Ask More

Anita Brick: Hi, this is Anita Brick and welcome to CareerCast at Chicago Booth. To help you advance in your career. Today, we're delighted to be speaking with Frank Sesno, who is an Emmy Award winning journalist and former anchor, white House correspondent, Washington bureau chief and talk show host for CNN. He currently serves as director of George Washington University School of Media and Public Affairs and is the creator of Anne Frank, which sounds really amazing.

Plant forward, an innovative forum seeking solutions to daunting challenges such as global hunger. And he lives in Washington, D.C. and I didn't mention the book called Ask More. So if we launched into one of the evening students, he asked, what is the goal of a good question?

Frank Sesno: A good question is to solicit information to create a connection to the next question, because the goal of a good question is accompanied by excellent listening.

Anita Brick: I think that goes along with another question that an evening student asked and she said, what components make up a great question? Is it a level of knowledge about a subject that gives you the intuition to ask a great question? Is it a methodology or is it something different?

Frank Sesno: It's actually a lot of different things. And that also applies back to the goal of what is a good question. It's really why I wrote the book. My experience comes out of years of interviewing, years of interviewing for CNN and for other journalistic organizations, years of interviewing live in front of audiences, of interviewing political leaders, some of them heroes, some of them scoundrels, of interviewing business leaders, CEOs, CEOs, Nobel Prize winning scientists.

And what I realized as I thought about it and as I taught a class, is that all interviews are not alike. All questions are not alike. Questions are not merely random acts of curiosity, not if they're done well, if they're done well and thought through carefully, they are tied to specific goals. They are tied to specific outcomes. If they are done well, they contain several components to your evening students' questions of knowledge, curiosity, and connection.

In the book, I create 11 categories of questions. Each one of those categories has a different outcome and goal. Each one of those categories engages different forms of preparation, framing of the questions themselves, and listening skills. So, for example, what I call diagnostic questions, figuring out what's gone wrong here I have three characters in that chapter. They are trying to figure out the problem by looking for the bad news.

So imagine that the goal of that question is to identify and connect symptoms and causes. The components of that particular set of questions would be an interest of curiosity, and making sure that you get a good description of the situation, the symptoms. You get a good sense of history, what's gone on before you get a sense of what the pattern has been and what you've done, or what has been done to address the problem in the past that perhaps didn't work. Each one of these types of questions has slightly different goals and components targeted to the objective.

Anita Brick: Well, and it's interesting you talked about bad news. One of the weekend students wanted to get a little clarification and he said, I'm starting a new career in strategy consulting, and I know that I bring curiosity and strong analytical skills. In your book, you talk about embracing bad news. How can I ask questions, dig out the problems, and not alienate my clients because I really do want to succeed?

Frank Sesno: That's just a terrific question, and it touches on a number of things. There are some things that I think that all types are questioning certain characteristics that they share. So one is preparation. The other one is what I'm going to call a genuine ness, if you're genuinely interested, if you're genuinely a caring person and you can convey that through your questions, that gets you well down the track.

Similarly, if you're genuinely curious, a variation of interest. So what I would say to the questioner here is if you are looking for bad news with a client and you do that through questions and you connect those questions to the right voice, tone and body language. So the questions are not a challenge, but a genuine inquiry. They are framed around the notion that you are part of a team or we're all in this together, or we're trying to figure out what we could do better or in more inspiring ways, frame it around something positive in that fashion, people will sign on.

Generally speaking, you can pose a question that makes someone defensive if it's accusatory, if your voice tone is harsh, if you do it at an unexpected time, you can take that same line of inquiry and make it comfortable and accommodating by one making an appointment for those questions. For example, let's have coffee tomorrow and I'd love to talk to you about it.

And it's a kind of clock on the bar. Well, that person has announced their expectations internally, that they know they're going to talk to you about that at 10:00, as opposed to you just suddenly coming around the corner and starting to ask away. Secondly, you know, I'm curious about your thoughts. Let's explore this together. When you pose a question in that fashion, you confer a sense of trust and authorship to that other person. Wow. You're smart. You might have the answer. Can you help me with this? You create a sense of team. Those will be some thoughts to your very, very good question.

Anita Brick: Now, I think it goes along with a question in executive MBA student hours. And if we take where we were and how do you make those connections, treating the person graciously and with respect. This person wanted to know, how do you engage with someone professionally? What's the structure in terms of timing and questions, to build a solid emotional connection with the person?

Frank Sesno: Well, it's really going to depend on what that professional relationship is. Is this your boss or is this a subordinate? Those are both professional relationships. Is this a peer? Are you on the same team and pulling in the same direction? Are you competing and you're in competition with one another? That human dynamic is very important and it's important to understand before you then launch.

But in both cases or in all cases really, you can use the question as a form of both. Search for information or knowledge and invitation to connect. A couple things to remember. I think that addresses this one. I find it very important to help people understand that this notion of making an appointment really matters. That set up at that moment when you know you're going to share and engage in this conversation is very important.

Secondly, asking with respect or genuine curiosity will overcome a lot of the personal dynamics that otherwise get in the way. And then, of course, and always be really careful listening. If you're trying to engage a colleague, a competitor, a boss, a subordinate, and you can hear in their voice discomfort, hesitation, you don't keep going. If it looks like someone wants to engage, it may be time to give them some space.

Anita Brick: Good. A weekend student wanted to know about the process. What's the process for coming up with high impact questions, given the people and circumstances and how it's going to be used, and so on? Are there other elements beyond what you've already spoken about that would be part of that process?

Frank Sesno: High impact questions first will connect with real information. You have to do your homework if you're going to develop high impact questions and high impact questions depending on what kind of questions, this is why my categories of questions, I think, come in very handy. Is it a job interview? Are you trying to create a common mission? Are you trying to motivate somebody or frighten someone into doing something because they've been underperforming?

Are you trying to have a brainstorming session where you want people to open up and go boldly into very naive, silly ideas because you want to get them all down on the wall? All of these cases have a really precise sense of where you're trying to go and what you're trying to accomplish, then breaking that down into manageable subgoals.

If you know that you want brainstorming, for example, innovation, do you want to build that around what I call the imagined reality of a bright future? You're the number one company. What are you doing? Do you want to build that brainstorming around what's the next great brand you're going to introduce? Do you want to build that brainstorming around a new undertaking that you want to do, because you need to reposition the company.

Then each of those goals will drive some of the elements of what we can be doing? What would that success look like? And then ultimately, how would we get there? Those are the impact questions that you can unpack a little bit there.

Anita Brick: I think it's good because sometimes people forget and they have an agenda and they ask questions, but they forget there's another person there. And I think this exact MBA student was actually being really self-reflective and self-aware when he said, As I'm making the next move in my career, when I network, what I really want to do is jump in and ask for a job.

And I know that's the wrong question. If I have an established credibility, how do I ask a question to get a contact interested in me? So the person actually wants me in their organization? This student was asking when I network, and this is before there's any job interview, and I want to jump in and ask for a job, how do I go about asking questions that will have that person actually maybe want me to interview for a job at their company?

Frank Sesno: Show curiosity about the company. Show curiosity about the individual. You just ask for a job in the email or in a phone call. They'll say, well, I don't really have anything, and you shut down the conversation. But instead you ask, can we have a cup of coffee? Can we get together? Most people, a lot of times it's very surprising, as a favor is a decent thing that a human being can do.

Plus they're, you know, flattered that you're interested in them. We'll say, yeah, come on in. Questions revolve around what do you do? How did you get here? What lessons are there? What should I be thinking of when I'm going forward with my career? What were the most important components of success in your life that I should be thinking about?

Then you can use a little bit of what I call premise. Question. Premise allows you to make a short statement because you don't want to make a speech unless someone's asking you to, and then to another question, you know, we can share an experience. I can share a premise and then turn it into a question. So how are you pursuing that with anything that I just told you to apply here?

Well, what you're now starting to do is demonstrate your own value, hoping that that person is gonna come back to you and ask you more about that. The other thing is to establish what I call a shared mission. And I have a chapter in the book. One of the examples I give is a guy named Ben and a guy named Jerry. And when they got together, they created this thing called Ben and Jerry's. They were friends going in, but their conversations led them in their discussions and dialog to realize that they shared core values, and then they were able to translate that into a business.

Anita Brick: It's true. And you're right. The shared values. I was working with someone earlier today. He said his challenges he views himself are very different from a lot of people. So he goes into the conversations kind of hunting around for the differences. And we talked about when you look for shared interest, shared values, then you have a platform or runway's been to take off on the other side of this, there was an alum who asked a question which I thought was very observant, actually, and he said, when I read your section on bridging questions and solving puzzles, it made me think that when I want to hire new members for my team, I know that they're super prepared and they have all the answers to the questions they've prepared for. What advice would you have for me to get to the real person through using questions?

Frank Sesno: You want to get past the talking points? That's really challenging. You can do that by asking unusual questions, unexpected questions people ask about risk and other things like that. I think the key here is establishing that relationship. It's asking about some unexpected or fun things, hobbies, values. So let's say you're in a really hard charging place. For many people, life is a balancing act.

Some people live to work, other people work to live. Exploring that a little bit in a non challenging, non-threatening way will help you get to know somebody's values. I interviewed Jim Davis for the book. Jim Davis, the CEO of New Balance Shoes. Jim has been an athlete all of his life. He's a super competitive guy. He's more of a listener than a talker.

To be honest, They had this wonderful comment about listening and looking for ego. He's a good athlete, thinks about the team and yeah, you want the superstar, but the superstars still have to put in the team. So he says, I listen for pronouns. You know, he's listening for I versus we, and he prefers the we. Can you steer a conversation towards one of your priorities or values like that, to establish a relationship with someone and to get to know them better.

Be careful with these conversations though, because we're trying to get to know somebody, especially in today's H.R. Land. They're, as we all know, are many things we're not supposed to ask about. We can't get too personal, so we have to be careful with that, too.

Anita Brick: Good point. So there was another Allen who asked a question which I thought was kind of interesting, and he said, in theory, I like and do employ the system one or cognitive ease that you talk about in the book. I use that approach to questions, and that's where I start most of my conversations. I have colleagues who want to get down to business. How can I dive into tough questions without the small talk? Because that will just annoy me.

Frank Sesno: That just does. If you can read someone that well and just go there. There are ways of doing small talk that are very short and effective. You know, how was your weekend and then you move on. There are people who just want to get down to it and then you get down to it. So much of this is about listening and understanding.

Empathy really does involve what that's all about fundamentally, which is standing in someone's shoes that person may be rushed. That person may have 27 meetings a day. That person may need to get right down to business, not because they're unpleasant or they're nasty. They may be that, too. We hope that they may. You've got to tailor your tasks to the people you're engaging in.

Sometimes you set the agenda and you can set the agenda through the questions you ask. They're a very powerful tool for doing that. Sometimes you're following someone in the agenda that they're setting, especially if they are in a position of authority and are dealing with limited time.

Anita Brick: I have seen and I've heard this from others, that they go into a meeting, they have a conversation, whether it's an informational interview, an actual interview or a meeting, and they feel like there are two monologues going on simultaneously. How do you use questions to bridge from going from two monologues to an actual exchange or dialog.

Frank Sesno: Understanding that this is going to be a discussion or a, you know, dialog and understanding how you can send signals of curiosity that other person is really important. Maybe you can describe what the conversation should be. Look, when we get together, I want to ask a few questions of you. Then that's an opportunity for us to ask questions that you've got about how I got to where I am or about this workplace or anything like that.

There are ways of advertising that, and that ad, which is about setting expectations, helps to project what it is you want. Now, if that other person you're playing with, you know, just isn't curious. And I've seen this, so some people just aren't questioners. You can prod them, you can try to make that appointment. You can try to set expectations and some will respond somewhat.

It's why one of my little exercises in the book is to sit down with somebody you've known for a long time, ask them questions for 30 minutes about their lives, their work, their whatever, their two words. You cannot utter during that 30 minutes. I or me, you are totally focused on that other person.

Anita Brick: And that's a good way. If you have two people so absorbed in themselves, someone is going to have to step out. If you do to me, it gives you a lot more influence and potential power. If you create engagement because the person probably is going to feel more valued and act accordingly, well.

Frank Sesno: Something in the premise here is a red flag for me. I mean, if you have two people who are so self-absorbed, we've all experienced that when you walk in the room or somebody calls you on the phone, and either they're not a player at all and they just let it all go to you, or they completely dominate the conversation.

Anita Brick: That makes sense. So here's an interesting question from another evening's student who said, what would you suggest regarding asking questions as a means to lead someone to an answer for themselves, rather than just trying to convince that person?

Frank Sesno: It's a great point, and it's one of the wonderful things that questions can do. Questions can help people realize things about themselves, how they're coming across in a workplace, whether they are being a leader in staff or team meetings. Very much built around this notion of how we use questions to self reveal or to help a friend reveal.

Let's say you're talking to a colleague at work and they've been having some trouble, or they fear a bad annual review and I don't mean to couch all of these around the negatives, because you can just as easily catch them around the wonderful positives. You could say, how do you think you're doing? How's it going? Probably, you know, they will start to talk about things that aren't going so well, but if they don't, you can come back and say, you know, do you feel things are going as well as they could be here?

The circumstances will drive the particular words that get incorporated in that question. But there are a number of ways to engage that will help someone look inside themselves by asking themselves that question. That's what you really want to do. You want to pose someone a question that will prompt them to pose the question to themselves.

Anita Brick: That's good to have time for a couple more questions?

Frank Sesno: Sure. Yeah.

Anita Brick: Okay, good. This one actually is about accountability. And this is an exact MBA student. And she said I'm all about strategy and creative thinking. That said, I believe those big idea questions are easy to discuss because there is an accountability attached to the answers. What questions would you ask to go from imagined reality to actual reality?

Frank Sesno: It's so interesting you asked me this because I just came from a brainstorming session, and we just went through this and we brainstormed out this, you know, elaborate new big idea that we've got. And we filled the wall with documents. So we just told people, nothing's out of bounds. You create a safe space for imagining and you want to do that and then you work backwards.

So once you create this imagined reality, it's five years from now. Your business is number one. You're doing all the right things. What are those things you're doing? And you do that list, but then you're going to work backward from that list. Well, one of those things you're doing is you've got this unbelievable, beautiful incubator on the second floor.

People coming in from all over the world. Problem is, you don't have any real estate at all right now. You don't have a second floor, and you certainly don't have a budget to bring people in from all over the world, because you've now identified that as the success component for what you need five years from now. And you've clearly said, well, wow, this is what we're doing.

Then you start asking, okay, well, how do we get the building? Where is that money going to come from? Who could come in on it with us? You identified that as this is what defines your success. Is that practical? Well, if it is, you start asking, how's that going to get paid for? I believe that the power of questions in innovative thinking is to imagine a reality that takes you into the future, and then you work backwards from the future to figure out how you're going to do it.

And there will be times when you think, wow, that's kind of creative. I wouldn't have imagined that otherwise. There may be other times we say it's impossible. We can't do it. You know, I know what I need to do to get from here to that building. I am never going to have $50 million to buy that building.

Anita Brick: So one final question. If you think about crafting thoughtful questions that yield answers that are useful and actually strengthen the relationship with the person to whom you're asking the question, what are three things that you would include in that question? Development.

Frank Sesno: First is preparation and research. Understanding the person. Understanding the topic. Understanding the outcome that you want from that conversation. Do you want information? Do you want connection and relationship? Is it relationship building? Is it confrontation and accountability where you want answers? Do you want to set some parameters? Understanding your outcome, your goal of the question and answer session of the conversation then connects you to the preparation and the set up for that allows you to set your own expectations and probably the others.

That one second posing the questions matters how you frame them? Are they very specific? Are they open ended questions? Tell me, how do you think you're doing? Is it very specific and closed that last month you exceeded your sales target by 127%? That's unbelievable. And so framing those questions with Deliberateness and follow through, keeping the questions short and one at a time, people make the mistake of doing what I call compound questioning.

And they'll say, well, I need to. I'm really interested in your career. So when did you get started and what were your first three jobs, and which one did you like the best and which one did you miserably fail at? First of all, I've invited you to talk for the next hour and a half. I think you're going to try to answer all of those.

But even more importantly, I've invited you to select which of those questions you're going to answer, as opposed to steer you with some deliberateness through it. So ask one question at a time. And what was your first drop? And off we go. And then I build the questions to follow so that I can have a full understanding of the arc of your career over time, because that's what I want from this conversation and from my question.

The final component that I would say here, and I cannot emphasize this enough in every good, meaningful question and answer session or conversation is listening. Don't be afraid of silence. Listen for what you're hearing. Listen for what you're not hearing. Listen with your eyes to see if someone is looking uncomfortable or comfortable, is withdrawing and is showing that through their body language it looks like they're bored or they need to go to the bathroom.

That sense of really coming into that other person. There is one thing that all really good questionnaires share, and that is a genuine interest in the person to whom they are talking and questioning.

Anita Brick: Well, and it brings us full circle. I mean, we started this conversation where you talked about how you need to care if you don't care. To me, the questions will either be superficial, irrelevant, or even worse. I like that. I like that approach and curiosity. It's very, very clear that this is who you are, and that's why you've built all the wonderful relationships that you have. I really appreciate your taking the time, Frank. This was very, very helpful.

Frank Sesno: Such a pleasure. I really appreciate the conversation. And yeah, I do love this. People are fascinating. Everybody's a story. Everybody walks around with hopes and dreams and imagination, with setbacks, triumphs and failures. In life. We think of one another as stories. We just become more fascinating to one another and we care more.

Anita Brick: A great way to end this. Again, thank you for the really valuable advice. Very practical. We can go away right now and tomorrow and the next day and use this straightaway. So thanks again and wish you all the best.

Frank Sesno: Thank you so much. Enjoyed the conversation.

Anita Brick: This is Anita Brick with CareerCast at Chicago Booth. Keep advancing.