Deeper Weekend 2014

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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.


I teach a lot of courses on pricing to firm owners, and everybody’s interested in pricing, value pricing. And one particular aspect of pricing is that it’s very collaborative process with a client. So if you can do a lot of work upfront to prepare a client, prepare them as a good lead and they trust you and they come really into a conversation with you as a firm, you get to ask them a whole bunch of questions and they’re there trusting you knowing you’re the expert that’s going to lead them through some kind of solution to change their company, your client that you serve.

And as you’re asking them questions, then what you get to do as a firm owner is you get to go, all right, I’m going to give you some options, that’s what you do in pricing, you give three options. We always give a high, middle, low. But then you go back to the client and you say, “Here’s what we came up with. Is our best assessment of what we’ve heard and we’re going to wheel this down to three options we think would really change you.”

A lot of those options have a lot of solutions they didn’t ask for and that’s collaborative. It’s because they’re going, hey expert, just kind of walk me through this process, if they trust you. That’s why it’s important to vet that lead appropriately, put up some walls so the right lead comes in that trusts you. And then they’ll let you pitch ideas to them and they’ll think about it. And then they’ll ask you a bunch of questions and then you can go, that makes sense. And then you go back and make a couple more options and you bring it to the client and they go, okay, now we’ve settled on one. And then you’re all pretty excited.

And actually the process of going through that is really enjoyable. And even the process of collaborative pricing drives such trust. And it really begins a relationship really well. My partner and I are going through that now. And it’s important that a lot of firms understand that pricing is very collaborative. It is not here it is, take it or leave it client. It is listening to them, spending time, then going back and spending time crafting things for them, then sharing with it them and then listening to them again. And then they say, give me this. And then you go back and you re-craft some options.

And so the process of onboarding a client through value pricing can take a month or two months depending on the complexity of the company. So I just wanted to throw that out. It’s actually a pretty enjoyable process. And your client really trusts you when they come in with some prices that they know you have worked really hard to collaborate on building with them. They feel heard, and the pricing is way better when the client’s being collaborative with you. So just keep that in mind.

If you’re interested in pricing, it is a very slow collaborative process. And again, what we’re not talking about right now is billing. Billing is a completely different thing. That’s billing by the hour and just sending a bill after you’ve done something from a client. Pricing is that upfront wall you can’t get over and start serving people unless you figure out what that price is. So that time period before you begin serving is that collaborative pricing process. And you really come to a joy when you have the right lead.

So if you need help doing that, we have courses, we have videos on pricing, I do webinars on pricing. Just hit us up and we’ll help you, [email protected] We’ll be glad to hook you up with any kind of pricing, content and resources that we make. Thanks so much for watching. We’ll see you.


Do you ever consider risk versus reward assessments? That’s a strategy and a skill that firm owners have to adopt. They have to figure out if they’re growing a services based company, they have to do risk versus reward. And a lot of firm entrepreneurs actually operate their business on their gut. They just like make gut calls about things to do in the future. And that works for a little while, but when you get bigger and you have more people and you have more clients and there’s more things to care for, your growth has to become more methodical. It has to become more strategic and strategic just means intentional about the future. And so a risk versus reward is something you do when you’re considering something big. We were coaching with somebody not long ago about adding a partner and that’s a risk versus reward assessment you do. And you don’t just add a partner. You have to think a lot about the implications of that.

So let’s just define a risk real quick, and we’ve kind of talked a lot about risks on videos before. But a risk is basically committing some money or time or resources right now in the present for some hope of a future outcome. Typically, some return on the future and that return could be more time, more money, more growth, more clients, whatever it is you’re trying to make a current bet is what you’re doing. A risk is a bet on the future. And so you can’t make poor bets and keep failing and actually grow. It’s going to hurt you. So you have to become more methodical when your bets become bigger. And your bets, by definition become bigger, when you have more people that are relying on you, and there’s a lot more that can go wrong.

So what you have to do is go, all right, I used to make decisions and make risk calls just with my gut when I was a smaller firm. But now that I’m bigger, you don’t get to do that anymore. You don’t have the freedom to do it. So you have to prepare some data. That’s what you need. And then you go through a process of assessment from that data, which is a lot of sticky pad paper. It’s talking about the pros and cons. What happens if we do, do it? And assigning probability percentages to what if it doesn’t work? What’s the probability that this won’t work? 60%? 30%? 90%? Those things are part of it. And then you have to assess the third step. Do you want what that means? So what if it does work? Or what if it doesn’t work? Do you want what it means to either succeed or fail in that risk you’re trying to take? And then the fourth phase is to make a commitment. Do it. You have to expend resources, expend time, move forward.

And sometimes you can do this assessment, risk versus reward assessment. You can do it pretty quickly, but at first it takes time to learn this methodology. And it’s so intentional. We have a whole module that my partner and I teach in our Thriveal Incubator Series. It’s such an important thing to help you grow your firm and we just wanted to throw that out there. If you need help, hit us up at [email protected], and we’ll be glad to help you figure out if that assessment is right for you. Take care.