How to Improve Your Leadership Skills By Asking Better Questions

Leaders don’t have many tasks on their to-do lists. Their responsibilities are few in quantity, but large in scope and impact. A leader’s job impacts the organization, the team, stakeholders, clients, customers, and sometimes, entire industries. Leadership is about making a few high-quality decisions each day, while continuously casting your vision and keeping your team inspired, focused, and rowing (and growing) in the same direction.

As a leader, one of the greatest things we can do is ask quality questions and listen, really listen, to the answers. If you go into a meeting or conversation with a decision already made or with the desire to be right, then you might as well cancel the meeting. Any conversation worth having is a give and take of questions, curiosity, discussion, and gaining understanding and a new perspective. From there, you can make the decision that is best for the organization (even if the majority disagrees), and gain commitment. The team will inevitably get behind you when you regularly engage in the practice of discussion, disagreeing, and committing.

Some of the best leaders are not those who know all the answers, but rather the ones who can admit what they don’t know, gather the best team around them to help find the answers, synthesize all the information, and are then willing to make the tough decisions in the face of conflicting information, competing agendas, and internal and external pressures while keeping the long-term vision and plans for the company in mind.

The Power of Great Questions

There is no doubt that questions hold a lot of power—from what you ask, to how you ask, and to how you answer. As Tony Robbins said, “Quality questions create a quality life. Successful people ask better questions, and as a result, they get better answers.” Are you asking powerful enough questions each day? Are the questions you ask yourself or others moving your business or career forward or helping your team self-discover and accomplish their goals? They should be.

Here are a few of my favorite leadership questions:

1. What do I need to know about this issue/opportunity that you haven’t shared yet?
We all know that information and data can be manipulated to tell the story you want told. To make sure your team doesn’t get stuck sharing only the information with you that proves their point or furthers their agenda, pause and ask them what else they haven’t shared yet. It’s great to know the good stuff, but what you really want to know is what might trip you up. It could be as significant as a less than favorable sales forecast or as seemingly insignificant as a dissenter in the ranks (who has influence over a key team). Getting that information out in the open means you can work with your team to solve it before it becomes a real issue.

2. What questions do people ask you? 
I love this one because it serves two purposes: first, as a quick check on how people perceive you (right or wrong); and second, as a way to dig deeper into potential issues at the company.

When it comes to your personal and professional image, think about all the questions people come to you with. Hallie, my former Chief of Staff, has said this for years. Not many people ask her out for drinks or to attend a social event, but former bosses, colleagues, family members, and friends all reach out to her for career advice, resume reviews, business questions, book recommendations, etc. Now, what do you think she is known for? Exactly – books and business. What are you known for? Just think about the questions people are asking you and you’ll know. Don’t like the answer? Take a good hard look at your activities and start making some changes.

Now, when it comes to the company or your team, pay close attention to the questions you are hearing from employees, sales reps, outside vendors, customers, and clients. These are indications of where you may not be sharing the vision enough, where you may not be explaining your product or service offering as well as you could be, or it may mean there are concerns among employees that need to be addressed. Questions give you great clues into where you can do better.

3. What are we missing? What might we be explaining away too quickly?
This is one I ask myself every day. Whether it’s trying to tackle a problem from another angle or when there is a leadership challenge in my organization. It gets me to stop and reconsider what other solutions there might be. Ask your team this one too – “What are we missing?” And when they answer, continue to dig deeper. Okay, what else are you missing? What might we be explaining away too quickly? What are we overlooking that could potentially become an issue in the future? And then create an action plan from there.

4. Who can do this? Who will be responsible for this?
I love leverage and ideas. So, in order to make all my ideas happen, I need other people to do them. My first thought when a new idea crosses my mind or someone on my team wants to implement a new initiative is, “Great! Who can do this?” If you are not yet in a position where you can completely delegate, then ask, “Who can help with this?” This gets you into the habit of delegating, going to an expert, outsourcing, and ultimately implementing a project or idea faster.

If your team is large enough, that creates its own complications. Sometimes, everyone assumes the new project or idea is someone else’s responsibility, which means no one is taking ownership. Before ending a meeting, I like to ask, who will be responsible for this? That doesn’t mean that they need to do it alone—in fact, it often means they will be running a team to execute. However, at the end of the day, one person ultimately needs to be responsible for the deliverable.

5. Is this a one-way door decision or a two-way door decision?
Before you get into hashing out the details of a decision, ask your team, is this a one-way door decision or a two-way door decision? One-way door decisions are decisions that can’t be easily reversed, such as merging with a competitor or selling one of your product lines. Two-way door decisions can be reversed. You can make the call, and still go back if you don’t like how it’s going. For example, two-way door decisions might be deciding to outsource IT, but then deciding later to bring it back in-house. One-way door decisions require you to slow down a little and proceed carefully. Two-way door decisions can be done much faster. Make sure you and your team know which type of decision you’re working on.

6. Who do you know that I should know? 
One of the best ways to find great talent for your organization is through the great talent that you already have on staff. My mission is to surround myself with the best people on the planet, so I ask this question of those people I respect and admire. You would be surprised how many times I hear, “Oh, yeah, you should meet ________; I don’t know why I haven’t introduced you before.” Bottom line, just ask. You’ll meet a lot of amazing people this way and be able to build your bench of talent that much quicker.

7. Are you investing your time appropriately regarding these priorities?
Keeping the team focused is key. Once you’ve agreed upon the priorities for the year or quarter, it’s all about resource allocation, with the most important resource being time. If you or your team aren’t seeing the results you need, then start by asking, “Are you investing your time appropriately regarding these priorities?” This may prompt a hard look at where they’re spending their time. With unproductive activities eliminated, unnecessary meetings deleted, and more purposeful blocks of time created to focus on these priorities, you should see the results turn around. Sometimes bringing awareness through a question like this is all you need to do to turn the tide.

8. Is this a skills issue or a commitment issue?
When someone is not meeting their goals, I like to pull out this question. It usually comes down to two issues—skills or commitment. 99% of the time, it’s not skills. The person usually has the skills, is working on them, or knows where to learn them. It’s usually an issue of commitment. Not being committed enough to their goal, which usually translates to not wanting to do the work required to reach that goal.

A skills issue I can coach through; a commitment issue, not so much. Someone either wants it or they don’t. I can’t want someone’s success more than they do. This question is a good way to get that person to self-discover that either the goal needs readjustment to something they are more motivated to achieve or that another position might be a better fit. It’s a hard conversation to have, particularly if the thing the person doesn’t want to do is the job they were hired to do. But better to know now for the sake of the company. And better for the employee to be able to be honest and hopefully find an opportunity that is better aligned with their goals.

9. What else can we do? 
There is always a way. If something is not working, if we not meeting our company goals, what else can we do? It is so critical to come from a solutions-based and abundance mindset. If you’re planning a board retreat, ask yourself, what else can we do to wow them? Or what else can you do to show your team how much you appreciate them? Or how can we create an additional $500,000 of revenue before the end of the year? There is always a solution or a way to improve the status quo. Ask yourself, ask your team, and you will find the answer you’re looking for.

We’re always one question away from a breakthrough. What are some of your favorite leadership questions? Share them with us in our free LinkedIn Community!

Original post shared on October 14, 2021. Updated for 2024.

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