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By Steven D. Goldstein

One of the elements of a truly engaged workplace is the asking of questions. The fact is that most people are afraid to ask questions; whatever natural curiosity we had as children tends to get discouraged in most large organizations. Leaders assume following the status quo is the right way to go and are not interested in trying to challenge anything, especially if it seems on the surface to be going along just fine. And the lower-level employees just try to do what’s asked of them and stay out of trouble—believing that people who ask questions may be sticking their necks out.

Getting people to ask questions requires effort and energy. It means changing what may have been part of a process for years. Change is almost always very hard. Questioning actually means choosing the path of resistance, instead of the path of least resistance. But when people get into the habit and realize they won’t get their heads chopped off for asking questions–that in fact their questions will be welcomed–everything gets better.

The best way to teach is by example. Buddha and every other great leader throughout history taught by showing or doing, not by telling. When your people see you, the leader, asking questions (i.e., questions about how and why things are done, not questions regarding people’s individual intentions and/or productivity), they will begin to feel comfortable answering your questions, and they will start asking similar questions with their folks. And those folks, in turn, will start to realize that challenging things and offering information about what is really going on in their department is something that is encouraged. When you are willing to admit in front of everybody that you don’t know a particular answer, and you are the boss, then that makes others understand that they also can admit they don’t know. This enables free flowing information, which is essential to the health and productivity of your organization.

This sounds pretty simple doesn’t it? So why does this reticence, this reluctance to ask questions, occur so often? Why is it so hard for leaders to know what’s going on at the lower levels of their companies? The main reason is that leaders are fundamentally not interacting well with their employees.

Obviously most leaders don’t promote a closed-door policy or a bad environment. They just don’t actively promote the opposite. But the absence of a positive message is still a message, just as making no decision is actually making an important decision—a decision to do nothing. The process of questioning is actually hard—and it is a process.

Getting your employees to ask questions starts with you letting your hair down. Start a dialog. Begin with your own engagement.

So how do you begin to practice this? There are many different methods to encourage people to open up so you can get to the nitty-gritty of what’s going on. If engaging does not come easily to you — if you are someone who is not comfortable talking to lots of people and asking lots of questions – try employing one or two techniques from the following list that suit you the best, ones that feel the most natural to you. (Note: You can’t do this superficially. If you are not truly involved in this process, it will not work.)

A Few Simple Ways to Encourage the Free Flow of Information:

Have a conversation with your assistant and ask him how things are going. If you have never really done this before, with someone you know, you will find out immediately that there are things he will tell you (and hopefully also things he will ask you) that you never knew—and will want to know.

— Ask your assistant if he can suggest a few individuals he thinks would be willing to be open with you. Then you can reach out to them and arrange to meet with them individually. These chats do not have to be more than fifteen or twenty minutes, but be sure to make it clear you are there to answer questions as well as gain information.

Make yourself talk to one new person every day—no matter who it is. Choose someone you would not normally talk to. At the end of the week, ask yourself, “Did I do this? Did I engage with someone new?” Believe it or not this will be fun, and you will almost always learn something that is beneficial. Once you realize it’s not a waste of time, you will naturally do more of it. Starting small is the way you begin anything new, whether it’s learning the saxophone, training for a marathon, or getting your people to ask questions.

Convene a small group of employees into a conference room in their department (not your conference room) and say something like this: “I just wanted to come down and visit with you to see how you are all doing. I’d like to hear from you about what’s working in your department, what’s not—where you think we can improve, etc. I will probably take some notes to make sure I can address the items you bring up.” Go around the table and ask them to tell you their name and what their job is. Usually before people finish introducing themselves, someone will make a comment that sparks a conversation among the group members, and you’re off to the races.

About the Author

Steven D. Goldstein is a proven leader who has held executive positions with leading global brands, such as American Express (Chairman and CEO of American Express Bank), Sears (President of Sears Credit), and Citigroup, as well as several early-stage enterprises. He currently works in the private equity industry as a Senior Advisor with the consulting and advisory firm Alvarez & Marsal, serves as Chairman of US Auto Sales, serves as a Senior Advisor to Milestone Partners and an Industrial Advisor to EQT Partners (a global private equity firm based in Stockholm). 

He has also advised CEOs and private equity owners providing counsel on performance improvement with their companies in addition to acquisitions and merger integration opportunities. 

He has served on numerous boards, such as: American Express Bank, Jafra Cosmetics, Union Bancaire Privée, Pay-O-Matic and Big Brothers Big Sisters of New York City. Steven has been an investor, advisor, and interim CEO for more than 10 venture backed e-commerce companies. Steven holds a Bachelor’s degree from City University of New York City, and an MBA from NYU’s Stern School of Business. He lives in New York City.



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