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Advice / Succeeding at Work / Management

How to Train People to Ask You Fewer Questions (and Figure Things Out on Their Own)

As a first-time manager eager to prove my worth, I loved when employees came to me for assistance. “I’ll help you with that,” “Here’s what you should do,” and “Let me show you,” were always on the tip of my tongue. I was ready to answer every question and resolve every issue, because, in my mind, that’s what a manager did.

However, I quickly learned that being a little too eager to help can leave you with, well, helpless employees. Once they’ve made a habit of leaning on you for advice, they start consulting you before doing anything, from brainstorming ideas for a project to inputting the time on their timecards—things that, in theory, they should be confident to handle on their own.

Don’t get me wrong—I know that a big part of management is guiding and advising your employees. But another part of being a supervisor is helping your employees learn to think on their own, troubleshoot difficult situations, and grow into self-sufficient leaders.

So, if you’ve noticed that your team is exclusively leaning on you (for things that don’t necessarily require your expertise), here are a few strategies that helped me encourage my team to be a little more self-reliant.


The first time I had to hire a new employee, I received a great piece of interviewing advice: After a candidate has answered a question, pause. The candidate will likely feel pressure to fill the silence and will eventually elaborate even more, giving you better insight into his or her character and personality.

I realized that I could also use this tip in everyday management one day, when one of my employees plopped down in the chair in front of my desk with a sigh, desperate for help. When he finished telling me about the issue, I didn’t have an immediate response, so I remained silent for a minute, thinking through how I was going to advise him to solve it.

But before I could formulate a resolution, he began reflecting on potential solutions himself. “I was thinking I should probably email the sales rep to verify what exactly was sold,” he mused, “and then I’ll be better prepared before I talk to the client about her system implementation.”

I affirmed that that would be a great start. As he walked away from my desk, he added, “I guess I just needed to talk it out!”

This can be a good way of introducing your team to a more hands-off approach. As they wait for your direction, simply pause and see if they come up with the answer themselves. And if they do, it’s a surefire way to give your employees more confidence in their decisions.

Ask “What Do You Think?”

If the pause doesn’t work—or you’re just met with a blank stare in return—try this. Instead of doling out a solution the instant an employee comes to your desk to ask what he or she should do, try, “What do you think?”

If the employee has a reasonable solution, great! Encourage him or her to move forward with it.

But even if he or she doesn’t have anything in mind, it will at least get the conversation moving. Maybe your employees starts with, “Well, I thought about contacting the client directly, but I’m not sure I have all the information I need if she asks more questions about the contract.” Even if you jump in at that point, your employees will start to get used to thinking through their actions on their own.

Emphasize Your Trust

In my management experience, indecision or helplessness often stems from insecurity and worry. Your employees are worried that if they do the wrong thing, they’ll get in trouble. And so, they make sure to ask permission before doing anything to avoid any negative consequences.

The thing is, they’ll have a hard time growing into independent, self-managing workers if they’re constantly asking permission—especially for day-to-day things that don’t require it.

For example, my team primarily works out of web-based project management software, where they’re required to document their work in tasks, then mark the projects as complete when they’re finished. Even though we moved to the software over a year ago, I still have employees who are absolutely terrified of closing their tasks prematurely. They’ll ask me over and over again, “Can I close this project now?”

To help ease them into decision-making mode, I’ve found that it helps to emphasize my trust during our team and individual meetings. I have a wonderful team of intelligent employees who I can trust with even the most difficult clients—and if I can trust them with that, they can certainly decide when day-to-day tasks can be considered complete. As I communicate how much I trust and respect them, the more confident they are in taking matters into their own hands, without consulting me every time.

Of course, it’s important not to convey that you aren’t willing or available to help. There’s a definite line between empowering your employees to make some calls on their own and abandoning them completely. So, make sure to communicate both (e.g., “I trust you to use your best judgement to close your project and tasks, but if you come across something that you’re really unsure about, I’m here to help”).

Reinforce With Recognition and Praise

As I mentioned, a lot of the helpless and constant questions come from a feeling of insecurity. So, it’s important that when your employees do display the type of behavior you want, they’re recognized for it.

However, make sure to keep your praise specific and genuine—e.g., “I thought the way you handled that decision was perfect—you have a really good instinct when it comes to dealing with difficult clients” rather than, “I’m so proud that you did something without asking me first!”

Recognition can even be relayed in a form that will help your other employees: “I saw that you figured out how to use the new expense report system—awesome job! Would you mind taking some screenshots and sharing them with the rest of the team?” In doing this, you’ll be encouraging your employees to take charge in unfamiliar situations, and you’ll set them up to lean on each other—and not just you.

With enough positive recognition, your employees will begin to feel confident in the things they do on a daily basis, without feeling the pressure to consult you first.

As a manager, you have an important and delicate job. On one hand, you want to guide your employees to do great work and make smart decisions—but on the other hand, allowing them to lean on you too much can hinder their professional development. By teaching them to take charge little by little, you can encourage them to become confident, self-sufficient professionals.

Photo of frustrated man courtesy of Shutterstock.