How Michael Krigsman Interviews Top Executives

Michael Krigsman, the esteemed host of CXOTalk and renowned for his exceptional interviewing skills, joined Dennis on the CoachYu Show to share his insights on achieving success in interviewing top executives. With an impressive track record of conducting over 800 interviews with business leaders on his podcast, his momentum shows no signs of slowing down. He has honed his podcasting techniques and fearlessly tackled every challenging question posed to him by Dennis.

How do you prepare for a podcast?

Dennis noted that Michael interviewed the who’s who of the business world and that no one has a more successful podcast than him because of the impressive list of companies involved. He asks about the process behind CXOTalk and how Michael prepares for every interview.

Michael explains that he is always conscious about who should be in the limelight with each interview. It must be about the guest, not the interviewer trying to elevate himself. So to prepare for every interview, he does his best to find out everything about the guest through research and uses whatever he can find. It is the starting point.

What type of person is the hardest to interview?

From his experience, Dennis knows that some people are challenging to interview, so he knows Michael has had his fair share of difficult interviews. He asks him to identify the type of person that is the hardest to interview.

Michael says that the question is difficult to answer. He explains that the most challenging guests are those who believe the interview is all about them. From the point of view of the interviewer, yes, it is about the guest, but if you look at the bigger picture, it should be for the benefit of the viewers.

Some guests are just walking and talking brochures and want to announce their greatness. It is not very interesting and useless to the audience. He says it is tough for any interviewer to deal with that.

How do you get interviewees to open up and be authentic?

Many executives who get on these interviews are coached by their public relations (PR) companies, so they come out with canned responses. Dennis asks Michael how he gets his guests to leave that zone and be more authentic.

Michael says that he works with PR agencies all the time since agencies good sources of interviewees. They want their clients to appear on CXOTalk, so he knows them well. Senior executives are careful about what they say because it can negatively affect the company’s stock price.

It is a challenge to get them to open up and be authentic because of that, so he does a few things to reduce tension for the guest, such as making the guest feel comfortable. Each interview is live. People are watching or listening, so if something goes wrong, there are no do-overs.

When the guest is relaxed and comfortable, he feels safe because he feels that Michael got his back and is not there to catch them off guard to make them spill the beans. He is not trying to do that. Instead, he wants to learn from their insights, experiences, wisdom, and expertise.

He also says that when somebody is stuck on the PR talk track, the interviewer must figure out how to ask a question that doesn’t map to their preparation. It will then force them to think and be spontaneous in their creativity and thinking. His guests are all smart men and women who know to do this.

Lastly, he says that the interviewer needs to develop a certain kind of empathy or intuition about where a guest’s comfort zone lies. You can push the boundaries of their comfort zone, and they’ll go there with you. However, they’ll close up if they feel the interviewer is trying to trap them with some hidden agenda.

So, make them feel comfortable and guide them down a path slightly outside of what they’re already doing.

Why do some episodes do significantly better than others?

Dennis mentions that Michael has recorded 800 episodes with C-level executives with notable personalities, such as Ziff Davis, and companies like PWC, Siemens, McKinsey, and NVIDIA. With that kind of lineup, Dennis asks how Michael knows when an episode will take off or do well.

Michael tells Dennis that he asked the eternal question. How does one determine when something is going to be a hit? At one time, he interviewed the CTO of NVIDIA. A few months after the interview, the company made an announcement. That announcement caused the views on the interview to skyrocket because it was about the CTO and that topic. It caused YouTube to recommend the content to other people. Things just went upwards from there.

He adds that he always goes back on a few things. For example, he looks at what has worked in the past, so when choosing topics, he consults YouTube Analytics to see what has been successful. He considers which interview has the most views. However, this is just part of the equation.

Just like Dennis, he loves looking at metrics. He looks at things like the view duration of the videos. For example, if 10,000 people watched a video, how much of it did they view? If someone watches at least 30 seconds of a video, YouTube counts it as a view.

Then, he also looks at the percentage of viewers who watched the entire video. So if 10,000 people watched the video, how many watched it until the end? That’s a good metric of engagement. And when you add all that up, what’s the total number of minutes viewed?

Michael is very meticulous about evaluating the success of the videos so that he can make a good analysis when figuring out what has worked in the past.

What particular metrics are you looking at?

Dennis is also a big fan of metrics, so he asks Michael if there are any particular metrics he looks at when considering completion and average view times.

Michael explains that looking at the metrics of a 45-minute video is not the same as before. It is much more competitive now. When he started doing this almost ten years ago, just a few people were watching videos on YouTube, for example. The pandemic accelerated many things, including competition for people doing full-length interviews.

Take a video that gets an average of 20 minutes of viewing duration as an example. If 20,000 people watch it for 20 minutes on average, that was commonplace back then. Now, if you get 20,000 to watch it for at least 20 minutes, it’s considered as good. It’s much easier on shorter videos.

For his kind of content (B2B interview style), the rule of thumb is you can get a third to a half on a 45-minute video. You’re doing well if you get an average view duration of 50%. Few people will be able to do that regularly. It’s 15 to 18 minutes for shorter videos.

If people stop watching a 20-minute video before reaching halfway, that’s not good. If people spend an average of three minutes watching your video, you must rethink your strategy. It could be an issue with your topic, approach, technical production, or maybe the editing and construction of the content.

What is your approach when considering the relationship between the different platforms and how much effort you put in?

Dennis mentions that Michael has 4.8 million views on his main YouTube channel but distributes on other platforms, too. He asks Michael about his strategy when considering the relationship between these outlets and the amount of effort to invest.

It’s the modern-day equivalent of “I’m going to make you a star, but how will he do it?” He knows how to make the hits. It’s a constant evolution of trying to figure things out and experimenting. Michael admits that he has no clear-cut answer.

For example, where does TikTok fit in? His team has been creating videos intended for the platform, but they’re not on TikTok yet, which he admits is a mistake because everybody should be on TikTok. However, they publish content on Twitter, LinkedIn, and sometimes even Facebook. He thinks that at the end of the day, it’s best not to think about it in terms of finding a magic bullet or formula.

Some people know how to make the hits like The Beatles. But Michael is not The Beatles. For people like him, it’s best not to rely on flashes of genius. Instead, rely on a proven process-driven strategy. For Michael and his team, that means consistency in promoting videos, the type of content, and the graphics to use.

Their team is careful when it comes to editing. They spend a long time with the first 20 seconds of every video and a lot more with technical production, all aspects of it. He says that when you add all that up, you develop a certain amount of consistency over time. Just try and figure out how to do it and stick to it. That is the winning formula for him.

What do you do when you lose track of your line of questions?

Dennis then says he was so amazed by Michael’s insights that he forgot his next question. He took that opportunity to ask Michael if that ever happened to him and what he did.

Michael recalled moments when his mind just went blank during an interview. He explains that when it does happen, he takes questions from the audience since every episode is live. Those questions are queuing up in the background anyway.

He’s also doing other things in the background during the interview, such as monitoring Twitter for questions the audience would like to ask the guest and publishing posts on LinkedIn. So, whenever he loses track of his questions, he looks at those questions from the audience and sees if there is something good to ask the guest.

He defaults to the list of questions he prepared earlier if there are no good questions. He never goes into an interview blind. He has topics and questions prepared in advance. He may deviate a lot, but he still tackles each interview well-prepared.

He recalls a time during an interview when he experienced a technical issue. The guest was talking while he was busy trying to solve the problem. He wasn’t paying attention to the conversation anymore because he was trying to plug every hole that sprung a leak. That was a difficult situation.

The podcast can go on in front of the live audience while his mind goes blank because he got distracted. Sometimes, he would ask the same question twice by mistake. In another interview, the guest answered a question, and Michael continued with a redundant question.

How do you balance thinking ahead versus listening intently to what the guest is saying?

Dennis knows how hard it is to balance paying attention versus thinking ahead. He admits that he struggled with it. Dennis wants to give the guest his full attention while considering what question to ask next. He has never asked anyone this question before, so he asks Michael how he manages that.

Welcome to my world! He knows what Dennis is asking about. As he mentioned before, he often multitasks while conducting an interview. He has a full-blown broadcast setup which is very complicated.

He continues by saying that the answer is two-fold. The first part is preparation. You go into it with your questions and are mindful of the topic. The second part is the flow because you are trying to tell a story, a narrative.

There will be a flow. The more you can consciously shape that flow, the better the result. So, know the questions and the flow, and key into the highlights of the discussion.

It’s crucial to think about what the key is. Michael uses Dennis as an example. While interviewing Michael, he’s keeping mental notes as the interview progresses, adjusting to the direction the conversation is taking. It may have been intuitive, and Dennis was probably unaware of it. But somewhere, he realized that something Michael said resonated with him for whatever reason. It is an essential skill that takes over in real time.

Production Quality vs. Content Quality

Dennis says that most people just turn on their webcam. Because of social media, young adults tend to think that production quality is only 10% of it and 90% is the content itself. He asks Michael to share his thoughts.

Michael explains that he understands that point. There’s no doubt that content is king. However, there’s a trick answer to it. If you don’t have a good interview, who cares that it looks great? A million people are also doing what you’re doing.

When he started podcasting, it was much harder to do this well just from a production standpoint, and there was much less competition. Now, if you use Zoom, you’re an interviewer. So, the question then is, how do you differentiate yourself? It became clear to him years ago when they started that the tools would become easier to use.

The typesetting industry went out of business because desktop publishing came in. It was easy and looked good enough. It became clear to Michael that the tools are going to become so easy to use that interviews would be accessible to anybody, anytime, and with no training and expertise needed.

And so, Michael realized that he needed to be the best at his craft to succeed. Being the best means leaving no stone unturned. From a content standpoint, that means being prepared, choosing the right guests, and selecting the right topic. Looking at it from a technical production standpoint, do it as close to CNN as possible. That is his goal.

Dennis adds that because Michael is interviewing C-level executives from huge companies, there’s an even higher expectation of high production quality.

Michael agrees. These people get many interview requests, but they turn most of them down. Before many of his guests come on CXOTalk, their internal PR folks need to evaluate it.

Michael says that he has been poked, prodded, kicked, and thrown to the ground many times by PR and communications folks. The things they look at are the content and the entire package. It’s a quality deal. They want to be associated with that. One of the most unique things about CXOTalk is that they can use all these company logos on their website.

That is no small feat. For anybody who has ever done business with a large company, one of the contract terms almost always includes a stipulation that you can’t use their logo without a written agreement approved in advance. CXOTalk.com has a lot of company logos on the site, but nobody complains.

He proudly says that there is trust. It’s trust and quality, the production values because this is what it comes down to. They’re meticulous about everything. It develops a sense of trust. And to people who say it doesn’t matter, Michael says it depends on your audience.

Dennis adds that when Michael reached out to him to be a guest on CXOTalk, he was not aware of who Michael was. Then, he saw the list of executives he interviewed, which led Dennis to think, “Man, I need to prepare because this is a great opportunity to be on his show.” It could do wonders for someone’s career simply by being on CXOTalk. That person could be like Robert Scoble in the B2B space.

Michael agrees with Dennis. He also adds that he likes identifying young talent doing something extraordinary, like this guy he saw on TikTok who is brilliant at explaining topics like OpenAI and ChatGPT. Michael learned a lot from his videos, so Michael invited him to CXOTalk. He likes showcasing people like that.

How does someone make it when that person is not a big deal yet?

Dennis says it’s easy for Michael now that he’s established himself as an authority in that space because it builds a snowball of trust. What about those people who don’t have what he has? How can they achieve success?

Michael says that they have to plan. The first step is to convey to the other person that they can take you seriously. Start there. Next, consider how to find people. Look for people who are slightly out of your reach. Don’t try to get the CEO of Coca-Cola right away. You won’t get that person to be on your show if you’ve never done this before.

You can try getting a marketing manager from a mid-sized company instead. That’s a great place to start. Those people don’t have many outlets, and there are a lot of them. And if marketing manager A doesn’t want to do it, go to another department of the same company and ask another marketing manager. After one company, move on to the next company. Just reach out to those folks.

You have to be thoughtful about how to do it. Identify who your target is. Michael shares that he would go to LinkedIn and reach out to those people and say, “I’m starting a new podcast. The topic is so and so. We’re doing this very carefully and thoroughly. We’ll present you well. Would you consider being a guest? We would love to promote your work. We’d love to tell the world about what you’re doing.”

Michael added that the strategy is what Dennis is doing exactly, interviewing people to elevate them. Michael does the same thing with his guests.

From a business standpoint, how do you measure the ROI of this podcast?

Dennis mentions that Michael has a well-established podcast. He has big names to back it up and an incredible reputation. People in the B2B space regard Michael as the gold standard of podcasting, not just from his production quality but everything else down the line.

He asks Michael to talk about how he looks at his analytics to determine which video will be a hit and evaluate the podcast from a business standpoint. How does he look at the ROI of the podcast? What does it do for his brand, business, and sponsors?

Michael shares that it’s a great thing from a personal brand standpoint because it establishes trust and credibility. For most people, the podcast will not be a source of income unless they have a big audience, way bigger than he will ever get with a B2B podcast aimed at very senior executives. Unless you have a big audience, you can never sustain yourself with the income from YouTube, for example.

You have to be realistic. For most people, the podcast is a way of establishing connections. Michael proudly shares that he has a great Rolodex. He’s also part of other people’s Rolodex. That builds credibility. It expands your network and gets you out there. It’s also great for your social media presence. Think strategically. Think about the business model. For example, you might want to interview people that could be your potential customers.

Interviewing people on a podcast is a great way to meet other people. And then stay in touch with them to build that relationship. The main takeaway for most people is that the business model is not the podcast. The podcast supports your brand, company brand, your personal brand. It helps you build a network.

Then, Dennis asks which one Michael would prefer if he had to choose between having a podcast or a New York Times bestselling book.

Michael decides that he would probably go for the bestselling book because if you have a bestselling book, it can lead to interviews on podcasts. After that, it will be easy enough to start your podcast. If you have a New York Times bestselling book, you can write your ticket, whatever you want to do.

What happens when you unknowingly invite a jerk to your podcast?

Dennis has always wanted to ask Michael how he manages a situation where he unknowingly invites a jerk to his podcast.

Michael says it’s easy to manage when pre-recorded since you can remove stuff during editing. When it’s a live broadcast, that’s a different story. When someone is so full of himself and tries to use your platform to expand their ego, it won’t matter how successful that person is because nobody will care. It will just be a black hole of noise.

It’s a tough balance because you have to take the high road. You can’t just tell the guest to shut up. Michael has had his fair share of undesirable guests. There was an interview with an angel investor who kept talking about his greatness without providing any meaningful information. He confesses that it was one of his worst episodes.

Michael tried to push him, but he was a strong entrepreneur. He would not budge. It was so bad that Michael never published that episode. He never told anyone about it. How do you deal with a situation where someone is fighting you in front of a live audience? You can’t be rude no matter what.

He once interviewed a journalist who would not let him ask questions. The guest kept on motor-mouthing about whatever he wanted to talk about. Whenever Michael would try to jump in, the journalist would actively fight him to stop asking questions. It was weird. At the end of the interview, when they were about to wrap up, the guest’s audio was cut for some reason. Michael felt that the journalist was probably thinking that it was deliberate. After a while, his audio came back. Michael says he had nothing to do with it, but he admits that it occurred to him to do something like that.

Is there a question you wish people would ask you?

Dennis then asks Michael if there is one question he hoped other people would ask him. Michael responds by saying that nobody has ever asked why he does it.

Michael adds that he loves interviewing people to get to know them better. He feels that he’s doing something worthwhile. He says that he’s aware of the flaws in what he does, how he does it, the direction, the limitations, the strengths, and the weaknesses. But despite all of that, there’s something inherently great about being able to interview these people.

Meeting someone virtually vs. in-person and vice versa

Dennis asks Michael if he prefers meeting people virtually via Zoom, which could lead to meeting someone in person over meeting them in person, which can create a better experience when he interviews them. How does he balance virtual versus real relationships, and how do they reinforce each other in his mind?

Michael shares that before the pandemic, he traveled quite a lot. But lately, he doesn’t travel unless there’s a good reason to do it. Of course, there’s no substitute for going out and spending quality time with people, but he thinks we have become much more comfortable with virtual meetings. We’ve all learned intuitively to construct a mapping between the two-dimensional version of interacting and map it in our brains to a three-dimensional relationship.

It’s the kind of relationship that happens when meeting in person. He thinks the key, whether virtual or in person, is the follow-up. He admits that he does a poor job following up and maintaining relationships because he feels like he’s being hit all the time. He keeps telling himself that he needs to improve on that. So, the follow-up maintains the relationship, whether virtual or in person. It is the key.

Many people want to be interviewed, but it’s impossible to accommodate all of them. How do you manage that?

For his final question, Dennis asks Michael how he can balance so many relationships. Many executives want to be on his show because Michael is a big deal. Of course, he should proactively decide where to spend his time. How does he balance all of that?

Michael says it’s tough because he doesn’t like saying no to anyone. Whenever he declines a request, it is never personal. These people may be great at what they do, but he has specific requirements regarding who he wants to interview. If a person doesn’t fit that filter, they won’t be a guest on CXOTalk.

These people can pay to be featured, but it won’t be on a live show unless they meet a specific profile that is a C-level executive from one of the largest organizations in the world or an extremely popular brand that is doing something that is changing the world.

Eventually, he tries to reply to most emails, the serious ones that come in. It may take him six months to a year to get back to them because of the sheer volume of emails in his inbox. He does his best to reply, but most of the time, he doesn’t. The messages fall through the cracks. It’s on his wishlist of things that he wishes he could do.

Advice from Dennis

Dennis agrees that everything is free time, and you’re doing stuff that you want. His friend, Mari Smith, showed him how she manages her time. She told him that when she looks at her calendar and sees a meeting that is not a hell yes, she won’t attend it. That way, whenever she wakes up in the morning, she looks at her calendar, and every meeting on her calendar is a hell-yes meeting. Life is joyful when you have that kind of control over your time. Mari shared her strategy after hearing Dennis complain about having too many meetings.

Michael says that he feels the same way. If a trip is not a hell yes, he won’t go. It was much harder when he started doing this. As you do something repeatedly, it becomes easier. Ten years ago, he had this idea about this video thing called podcasting. While he was late, no one else was doing live podcast interviews. He reveals that it was difficult to convince executives to show up and do it live because it was new.

Now, with an impressive track record, it is much easier. And so the nature of the challenge shifts from proving credibility to filtering. But of course, there are always more well-known guests, so the challenge continues. You’re always trying to move up the market one way and expand in one way or another. It’s just the nature of who we are and what we do.

Appreciation from Dennis

Dennis says that he counts it as a huge blessing to spend time with Michael. He has learned so much from him and hopes everyone in his community can learn from him, too. Even if they are not interested in being famous podcasters, they can learn from what Michael shared.

Dennis also says that Michael is high on EQ (emotional quotient). It’s a requirement for anyone who interviews high-profile people, such as C-level executives. You have to be able to read between the lines and warm them up. You need a certain level of executive panache that people can see.

Michael has a unique way of saying things that makes the conversation interesting. Dennis shares that he’s gone through numerous autobiographies of famous people. By doing so, the content he’s consuming is subconsciously programming his brain to think and act like them.

Michael ends the interview by saying that having EQ is equivalent to being honest. He doesn’t have a hidden agenda when he interviews people. His goal is to serve the audience. It’s not just a show. Just be honest and straightforward. Combine that with a track record that people can see, so they can confidently let their guard down when they get on an interview with you. It’s trust and relationship building. It is at the end.