Two Questions Every Leader Should Ask Repeatedly

Guest Post by Art Petty

Make Continuous Improvement Part of Your Approach

I’m a big fan of baking in continuous improvement practices into my leadership and management approaches. From how I run meetings to how I engage with others in feedback discussions or support (or inhibit) problem-solving, I want to know how I’m doing. Unfortunately, timely quality input is hard to find unless you ask for it. While there are myriad challenges in opening up the dialog between you and your team members on your performance, the input is worth the effort.

We’re Mostly Oblivious to How Our Actions are Received

There are a small number of behaviors you exhibit in an endless stream of encounters that either strengthen or detract from your credibility as a leader. These tells—often as invisible as breathing—scream out to the world and announce: Effective! Trustworthy! Or as is often the case, they shout Run! Can’t Be Trusted!

Of course, the challenge for you is determining which behaviors are working and creating positive outcomes and which ones are undermining your credibility and effectiveness. Without help, it’s nearly impossible to know where to improve, where to do more of the same, and where to let go. As part of your leadership improvement program, it’s important to ask for input. The answers and perhaps even more so people’s reactions and responses to your questions offer valuable clues to where you need to strengthen your performance.

“But Why Ask? We Have 360-Degree Reviews.”

While 360-degree reviews can be a helpful supporting tool for your quest to improve, they are imperfect. Quality declines with time and biases or agendas can influence written input on your performance. I prefer prying open the lid on discussing my performance directly with my team members as part of our regular one-on-one conversations. And while the first few times you inquire about your performance, you might be met with unusual reactions and pulled punches, persistence pays.

Set the Stage—Tell Them You are Striving to Improve

Because there’s an inherent awkwardness in asking subordinates to share what they like or don’t like about your approaches to managing and leading, it’s essential to give people some context for this line of discussion. I prefer the straightforward approach: “I’m working on improving my performance in support of you, and without specific input, I’m just guessing. Please help.” Mostly, people will nod their heads and privately respect that you care enough to ask.

Ask Two Questions and Then Shut Up and Listen

How am I doing? is a great starter question.

Or, you can get more specific with What’s working with my approach to managing and leading?

And, after the topic is exhausted, I ask the even more critical question: “What’s not working?

One manager rephrased the latter question to: What do I do that makes your job harder?

Tune the words to your liking.

A crucial part of success with this primary research on you is showcasing your genuine interest in the good, the bad, and the ugly. Practice fierce listening and above all, resist the urge no matter how strong to defend, argue, clarify, deflect, or dodge. Anything you do other than listen, take notes, and ask clarifying questions will shoot your personal improvement program right in the foot.

If at First They Don’t Offer Input, Keep Asking

The first ten or so times you ask these questions you might get uncomfortable, qualified responses. People tend to pull their punches or shower you with false assurances until they’re comfortable this is a safe discussion and that you really do want the input.

If you are persistent and if people perceive you as genuine in your interest and willing to do something constructive with the input, the barriers to quality input often come down upon repetition of the questions.

Practice Extreme Accountability

In my management of this process, I prefer to playback the key themes to the broader team. If I hear repeatedly that our meetings are inefficient, or, that I tend to shut-down creativity with my abrupt approach, I let everyone know. Yes, I share my misfires and insights about my poor practices because I am genuine in my drive to improve my performance.

While it’s awkward to amplify your misfires, there’s something powerful about asking people to hold you accountable for eliminating, adapting, or adding in new behaviors. You tend to do what you share and commit to! Stick to your commitment to improve or change, and people take you seriously, and the input flows freely.

You Strengthen the Group’s Communication Environment

Yes, the input on your performance is priceless. However, my favorite by-product of this leadership improvement process is how it positively impacts communication across the group.

Your willingness to ask for and act on input from your team members sets the tone for communication between group members. Suddenly, the idea of offering positive and constructive feedback to each other doesn’t seem so far-fetched. After all, they regularly share with the boss how she’s doing. And, importantly, people recognize the input is intended to promote positive actions. The goodness that emerges from your genuine interest in strengthening as a professional ripple across the team and supports the emergence of high-performance.

The Bottom-Line for Now:

It’s amazing what happens when you ask how you are doing as a leader or manager. If people believe you care, you’ll gain ideas and input on improving in your job. Of course, first, you have to find the courage to ask and the discipline to listen and do something about it.

What’s stopping you from getting started today?

What’s working?

What’s not?

And Importantly, what are you going to do to improve?

Art Petty


Art Petty is an executive and emerging leader coach and popular leadership and management author, speaker, and workshop presenter. Art writes the popular Leadership Caffeine series at the Management Excellence blog. His work is regularly featured at SmartBrief on Leadership and others. Additionally, he has written multiple books, including Practical Lessons in Leadership and Leadership Caffeine: Ideas to Energize Your Professional Development. You can reach Art at 


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