7 Questions Every Leader Needs to Ask Their Direct Reports

It’s crucial for every successful leader to understand the motivations and drivers of their direct reports. The best leaders take the time to regularly check in with their team members and ask the right questions to gain valuable insights into how to support and motivate them.

As an executive leadership coach, I have helped my clients come up with seven of the most important questions that will create a positive and successful working environment with their direct reports. And here they are:

How can we invest in your future here? As an effective leader, it is important to understand your direct reports’ career goals and aspirations. By asking this question, you can gain insight into what they need to grow and advance within the company. This can help you create development plans and opportunities that align with their goals, and ensure that they feel invested in the company’s future.

What do you need from us to do your best work? Successful leaders understand that every direct report has different needs and preferences when it comes to how they work. By asking this question, you can gain insight into what support and resources your team members need to be successful in their roles. This can help you create a more supportive and effective working environment for everyone on your team.

What additional resources do you need? As an effective leader, it is important to understand the resources that your direct report needs to do their jobs effectively. By asking this question, you can gain insight into what resources are lacking and make changes to ensure that your team has the tools they need to be successful.

What are we currently not doing for you, that we should do? Successful leaders are always looking for ways to improve their teams. By asking this question, you can gain valuable insights into what changes your direct report would like to see in the company. This can help you identify areas for improvement and make positive changes that benefit the entire team.

What is the best part of your job? As an effective leader, it’s important to understand what your direct reports enjoy about their work.  By asking this question, you can gain insight into what aspects of their job they find most rewarding, and make changes to ensure that they continue to feel engaged and motivated in their role.

What part of your job would you eliminate? Successful leaders understand that not all aspects of a job are enjoyable or fulfilling. By asking this question, you can gain insight into what your direct report finds to be the least enjoyable or most tedious parts of their job. This can help you make changes to make their work more enjoyable and effective.

What is the one area where you think the company could improve? As an effective leader, it is important to continuously look for ways to improve your company. By asking this question, you can gain valuable insights from your team members on areas where they think the company could improve. This can help you identify areas for improvement and make positive changes that benefit the entire team.

When leaders make checking in with these seven questions a regular part of how they interact with their direct reports, it helps ensure that people feel seen and valued. And when leaders help their direct reports feel that way, they’re more likely to be rewarded by employees who become advocates for the department and organization, no matter how long they stay.

Lead From Within: By asking the right questions and actively listening to the answers, leaders can create a positive and supportive team of direct reports.


#1 N A T I O N A L  B E S T S E L L E R

The Leadership Gap
What Gets Between You and Your Greatness


After decades of coaching powerful executives around the world, Lolly Daskal has observed that leaders rise to their positions relying on a specific set of values and traits. But in time, every executive reaches a point when their performance suffers and failure persists. Very few understand why or how to prevent it.

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Lolly Daskal is one of the most sought-after executive leadership coaches in the world. Her extensive cross-cultural expertise spans 14 countries, six languages and hundreds of companies. As founder and CEO of Lead From Within, her proprietary leadership program is engineered to be a catalyst for leaders who want to enhance performance and make a meaningful difference in their companies, their lives, and the world.

Of Lolly’s many awards and accolades, Lolly was designated a Top-50 Leadership and Management Expert by Inc. magazine. Huffington Post honored Lolly with the title of The Most Inspiring Woman in the World. Her writing has appeared in HBR, Inc.com, Fast Company (Ask The Expert), Huffington Post, and Psychology Today, and others. Her newest book, The Leadership Gap: What Gets Between You and Your Greatness has become a national bestseller.

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