The Gunn Show - 9.15.24

Want better answers? Ask better questions.

Hey everyone!


Happy Sunday and welcome back to The Gunn Show. As always, hope you all had a fantastic week.


It was a great one on my end here out in Arizona as we wrapped up the first week of our three week Fall Instructional League. A yearly post-season camp that consists of a subset of our younger players, Instructs is one of the more unique portions of the baseball calendar as the timing allows for us to create a highly controlled - and thus specifically tailored - development environment for both staff and players. I always find it to be one of the more impactful camps we run, as each year I look back on things that were accomplished across the system and know much of the groundwork was laid during the prior Instructs to serve as a launching pad into the following season. Looking forward to the next two weeks of work to set ourselves up for a big 2025 (as well as the cooler weather that is on its way to AZ).


With that said, let’s get into this week’s edition which centers around a topic I’ve been thinking deeply on recently: questions and answers. Hope you all enjoy, and thanks for reading. Catch you next week!


- CG

Thinking - On Questions and Answers

Life punishes the vague wish and rewards the specific ask. - Tim Ferriss

6 years ago, I read a book that changed my perspective.


It was a very thick book - one with a bright orange cover, a black embossed spine, and 672 pages of tactical wisdom for life from some of the world’s most elite performers. Written by Tim Ferriss and titled Tools of Titans, it still to this day stands as one of the best curations I’ve come across on the habits, tactics, and routines that high achievers from billionaires and icons alike accredit their success to. If you want to know what excellence looks like behind the scenes, Tools of Titans contains the answers within its pages.

But for all the powerful insights packed in the book - from things like Jamie Foxx’s commentary on the value of adaptability or Arnold Schwarzenegger’s discourse on the importance of vision and goal setting - one stood out in particular: to get all of that information in one place, someone had to go collect it. And so, after a 672-page journey of insights into some of the world’s most famous and successful people, I unexpectedly came away most intrigued by the person that had managed to put those pages together. Tim.


After I finished Tools of Titans, I went down the Tim Ferriss rabbit hole. I bought and binged three of his other books (The 4-Hour Workweek, The 4 Hour Body, and Tribe of Mentors), scoured the archives of his blog, and listened to over a hundred of his podcast episodes where he interviews world class performers. As a self-admitted nerd that has a major interest in high-performance, the content he was consistently putting out fit my inclinations to a tee. But the more of Tim’s content I consumed, the more I started to notice something: the magic of what he did was not in just getting access to some of the most impressive people on the face of the earth - that was table stakes in his profession as an interviewer and podcaster. Instead, it was what Tim was able to get those people to reveal when he had the opportunity to sit down with them that truly sets him apart.


From my perspective, there is something important to be learned from observing Tim’s success as an interviewer: the value of asking good questions. Because while the information he is able to parse out of his guests is ultimately what shines in the light, it is important to recognize that the insights only come as a function of the inquisitive journey that Tim takes them on. There is an order of operations at play, such that good answers can only come from good questions. Or, as Tim himself has said before: ‘Want better answers? Ask better questions.’


This interplay between questions and answers stands out to me as a key concept for creating a life of value for a couple of reasons.


The first is quite simple - at some point, life is just one big exercise in asking the right questions to get to the right things. Humans are a problem-solving species, such that the mechanism for us moving forward in the world is to find ways to solve problems that stand between where we are now and where we want to be. But to solve those problems requires us to find solutions - how do we do so? You guessed it - we find solutions by asking questions. To tweak an old adage - it’s questions, all the way down.


The second reason is for something I’ve been observing of late, which has caused me to think more deeply on the concept: it seems to me that one of the clearest commonalities amongst the highest performers is that they are excellent at asking the right questions.


Any easy place to see this in action is the business or investment industry. If we consider a ‘question’ as a foundational starting point for an idea, then it becomes quite clear that many businesses are simply products of people asking the right questions at the right time. Mark Zuckerberg started asking the right questions on what an online social experience could look like, and voilà, Facebook was born. The same could be said of Peter Thiel and Pay Pal, Elon Musk and Tesla, and Jeff Bezos and Amazon. For this group specifically and many of their peers, it’s notable how many of these successful CEOs are ‘serial entrepreneurs’ rather than ‘one hit wonders’ - they have carved careers out of multiple successful ventures and big wins rather than just one at a single point in time. And when we view it through the lens of questions and answers, it makes sense why - they are elite question askers that dominate a simple formula: Right Questions + Right Time = Powerful Answers.


The more I’ve been around high level decision makers and executives, the more I’ve come to believe this to be true. The way I see it, the people that are the best at getting answers do so only because they are the best at asking the questions that give rise to them. They ask good questions and then get good answers, not the other way around.


When viewed through the lens of personal growth - whether in your career or elsewhere - I think this provides a helpful framework: focus on asking better questions first, and let everything else fall into place later.


Admittedly, this piece of advice is tougher to execute than it might seem - likely because I don’t think question asking mode is our default programming. From a young age we are taught that the way to sound smart or be smart is by having answers - not necessarily questions. You only get points on a test by answering the questions your teacher asked, after all - not by asking her your own in return. The same is true when you first start a job as intern or in an entry level role - your boss or some executive has questions for you that they want answers for, and you get your credibility by providing them. They ask, you answer.


But again, there is a catch here: in order to provide answers you have to ask questions. So regardless of whether your primary responsibility is as the question answerer (like an intern) or the question asker (like a CEO), at some point your ability to get what you want out of your life will depend on whether or not you can ask the right questions to get the right answers. The more we can think about life in this way, the better off I think we’ll be.


So I’d encourage us all to take a page out of Tim’s book, and recognize that the formula for success is relatively simple: Better Questions → Better Answers. That is the game to be played, and the order in which to do so. Because as Tim himself has said life rewards the specific ask, and who wouldn’t want that?

Reading

Thought Partner - Greg Shove (~8 min)


If you can spare the 7-8 minutes to read through this, I’d highly recommend that you do so. A great share in Scott Galloway’s weekly column, the piece focuses on a core idea I’ve discussed frequently in this newsletter: how to use AI as a tool to upgrade what you are capable of. I liked the manner in which Greg frames AI’s potential as a ‘thought partner’ such that it can help us think more clearly and effectively - but only so long as we know the right questions to ask it. There are some helpful ideas in here on how to properly pair up with AI as a cognitive teammate - something I think will be critical for success in the future, because as the piece notes “AI won’t take your job, but someone that understands AI will.”


Tell Good Stories - Jack Raines (~6 min)


I have become endlessly fascinated in recent years by the inner-workings of good storytelling, and this was a great article by Jack on the power that good narrative can carry. As Jack writes, it is hard to beat a good story when it comes time to make an idea stick because stories, at their core, are ‘mediums for helping an audience ‘get it’, whatever ‘it’ may be'. Good stories create a sense of relatability and lead us as humans to form some type of feelings associated with them - it is these feelings that in turn give the stories their power by creating a ‘hook’ that an idea can neatly attach too. So let this piece be both a reminder and a challenge - a reminder to recognize that stories are the best medium humans have invented for communicating our ideas, and a challenge for each of us to get to telling them.

Public Speaking Mastery - Sahil Bloom (~6 min)


It’s not too often anymore that I come across a completely new framework or mental model that makes me stop and pause, but that happened to me this week after reading through this piece from Sahil. In it, he provides a great concept for how to improve your public speaking: Winston’s Star. Coined by late MIT computer science professor Patrick Winston, the technique centers around making sure each speech you have is centered around 5 key ‘points of a star’ - symbol, slogan, surprise, salient, and story. I like having the ability to condense big, often amorphous public speaking opportunities into concise and executable checklist type items, and will be giving this a go at some point in the near future.