top of page
  • Toby Sinclair

Summary: Ask by Jeff Wetzler

 

📚 Should You Read This?


👋 Hey - I'm Toby. This summary wasn't written by AI. I'm a real leader, managing teams in large organisations. I read to solve tough problems. I share book summaries weekly to help other leaders tackle scary challenges.

Toby's Rating: 9/10


Asking is a Superpower. I believe it. Jeff Wetzler does too. Most people think they are good at asking questions. The reality is that many of us ask crummy questions, most of the time. This isn’t a skill you learn at school so for most leaders, asking quality questions isn’t a skill that comes naturally. Ask by Jeff Wetzler is your playbook for better questions and importantly, better results!


 

✅ Toby's Top Takeaway from Ask by Jeff Wetzler


I walk into the bookstore. I see it on the shelf. The book I wish I’d written.



It’s five-step approach is exactly how I lead like a coach:

  • Step 1: Choose curiosity.

  • Step 2: Make it safe.

  • Step 3: Pose quality questions.

  • Step 4: Listen to learn.

  • Step 5: Reflect and reconnect.


It’s not the first time I’ve experienced this deflationary feeling.



Every book I would write seems to have already been written.


I’m sure this feeling shows up for you too. You think of a great business idea, only to google it and find out someone else has already thought of it.


I’m still learning how to overcome it.


I just started “How To Tell a Story” by The Moth. I'm hopeful it may have a solution.


I was drawn to it from this quote:


“You have important stories to tell. They are stories no one else can tell. But you have to be willing to do the work of developing them - and then work through your fears to tell them.”

One day it will be different.


I will walk into a bookstore and say “That is the book I wrote!”


💡 3 Big Ideas from Ask by Jeff Wetzler


By asking more quality questions, you will get these benefits:


  1. You’ll create better results. You’ll make smarter decisions based on a full and accurate range of insights that you’ll discover. You’ll co-create more innovative solutions. You’ll also get unstuck from conflicts more quickly and spend more of your time being productive and creative.

  2. You’ll forge stronger relationships. You’ll connect more deeply with people, whether or not they look like you, talk like you, or think like you. You and others around you will be rewarded by unblocking the flow of information. Greater trust and connection will flourish.

  3. You’ll grow and improve faster. You’ll hear more honest feedback, you’ll get helpful suggestions, and you’ll become aware of your blind spots. When learning becomes your way of operating, it feels much safer to experiment and even falter. Relieve yourself of the burden of pretending you have all the answers, and you’ll grow in profound, even unexpected, ways.

 

💬 Best Quotes from Ask by Jeff Wetzler


Asking BIg Idea

Asking is the behaviour that unlocks everything.
In one study of managers over 85 percent of people interviewed admitted to remaining silent with their bosses about a concern on at least one occasion, even though they felt the issue was important. What’s more, nearly three-quarters (74%) of those people said that their colleagues were also aware of the issue and also felt uncomfortable speaking up. And when asked if they felt comfortable speaking up in general about issues of concern, nearly half (49%) of employees said that they did not. Imagine the cost to an organization when half the people don’t share information or opinions about what concerns them!
The biggest and most common reason that people decide to hold back from sharing what they really think, know, or feel, even when it would be incredibly valuable for you to hear. They could be worried that what they have to say will irritate, upset, discourage, burden, or embarrass you. They might worry about the consequences for themselves—what if you judge or shame them, or even punish them for sharing? They could also worry about the potential harm that could be done to their relationship with you, from creating unnecessary awkwardness to damaging it irreparably.
“Listening to learn” means: Intentionally opening ourselves to all that another person shares, in order to understand what’s essential about their message and experience.
We are taught how to read, to write, to speak and defend our opinions, but not to listen. Worse, we are taught to associate speaking with intelligence and ambition but staying quiet with being dumb or disengaged.
Increased curiosity in the organizational setting has been linked to richer information exchange, more creativity, and reduced conflict. Organizations that are better at learning from their members are better at adapting within uncertain environments, a critical skill in a world characterized by rapid technological development, cultural change, and environmental precariousness.


💡 More Ideas from Ask by Jeff Wetzler


Asking is a Superpower


Asking is the behaviour that unlocks everything.

Asking Questions is a Superpower because:

  1. When we all have this superpower, we’ll be more informed, more creative, and more connected. The world will be a better place.

  2. This is a learnable kind of superpower—not like shooting spider webs from your fingers or flying over buildings. You just have to master some specific practices.

  3. Most people haven’t learned these practices. And herein lies an incredible opportunity.


The Ask Approach:

  • Step 1: Choose curiosity. I’ll guide you through a powerful mindset shift that will prevent you from making the quick assumptions that limit learning and damage our relationships.

  • Step 2: Make it safe. Lots of people withhold, even if you do ask them questions. This is a seminar on how you can support others to open up and say what they’re afraid or unwilling to say by making it more comfortable, easy, and appealing to share.

  • Step 3: Pose quality questions. Discover the highest-impact questions you should be asking, but aren’t—complete with scripts, workarounds, and follow-up ideas.

  • Step 4: Listen to learn. We all know it’s important to listen to what people are saying, but this practice triples the information you’ll be able to hear and ensures you’ve got the right takeaways.

  • Step 5: Reflect and reconnect. You’ll learn how to evaluate which insights have real value—and then you’ll translate that value into action and take steps to keep the learning momentum going and deepen your relationships along the way.


Benefits of the Ask Approach:

  1. You’ll create better results. You’ll make smarter decisions based on a more full and accurate range of insights that you’ll discover. You’ll co-create more innovative solutions. You’ll also get unstuck from conflicts more quickly and spend more of your time being productive and creative.

  2. You’ll forge stronger relationships. You’ll connect more deeply with people, whether or not they look like you, talk like you, or think like you. You and others around you will be rewarded by unblocking the flow of information. Greater trust and connection will flourish.

  3. You’ll grow and improve faster. You’ll hear more honest feedback, you’ll get helpful suggestions, and you’ll become aware of your blind spots. When learning becomes your way of operating, it feels much safer to experiment and even falter. Relieve yourself of the burden of pretending you have all the answers, and you’ll grow in profound, even unexpected, ways.


Tangible outcomes from the Ask Approach include:

  1. Discover where you really stand in a critical relationship… and what you need to do to make things right.

  2. Break out of a persistent conflict through finding better, more mutually satisfying outcomes than either of you could have imagined

  3. Identify the fatal flaws in your plan before you waste a ton of time and resources implementing it

  4. Gain insight into why people treat you the way they do… and how you are affecting them

  5. Help and support others you care about (teammates, family, friends) in whatever ways they really need, even if they’re hesitant to ask for it

  6. Unite people with diverse perspectives, to create deeper connections, accomplish amazing things, and draw strength from everyone’s differences


Uncovering Hidden Truths

What do you most need to know that people are least likely to tell you?

Every leader faces a phenomenon called “The Unspoken”. This refers to the thoughts, feelings, and ideas that others around us hold but too often don’t share. Asking helps people share important, unspoken truths.


In one study of managers over 85 percent of people interviewed admitted to remaining silent with their bosses about a concern on at least one occasion, even though they felt the issue was important. What’s more, nearly three-quarters (74%) of those people said that their colleagues were also aware of the issue and also felt uncomfortable speaking up. And when asked if they felt comfortable speaking up in general about issues of concern, nearly half (49%) of employees said that they did not. Imagine the cost to an organization when half the people don’t share information or opinions about what concerns them!


Four things most people withhold:

  1. What they struggle with… and what help they need

  2. What they really think or feel about an issue… and where their views come from

  3. Their honest feedback for you… and suggestions for how you can improve

  4. Their most audacious ideas and dreams… which they fear might sound crazy


Overcoming Barriers

Why don’t people tell you what’s most important for you to find out?

Common reasons people hold back:

  1. They’re worried about how what they have to say could negatively affect you, them, or your relationship.

  2. They can’t find the right words because they lack the skills or language to express themselves in ways that feel acceptable, or because they are still processing internally.

  3. They don’t have the time or energy to share.

  4. They think you’re not truly interested in hearing from them.


Barrier 1: They Are Worried About the Impact of Sharing


The biggest and most common reason that people decide to hold back from sharing what they really think, know, or feel, even when it would be incredibly valuable for you to hear. They could be worried that what they have to say will irritate, upset, discourage, burden, or embarrass you. They might worry about the consequences for themselves—what if you judge or shame them, or even punish them for sharing? They could also worry about the potential harm that could be done to their relationship with you, from creating unnecessary awkwardness to damaging it irreparably.

Ninety-seven percent of people who notice a smudge on the face of someone near them won’t mention it, according to one study. And the number one reason people stayed silent? They felt bad about how saying something might affect the person with the smudge—they didn’t want to embarrass them. How ironic that in trying to be kind and help the other person avoid embarrassment, they let them walk around with a potentially embarrassing smudge on their face!


Barrier 2: They Can’t Find the Right Words


Another reason people hold back from telling us what they really feel, think, or know is that they simply can’t find the right words to express themselves.

There is a reason that an entire industry’s worth of consultants, coaches and trainers are teaching people how to communicate hard things to one another: it’s not easy to do! Finding the right words to express what we are thinking or feeling is a skill, particularly when what we have to say isn’t all glowing. When others aren’t sure how to say what they want to say well, staying quiet can feel like the easier and safer choice.


Barrier 3: They Lack the Time or Energy


Sometimes people hold back because they don’t have the time or energy to share, or they feel that sharing will draw them more deeply into the situation than they are mentally or emotionally prepared to go. This could be because of overwhelm from the stress and pace of life, from burnout at home or work, or from the exhaustion of feeling like they aren’t fully accepted.


Barrier 4: Their Sharing Doesn’t Feel Valued by You


Whether accurate or not, people often believe you aren’t really interested in what they have to say. How do they develop this belief? Let’s take an extreme case—a friend of mine, Michael, had just completed a four-month project as a junior analyst that entailed a lot of unexpected evening and weekend fire drills, work that he thought could have been avoided with some specific changes in how the partner in charge managed the project. So, when it was over, he typed up some constructive feedback, printed it out, and hand delivered it to his boss Doug, saying, “I put together some feedback for you about your leadership of the project.” Doug had never seen a junior person do anything like this. He stood up, took the paper, and said, “Thank you, Michael”—simultaneously ripping it in half and letting the pieces fall into his trash can.


There are three types of curiosity:

  1. Connective curiosity - connective curiosity is a desire to understand more about the thoughts, experiences, and feelings of other people.

  2. Diversive curiosity - the drive for new information.

  3. Epistemic curiosity - a more focused form of curiosity having to do with understanding a particular subject area.


Developing connective curiosity helps you break down barriers.


Make it Safe

How do you make it easier for people to tell you hard things?

It’s important leaders make it as comfortable, easy, and appealing as possible for others to share openly.


Create the conditions so that asking another person to share is less like proposing a cliff dive into icy waters and more like proposing a swim in a heated pool—lower risk, worthwhile, and maybe even enjoyable.


How to cultivate safety:


  1. Create Connection - When people feel connected to you, and you to them, you both feel safer. You can relax in one another’s company.

  2. Find the Right Space - There’s a lot of individual nuance to it, but the bottom line is: Where will they feel most comfortable? What is convenient for them? Would that place be private or open? Inside or outside? Seated or in motion? I try to think about their needs first.


Three reasons people hesitate to open up:

  1. You’re too focused on efficiency. You need answers, now!

  2. You don’t want to make yourself vulnerable. It might not feel good to expose a gap in your knowledge, or to admit that they have information you can’t get anywhere else.

  3. You don’t want to bias them. Many people, especially those in positions of power, are afraid that opening up about their own viewpoint will bias the conversation.


Conversation starters, to make it easier for people to open up:

  1. “If I were in your shoes, I might be feeling frustrated or even resentful. If that’s how you’re feeling, I would understand completely. Please don’t hold back.”

  2. “I realize you might be thinking that I’ve got it all wrong. If that’s the case, I’m ready to hear it and open to rethinking my assumptions.”

  3. “I recognize we come down on different sides of this very charged issue. Whether or not we change each other’s minds, I want you to know that I am sincerely interested in understanding where you’re coming from, and what I’m missing.”


Pose Quality Questions

What questions will best tap into the wisdom of anyone you ask?

We’re all born with the instinct to ask. Kids are natural-born question askers. But by the time we become adults, many of us have stopped asking real questions, other than “Where is the bathroom?” and “Has he lost his mind?”


One poll found that, among the two hundred executives surveyed, only 15 to 25 percent of interactions included real questions.


We worry that asking questions will make us come off as prying or rude. At the same time, we are taught to “perform” confidence and certainty at all times, especially in competitive academic and corporate settings where we face constant pressure to prove our worth. In these environments, asking questions can feel like an admission of imperfection, vulnerability, or ignorance that runs counter to deeply held beliefs about what competence is supposed to look like.


When people are reprimanded or ridiculed for asking questions in school, in their families, or in their workplaces, the dangers of asking come to outweigh the risks. For those in more vulnerable positions, whether due to age, race, gender, or position in the organizational hierarchy, the risk of asking questions can feel even greater and more chronic.


Questions commonly fall into three categories:

  1. Clumsy questions

  2. Sneaky questions

  3. Attack questions


Clumsy questions may be well-intentioned, but their wording immediately closes down the inquiry, preventing learning. These include closed-ended questions, rhetorical questions, and questions that get lost because they’re buried inside statements. Here’s one example: Fred: “We’ve got to raise our prices, right? All our costs are going up, and we’ve got to hold our margin steady.” Renata: “True.” Fred’s got two clumsy things going on here. First, his use of the question “right?” sounds rhetorical at best. The way he phrases the question makes it hard for Renata to do anything other than agree with him. In addition, by following his question with two other statements, he does not give her any room to answer


Sneaky questions, on the other hand, are not designed to learn anything. Instead, they’re designed to influence, convince, or maneuver the other person. We see trial lawyers do this all the time, with questions that lead the witness (such as, “Wouldn’t you agree that…?”). Other times, people are reluctant to assert their views as direct statements, so they phrase them as questions (“ Don’t you think it would be better if you stayed home tonight? The roads are so icy.”). Finally, sometimes people layer question upon question in a strategy called “easing in,” as in the following example: Dante: Do you think the timeline you’re asking for is feasible? Yuki: I think so. Dante: Have you considered the time it will take to set up the project in phase 1? Yuki: Well… Dante: Are you sure we can even get the talent lined up?


Attack questions are weapons we use to pounce on others. Examples of these questions include:

  • “Why would you ever think that’s a good idea?”

  • “How could you possibly believe that?”

  • “Why can’t you be more considerate?”


High-Quality Questions


In contrast, quality questions have the following five attributes:

  1. They signal true curiosity, reflecting a genuine intent to learn from and understand the other person—not to prove a point or influence or fix them.

  2. They are clear and direct, with no hidden, layered, or confusing meanings, so it’s self-evident what the asker wants to know.

  3. They invite honesty by making it as easy as possible for the other person to share openly, regardless of how the asker feels about their answer.

  4. They tap into the other person’s full story—to surface the underlying meanings, reasons, emotions, and experiences.

  5. They create mutual benefit by contributing to a meaningful, two-way dialogue in which everyone learns from each other and leaves the conversation with a better understanding of themselves and the other person.


How to check what you said was heard:

  • “I want to check if I’m communicating clearly. What came through most in what I shared?”

  • “I’m not sure if my intent is coming through, so I want to check: What were your main takeaways from what I said?”

  • “In case I’m not expressing myself well, I want to ask: How are you hearing and understanding what I’m saying?”


Listen to Learn

How can you hear what someone is really trying to tell you?

“Listening to learn” means: Intentionally opening ourselves to all that another person shares, in order to understand what’s essential about their message and experience.

The challenging reality is that most of us were never taught how to listen. One survey found that 96 percent of people think of themselves as good listeners, yet research has also shown that we retain less than half of what people tell us and that the average person listens with only 25 percent efficacy. Research shows that we are actually worse at listening to the people closest to us than to total strangers.


We are taught how to read, to write, to speak and defend our opinions, but not to listen. Worse, we are taught to associate speaking with intelligence and ambition but to stay quiet with being dumb or disengaged.


How To Listen Better:

  1. Ditch the Distractions

  2. Zip Your Lip

  3. Watch Your Face

  4. Paraphrase and Test (I heard this…what did I miss?)

  5. Pull the Thread (Tell me more)

  6. Back Off to Move Forward (Let’s take a break)

  7. Check-In (What was most useful for you?)

  8. No BS (Back to self) Listening. Focus on the other person .


Asking When Leading

How can you unlock the collective genius of your team?

Team members who feel safe admitting mistakes, expressing uncertainty, and communicating openly consistently perform better, learn faster, and are more innovative than those with lower levels of psychological safety.


Increased curiosity in the organizational setting has been linked to richer information exchange, more creativity, and reduced conflict. Organizations that are better at learning from their members are better at adapting within uncertain environments, a critical skill in a world characterized by rapid technological development, cultural change, and environmental precariousness.


In my experience, the most valuable, and essential, source of ideas, knowledge, and information in any organization lies in its employees, particularly those closest to the front lines. Efforts to involve the front line are typically too superficial or disconnected for employees to trust that any time and energy they invest will affect decision-making. Many companies do some version of “ask quality questions” but forget all the other steps of the Ask Approach.


How To Lead By Asking:


  • DO: Reduce the effects of power dynamics as much as possible by acknowledging that you have a dilemma or puzzle and need their partnership to take it on. Name the value you see and place in their perspective.

  • DO: Let them know in advance how final decisions will be made and what roles they will play in making and/ or influencing the decisions. Ideally, let the decisions get made as close to the front lines as you can.

  • DO: Let them in on the challenge by exposing them to all the data points you can, while asking them to help you revise your understanding of the issues by adding additional information that they uniquely see.

  • DO: Empower them to develop new solutions by asking “How might we…” questions and generating as many creative ideas as possible before any ideas are evaluated or discarded. Invite them to prioritize the solutions they see as most relevant and share their reasons why

  • DO: Consistently report back to employees how their ideas and feedback informed organizational decisions. When you can’t act on their ideas or feedback or can’t respond right away, let them know why and what you plan to do next.

  • DON’T: Feel like you need to have all the answers. Instead, bring your thorniest questions to the people who are closest to the action: those on your front line.


How To Become the Learner in Chief:


  • DO: Publicly share your own learning and development goals, needs, dilemmas, and challenges.

  • DO: Foster a culture of openness by modeling vulnerability yourself. Allow people to see you as a full, complex, flawed human being. To the extent that you can, let people in on your process—for example, speaking openly about work or personal challenges you have experienced.

  • DO: Seek feedback and input publicly—don’t just invite it but actively go seek it out. Even if you don’t receive it publicly, reflect on it publicly by sharing what feedback you have received and how you are making meaning of it.

  • DO: Thank and publicly acknowledge those who gave you input. Let them know what you plan to do with the input, and why.

  • DON’T: Expect it to feel comfortable. Asking and learning goes against many norms that suggest leaders need to



📹 Prefer Video?





Comments


bottom of page