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Problems Are Coaching Opportunities: 
Asking Artful Questions

By Doug Silsbee

Every day, in businesses around the world, people take problems to their bosses. Every day, the boss asks enough questions to get the lay of the land, then tells the employee how to handle it. You see, most of us like to solve problems. While we might complain to our spouses and our colleagues that work is just one brush fire after another, there is also a part of us that is proud that we’re the “go to person” that can put fires out.

So, what’s missing? The learning and development of the employee. Daily problems provide a major opportunity to coach and develop your employees. This shift begins by asking artful questions that get your employees thinking, rather than simply providing answers. This article will show you how. First, let’s look at how a typical well-meaning manager might ask questions when faced with one of countless daily brush fires. She is likely to ask questions in several of these categories:

Traditional Question Category #1: History. “What have we tried before?” “Who did that?” “How did we get here?” and “What did we charge them last year?” are history-based questions that draw upon the employee’s knowledge to establish context for the current situation.

Traditional Question Category #2: The problem itself. These questions elicit information the manager will need about the problem. “What happened? “What do they want?” “What’s broken?” and “What’s at stake?” will get factual answers from the employee’s mental picture of the problem. With this information, the manager can decide what to do.

Traditional Question Category #3: Available resources. “How much inventory do we have?” “What resources do we have?” “How much time do we have to fix this?” and “What equipment is on-site?” help establish what resources are available to be deployed against the problem. Resource availability, of course, will influence the feasibility of various solutions.

Traditional Question Category #4: Possible solutions. Here, questions for the employee center on identifying ideas for solving the problem. “Do you have any ideas about how to solve it?” “What might work?” “Have you gotten any ideas from the team?” are examples of these. Here, the manager is gathering input while looking for a solution.

These questions are all fine. They provide important data, and will typically be part of any problem-solving conversation. They may well provide the manager with sufficient information to suggest a solution. Great, right? Wrong! Read on.

The down side? These questions keep the manager in charge. They lead to a one way flow of information from the employee to the manager. Armed with this information, the manager can then make a decision. The employee is treated as a source of data, rather than as a creative, capable problem solver. While the problem was solved, the employee didn’t learn anything new, and has little investment in the solution.

These questions fail to:

  • Challenge the employee to think. Factual questions, geared toward obtaining information for the manager, invite a data download. They don’t impel the employee to access his creativity and resourcefulness.

  • Keep responsibility on the shoulders of the employee. While this might feed the manager’s sense of self-importance, continuing to solve problems in this way (multiplied by the many little problems that often show up in the course of an average day!) makes the manager’s job bigger and bigger and fosters employee dependency.

  • Stimulate joint problem-solving and collaboration. The manager will tend to do things the way she always has, rather than enlisting the employee in a process that could lead to new solutions. “There’s nothing more dangerous than a good idea when it’s the only one you have.”

The solution? Different approaches to questioning can enhance the manager/employee relationship, lead to more creative solutions, and invest in the employee’s long term capabilities. So, let’s consider some alternatives.

 “Artful questions” push the employee to think because, by design, the employee doesn’t already know the answer. These coaching questions challenge the employee to think out of the box, put responsibility back on the shoulders of the employee, and often lead to better solutions. Designed to impel the employee into a process of learning and exploration, they also provide more opportunity for the manager to learn.

Generally, artful questions will illustrate a thinking process, rather than simply obtaining information necessary for an answer. The question represents a line of inquiry that can be used in many problem situations. By asking artful questions, the manager helps the employee learn how to solve problems, leading to more independence down the road. As the ancient Chinese proverb says, “If I give you a fish, you eat for a day. If I teach you to fish, you eat for a lifetime.”

Obviously, the questions need to be created for the specific situation, but here are a few examples that can be used to coach in problem situations.

Artful Question Category #1: Criteria for a solution. Ask the employee about the criteria that would define a great solution. Later, possible solutions can be evaluated against these criteria. Getting clear about criteria early in the conversation will focus and energize problem-solving. “Who needs to be happy here?” “What are the primary concerns to take care of?” and “What’s the bottom line that our solution must address?” are examples.

Artful Question Category #2: Switching perspective. Ask the employee to step into a different perspective, and view the problem from there. You can ask the employee to view the problem from the viewpoint of a different function, time, or person. The popular bumper sticker “What would Jesus do?” is a great example of a perspective switch that can illuminate how to handle a tricky situation.

Perspective switching is a great “out of the box” approach. Often, with a different view, new ideas will surface that previously hadn’t occurred to the employee. Try out, for example, “What would an engineer/sales person/accountant say to do?” “If you were to look back from six months out, knowing that your solution worked beautifully, what would be in place?” “What do you think our customer’s/boss’s primary concern is in this?”

Artful Question Category #3: Creative Resourcing. This category of questions challenges the employee to identify new resources that could be brought to bear. Notice the similarity to the Available Resources category above; the distinction is that this category seeks to expand the resources available for a solution. “We can’t go lower on price, so what can we offer that would add value without costing us much?” “What else is lying around that might be helpful?” “What non-critical projects could spare someone to help out for a week?”

Artful Question Category #4: Unique contribution. Ask a question that directs the employee’s attention towards his strengths and to view a solution in that context. “You have terrific skills in X; how does your experience suggest we should move forward?” “What solution would best take advantage of your expertise in sales?” “What solution is most consistent with your values?” All of these affirm and validate the experience and judgment of the employee, and send the powerful message that he is uniquely capable of providing the solution.

Artful Question Category #5: Challenging limitations. Together, list the rules and assumptions that you’ve made about the situation. Go down the list, one by one, and question them. Be a devil’s advocate. “Who says that this can’t be changed?” “What assumptions can be eliminated?” “What rules can be broken?” This isn’t an argument for random abandonment of reasonable rules. However, if the specific problem provides an opportunity to streamline a procedure or eliminate unnecessary restrictions, there may be real benefits to changing things.

Artful questions stimulate a creative thinking process and a dialog. Rather than a one-sided data gathering process that allows the “expert” manager to decide what should happen, artful questions challenge the employee to think and take ownership. The results include an employee more able to problem-solve the next time, lowered dependency on the manager, and often more creative and effective solutions.

Two words of caution. First, not every problem lends itself to this approach. For example, if an employee, on his first day on the job, needs to know how to turn the computer on, it will be more appropriate to show him the switch than to ask “Who might be able to tell you where the manual is?” It takes some discernment from the manager to decide if a particular problem is really an opportunity for asking coaching questions, or whether it might be better to simply provide an answer and get on with it. Assessing the nature of the problem, the capability of the employee, and the urgency all factor into the decision.

Second, when employees are used to getting simple answers, to be suddenly asked challenging questions can be confusing. In order to not appear “gamey,” it is important for the manager to give the employee context. Let him know that you’re asking questions in order to coach and support his learning.

It may be useful to say something like, “Let’s try something a little different. I’m not sure what the best solution is. I have confidence in your capability. Let’s try some questions that will help us come up with a great solution to this.” Providing a little context will do much to enroll the employee in a process that changes how you work together in subtle but significant ways.

The bottom line? Far too many managers create a subtle dependency and keep themselves in the driver’s seat when they could be coaching their employees to take more responsibility in solving problems. Most managers could be much more effective by using day-to-day work situations as coaching opportunities for their employees.

Using artful questions to challenge and intrigue employees is a great starting point. Use them to send the consistent message that you see your employees as capable, resourceful, and creative.

Read other articles and learn more about Doug Silsbee.

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