Episode 130:

Hello everyone and welcome to The Upstream Leader Podcast. My name is Jeremy Clopton and I’ve got with me today a repeat guest. I’m super excited for this repeat guest because my guest today is Courtney De Ronde, who was actually our very first guest, way back in Episode 1 of the podcast over five and a half years ago, now 130 episodes ago. At that time, we were talking about accounting firms and Courtney’s role as a leader. Today we are talking to Courtney as a new author of the book, Planning to Scale. Courtney De Ronde, welcome to The Upstream Leader.

Hey, Jeremy. Thanks for having me back. Five and a half years, I can’t believe it. That’s awesome.

Yeah, it is hard to believe. That was March of 2021 when we launched the podcast. You were the first guest. We were talking about focus, which is interesting because I’ve got a feeling we’re still going to be talking about focus today, but we’re going to be talking about it through a slightly different lens than we did a few years ago. But before we do, I’m not going to ask you the same question that I ask every guest, because I’ve already asked you that question, but I am going to modify it just a little bit. Since when you joined the show five and a half years ago, to today, how have you evolved as a leader?

Oh yeah. I’ve had so much growth since 2021. I would say one of the biggest things in my evolution in that span of time has been realizing that you can have the right strategy, you can have the right goal, the right approach, but if you don’t have alignment with the human beings, it won’t matter. So that’s been my biggest growth edge in the last five years.

That’s incredible. And alignment, it is a term that keeps coming up. I swear every time that I have a discussion with leaders of firms today it seems like alignment, alignment, are we aligned? So much more important than agreement, because agreement is very hard to come by. Alignment, we can at least work toward. So what happens if you have the right strategy but you don’t have alignment? What’s the outcome?

Yeah. Well, for me it resulted first in me thinking like I was the worst leader ever, and I should probably quit and not be a Managing Partner in a firm. So what happened for me was, I had this strategy that we would split our firm. We’d grown, and we had two very different business models, so we would split the firm, and it made tremendous sense. We wouldn’t have to keep fighting for this common brand, this common vision, these common values. Both business models were successful and profitable. We had this nice split between our clients and our team members and our locations. It just all was like, “Oh, this all just makes perfect sense. Let’s just split this up and we’ll all make more money and do what we want to do, and everything will be great.” But I did not consider the emotional impact that proposal had on my partners, and essentially, I broke trust, and my first thought was, I’m a loser. I should quit. I wasn’t cut out for this, this was a huge mistake.

Thankfully I had a coach at the time who helped me reframe it as, you can learn more from this mistake in the next than most people learn in a decade. Like, that’s how big of a mistake it was. But if you’re willing to believe that mistakes happen, good leaders mess up, and what they do is they learn from it and they move on, they don’t quit. If every leader who made a mistake quit, we wouldn’t have any leaders. I’m a perfectionist, I’m a people pleaser. And at that time I just thought people don’t make these kinds of mistakes. So anyway, I rebuilt trust, I put the human element into it: Who are these people? What is it that they want? What do we each want? And I ended up coming up with two different visions, one where we move forward together, and one where we move forward separately, and I set aside my belief that I needed to control the outcome. My only goal was to lead well, to be proud of how I handled the situation and the leadership, and to be aligned. That’s what I was going for. Not “my idea wins,” the aligned idea wins. Because if we aren’t aligned, we’ll have all this activity that doesn’t actually get us where we’re going, people will actually be working against each other. And so I ended up presenting those two visions, and we had a unanimous vote to split the firm. The same strategy that I had put forward.

So it wasn’t a decision error, it was an execution mistake.

Yes, it was. We were not aligned at that point that that was what was needed, and I wasn’t considering the fact that alignment requires human involvement. People understanding their strengths, their gifts, their motivations, and, your audience gets this, like, we’re numbers people, right? Most of our decisions we think are logical. But they’re really emotional. And I was just taking that piece out of it. Like, this is so logical. Well, people don’t make decisions based on logic. They make decisions based on emotion that they can, on the back end, justify logically. So all that to say, what I came to realize was the two things we’ve talked about so far, one is like, it’s not just about the strategy, it’s about recognizing that this strategy involves people, and those people have to be aligned for this to work because it could be the right strategy, and we won’t actually get there.

Well, and that also speaks to the fact that a lot of times the people probably even know what they need to do. Like you said, the logic is there. There are a lot of things we know we need to do, right? Professionally, personally, all the things, there’s lots of knowing, not a lot of doing always, and getting ourselves to drive the action once you have that alignment… how did you overcome that? So you said that you had to rebuild trust, you ultimately got to the same decision, right? Which I’m sure that as you reflected on that and you’re like, “Wait, if it was such a big mistake, why are we still doing what I said at the beginning? But now everybody feels better about it? Wait a second, right?” So there’s that emotional piece, like you said. But even past that, I would expect that even once people were on board, they were aligned: Yes, we have two visions. Yes, it makes way more sense to do this as two entities, not one. Getting people to actually then take action, move forward and do that probably wasn’t still easy. Is that fair?

Yeah. And it’s still not easy. It still requires intentional effort every day, week, quarter. It is the work of leadership. And it’s ultimately why I wrote the book Planning to Scale, is because I’m a learner. One of my top five Clifton Strengths is “Learner.” I love to learn. And what I got frustrated with was learning all of these methodologies for planning that didn’t have any true implementation legs. What my experience is as a learner, is I’ve encountered a lot of authors and speakers who are great writers, researchers, charismatic speakers, they have wonderful ideas, and they can put them into beautiful words, into wonderful books that change the way we think. And I would consume those, and then I think, okay, I believe that, so how do I do it? But these people are not people who have 40, 60, 70, a hundred people back at the office to actually execute these ideas on, these are philosophies, these are perspectives. And so what I ended up doing was figuring out, by Clifton Strengths, I lead with execution, so of the four Clifton Strengths themes, execution is mine. So I’m a doer. And so I figured out, how do I do this, and eventually I built it into a framework, a workshop, and then a book, because I couldn’t find anything out there when I was going through it to actually do it. And so it requires a lot of things, and we can talk about whichever ones of them you want to, but that’s essentially what the book is, my strategic planning framework that I had to figure out because I just couldn’t find anybody out there who could cover all the pieces and tell me, “Now when you go back, here’s what you have to do every day, week, quarter, month, year.” Like you said, we can know things, but that doesn’t always mean that we actually do them.

Yeah. You mentioned there’s a lot of other books, there’s a lot of other speakers. We can all walk away from a conference, we just feel so good, we have so many notes and all the warm fuzzies and the enthusiasm. And then like you said, you get back, you look at your notes and you’re like, “uh huh, uhhhhh, the excitement’s still here, but I just realized I don’t have a how-to guide on how to do any of that. I’m really glad they did, and I’m sure it’s really cool that they did, but I don’t know how to do it.” I’ve heard you say before that Planning to Scale is not just a book, but it’s a system. And hearing you say that you lead with execution, that makes a lot of sense, that you wouldn’t just write a book that’s inspirational and makes people feel good, but it’s a system. So help me understand, how does the book show up as a system rather than just an inspiration?

Yeah. So each chapter in the book explains a part of the planning process, and it does have some stories throughout that hopefully are inspiring, that show “this is the challenge I had” and “here’s how I led through it.”

Great stories, absolutely.

Thank you! But it also says, and here’s the way you’ve got to do it, you’ve got to do this, then this, then that. And by the way, go to planningtoscalebook.com/tools and download the tool. It’s the same tool that we use in our strategic planning workshop, our Planning to Scale workshop in person. None of it’s held back in the book, it’s a full resource to help you. And so I think that’s the balance, because we do have to change the way we think before we can change the way we act. We have to believe something before we’re willing to actually do something different. But a lot of resources out there change our belief, but they don’t tell us how to act. And so essentially that’s what I’m doing, is giving you both the mindset shift behind it—there’s principles, each chapter is rooted in a principle: “Know who you are and where you’re going.” “Better is possible.” “Forecast your future.” There’s all these principles that should help shape your thinking as a leader, and then there are tools and systems that you install in your business through yourself and your leadership to actually live out those principles and beliefs. Both are necessary, and I wasn’t able to find that when I was out there figuring out on my own. And so eventually I went back and said, okay, what are the things I did? What are the things I believed, and how can I put this into a structure where I can help our clients, our small business, nonprofit organizations, entrepreneurs? How can I help them do the same thing without having to go through the winding road that I went through.

Yeah. And as I went through the book, I loved the fact that all the tools were right there. They’re easy to access, they’re usable like you said. They’re not hidden somewhere where you can’t actually, you’re like, oh, I got this. Oh no, I don’t have it figured out. Actually, if I only had a tool for that, and you just said, nope, here’s the tool for that. So what I loved about it though is in a way, it takes a topic that—and I’m sure I’ve overcomplicated it numerous times myself, and I hear a lot of business owners and leaders overcomplicate strategic planning—”Oh, it’s got to be this, it’s got to be that, and it’s got to be this particular way.” And oh, we’re special and unique just like everybody, right? We’re all special and unique and we need our own custom thing. What I got though, as I read the book and looked at the tools, Courtney, this is going to sound maybe not exactly how I intend it to: We’re not as special as we think we are. Yes, every business has its nuance, but that doesn’t mean that we have to recreate the system just to add unnecessary complexity. And one of the things that I loved is the book made it very straightforward and simple. That’s a huge compliment because strategic planning is anything other than simple, and it’s sure not easy, but you made it very accessible and simple. And I had never thought before that strategic planning could be one-size-fits-all. I’m not sure that you’re saying that it is, but it sounds like what you’re saying is one system can benefit all. Is that a fair assessment of how you approached it?

Yes. And simple is harder to create than complex, and so I appreciate that. I do take it as a compliment, Jeremy.

Good!

So the actual whole content framework that I created is called the “Simple ScaleUp System.” It’s a whole body of tools and frameworks for helping leaders scale themselves and their businesses. When essentially you’ve grown, you’ve built this great firm, this great company, and you can’t keep running it this way, and you’ve got to do things differently, these are the tools that when I felt like that, this is what I ended up doing. And then here it is, we built it out. The strategic planning framework is a subset of that Simple ScaleUp System. So my goal with everything is to keep it simple, because things that are simple actually get done. It’s things that are simple, are easier to execute, they’re easier to scale, they’re easier to replicate. And it takes more work on the front end to make something simple, but once you’ve got it, then it’s easier for people to actually leverage. And so that’s why we built it in this way so that people can really do it. That’s what we need, is we need things that people can learn and then do.

And that’s the way we run our workshops. And so that’s why when we turned the workshop into a book, I just knew from my experience leading these workshops every year, what we need is to teach somebody some little piece of something that shifts their mindset, changes their thinking, helps them understand why, and then immediately have them do it, apply it. Because it all sounds so simple, right? When you hear it, you think, oh, yeah, yeah, yeah. And then you take your own context, your own industry, your own nuance, your own everything, and you start to try to do it, and you think, oh, this isn’t as easy as it sounded. And so that’s why in the workshops, we want people to start doing it right then, and that’s why in the book, at the end of each chapter, I’m like, now go download this tool and start doing it while this is fresh in your mind. You can still flip back through and it all builds on itself anyway, you need to really keep following the process as you go.

Yeah. Well I love the idea of simple. It’s one of those things that I believe is often overlooked. We try to make it so complex, and like you said, the more complex we make it, the harder it is to do. And in a way it’s almost, I wonder if sometimes it’s a bit of an escape clause: “Oh, it’s just too complex. It’s too hard. We can’t do it.” And when it’s simple, it’s like, “Oh wait, I should be able to just do this? Because it is simple.” Like you said, it doesn’t mean easy. In fact, really hard. I want to focus on something you said. At the beginning of that answer, you said that in the Simple ScaleUp System, that it addresses both the leader and the organization. So which came first? The leader or the organization?

I believe it’s the leader.

Okay.

I think there’s two transformations that have to happen—if you want to scale your firm, you want to scale your business, there’s two transformations that have to happen. One is the leader, and two is the structure and systems of the firm. In my experience personally and leading, coaching, guiding hundreds of other leaders, the leader always has to be on that journey a little bit ahead of the firm. And I actually wrote about this a couple weeks ago, or maybe it was a video, I can’t remember, but I call it time traveling. Leaders are time travelers. We have to be learning and becoming the leader that our firm needs us to be so that when our vision is realized—so I have a three-year vision, this is where my firm is going. When I get there, it takes a different leader to lead that firm that I’m becoming than the leader I am now, and I can’t become that leader when we arrive. I have to be that leader when we arrive. And so I’m time traveling between planning for the future and growing my own leadership, and then living in the here and now while my team, rightfully, executes on the things today that I planned last year, two years ago, three years ago. So as a leader, we keep traveling in time, back and forth between who we’re becoming and who we are right now, and that’s hard work. But if we don’t, as leaders, keep going to the future, seeing what we want to become and who we need to be to lead it and becoming that person before the rest of the firm catches up, then we’ll be behind when the firm gets there.

So how does a leader who develops themself into the leader that the firm needs, what do they have to do to keep perhaps the frustration at bay if they are ahead of where the systems and the structure are of the firm that they’re leading within?

Yeah. So the first thing is just to acknowledge that this is one of the challenges, one of the hard parts of leadership is that we are time travelers. This is normal. This is part of the job. I was lamenting this phenomenon a few years ago to my friend Kyle Kubroth, and he’s the one who said this like, “Courtney, it’s time traveling. It’s just part of leadership.” And so then I realized, oh, this is supposed to happen. I’m supposed to feel this tension. So it’s kind of like, isn’t that like one of the first steps of the 12 steps, is to recognize you have a problem. Just acknowledge, oh, this is happening. Increase your awareness that this is part of the job. That’s the first thing.

So embrace it, don’t fight it.

Yes, exactly.

Okay.

The second thing is to know which horizon, which leadership time period you are in. So recognize, “Okay, this is where I go to the future when I’m doing my strategic planning, when I’m doing my weekly thinking time, when I’m learning. These are the activities that are my future-focused things, and I’ve got to be really careful when I come back from the future to the present that I don’t spew out a whole bunch of ideas and changes and things to my present team about things that aren’t going to happen for a long time.” So I have to, one, know that this phenomenon happens, two, know which one I’m in, and then three, communicate appropriately.

Yeah. So the leader is effectively long-range planning in future tense under the system that will be in place, the structure that will be in place, operating as the leader that they will be in that moment. And then, like you said, they time travel back and they essentially say, all right, to implement what we need to do for the coming few months or year, or whatever it may be, I’ve got to ensure that I don’t ignore that structure, but I’ve got to remember the structure I have now is different than the structure that we will have. So my long-range planning can be in one set of reality, future reality. And then the implementation has to be in the current reality. What you’re saying is one of the healthiest things for a leader to do is to acknowledge, hey, two realities, let’s not confuse them, let’s just operate within them.

Exactly, yes. Because how many of us have had this big idea for something that we’re going to do, we come back, we tell our team, and they’re freaking out because they’re knee-deep in what we told ’em last time we came back. That’s one of the reasons that people fall into this gap. I call it the planning gap. The gap between what you intend and what you actually end up with. There’s lots of ways you can fall into the gap, but this is one of them. It’s because we disrupt our team from executing and implementing strategies that we came up with two years ago that need to be executed now, today, with what we now are excited about for the future, and it’s not time for them to do that yet. And so we as the leaders have this unique role of traveling between the different time horizons. And we need to normalize that, we need to recognize and acknowledge which one we’re in, and then we need to communicate accordingly, or we’ll disrupt our team from doing the work that they should be doing now because we’ve pulled them off into something that we’re excited about when we came back from the future.

Yeah. Well, you talk about that and it’s so funny because I can think of times where I’ve done this. I can think of times where I’ve talked with firm leaders who have done this, and the intention was always, “You know what, if I tell the team about this super exciting new thing that we’re going to do and all this grand vision, they are going to be just as excited as I am, and it’s going to motivate them, and it’s going to inspire them, and they’re going to rally the troops and we’re going to just charge ahead and it’s going to be incredible.” But you’re right: More often than not, it’s met with, “Oh no, we can’t do that. We have, no, no, no, no, no, no. Like I’m glad you’re excited, but I am now terrified.” And now it’s the focus as you talk about, right? Narrowing the focus. All of a sudden, everybody is no longer focused on doing what we need to now, they’re focused on freaking out about what we’re going to do at some point in the distant future that is now pulling their attention away from the present. So what I’m hearing you say is, it’s okay for leaders to be in the future. It’s okay for leaders to be excited, but it’s incredibly important that leaders understand who to share that excitement with and when, so that it allows people to stay focused on the right things.

Absolutely. You nailed it, yes. And the book is broken into three parts and the third part is called Implementation Planning. So there’s long-term planning. It’s like, where do we want to go? Who do we want to become?

Okay. So our real future selves.

Yes. Like three years out, what’s our vision? How are we going to get there? The second part of the book is Annual Planning. This is where we narrow the focus from three years down to one. What do we need to do next year to get a year closer to that three-year vision? What outcomes do we want to achieve? What projects need to be executed to achieve those outcomes? And then part three, this is the part that I never found anybody that had anything around, is Implementation Planning. This is how we actually communicate the plan to our teams, is how we make sure we have the capacity to do the plan, and it’s how we have the accountability to make sure the plan actually gets implemented.

And so what we’re talking about here, this time traveling and communication, part three of the book has this whole rollout plan that tells you: Here’s how you cascade communication around your plan. If we have a whole all-team meeting where they know, this is where we’re going to talk about the recalibration of the vision for the next three years, this is the annual plan for 2027 for us, it’s actually coming up next week, we’re going to do this. This is the plan, the outcomes of Project 2027. And then the way we handle communication, accountability, capacity planning, our meeting rhythms, our communication rhythms, everything we do every week, quarter, throughout the year, that’s what holds all of that together and keeps it in front of us so that we’re all still working on the same plan, we just keep getting farther down the path to what was originally set up. But for leaders, it’s part of our job to go into the future. It’s part of our job to set vision and strategy, and to align the people around it, and to enroll them in it, but sometimes we do that in a way that actually disrupts the work that they’re doing, because we don’t recognize this phenomenon that we’re the ones mostly time traveling, they’re not.

What’s going through my mind is instead of creating excitement around a big, hairy, audacious goal, we’ve created a big, hairy, audacious freakout, is what we’ve done, which is not exactly the intent.

Yes! Well, and especially in our profession, in public accounting, this is kind of a generalization, this isn’t true of everybody, but most people in our profession are risk-averse, change-averse. And so when we introduce things that create uncertainty, that feels like risk, it feels like change. And so we just naturally have, we don’t have a profession full of innovators who are just out there bouncing around trying to see what could they disrupt and change, we have the opposite—which serves us well, but it can make this even more, a bigger freakout, because of the way our profession is wired.

Interesting. Courtney, this has been incredibly valuable, and as I said, the book itself, it takes what are some really challenging topics, makes them very accessible, simple. Probably still not easy, unfortunately, but woe is the leader in business, right? It’s going to be a little bit hard, otherwise everybody would do it. But it’s a phenomenal resource. Folks who want to learn more about the book, if they want to figure out how they can start applying the Simple ScaleUp System within their firm or their company, what’s the best way for them to get in contact with you? I know the book’s available pretty well everywhere books are sold. I highly recommend the hard copy. It’s my favorite, but I like a good hard copy book. I believe you even have an Audible edition that you recorded. Is that correct?

We do, yes. I narrated the book so it’s on Audible, so on Amazon you can get Kindle, Audible, or hard copy. You can also get a hard copy from planningtoscalebook.com, but wherever you get it, just make sure you go to planningtoscalebook.com/tools so you can download the actual tools that we created, the same tools we use at Forge, the same tools we use in our in-person workshop, Planning to Scale, so you can actually do what you’re hearing and learning in the book. And so yeah, you can find the book in those places. You can find me on LinkedIn and glad to connect there. And if you read the book, if you hear this episode, I’d just love to connect and see what resonated and what you’re working through, because really the ultimate goal is to create a resource that helps leaders close the gap between what they want their firm to become and what it is. That is a hard gap to close, even if you have the willpower to do it. And so my hope is that these tools, like you said, Jeremy, are simple enough, accessible enough that you feel like, “Okay, I can follow this process and figure out where I want to go, how I want to get there, how far we’re going to go next year, and then what we need to change in our days, weeks, and quarters to actually stay aligned to that plan.” So I would love for your audience to grab the book and use it to get their firms where they want them to go.

I agree, I would highly encourage it and we’ll also put a link in the show notes to your newsletter, Field Notes, which is, in my opinion, one of the best newsletters out there that you can get from a leader. I always look forward to your stories, your insights in your Field Notes newsletter. So I would encourage, don’t just buy the book, please do that, but then also I would encourage you to sign up for Courtney’s newsletter. It is full of remarkable insights. It’s personable and it’s just, I don’t know. There have been so many times I’ve gotten that and I think I’ve even replied directly to you and just said “Yes.” Yeah, that’s so well said.

Thank you, Jeremy.

Absolutely. Courtney, thank you so much for joining me.

Well, thanks so much for having me. And yeah, if you want the newsletter, just go to forgeahead.com and I think there’s a footer where you can sign up for the newsletter there.

Wonderful. Well, we will get all that in the show notes. Again, Courtney, it’s hard to believe it’s been 130 episodes since we’ve first had you on the show, but it has been an absolute pleasure having you back on the show, and hopefully we’ll have to do a round three sometime here in the future.

It would be my honor. Thanks for having me back.