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Team meeting to identify questions to ask leaders
6 Min Read

10 Must-Ask Questions To Supercharge Your Leadership

David Hassell, Co-Founder and Executive Chairman of 15Five

Image credit: Shutterstock

When I talk about 15Five’s mission, I like to say that we are in the business of employee feedback. Because when it comes to enacting positive change, managers are most effective when they’re aware of what’s really going on around them. You can start gathering feedback from your employees by learning to ask the right “leadership questions”—inquiries that provide a deeper sense of what’s happening for people and in the org as a whole. 

Throughout my time in leadership, I’ve found that by uncovering what’s most meaningful for my team and the company, I’m better able to understand how to lift team morale and take action on what matters most. Here are some of the best questions I’ve found that boost employee morale and employee engagement:

1. What’s going well for you and your team this week? Any wins (big or small)?

This is a great place to start because it sets a positive tone for the conversation and it allows employees to celebrate their wins and accomplishments. Be sure to highlight the small but critical things that might get overlooked. And as you listen, pay attention to what your employees consider triumphs relative to the goals of the organization.

2. What barriers are getting in the way of your success? Where are you stuck?

The first step in overcoming challenges is identifying the barriers that are getting in the way. It’s also important to normalize that everyone feels stuck occasionally and to remind your employees that help is available when they need it. In talking about challenges, make sure that you are offering coaching in a way that helps your employees feel supported. Brainstorm actionable solutions together and listen for patterns within these conversations.

3. What can I do to help you be more successful?

Employee success is a dynamic and always evolving process that is influenced by organizational KPIs and personal definitions alike. But you can support your employees’ success by giving them permission to ask for the things that will move the needle forward and build more engaged teams. Of course, regardless of the type of support that’s needed, always be prepared to follow through with any solutions you propose. 

4. How are you feeling at work lately? How’s the morale around you?

Asking this leadership question in an authentic way increases drive and job satisfaction because it makes your employees feel validated and heard. When you know how your employees are doing, you can time certain initiatives and changes within the company to set them up for success. And aside from providing you with valuable insight and feedback, asking these questions can also enhance self awareness and promote better communication within the whole team, which leads to positive employee morale.

5. On a scale of 1-10, how satisfied are you? Why?

The research on positive psychology is clear: positivity is a precursor to success and accomplishment, not the other way around. When your team is happy, they not only come up with better solutions, but their satisfaction also helps to build a culture of high performance and low turnover. 

Plus, asking this question sends the message that your employees matter beyond performance and work-related issues. Of course, remind your employees that they don’t have to disclose anything they’re uncomfortable sharing. But by quantifying how they’re feeling in a broad sense, you can get a quick snapshot of this metric across the team.

6. What’s the best thing that happened to you this week, either at work or outside of it?

Learning about direct reports can help you develop a more committed and engaged team. But on a more personal level, when employees feel that their manager knows them and understands their personal goals, it helps foster team building and employee retention. Use this leadership question as an opportunity to build meaningful connections and discover common ground.

7. If you had the chance, what’s one thing you would do to improve the product or service provided by our company?

The best source of innovation is often found by people who already work for you because they have insider knowledge of your product or service but with a unique perspective. Since suggestion boxes have gone the way of the fax machine, asking this question opens the door for team members to share ideas for improvement, no matter how big or small. 

8. If you owned the company, what’s one thing you would do differently?

While the previous question is aimed at fostering ideas and innovation, this question is designed to give you insight into the human side of your workplace. If you’re recruiting and retaining effectively, then you have leaders and future executives among your ranks. So when you ask this leadership question, you’re encouraging a leadership mentality that can uncover some potent ideas on helping the company succeed. This question also offers a sense of empowerment and ownership of the company by allowing everyone a few minutes in the driver’s seat.

9. What were some great contributions made by other team members recently?

Rather than asking for feedback on the performance of a specific employee, asking this question in an open-ended way allows employees to give employee recognition and acknowledge each other positively and organically. And in asking it regularly, you’ll normalize noticing and highlighting what’s going well with the team both individually and collectively. You can also use the answers to this question to develop an understanding of the top traits to look for in a new hire. 

10. What can I do to be a better leader?

There are few better ways to model seeking and accepting constructive criticism than by asking this question. And while it might be difficult to ask at first, it will get easier over time and the responses will be incredibly worthwhile. You will learn what your employees perceive as core leadership values, and determine if they are in sync with the values of management and the company as a whole. The insights offered here will also aid you to promote internally as it takes a courageous and skillful employee to tell their manager where they have room to grow.

David Hassell, CEO of 15Five

David Hassell is a business columnist, speaker, and serial entrepreneur who believes that when leaders institute cultural practices that support each person in being and becoming their best self, high performance and uncommon loyalty naturally result. As co-founder and CEO of 15Five, David created the science-inspired Best-Self Management methodology that helps leaders and managers address the hidden factors that stimulate sustainable growth and development – things like intrinsic motivation, strengths, and psychological safety. David has been featured in The Wall Street Journal, Inc., Entrepreneur, Fast Company, and Wired. Follow him on Twitter @dhassell.