Ep 525 | My 6 Thinking Time Questions That Could 10X Your Business

Brian Gubernick shares six questions to ask yourself during 30-minute thinking sessions, inspired by Keith Cunningham's The Road Less Stupid. Block your calendar, write one question on a whiteboard, and sit with it weekly to surface blind spots and spark exponential growth.
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Thank you for joining me today. It's Brian Gubernick, and welcome to the No Days Off podcast, where we believe that every single day brings a new opportunity to get better. Most business owners are addicted to motion, but the reality is the ones who win long-term, in my opinion, are actually addicted to clarity. So today, what I'd like to do is give you my 6 favorite best thinking time questions, at least the 6 that I'm favoring right now. These are questions that I think can 10x your business as long as you sit with them for a long enough period of time. Now, this thinking time concept, we've talked about it quite a bit here at No Days Off over the past couple of years. But what am I really talking about? I am talking about you blocking time on your calendar to sit and do nothing more than think, which is arguably the most valuable time you will spend in your business this week. When I think about thinking time, for me personally, I like to write a big question up on my whiteboard and just stare at it and think about it. And as I do that, jot down notes or thoughts that come to mind, moves I need to make, assumptions I need to challenge. Whatever comes out from that thinking time exercise, I want to just drop it in my notes. So I like to have it on a whiteboard, but then I'm jotting down notes in my notebook. You may write it in a journal. You may not even write it down. You just have it top of mind. You may be going for a walk. Again, I sit in a room and just stare at my whiteboard. But you may do it on a walk. To me, it doesn't so much matter as the exercise that is thinking time, that getting accomplished is what matters. So a shout out to Keith Cunningham, who, who, while I'd heard of the Think Week with Bill Gates and thinking time in general, it was really Keith Cunningham and his book The Road Less Stupid that really, really pushed me to spend more time on the whiteboard and less time in my inbox. Now, why does this thinking time really matter? Keith Cunningham says it, says it really well. He says, if you're asking the wrong question, the answer doesn't matter. So, these questions that you ask during thinking time are not really tactical. I'd say they're surgical because they should cut deep and most people avoid them. But that's where I think the edge is. The bigger the question, the better the question, the bigger and better the response or the answers you're going to find. So, thinking time provides an opportunity for you to put a really big question up on the board, stare at it, and ideally come away with some big answers. So, let's talk about the 6 thinking time questions that are just important to me right now that have really been making a difference. And I've had some kind of big ahas as of late as I've worked through them. And there's no particular order here. I'm going to list them in an order, but I don't think any of these are weighted over the others. The first question I would ask myself if I had a, a board of directors, let's say, and that board decided one day to fire me as the CEO of my company. Now, mind you, my company may be 50 people, or maybe it's just me. So whoever's listening, this applies to you. If I had a board and that board chose to fire me as the CEO of the company, and the board hired someone new to take my place. What's the very first thing the new CEO would change? What's the very first move the new CEO would make? So if the board fired me as CEO and hired someone new to take my place, and that new person immediately took over, what's the first thing that person would change, or first big decision that person would make? What are we really trying to uncover here? In my opinion, you're uncovering blind spots. I think you're uncovering decisions you may be too close to emotionally. I think you might uncover stagnation that you've rationalized. Here's why. New CEOs don't protect old decisions, they actually optimize. So what they would cut or who they would move and what would they launch. They're not emotionally attached to all this stuff. They're looking to optimize. So again, what moves would they make? Who would they move? What would they cut? What would they launch? What have you been sitting on that maybe that new CEO who's not as anchored to the past, you know, that new CEO would take action around? So number 1, if you're fired as CEO, someone took over, what's the first move they'd make? Number 2, What part of my business would I start over from scratch if I had the courage? What part of my business would I start over from scratch if I had the courage? That's an awesome question. What does it uncover? I think it uncovers systems or people or branding. Things that are broken— systems, people, branding, offers, whatever it may be that are broken. I think it also uncovers things that you've kind of duct taped together that now frankly need rebuilding. Now there's a key word in that question. I think that key word is courage, because if fear or, or sunk costs weren't in the way, you'd likely be rebuilding? You'd rebuild it better if fear and sunk costs weren't in the way, right? So courage is the key word here. Number 2, what part of my business would I start over from scratch if I had the courage? Number 3, what am I tolerating that if eliminated would create immediate momentum? What am I tolerating in my business right now that if I eliminated it it would create immediate momentum? What are we going to discover through this question? I think what you're going to find are bad clients or low performers or messy handoffs or unproductive meetings. I think tolerations, these things we tolerate, they're like pebbles in your shoe. They're small, but they, they start to wear you down, and the things you put up with are robbing you of energy. So the question here, what am I tolerating that if eliminated would create immediate momentum? It's a great, great question. Number 4, where is complexity costing me profits, time, or peace? And what would simple look like instead? Where is complexity costing me profits, time, or peace? And what would simple look like instead? This is a different, you know, different question than the others. What does this uncover? I think it uncovers overly complicated sales processes. I think it uncovers places where ego or fear may have created or added some unnecessary layers. I think it uncovers bloat in, in your model, in your business model. I think complexity sometimes is seductive, but it usually means we're covering for something, either a lack of clarity or maybe a fear of, of letting go. So the question one more time: where is complexity costing me profits, time, or peace? And what would simple look like instead? Number 5: if my number one product or service became obsolete tomorrow, What would I do next? If my number one product or service became obsolete tomorrow, what would I do next? I think what you're going to find by asking this question is some dependency risk. I think you might find missed opportunities for expansion, or maybe it's reinvention. I think you could find innovation gaps. I think too many businesses die slowly because they didn't ask this sort of thing early enough? If AI or competitors or new behavior made you irrelevant, what would rise from the ashes? It's a really good question to ask, especially in light of, you know, all of the changes that we constantly are seeing and all the innovations that we're seeing at this very moment. And number 6, the final question: if I were guaranteed to succeed, What bold move would I make in the next 90 days? If I were guaranteed to, to succeed, what bold move would I make in the next 90 days? I think what you're going to learn from asking this question is where you have some suppressed ambition, maybe where you have some risk aversion. I think ultimately what you're going to uncover is the big move that maybe you're too scared to even admit you want, you want to make? I think when you remove the fear, the real desire starts to surface. And that's usually the move that leads to exponential growth. So, one more time, the question: if I were guaranteed to succeed, what bold move would I make in the next 90 days? So, my challenge for you, right? I don't know if all 6 of these questions are applicable in your world. I bet a lot of them are though. But I want you to pick one or two of these questions today, your two favorites of the six, and write them up on the whiteboard. Set a timer for 30 minutes. Put your phone aside. Don't be looking at email. Just you and these two questions. And just allow yourself to think around each one of them, one after the other. Stare at the question, jot down what's going through your mind. Make sense? I think that when you do exercises like this, you are thinking differently. You have the opportunity to think different than everybody else around you. And that's what the No Days Off movement is all about. I think as you become, as you bake this into your calendar and it becomes a habit, what you're going to again find, and I alluded to this earlier, is that your most valuable time is going to be making big decisions. And these big decisions come with asking big questions. So, your most valuable time arguably is going to be this 30 minutes you're going to start spending every week contemplating a big question. That's all I have for you today in the No Days Off Podcast. Thank you so much for listening. And remember, every single day brings a new opportunity to get better. So let's get after it.
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