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Advice / Succeeding at Work / Management

The Critical Skill That Too Many Leaders Overlook

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Two mid-level managers were up for the same promotion. They’re both good bosses whose employees love working for them and achieve results, but they have two totally different styles.

Bradley saw his job as being the answer man for his team. He had an open door policy to ensure he was always accessible to his employees. When they came to him with problems, he could be counted on to provide a concrete solution. Bradley always provided the answers they needed to get the job done quickly and efficiently.

Leila preferred to schedule time with her team and sometimes she was unavailable to them. When they came seeking guidance, she’d often say, “That’s a great question, what do you think the answer is?” or “Why don’t you work on some possible solutions and we’ll talk about them.”

Her goal was to develop her employees’ abilities so they could work more independently. By asking instead of telling, Leila saw her team’s confidence and capability grew, and as result, she was able to get more done, too

As you might’ve guessed, Leila got the promotion.

Bradley asked his boss to explain the decision, and he jumped on the chance to share his reasoning: “Day-in and day-out, Leila gets more done. She’s also developed a reputation as a people developer: Her employees move into more senior roles regularly, while yours don’t. You run a great team, but we’re growing and Leila’s management style helps us deal with those growing pains.”

Yes, it can take more time and also mean delegating some big-picture thinking, but asking instead of telling is a critical management skill all leaders need.

Here are three reasons why:


1. Asking Questions Helps People Learn How to Think Through Problems

When someone tries to do things they’ve never done before, they’ll have questions. And sometimes the smart thing to do is to answer them. (Obviously, if your employee asks how to use the new database you’re familiar with, I’m not suggesting you ask them to guess how to find a record.)

But if a task can be solved multiple ways, help your employee think through the best approach by asking questions like “What are the trade-offs of doing it this way?” or “Have you seen others have success solving it the way you are suggesting?” Asking them great questions helps them come up with better solutions.


2. Asking Questions Builds Confidence

Instead of becoming reliant on you, an employee who works through difficult problems on his or her own gains confidence. That’s because if you provide the answer every time, you’re reinforcing the idea that he can’t trust his intuition to move forward.

Conversely, if you say “I don’t have an answer, do you?” you’re showing that you think his ideas are just as valuable as yours. Moving forward, this’ll help your employees learn to tackle the next tough situation on their own.

Initially, this work shift makes some bosses who are used to stewarding every project a bit nervous. Like delegating work, delegating strategic thinking takes practice too. If you fear your employee will take something down the wrong path, remember I’m not suggesting you become completely hands off.

The goal is to ask questions and let the employee take the lead in answering them, but you still get to participate in the conversation.


3. Asking Questions Allows for Learning From Experience

The best bosses can identify opportunities to let experience do the teaching (even if it means sometimes the job will be done less efficiently). And even though it seems completely contrary to everything you’ve heard about being a good manager, sometimes you need to let your employees fail.

Imagine a situation in which one of your direct reports wants to ignore the suggested guidelines and hire subcontractors through a new system she thinks will be faster. As the boss, you have the authority to override her and say, “It has to be done according to the guideline.” If you’re on a tight budget or timeline, that approach may be necessary.

But if trying a new approach won’t do any permanent damage (or put any annoying obstacles in other people’s way), you might consider saying, “Who knows? Maybe you’ll find a better way!” What’s the worst-case scenario? Even if the idea turns out to be a dud, everyone will be reminded of the importance of using the subcontractor hiring guidelines.

Plus, being allowed to try something new will fan the flames of her creativity and initiative. This employee will keep coming to you with creative approaches and can become the go-to person when you need an out-of-the-box answer.


Bosses who get hung up on having their people do things the same way they do it create clones, not smart, capable employees. Instead, your ultimate goal should be to create a learning environment where your team can bring their best to work every day. Great questions help people learn to use their creativity, discretion, and judgment to get work done. What’s more, they help employees learn to ask themselves, and that helps the whole organization.