Ask More — Book Summary and Review

Ask More — book  cover

Ask More — The ability to know what to ask and how to ask is a crucial life skill and this book is a great help on that. Former CNN anchor and White House correspondent Frank Sesno spent his career asking questions.

Based on his “taxonomy of questions,” he explores the value of inquiry and its power when properly put to use. Each chapter covers a different type of question, including “diagnostic, bridging, confrontational, mission, interview, legacy,” and more.

I would rate the book at 8/10 purely on the wonderful insight the book covers.

Ask More —Key points

  • Diagnostic questions help you get to the heart of the matter and zero in on the problem.
  • Bridging questions act as connectors between a reluctant subject and needed answers.
  • Confrontational questions demand accountability and uncover the truth. I used too much of this. Currently learning to take a step back and try to be patient. It’s harder than it seems.
  • Mission questions identify shared values and goals.
  • Interview questions can be helpful or can intimidate both employees and employers. But when used properly can produce meaningful revelations.
  • Legacy questions give you the opportunity to reflect back on your life.
  • Asking questions promotes personal growth.

Ask More — Diagnostic Questions

Essential when we need to assess a situation quickly. Some professionals such as air traffic controllers, reporters, health care providers, plumbers, electricians and the likes do this for a living.

How to ask diagnostic questions

Diagnostic questions start out open-ended, but they gradually become more close-ended as you home in on the answers you seek. To ask diagnostic questions properly, pace the progression you want to use as you narrow down your inquiries.

Outline your diagnostic questions in a logical sequence with the goal of describing and defining an issue.

Useful strategies for arranging questions to diagnose a problem include:

  • Ask for the most damaging or negative information first.
  • Review the pertinent history to provide a baseline of experience.
  • Ask the same or similar questions for confirmation.
  • Request different sources for clarification.
  • “Connect symptoms and specifics.”
  • Challenge the experts. A second or third opinion may be necessary. (*Note: Thread carefully as not to undermine the experts)

Professionals in any field are experts at narrowing down options to find solutions.


You might have to ask –

  • What are you telling me?
  • What does this mean?
  • What aren’t you telling me?

List each question you want to ask.

Don’t let your expert get away with being evasive.

Ask More — Bridging Questions

The judicious use of bridging questions can open doors. Know what you want and avoid triggers and accusations.

Instead, affirm and validate the person you are questioning.

The book shares an awesome example on the “bridging questions” based on the work of Barry Spodak.

Barry Spodak is a master of bridging questions. He trains FBI and Secret Service agents and knows how to assess dangerous situations. As a grad student in the late 1970s, Spodak was interested in violent criminals found not guilty because of insanity. He worked at St. Elizabeth’s Hospital, then a premier psychiatric facility. To get admitted there or to any psych ward, patients had to be a danger to themselves or others. But, at that time, little research validated the accuracy of assessments of how much of a threat someone posed.

Spodak’s patients included John Hinckley Jr., who thought he could impress actress Jodie Foster by killing then-US-president Ronald Reagan, which Hinckley attempted on March 30, 1981. Hinckley said little in group therapy sessions and didn’t interact with other patients. Spodak got him to open up in one-on-one discussions after group therapy by listening and speaking softly. Because they were about the same age, Spodak felt Hinckley didn’t feel threatened by him.


Spodak follows Nobel-Prize-winning psychologist Daniel Kahneman’s theories about how the human brain works. Kahneman says the brain has two main systems: System One kicks in when you make decisions quickly and easily without much thought – like a type of autopilot. In System One, you are relaxed and comfortable. But System Two represents your brain’s warp speed, triggered when you must respond to difficult, frightening, unfamiliar or complicated situations.

Spodak’s work involves helping law enforcement officers shift their subjects from System Two to System One. He begins by asking suspects innocuous questions about shared experiences.

For example, if you are about to interrogate a man in his house and you notice a piece of art on his wall, you might start by asking him who the painter is or why he bought the art. This gives your subject the opportunity to discuss something he cares about in his own space. Such bridging questions are like social icebreakers.

“The principles behind bridging questions support a specific and clear outcome: getting a closed person to open up.”

Other tactics for moving people into System One thinking include using “micro-affirmations” – that is, asking questions without question marks. Micro-affirmations are small gestures designed to affirm or validate the other person.

These might include leaning forward, making eye contact or offering a verbal confirmation such as, “That’s really interesting” or “That’s a good point.”

*Definition: Questions without question marks are declarative statements that sound less threatening than typical questions.

These may include statements such as, “Tell me more. Explain that to me. Go on.” Such conversations encourage someone to open up.


Ask More — Confrontational Questions

“Sometimes you can’t build bridges. You’re not looking for empathy or trust. You just need an answer.”

Use confrontational questions to demand accountability.

They work best when you have a specific goal, know your facts, ask precisely, care about what you’re asking and expect hostility – perhaps in the form of defensiveness, confrontation or evasiveness.

Politicians and celebrities may try to dodge questions rather than giving a straight answer or admitting faults.

On “Confrontational Questions”, let’s consider the example of Jorge Ramos;

Jorge Ramos, an anchorman for the Spanish-language network Univision, known as the “Hispanic Walter Cronkite,” doesn’t pull any punches with world leaders. Despite his years of confronting Latin American dictators and others in power, even Ramos was surprised when he was thrown out of a news conference during Donald Trump’s presidential campaign.

Trump had made headlines by saying, “Mexicans were bringing drugs. They’re bringing crime. They’re rapists. And some, I assume, are good people.” Ramos wanted to ask Trump about his plan to build a wall along the Mexican border and his immigration policy.

Ramos, a Mexican-American immigrant himself, sought answers to questions that directly affected him. “I have a question about immigration…,” Ramos began. Trump told him to sit down and didn’t call on him. Ramos continued, “I’m a reporter, an immigrant and a citizen…I have the right to ask a question.” That was as far as he got before Trump had his security people escort Ramos out.  After a few minutes and some prodding from other reporters, Trump let Ramos back in. Ramos continued with his line of questioning. He said, “You cannot deport 11 million undocumented immigrants. You cannot deny citizenship to the children of these immigrants.” They continued in a heated exchange.

Ramos feels comfortable confronting those in power because of his background. He had a strict father, attended Catholic school and grew accustomed to facing up to authority figures.


Mission Questions

When you define your mission, you clarify your goals, encourage your team members to work together and forge connections with others.

The example in the book on “Mission Questions” is based on Ben Cohen and Jerry Greenfield

Ben Cohen and Jerry Greenfield first met in seventh-grade gym class. They admitted to being the “slowest, fattest kids in the class” and, by high school, they were best friends. After Jerry graduated from college (Ben dropped out), they briefly considered a bagel business before realizing the equipment was too expensive.

They both liked ice cream, so they took a $5 correspondence course in making ice cream. They started their company, Ben & Jerry’s, with a sense of purpose and built a successful firm based on their mutual values and mission.

In 1978, they opened their first store in Shelburne, Vermont. By 1990, their company had grown around a set of shared values gleaned through employee surveys. They publicly promoted a variety of causes by putting their names on ice cream packages. They also made sure their compensation plan reflected their beliefs.

For instance, one Ben and Jerry’s rule says the bosses can’t make more than five times the lowest employee salary.

“Mission questions ask more of everybody. They help you draw people into a genuine conversation about shared goals and what everyone can bring to the task.”


Ask More — Interview Questions

People tend to fear interviews. It could be tough on both the interviewer and the candidates.

Job candidates are afraid of giving the wrong answer and looking foolish; supervisors fear not asking the right questions and hiring the wrong person. Successful job interviews feature a range of queries meant to gauge an applicant’s talents, abilities, personality, judgment, and so forth.

Some questions will be straightforward – such as “Why are you interested in this position?” or “Why should we hire you?” – and some won’t.

Candidates should prepare for interviews and be ready to respond to questions about their successes and failures. The interviewer may ask, for example, how they handle failure, which is useful for assessing whether they’re a good fit.

Candidates should be prepared, in turn, to ask interviewers questions that convey their interest in the job, department and company overall.

Examples might include: “How has your digital strategy affected your retail strategy?” or “How do your employees translate the corporate social responsibility you promote into their own work lives?”

Well-prepared candidates can ask relevant questions about the company to demonstrate their interests and passions. Never start by asking questions about salary or benefits.

Job interview questions come in one of these formats:

  1. introducing yourself,
  2. sharing your vision,
  3. acknowledging setbacks and challenges, and
  4. answering “curveball” questions.

Curveballs are designed to test quick thinking, spontaneity and creativity.

Such questions can “come out of nowhere,” and are designed to provoke an unrehearsed response, a bit of humour or some humanizing insight into the candidate’s personality and thought process.

Job interviewers generally ask candidates to look back on what they’ve accomplished or to discuss how they’d handle a hypothetical situation.

“Some of the most important questions in a job interview come from [the applicant’s] side of the table.

Curiosity and compatibility are mutual.”

Ask More — Legacy Questions

You may reach a point in your life when you want to reflect back on what you’ve done and whose lives you’ve touched. This is the type of questioning I asked myself when I decided to ditch my online business for blogging. What’s my legacy will be? How would my existence affect or improve others? Is the world a much better place when I’m on it? Or would the world be better off without me? Tough decision with some significant financial impact. But I’m hopeful that I’ve made the right decision.

Legacy questions centre on meaning, spirituality, lessons learned, regrets and gratitude.

These questions might come after a major illness or at the end of life, and to be honest I’ve faced 4 near-death experience in my lifetime – 2 times almost drowned and 2- car accidents. This leads me to question “What have I accomplished?” and “How do I want people to remember me?”.

They encourage reflection and allow you to take stock of your life. On top of that, the type of books I read also prompts me to reflect and consider such queries. Among awesome reading materials for life purpose, I would recommend, read Man’s Search for Meaning by Viktor Frankl and The Secret Letters Of The Monk Who Sold His Ferrari by Robin Sharma. (*Note: Yes, letters of the monk who sold his Ferrari, rather than the original, The Monk Who Sold His Ferrari)

Legacy “questions open the door for reflection and resolution.

They seek context.”



In summary, it’s an awesome book, hence the 8/10⭐. It will be an awesome weapon in my arsenal 🙂

Can’t wait to put this knowledge to test and see up to what extent I can put it to use.

Read Ask More


Author: Muhamad Aarif

A notorious book addict by night and an oil and gas executive by day. As Mark Twain said, "The man who doesn't read good books has no advantage over the man who can't read them." So, read, read, and read some more.

Leave a Reply

This site uses Akismet to reduce spam. Learn how your comment data is processed.