This article was published on July 12, 2014

10 must-ask questions to supercharge your leadership

10 must-ask questions to supercharge your leadership
David Hassell
Story by

David Hassell

David Hassell is the founder and CEO of 15Five, lightweight performance management software that delivers a full suite of integrated tools - David Hassell is the founder and CEO of 15Five, lightweight performance management software that delivers a full suite of integrated tools - including continuous employee feedback, objective tracking (OKRs), pulse surveys, and peer recognition. Named "The Most Connected Man You Don't Know in Silicon Valley" by Forbes Magazine, David has also been featured in The New York Times, The Wall Street Journal, Inc., Wired, Fast Company, and the Financial Post. You can learn more about 15Five and David Hassell at

David Hassell is the CEO of 15Five. This post originally appeared on the 15Five blog.

I used to imagine that I could peer into the silent void of a discussion with an employee and their thoughts and feelings would magically pop in my head. It never happened.

We are in the employee feedback business. Through running 15Five by using our own product, I have found that regularly asking questions is an agile and lightweight way of keeping up with what’s really going on.

Answers become conversations about what is most essential and meaningful for the team and the company, and those conversations transform into action.

The first place to start is by asking the right questions. Here are some of the best I’ve found:

1. What’s going well in your role? Any wins (big or small) this week?

This is a great place to start. Employees get to celebrate and even brag a little about all the positive stuff that happened that week by simply answering that question.

This includes the small things that often get overlooked because they aren’t related to top priorities. As a bonus, you will glean what employees consider triumphs relative to the goals of the organization.

2. What challenges are you facing? Where are you stuck?

The quickest way to overcome challenges and get unstuck is to say, “I’m stuck!” When we can identify where we’re stuck and then bring someone else’s attention to the challenge at hand, we are in a position to receive the coaching and guidance that helps us think about the issue in a fresh new way.

Often just writing about where we’re stuck begins the process of getting clear on how to resolve it ourselves.

3. What is the business doing, or can be doing, to make you more successful?

Employee success is a dynamic and always evolving process. Sometimes what your team needs is more training or a one on one meeting. Other times they require help with learning a specific skill set. This question gives permission to ask for the things that will move the needle forward and build more engaged teams.

4. How are you feeling? What’s the morale around you?

Asking an employee how they feel is critical. It increases drive and happiness because their individual and collective experiences feel validated and heard.

Answering this question can not only bring self-awareness but also provide valuable qualitative insight for others. When a team member knows what’s going on with others, the entire team is more cohesive. This creates more effective and satisfying team work.

The answers to this question can also allow you to properly time certain initiatives and changes within the company. Are they on the edge of burnout or feeling happy and energized? Are they stressed by the new product launch? Perhaps you should postpone hack day until things settle so that they have space to access their most creative ideas.

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

The research of positive psychology is clear: happiness 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.

This question simultaneously sends the message that your employee matters beyond mere performance and work-related issues. By quantifying happiness, you can get a quick snapshot of this metric team-wide.

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

There are strategic reasons to ask this question since learning about team members as whole people can help you develop a more committed and engaged team. Feeling that others know them and understand their personal desires and goals helps to maintain team cohesion and employee retention.

This is also an opportunity to discover a common ground with which to enrich in-person communication.

7. Provide one idea to improve the product or service provided by your company.

The best source of innovation is often found by people who already work for you. Since suggestion boxes have gone the way of the fax machine, this opens the door for team members to throw out ideas for improvement, no matter how big or how small.

Imagine that the next Airbnb is humming in one of your employees’ heads. You have now presented the opportunity to hear all about it. This not only elicits what could be valuable responses, but also makes the respondent feel connected and appreciated.

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

If you hired well, then you have leaders and future executives among your ranks. Ask this question once a month to encourage leadership from everyone in the company.

Placing them in the driver’s seat can really open up some potent ideas on helping the company succeed. This question also offers a sense of empowerment and ownership of the company.

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

This opens up the door for praise and can grow cohesion. You can also develop an internal conversation regarding the top traits to look for in a new hire.

It is better to ask this question to elicit specific and positive information. Asking for general comments on the performance of other employees may be insightful and entertaining, but will probably open a competitive can of worms.

10. Provide feedback on how I can be a better leader.

This one will probably be the toughest on your team, but the responses will also be incredibly worthwhile. You will learn what your employees perceive are 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. You will separate the chaff from the wheat, as it takes a courageous and skillful employee to tell their manager where they have room to grow.

I still hope that one day my superpower clairvoyance will kick in. Until that day comes, I’ll stick with getting straightforward answers by asking the right questions.

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