all the answers. Instead, they ask more questions than they have solutions to and trust what their people produce. Including your team in the conversation demonstrates genuine concern for their being and empowers their individual perspectives.

For leaders, taking time to speak regularly with every one of your employees is critical because face-to-face conversations, not emails or memos, develop the relationships that allow your team to thrive. 

But what you ask doesn’t need to and shouldn’t always be tied to work. Instead, ask questions that demonstrate concern for your people, such as “what is the best thing that happened to you this week, either inside or outside of work?” This question shows authentic interest in the person as both a contribution to the project and a human being. At a larger scale, this question establishes a sense of belonging and worth throughout the organization by recognizing each individual’s experience.

Open A Positive Conversation

Establish transparent communication throughout your company by inviting further discussion through open-ended questions. Open-ended questions are powerful because they provide both participants an opportunity to learn about the other and gain deeper insights into their shared project.

However, open-ended questions collapse if your employees feel their answers must align with how you want them to response. Without exception, you should always avoid leading questions because inquiries should be made to learn, not to encourage agreement. 

For example, asking your employees, “how can I improve as a leader,” cannot be answered with a simple ‘yes’ or ‘no.’ It requires further thought and explanation. This question is successful because it does not assume that you are above improvement, and instead provides space for both positive and constructive feedback. 

Similarly, the question “what is going well” allows leaders to open a conversation positively while gaining insights on what is working. The natural follow-up questions are “what is not going well” and “what could we be doing better?” Beyond discerning concern for your individuals and your team, these questions demonstrate an open-mind and flexibility to ensure continued improvement.  However, they do not deny your employees the opportunity to provide unfavorable feedback.

Avoid Assumptions

Questions suggest vulnerability and admit that you don’t have all of the answers. But they also show courage and allow you to become more effective in your leadership position. And asking the hard questions provides you invaluable intel on where you can drive positive change and actually achieve your vision. 

Your team often know more about a project’s details than you do, and any assumptions you make about the project are guesses, which can ultimately hinder progress. Rather than taking your best guess, ask, “what do I need to know” and “what assumptions are we making?” These questions demonstrate that your intentions are not to compel results, but to consider the advice provided by the experts on your team. Deferring proves you value your people’s input, reduces the risk of assumptions, and reveals how the workflow or product can still be improved. 

 A natural follow up question is, “how I support you throughout this project?” But if you suggest you will help, you must then follow through. These questions, in particular, foster trust and loyalty because they demonstrate the importance of what your team says as you improve working conditions, sometimes at a cost to you.

Hold Yourself Accountable

According to Jorge Paulo Lemann, who Forbes deems as the “conqueror of America,” your company’s greatest asset will always be your people. As a leader, you take on the responsibility to nurture the careers and growth of this asset, including yourself. Just as you catalyze your team’s growth by asking questions, you should be asking yourself tougher questions to generate growth each day. These questions do not reflect self-doubt, but self-confidence and allow you to improve how you lead. To assess your own contributions to your team, ask yourself: 

How can I do better?

By sparking a bold and candid self-assessment of your own work, this question makes you reflect on what you do well and where your self-improvements should focus. There are no limitations to your answers, but it presents an opportunity to examine how effective specific interactions and resolutions were. Being honest is critical for how useful this question is because dishonest answers will disadvantage yourself first and foremost. 

Is this important right now?

This question looks to not only make more efficient use of your own time but respects the time and effort of your employees. This type of consideration is infectious. It shows how you empathize with and support your employees. And it exemplifies how you expect your team to interact with set goals when there is still work to be done (which there always is). 

How might I better use my time?

A similar question is, “how may I better serve my team?” Where the original question considers your personal efficiency and the example you set, the revised version regards the immediate needs of your team. In both cases, if you spend too much time concentrating on things that do not promote the success of your team, the project, or the overall company, why should your people? Your time, energy, and resources will always be best spent innovating more productive ways to support your team.

Am I helping or hurting my people?

As your greatest asset, how you impact your people, as well as your team, must remain at the forefront of each decision. However, accurate assessment requires that you have established strong relationships with your people because otherwise, how could you determine whether you are helping or hurting their success? More times than not, this question will reveal how deep your relationships are with your people, and consequently, how well you are achieving your vision.

Asking questions is the beginning of gaining insight and fostering relationships with your employees. But thoughtfully listening to and considering their answers actually helps you to become a better leader. Ian Hutchinson, the author of People Glue, advises that “your number one customer is your people. Look after your employees first and your customers last.” And while this may seem counterintuitive, your employees are the face that your customers see, making it imperative to your vision and company’s success that your employees are satisfied.


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