Deeper Weekend 2014

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    Scott Kregel


Okay, we’ve done all the heavy lifting in the first three videos in Strategic Planning Season. And as we’ve been mentioning, November, December is strategic planning season, this is the season. The holiday season? No. This is the season where entrepreneurs plan their future. And go back to video one, to find out what planning and what strategic means. Why did we put those words, strategic planning together, they’re real important.

So, what have we been doing up to this point? We’ve really been just dumping all the things out, prioritizing, listing core initiatives. Really just getting more and more granular as to what we’re going to accomplish next year. Now boots on the ground happens in phase four. This is when now we take our core initiatives, go see what that means in video three, we get our core initiatives and we put them into what we call eight to 10 calendar containers. And calendar containers, a lot of our the people who follow us and we teach entrepreneurs, there’s a process we go through called strategic calendar work blocking.

This methodology about owning your future and how to operate and create some sense of strategy, moving forward in your business has to do with owning the future of your calendar. And so now we define all the initiatives and the things we want to do in eight to 10 calendar containers. Now these calendar containers are going to be, these are the eight to 10 hats that my partner and I are going to decide to wear in our business, right? I mean, that is so strategic, right? To limit everything to eight to 10 types of work. Now, those calendar containers are pretty big. They’re big rhythms. So what you’re going to find, you’re going to find those on a calendar that recur week after week.

So you probably know if you watch a lot of my videos that I have a huge content blog. That’s one of my calendar containers. Well, my partner and I have a strategy and planning calendar container. That’s a required part of our strategic calendar work blocking. And then we make other calendar containers that relate to other things we’re going to do. Like there’s a big team care calendar container, because we spend a lot of time with our team, leading our leadership team. And so there’s a big block for that.

And what we do is we roll our eight to 10 calendar containers throughout our whole calendar. So we’ll go to January, the first week of January, we’ll lay out all of those calendar containers and they fill up the whole week, right? Eight to six, Monday through Friday, we filled the whole week up and then we just hit the recurring button. We recur it every week and it zips all the way through our calendar, all the way through 12/31. Now we have these big buckets that we go stick stuff in, right? We have this team care bucket that might have four hours on a Wednesday. And we’ll go put different meetings in there, meeting with a team member, a weekly team meeting, weekly leadership team meeting. So the container holds all the things we’re going to do. And of course I have a huge content calendar container. And so I’ll go fill it up. The content I’m working on, these videos are in a calendar container that I’m making.

So the calendar container now becomes our future. It is a depiction of our future as seen on a calendar. So now when us and our team roll into our future, we’re rolling into these containers and we’re operating in the way that we’ve already planned by going through a very methodical, strategic planning type phased system. So our calendar now depicts, this is what we should be doing to actually fulfill our strategy.

And so that’s video four of four videos on strategic planning. So I hope you will try to fall into strategic planning this year. Just give it a shot. I think last year it took my partner and I four days to complete all of our strategic planning. This year, it’s going to take us five to six days. So it’s expanding because we have a lot of things we want to do. And it’s taking a lot of time to call through them and say no to a lot of them. So it’s just taking a lot more time. And also as we grow, strategic planning will take more and more time.

So I hope these videos are helpful, so you guys know what we’re doing during this really important strategic planning season. So let us know if you like these videos and, you know what? Reach out to us. You can hit us. You can go to or you can go to and you can find out more about how we help entrepreneurs do things like strategic planning and how we help them be successful. Thanks for watching. We’ll see you.


Part three, this is part three of four of how to do strategic planning. If you’ve been watching our videos, you know by now November and December, at the end of the year, are strategic planning season. All entrepreneurs should be doing strategic planning, if you’re an owner of a business, this is the time you do it. And so, we’ve been talking about what we did in part one and part two in the strategic planning process. Now in this phase three, what we’re getting to is listing core initiatives. So part one was we did a brain dump, part two was we prioritized that brain dump, which was strategic. That was the strategic choices of what to do and what not to do. Here we are in part three, we’re like, “Oh, we can look at all of our paper and go, Oh, I see what we’re going to do. I see our core initiatives.”

Then what we do is we start listing out, this is a big thing I’m seeing in the strategy of all we want to do. This is a big thing, we start listing these huge, big bucketed subject areas. And we’re really starting to understand what are the huge initiatives that are going to really eat up our time, our capacity? What do we want our team to do more of? We’re really seeing through listing out on just one other piece of paper, our core initiatives. We’re like, “These are our biggies for the year.” If we move these big boulders and rocks forward, these are going to be the things that move our companies forward. So, this listing, the core initiatives, just starts to really make it aware to you how big your year is going to be coming up.

And even in this third phase, this is another strategy phase where you may drop off things and go, “I’m looking at all of these core initiatives now.” After looking at 30 pieces of paper, sticky pad paper, I’m looking now at one piece of paper with our core initiatives, you may further cut those core initiatives and go, “We still can’t do all this. Those are bigger than we thought when we were looking at all the paper.” Now that we’re looking at one piece of paper in this third video of four on strategic planning, we’re seeing we’re going to have to cut more out. So that’s when we start cutting again, or we further, deeply commit to those. So come back and find out what we do in phase four of strategic planning to wrap it up.


Here we are in part two of four videos on strategic planning season. November and December are strategic planning seasons for entrepreneurs. So you should be planning, you should be doing strategic planning. Go see video one about what the heck strategic planning even means.
So here we are in part two. In part one, I shared that we did a brain dump of our ideas, my partner and I. Here we are in part two, and in part two, this is the strategic part. What we do is we go through the whole brain dump, all the sticky note papers all over our conference room walls, and we assign priorities of when we want to get these things done, by a month and a year, of course.

Now, sometimes the year for us pushed out into 2022. Now, here’s the cool thing about strategic planning. When you have a brain dump of all the papers you’re working with and you start prioritizing things, right, you’re thinking you’re going to be prioritizing 2021. Well, as you do it, and as you have conversations, either with yourself, your coach or your partner, you find out, you’re like, “Wait, we can’t do this. We can’t do all this.” And what you do is you start eliminating, and on the fly. Now you’re into a huge part of the strategy of strategic planning. You can do this for your business, for your family. You can do it, really, for anything where you’re trying to be more efficient and more successful.

So as my partner and I were talking, we started labeling some of these things 2022. We were pushing them out two years, which was really cool, right? What it’s doing is it’s really helping us focus, and so now we’re saying, “No”, or we’re saying, “Later”, to a lot of things. Then, as we’re assigning months and year, like January 2021, July 2021, we’re starting to prioritize our strategy. Now it’s starting to come alive.

And again, we’re still working on this big list of sticky note paper all over our conference room. But in this second part video is when the strategy really gets serious. You should hear the conversations we’re having. They’re really strategic, sometimes we don’t agree, sometimes we’re fighting for a certain position of something we think is more of a priority. But since we care about each other, we come to a consensus as to what we think is the thing we can accomplish. I’m going to be more objective to the things she wants to do, she’s going to be more objective to the things I want to do, and we’re going to hear each other, and the best strategy comes out of that.

So keep watching for the other videos on how to do strategic planning.


This is strategic planning season. At the end of the year in November and December my partner and I always do strategic planning. That’s what you should be doing too. If you’re an entrepreneur, you should be doing strategic planning right now in November and December. And this is part one of four videos. I’m going to tell you exactly how we do it. Listen in and follow up on those videos.

First, why planning? Strategic planning? Why planning? Because any entrepreneur who’s a successful entrepreneur, typically you’re going to find them out in the future, deciding the future before it gets here into the present. Planning is a key concept to winning. You don’t plan and figure out your future in the moment, you will have already figured out some calendar system in the future and that’s planning. Planning is always in the future.

Now what is strategic? Strategic is choosing. Choosing is prioritizing. Being strategic is all about eliminating all the things you won’t do, basically. And that happens when you choose the things you will do and that’s the strategic part. And these videos are going to tell you exactly how to do it.

Here in part one, as with a little intro there, the first thing we do is a huge, massive brain dump. My partner and I went in a conference room, we had about 30 pieces of sticky paper and we wrote at the top, all the categories of the big ideas we had had all year or that were in our drive list. We keep a drive list. What is a drive list? It’s something we keep track of where we just, we dump all of our ideas to this drive list and we keep it categorized throughout the year. We’re always, always keeping up with it. A drive list is kind of your brain and when you’re a bigger company or you’re running a bigger company, you can’t keep everything in your mind so you have to have a place to keep it. And so a drive list is where you just dump everything. You categorize it. You probably spend, you spend an hour a week just managing and organizing your drive list because that’s your treasure chest. Everything’s in there.

At the end of the year, during strategic planning season, you pull it out and you dump it on a bunch of sticky pad paper. And so that’s the first thing you do is kind of categorizing and we’re not to the strategy yet. That’ll be in part two.


Our firm just had a great team retreat. It was supposed to be in person, but COVID meant we had to pivot that to a virtual retreat and that’s fine. It turned out being pretty awesome. And one thing that was proven that we knew walking into was we prepared a whole agenda of some teaching from me and my partner, but some teaching from our team, and then collaborative practice where all these communities come together. All the people in the community come together through collaboration and the wisdom they produced together is amazing. So anytime you’re leading an event, anytime you’re bringing a community together, limit some of your teaching, push people together, push them in groups, push them in community. The things they will learn together is mind blowing because they’re just as smart and as wise as any speaker. They have history, they have abilities.

And when you push people together, that event becomes stronger, better, wiser. You get more information out of it. People are more bought in. It’s just a beautiful time together when the leaders of an event or a company step back and let their team lead because the team is also amazing. So that’s just a hint we knew going in, and it turned out even better than we thought. It’s just amazing what our team can do. Their brilliance, their thought, their care, their love for one another. And it just drove all of that even deeper. So virtual team retreats, push your team together in those. Do breakout rooms and zoom, or however you do that, and you’ll see some amazing things happen. So thanks so much. Take care.


We didn’t plan on the pandemic wrecking our team retreat. So we’ve been virtual for almost a decade. And this year, we were supposed to have all of our team fly in for a few days of a team retreat, where we serve each other, care for one another. And some people, we just haven’t met in person yet. And we miss our team. We’re with them every day and the pandemic blew that up. So what we’ve been doing is pivoting not only services and things that everybody else is doing, but we’re pivoting a team retreat. So we’re turning it into a virtual team retreat, but we’re trying to bring as many aspects of the intimate part of being in person to the virtual part of it as well. And just a couple of things we’ve done is we got our team involved. Our leadership team started leading their own teams to build out certain parts of it.

So our team is going to lead parts of the team retreat. It’s not just my partner and I. And then also, everybody’s leaving their homes. They’re still leaving. And those that can, and that it’s safe and feel comfortable, they’re going to some hotels, so they can virtually still feel like they’re away and it’s different. So these are some of the things we’re changing and it’s coming up soon. And we’re really excited to teach our team new things, to hear parts of our team teach things that none of our team know we do, like the marketing processes. We’re going to teach our team how all that happens. We’re so excited. But even though the pandemic blows things up, you can still pivot and make things special. It’s just going to be different. So there’s some sense of us embracing.

It’s not going to be what we thought it was, it’s going to be different. But in that can also come things we don’t anticipate. So our team has just stepped up and they’re leading their own teams to build such amazing things. And we’re so excited about how we can serve each other. And we’ll do some updates to let you know how our virtual team retreat is going as we’ve pivoted from a live team retreat. So those are just some things we’re working through and some thoughts on how we’re pivoting that. So let us know how you’re pivoting the things in your firm too, because this is a tough time for everybody. We’ll see you.

COVID-19, CPA firm, Leadership