Step 6

Elevate the Power of Questions

“Positive questions bring out the best in people, inspire positive action, and create possibilities for positive futures.”

—Diana Whitney

Bill saw the struggles his mentee Randall was having with his staff members and knew exactly what Randall should do. The problem and resolution were so clear for Bill that when he closed his eyes to think about it, he could actually visualize Randall taking those steps toward complete resolution. He even felt the sensation of Randall’s hearty handshake, thanking Bill for this terrific advice. Then, as reality set in, Bill stopped himself.

Like Bill, as a mentor, the depth of your expertise is better leveraged toward creating a learning experience for your mentee rather than dispensing advice directly. This is sometimes called coaching versus teaching, or “ask versus tell,” and it uses the art of asking thoughtful questions. More memorable and engaging, this approach will help the learning to become integrated into your mentee’s behaviors, going beyond providing interesting ideas for them to explore.

Given a more coaching and developmental focus in today’s work environment, books and workshops about the art and power of using questions have exploded over the last decade. Why all this attention to the use of questions? Questions are very powerful in establishing and maintaining a relationship. Instead of assuming you, the mentor, have all the answers, questions open up a dynamic conversation. By their nature, questions create a two-way dialogue. And, by this point in the book, you may have noticed you have been provided with sample questions to use with your mentee on each specific step of mentoring. That is no coincidence. Questions both create and change a conversation.

How you word your questions will determine where your mentee’s attention gets focused; so, proceed thoughtfully. For example, the field of Appreciative Inquiry demonstrates that positive questions lead to more favorable and expansive outcomes (Whitney and Trosten-Bloom 2003). In your mentoring, questions are used to invite learning, gather information, and stimulate thinking. They can help you maintain momentum, demonstrate interest, and resolve misunderstandings. They are used to spur reflection and introspection, change perspectives, infuse hope, and create new solutions. This list could go on and on. Your ability to elevate the power of questions can determine your success as a mentor. But first, you need to know the right type of questions to ask.

Determine the Right Type of Questions to Use

A while back, during a group conversation among scientific pharmaceutical leaders who were learning to deepen their mentoring skills, Sophie shared her frustration that using questions was only making the mentoring process more challenging. I asked, “Can you give us background about the situation and examples of questions you used?” Sophie went on to describe that her risk-averse mentee, who worked in another research department of their company, had a repeated pattern of approaching his clinical trials too narrowly, leading his study designs to be rejected or reworked. The nature of her questions to him were: “Have you tried using the Johns Hopkins guidelines?” “Would speaking with Kim help you see the trial differently?” Once she explained this, we could understand that she was using questions to hold back on her usual directive approach (a good thing); yet, we could also surmise that these were not the right questions to help expand his thinking about establishing the right framework for the study.

To avoid Sophie’s mistake, make your questions development-worthy. The key is to consider the “quest” of your question. What do you want to achieve in this part of the conversation? What do you want your mentee to think about? In this case, Sophie wanted her mentee to reflect on the breadth and scope of the clinical study so that its outcomes could give maximum usefulness to the company, without overcomplicating or overspending. It is a tricky balancing act, and one he had not yet mastered. Her old tendency would be to simply tell him the reasons why her design suggestion would work; but she now knew he would not internalize the skill nor be able to successfully design on his own. Thought-provoking questions the group suggested she use included:

• “What assumptions need testing to identify the best objectives for this study?”

• “What elements need to be in place to give the department maximum return from the study?”

• “What are the most effective ways to determine optimal criteria for the study?”

There would be no quick answers, and the questions may even require him to think about it and come back to the next meeting with the answers. Not a bad thing, since he would spend the next couple weeks making a change in his thought process that could serve him well in the years ahead.

Ask the question that fits the need in that part of the conversation. Take note that a question worded to receive a yes or no response (for example, “Did you review the checklist?”) is hardly ever used in the midst of a meaty mentoring conversation. The mentee’s answer would start and end with that single syllable. Instead, you want questions that lead further into a thoughtful discussion.

A useful way to think about mentoring questions is how they fit into the following four types shown in Figure 6-1. Often, from left to right, these range in complexity and thoughtfulness required of the mentee to formulate the response.

FIGURE 6-1

FOUR TYPES OF QUESTIONS TO USE IN MENTORING

Promote Clarity

These questions are used often at the front end of a conversation to lay out the facts or observations and ensure you both have a shared understanding. They can help establish a chronology of events or interactions, and can also spur a new realization of what occurred for the mentee. For example,

• “What is the target date for delivering the report?”

• “What is the expected revenue?”

• “Who is the intended audience for the report?”

• “Who have you spoken with so far, and who is next?”

Questions focused on clarification are important for alignment between the two of you, and form a good basis for further discussion. These also help to check your own assumptions about what might be going on.

Illuminate Perspective

Sometimes a mentee can believe their way of seeing things is standard—the way everyone else views it, too. Help your mentee to appreciate their stance relative to others. For example,

• “Max, this step in the project is top priority for you; how does Tara view its priority?”

• “How will the department managers view your approach as contributing to this quarter’s objectives?”

• “Josie, your solution is quite tailored to Jackson’s needs; how will your team be able to replicate this solution for other clients?”

The goal of these questions is to help the mentee see a situation from many angles, both with the immediate issue and others that follow. In other words, you are encouraging a habit to move outside their own box, broaden their viewpoint, get into someone else’s shoes, or consider how well (or not) their approach aligns with that of others.

Deepen Self-Awareness

This line of questioning can be more sensitive for your mentee and more challenging for you to ask. They might feel vulnerable during this part of a conversation, not wanting to reveal themselves. As we have discussed, it requires trust and safety within the relationship; otherwise, they may not be fully responsive to your questions. If you are unsure, tread lightly or hold off for another time, rather than do damage (Guiding Principle #2: Create a conversational safe space). You might ask questions such as:

• “Rosa, what were your assumptions going into the negotiation?”

• “How were you thinking and feeling just prior to the interaction?’

• “Saeed, how do you believe your perspective affected your stance with the client?”

• “What impact were you hoping to have? Do you believe you had that impact? Why or why not?”

These questions help the mentee to see how their mindset or emotional state may have influenced the outcomes—for better or worse. You can take that even further by asking whether they have had a similar circumstance previously, and have them describe it. Then, there is a potential to see an ongoing pattern, a moment for increased self-insight.

Bridge Actions to Impact

After your mentee has perspective and self-insight about the situation, they are ready to move on to what they can do to produce more effective results. These are high-gain questions that ask the mentee to do some forward thinking. It combines considering their new actions along with the desired end results. These questions have two parts: (1) What behaviors or actions are needed on the part of the mentee to (2) have results that target a larger outcome than the mentee had previously considered? Of course you can ask these questions at any time, but their responses will be more powerful once they have perspective and self-awareness. That’s the beauty of building your line of questions as you go, and possibly over a set of conversations, rather than all at once. Sample bridging questions include:

• “What steps can you take to put the client at ease and then willing to move onto the retooling of their process?”

• “What will be required of you to guide the team’s effort to produce a more innovative solution?”

• “What sequence of actions with your manager will help him work through his objections, and then encourage him to give you a role on that task force?”

There is no one right question that needs to be posed for each circumstance. If a question you asked seem to fall flat or took a wrong turn, no worries; try again with another. Mentors, even experienced ones, write some useful questions in advance of their upcoming meetings. Tool 6-1 provides recommendations on how you might use each type of question during your mentoring conversations.

TOOL 6-1

SUGGESTIONS FOR USING FOUR TYPES OF QUESTIONS DURING MENTORING CONVERSATIONS

Layer Questions for Bigger Outcomes

Have you ever thought about the number of sequences that can result from shuffling a deck of 52 cards? Unless you have Googled this, you may be shocked (like me) to learn that the number is far greater than the number of stars in the universe, or grains of sand on our planet. Considering the number of possible circumstances you will encounter as a mentor, if you want to know the right questions in the right sequence to ask, it is impossible to respond with certainty. Instead, you learn the general principles of working with the cards you are dealt, and become more expert in recognizing what approach to take in given situations.

For a productive conversation, using questions to clarify the situation and gain alignment between you and the mentee is a great way to start. Though it may seem obvious that one question follows another, a successful approach is to be intentional yet flexible. As the conversation builds, questions should be geared to the lessons the mentee has asked to learn. Layering a sequence of questions will help to expand the conversation and move it to a more valuable outcome. You may not always know where the conversation will land, but carefully pushing forward with a series of questions enriches the discussion.

As an example, I had a mentee who complained about not getting enough growth in her job. “I want to learn how to get my manager’s support for further development opportunities,” she told me. After a “dumping out” session with me about her manager, I could have taken the conversation in a number of directions; yet, I selected questions that fit with her stated development goal. I asked questions to illuminate perspective, for example, “How do you think your manager views your readiness to take that next step?” and questions to increase self-awareness: “How do you prepare yourself for conversations with him about this? When you raise this subject with him, how do you think you are coming across?”

I layered a number of different questions that called out perspective and self-awareness from different angles. After two conversations of this type, she reported a breakthrough in her perception. She realized she had been whiney with him, and her boss probably felt cautious about putting her in front of larger groups. Over time, she changed her behavior and one day, seemingly out of the blue, her manager offered her the developmental assignment she had hoped for. Real progress, and very satisfying to me, as her mentor.

When your conversations with your mentee have been complex or you feel stuck about what questions to ask, try working out your questions in advance of the next meeting. Sit down at the computer or with pen in hand, review their goals, consider the four types of questions and how they are used, then brainstorm a bit. It won’t take you long, but the result can totally change the conversation or even facilitate a breakthrough. Have these questions ready, but not necessarily committed to memory, because the flow of the conversation helps you to tailor what you will ask.

While many people do not put much effort into asking questions and prefer to “tell versus ask,” in your pursuit of ever-increasing mentor mastery, you know the power of posing questions effectively. Tool 6-2 offers tips to consider when layering questions.

Consider Fredy, who is mentoring Jorge. Fredy sensed that Jorge had become obsessed with delivery of a strategic recommendations report for his client, to the exclusion of all his other work. Being diligent and knowing he was the department expert on these analytics, Jorge felt compelled to work all hours to get this report together in the next few weeks. Jorge had explained the importance of this work to his other clients, boss, and co-workers, but was still getting pressure to get the other work completed. What questions might Fredy brainstorm in advance of their next meeting? What would you add to the list?

TOOL 6-2

FOUR ACTIONS FOR LAYERING QUESTIONS FOR BIGGER OUTCOMES

• “Jorge, what’s been your approach to handling your workload this month?” (for clarity)

• “How can you confirm that what you are putting into the report is on target for the client’s interests?” (for perspective)

• “Jorge, you report being totally obsessed by this project; how has that affected your overall presence at work?” (for self-awareness)

• “What has happened for you at other times when you experienced being so consumed by a project?” (for self-awareness)

• “How can you work with your manager or others to get support on delivering against your top priorities?” (for bridging behaviors to action)

Be Respectful When Asking

In addition to what kinds of questions to ask, how we do the asking is equally crucial. Ever feel jabbed or interrogated after someone asked you a line of questions? You may have gotten the feeling the person was not really that interested in you; more just serving their own curiosities or interests. How do you want your mentee to feel as a result of your next conversation?

Your mentee’s willingness to engage fully in the questioning rests on their perception that this will lead to a positive or productive outcome. They suspend any doubt about where you are headed and trust your intentions. In short, they feel respected. You lead not just from your head, but also your heart, being considerate and pausing to take in their reactions. This is especially needed when questions get into more complex and sensitive content. Tool 6-3 offers five Bes to consider when thinking through this line of questions.

TOOL 6-3

THE FIVE BES OF RESPECTFULLY ASKING QUESTIONS

• Be authentic. Questioning is best done with a sincere interest to hear what the mentee has to say. Your genuine interest makes the conversation natural and keeps you invested, and your level of interest will be transparent to your mentee. In addition, your tone of voice, which is picked up by the mentee in the transmission, reflects your involvement, whether serious, spirited, curious, or concerned. • Be brief. An effective question fits in with the flow of the conversation and stands on its own. There is no need to have a long preamble to the question followed by an explanation. That added content around the question can become the focus of their attention rather than the question itself. • Be patient. Thoughtful questions are intended to yield thoughtful answers, which can take time to formulate. Often the question can engage your mentee in several ways, causing them to consider emotion, perspective, and behaviors. Exploring all of these factors will not necessarily be top of mind for them. Allowing silence and giving them time to work it through adds real value. • Be safety oriented. Opening up exploration with questions can feel risky to the mentee. Safety in the relationship is one of the hallmarks of the mentoring relationship and what makes it so unique from other relationships they have at work or elsewhere (Guiding Principle #2: Create a conversational safe space). At other times, they may experience judgment, competition, or performance expectations, but not from you! • Be open to any answer. Your mentee’s response, whatever it is, is exactly what you are looking for. Allow it to surprise you. You may have thought you knew the answer, and now your mentee is saying something altogether different; that’s a discovery bonus for both of you. If your mentee does not have an answer at that moment, that’s fine, too. If it’s an important question, they will think about it and come back to it another time.

Listen With Interest and Compassion

Leading a mentoring program for over a decade, I find it both pleasing and disconcerting to have mentees and mentors tell me (with great enthusiasm) that their partner is the perfect match. It is wonderful to know that our mentoring program team did an appropriate pairing, they like each other, and they will want to do what it takes to dig in. On the other hand, I worry that they could fail to see how different they are from each other. Worse, they might assume they are “on the same wavelength.” This could cause the mentor to take too much for granted, or the mentee to believe they are fully understood. This can lead to cracks in the relationship, a loss of trust, or diminished energy.

When you effectively use the counterpart to questions—listening—you avoid this misstep. Remember the adage, “We have two ears and one mouth so that we can listen twice as much as we speak,” by the Greek philosopher Epictetus, who lived over 2,000 years ago. I would take that even further: Yes, take the time to listen, and also focus on the manner in which you respond to what you are hearing.

A key to listening well is to internalize that the focus needs to be on the mentee and where their interests are. It is not a typical give-and-take conversation. You do get a lot of rewards from the conversations, but these discussions are not about advancing your interests and curiosities or getting them to where you think they ought to be (Guiding Principle #1: Start where your mentee is). As part of a discipline named Conversational Intelligence, the practice of “listen to connect” is all about allowing an open space for what is being said, without judgment or expectation. And, it invites you to explore further for full understanding (Glaser 2014). Learn to listen well, and practice on family members, friends, co-workers, and clients. It will pay big dividends in those relationships as well.

Consider the following advice for listening with interest and compassion.

Welcome the Response

Now that you opened up the air time for your mentee with your question, how will you take in their response? Receiving what they have to say is the privileged part of this work; they may have no one else to share this with. You become the one who will help them make sense of it and use it for further growth. If they are exploring a knotty challenge at work that you identify with, you might be all ears and highly engaged—great eye contact, appropriate body language, and so on. If they are complaining about something you consider trivial, would you tend to tune out? Consider this: Joelle, a busy senior marketing manager, told me, “When my mentee started emphatically telling me the fourth version of the same story he was having with noncollaborative co-workers, I resorted to pinching myself to stay tuned in.” Joelle told me she then diverted the conversation to a subject she considered more productive for the mentee (and easier to listen to). Big mistake; her mentee then came back to the story for a fifth time.

Check Yourself

What are you thinking about and feeling as your mentee responds to the question? Lukas, an experienced mentor, takes a second or two to “go internal” and be aware of his own thoughts and reactions. Though Lukas might be formulating a solution for the mentee or having his own opinion about the mentee’s manager, he puts that to the side and stays tuned into the mentee. As he listens further, Lukas can separate his internal messages from what his mentee is expressing. The result? Lukas’s mentee reports that the very high level of attentiveness increases her experience of truly being heard and understood.

Attend to All the Moving Parts

Your mentee wants to know that the complete picture of what they expressed is understood by you. In their fast-paced world, when many elements of work are disconnected, this may be the only time they can get that treatment. Mary, a seasoned mentor, asked questions to round out her understanding of Bruce’s concerns about his challenges on a multidisciplinary team. She then had him physically retrace the chain of events on a whiteboard. This affirmed to Bruce that Mary had received the complexity and was in a better position to help sort things through. When a mentor fails to do this, the mentee will bring up the situation again; or worse, the mentee will move on, but take note that the mentor did not grasp the full picture.

Recognize Their Emotion

Because mentoring conversations are often geared toward working out mentee challenges, their conversations can be emotionally charged. Put yourself in their shoes and lead with empathy, whether you agree or not. Recognize their emotion and the associated entanglements. In the end, because you have listened with curiosity, which encouraged them, and were compassionate about their discomfort, they can move on to explore further. They will be open to travel into some of the scary unknowns. That’s how self-discovery happens. For example, when Joelle had the opportunity at the next mentoring meeting to discuss the co-worker situation with her mentee, she listened with compassion and encouraged him to say and explore more. He talked it through and then suddenly realized that because he felt far more experienced than his co-workers, his interactions with them had been curt and somewhat condescending, which was likely at the base of the dysfunctional relationships. This type of insight is golden. Good job, Joelle!

Listening well can make all the difference. When a mentee experiences you as fully present and taking in the multiple dimensions of what they are saying, they will trust you and take risks to explore. And, when a mentee experiences compassion, they leave the conversation feeling lighter and more confident. The conversation can be therapeutic, without being therapy.

Ask Yourself Questions to Enrich Your Mentoring

If questions help our mentees gain clarity, illuminate perspective, deepen self-awareness, and bridge action to impact, they can do the same for us. The best mentors are in a continuous growth mode. I have worked with mentors who are managers, sales people, C-suite executives, scientists, engineers, and leadership coaches. While they love providing a benefit to their mentees, they are also in it for the learning they receive from the experience. By sharpening their mentoring skills, they go back to their day jobs with added capabilities acquired through their role as mentor.

If you had a coach mentoring you while you were mentoring someone else, what questions might they raise about your experience? How could they help increase your learning, so you could do a better job? What insight could they nudge about your effectiveness in both asking questions of your mentee and listening with compassion? What new self-awareness could they prompt? Consider Marshall Goldsmith, often referenced as among the world’s top leadership coaches, author of 35 books (two of which are Amazon’s top selling leadership books of all time). Goldsmith has hired someone to call him each day to ask him growth-provoking questions (Morgan 2016). If it’s good enough for Goldsmith, a premier coach, it can work for us, too!

Some mentors are fortunate to have peer mentors who work with them in this way, and I highly recommend this arrangement. However, it is also a very useful approach to have questions for yourself that you have developed. It may seem a little odd at first, as it is more straightforward to simply reflect on what transpired with your mentee and take notes; however, as I described earlier, questions create an engaging dynamic.

Tool 6-4 provides a starter list of questions to ask yourself. Add your own questions that are relevant to your current mentorship.

TOOL 6-4

SAMPLE QUESTIONS TO ASK YOURSELF TO ENRICH YOUR MENTORING

• Is my view of my mentee’s goals consistent over time, or is it changing? • What is my understanding of the significant aspects of my mentee’s work life? • What is the comfort level in our conversations—mine and my mentee’s? • If my questions are not having the desired impact, what might be contributing to the situation? • What is the evidence that my mentee trusts me and is willing to take risks in our conversations? • What is evidence that I am using the four types of questions appropriately (or not)? • How does my level of trust in my mentee impact my effectiveness with questioning and listening? • How have I moved past my own biases about my mentee’s challenges, and focused on developing a solution that could be theirs alone? • What is the evidence that I am listening to my mentee with compassion (or not)? • What am I learning about myself in this process of questioning and listening? • Other questions you have developed:

The Next Step

In these last few steps, we have identified ongoing actions (leveraging experiences, expanding growth, and elevating the power of questions) that are used throughout the mentoring process to truly distinguish you as a masterful mentor. Likewise, the next step continues to add depth and breadth to your skill. Extend and cement the development by guiding your mentee to experience a variety of learning approaches. Dig into step 7 (Diversify the Development Methods) to understand the additional learning approaches that will augment your mentee’s growth and make the mentoring process even more engaging and memorable.