"Review, Refine, Repeat" - Making Strategic Planning a Leadership Habit

In this final episode of the Strategy Sessions series, Ashley Carlson and Nichole Hughes explore the leadership habits that transform strategic planning from a once-a-year exercise into a sustainable framework for long-term business growth.

They discuss why the most successful businesses don't simply create a strategic plan and move on. Instead, they consistently review, refine, and adjust their plans as their business, team, customers, and market evolve. Ashley and Nichole share practical approaches to monthly and quarterly reviews, using data to drive better decisions, involving your team in the planning process, and avoiding emotional decision-making.

The conversation also highlights the importance of celebrating progress along the way. By recognizing milestones, sharing wins, and creating visibility across the team, leaders can maintain momentum while keeping everyone aligned around the bigger vision.

If you want your strategic plan to become a living framework rather than a forgotten document, this episode offers the habits and systems to lead with clarity, consistency, and confidence.

✨ Takeaways

• Strategic plans should evolve as your business grows and changes.
• Monthly and quarterly reviews keep your team aligned and focused.
• Consistent reviews matter more than having a perfect planning system.
• Data should guide strategic decisions instead of emotions.
• Tracking key business metrics creates clarity and confidence.
• Involving your team improves ownership and decision-making.
• Different perspectives lead to stronger solutions and better outcomes.
• Celebrating milestones keeps motivation and momentum high.
• Breaking large initiatives into milestones makes progress easier to recognize.
• The strongest leaders build habits around reviewing, refining, and repeating their strategy.

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Transcript

SPEAKER_00 0:01

Welcome to the Delegation Download Podcast, where business owners, CEOs, and leaders learn to work smarter, not harder.

SPEAKER_01 0:07

We're your hosts, Nicole Hughes and Ashley Carlson, here to share real stories, expert tips, and simple strategies to help you delegate with confidence and grow your business with support. Because you can do anything, but not everything.

SPEAKER_00 0:19

Welcome back to the Strategy Sessions, Mapping the Business You Actually Want series. In this series, we're breaking down how we approach strategic mapping at Elevate, the exact framework we use to move from scattered ideas to aligned action. Because growth doesn't happen by accident. It happens when vision meets structure. Whether you're planning your next quarter or your next five years, this series will help you think bigger, lead better, and execute smarter. We've talked about vision, priorities, and execution. And today we're closing with the piece that actually makes it all sustainable.

SPEAKER_01 0:50

Yeah, because without it, even the best plan will eventually fall apart. So I'd like to talk to start off like with a bang on this episode. What is the biggest misconception that you have seen when it comes to strategic plannings for both us as a company and with those that you've worked with?

SPEAKER_00 1:07

Something that happens a lot is that it's just a checklist. It's just a thing that you do once a year and you move on. So building the plan, saving it, and then assuming you're set. But businesses are dynamic. The people are always changing, the economy is changing, your customers are changing. So all of those things in the market changes and internal priorities should evolve with it. So your strategy needs to evolve and you have to be flexible. So a plan that doesn't move with the business is just no longer a plan at all.

SPEAKER_01 1:41

Absolutely. And it's it's such a good point because planning gives direction, but there may be roadblocks that you face and you have to overcome them. And so it's the leadership that keeps everything aligned over time and keeps things moving the needle forward. Even if it's a slow movement of the needle forward, you still need to have that leadership to move the needle forward. Now let's talk. We talked about the monthly reviews that we do here at Elevate, the quarterly reviews. Why would it, why is it important for somebody to start doing that? And why is it practical to do that when you have a strategic plan?

SPEAKER_00 2:15

I think exactly because of what we just talked about with the ever-changing environment that you're undoubtedly in, you have to re-look at everything every month. And they don't have it doesn't have to be complicated, but just taking 30 minutes to review how the last 30 days went, what progress was made on the original goals that you set, or maybe progress on new things that came up, what didn't move forward because maybe your attention was drawn somewhere else, where we stuck. So being able to look at all those things on a regular basis and change course going forward if needed, or push things back, or create new. Maybe a new initiative needs to take place of an old one. So just being really intentional of re-looking at that plan and how things are going right now is going to make sure that you're never stuck and you're not too far off course as well.

SPEAKER_01 3:04

And I think what I'm hearing is consistency. It's not about having the perfect system. It's not about making sure that everything is always moving forward, but it's about actually showing up, reviewing what has happened and why it either has gone forward, why it has paused, why something else took its place. So it's consistently having those conversations. Now, from the business or sorry, not business, from the monthly review to the quarterly review, how do those differ?

SPEAKER_00 3:30

So in my experience, the monthly should be a bit more tactical. You're looking at progress, you're sharing what has gone move forward versus what's stuck, looking a little bit more at the milestones, if you will, whereas quarterly is more strategic. It's more of a step back because you've collected data from, you know, you should still look at data on a monthly basis, but looking at data over the last quarter and what's upcoming, you're able to look at are we focusing on the right priorities based on what we know? What's working that we should definitely double down and throw more resources at resources at, and then what's not working that maybe we need to adjust. So I think that monthly is maybe more about the tests and the milestones versus quarterly is more directional, more of that, like following the compass, if you will.

SPEAKER_01 4:16

And not starting over from scratch because it already exists. You're just refining what already exists and making sure everything is still moving in the right direction for the business, for the team, and everything else that goes along with it. Yeah, exactly. Now let's talk about what can derail process because you know, all the things that people don't talk about. Emotional decision making. Talk to me about that and how it affects strategic planning or strategic mapping as a whole.

SPEAKER_00 4:43

I think that this happens a lot. We're all human and we all are can be emotional in our decision making, especially in fast-moving businesses, whether you're scaling fast, when you're in a season where a lot of things are changing all at once, it's really easy to feel reactive to things instead of proactive. And I think, I mean, I know us personally as a leadership team have caught ourselves being in a very reactive season. And sometimes it happens out of necessity just because so many things are happening. But it is important to be aware and kind of take a step back and handle what you need to handle, but then be less reactive and less emotional. So when things are feeling off, when suddenly everything feels urgent, I think that it is easy to change direction and pivot and spend resources in the wrong direction just because you don't have time to look at the data. So I think it's very normal, but it is something that we need to be aware of so we can take a breath and not be so reactive.

SPEAKER_01 5:45

Yeah, we are all human. And that is the number one thing that we have to remember. But when it comes to when it comes to the data that people should be looking at, what exactly should they be looking at?

SPEAKER_00 5:54

Yeah, that's a great question. And I think it's important for all businesses to have some sort of data that they're collecting, some sort of dashboard that they can look at and pull numbers every month and every quarter. And I'm a big advocate of pick those numbers for the year, but don't be the one that is pulling all these numbers. Have your team who is maybe owning these departments, your EA, whoever it is, gather the numbers so that way you truly are just looking at the dashboard and processing them and making sure that you are the one making something of the numbers and making decisions off the numbers. We have a lot of clients who don't look at the numbers ever because they don't have time to pull them. And that's understandable. So have someone else help you pull them so then you can look at them and make decisions from them. But some of the, I think every business will look different, but a few areas that I think are critical for you to know whether or not things in your business are going successful is revenue trends, of course. So is the money coming in the same way that it was? What is MRR look like? Things like that. So really looking at what the revenue trends are. Client retention and feedback. I actually just read something that talked about how retention is the most important number. That is so critical because you can get as many clients as you want, but are they staying? That's a huge indicator of your delivery of the health of your business and your team. Completion rates, I think that all these initiatives that we've been talking about through this series, are they actually being completed when you originally said they were? Are they lasting way too much longer? Because that's a case that maybe you are overpromising or your team is at capacity. And I mean, team capacity is is one of the things that you should also be looking at. So what does it look like? What does everyone's plate look like? Is it twofold? Do you need to hire again? Things like that. So the list could go on and on, especially per business. There's going to be different variations. I think marketing effectiveness is a big one too, where you're spending your marketing dollars and time looking at those numbers as well. So I think ultimately, whatever data you choose and collect, you have to collect it. And it should be helping you make decisions with clarity instead of, like we just talked about, reacting to pressure, emotions, whatever that might look like.

SPEAKER_01 8:07

Mm-hmm. Yeah. And another thing, and you mentioned it just a moment ago, is bringing your team into the plan. We each have a hand in what we're doing. We each have ownership of what we're doing. And I know that that takes a lot of weight off of your shoulders because you're not holding all of the weight. You're not owning all of the projects. Are you part of a lot of them? Yes, absolutely. But you're not owning the all of the milestones. Maybe you've got one or two in there. But it bringing a team in makes a huge difference in the process for strategic planning.

SPEAKER_00 8:39

Yeah, I think that the bringing everyone into the process of, you know, so many different avenues is real, I I've always said that that's one of my favorite things is that everyone can look through their own lens and have their own experience. They also can see things that I might have missed because I'm not so in it. And so because the team is in the day-to-day of different areas, allowing them to also look at the numbers in the areas that pertain to them and give me some feedback as well. So, like when we have our monthly and quarterly, I'm not the only one reporting on these numbers. I ask the ones who it pertains to to also. So you and Amanda in this case also let me know, hey, what are what do these numbers mean from your perspective? Because I may not know the details of the why behind it. And so collectively, between all of us looking at it, really helps make better decisions, identify what's working, what's not, where do we need to pivot or adjust. So I think, and then it also is ownership, right? So you guys also have a stake in it. And I think being able to have you all be in and involved in these data dis data-driven decisions is really critical and much more impactful than having me be the only one who does it.

SPEAKER_01 9:54

Yeah, absolutely. The why, understanding the why behind decisions that are being made is it just allows for execution to get easier. And because we are owning things, we also, like you said, we may have a different perspective, a different lens that we're looking through when we're looking at these numbers. So we can bring even we can bring fresh ideas. We can say, hey, this, we've got this initiative on our plate, but I don't think that's where we need to focus. We can focus here. And it's because we're seeing things from a different angle. And you need that sometimes to have that fresh perspective and move forward with things. And like you said, there may be something that you miss just because you're not looking at it from the same lens.

SPEAKER_00 10:30

Right. And I think problem solving too is really brings out some unique perspectives. So even if the three of us saw the same data issue, right? The same problem, whatever it might be, we all three might have a different idea of how to solve it. And from that three different ideas comes the one perfect idea with pieces of all three, usually. And again, I couldn't have done that by myself, nor could you guys do it yourself. So being able to have this collaborative without too many cooks in the kitchen, I think also, but I think having this collaborative view of looking at the numbers, making decisions together. And also, I think for I'm also gonna say for those who are visionaries listening to this, you also need someone who's going to tell you that's a great idea, but we have to wait because we also said these things are priorities. So sometimes I also need that because I have all these ideas, and I sometimes need that little voice on my shoulder, which is you guys. Sometimes you have to step into that and say, nice, very nicely, Ashley. Love that idea. We're gonna put it in the parking lot, or that's gonna be next quarter. Now is not the time. And so, because of that, though, I think, and and that goes all three ways. I think we all get super passionate and excited about whatever ideas we might have, but we can all, I guess it's checks and balances, is what I'm trying to say. We all need that sometimes. And I think that it really helps us not be too reactive with our shiny object syndrome nor emotional decision making. All of it really just helps keep the things moving forward in a really good way and collaborative in solving problems together.

SPEAKER_01 12:18

Yeah, I think it's just the collaboration. We love collaboration here at Elevate. We collaborate with each other all the time on all different things, including the initiatives that we're working on that were established in the strategic plan. And it's just nice to get somebody, like you were saying, to get somebody in there and give a give their perspective and what they saw. And then that makes just a beautiful thing happen. So and then there's one other thing that we need to talk about today when it comes to refining and reviewing everything. And it often gets skipped, surprisingly, even though it is something extremely positive, and that is celebrating the wins that you're making on your initiatives.

SPEAKER_00 12:52

Oh, yes. I think that in a group of high-performing women like us, and I'm sure many other teams experience it as well, there is always another goal, another project, the next milestone. And so you just move on to the next thing before stopping to acknowledge what worked and what's going well so far.

SPEAKER_01 13:12

Yeah. And I think that over time what happens is that can create a feeling of always feeling like you're behind because there's always something next. There's always something to do next. There's always another due date. There's always another milestone. And so slowing down and celebrating what you actually have accomplished is crucial to keep that momentum going. And I think that celebrating the wins just allows you to keep that positive and engaging momentum so that things continue to move forward with initiatives as you celebrate, as you hit roadblocks, all the way around. But keeping that momentum is so important.

SPEAKER_00 13:44

Yeah. And for the team, it's it's important to keep them engaged by recognizing the progress so far. And yeah, I know that we've talked about this, and I don't know if we've talked about it here, but it's something that we used to do was just put an initiative on the, you know, plan. And we felt like it was so ambiguous, the finish line. And so by building milestones in our plan for each initiative has helped all of us feel more accomplished because there would be progress. We knew it, we heard it, but without seeing the progress, the many milestones that have come been completed along the way, it's almost hard individually to see the sense of accomplishment that you have done so far. And so I think for all of our team and me included, being able to break things down into milestones, it really is, it's more motivating. You're able to say, I accomplished this, even though it isn't the finish line, but you accomplished those first couple laps or whatever it is. And so it really allows each to celebrate what you've done with each other. It also makes it a lot more clear to report, right? So we have weekly reporting as well. We talked about monthly and quarterly, but we also let each other know what we're up to every week. It makes it a lot easier to say what you accomplished this week if the mini milestone is clear, instead of thinking, which I think is human nature, of how much further you have to go, right? And it becomes demotivating a little bit and less you're less connected to it. So being able to know, hey, I accomplished these things that are getting me closer, you are able to celebrate it a little bit more. So we do make sure that in the weekly updates, the monthly check-in or monthly um planning and reviews and the quarterly that we're celebrating the milestones. We even share with our team, the leadership team every month shares with the team, hey, here's the progress we've made. Here's what we are working on. So not only are we celebrating the progress and getting letting them in on that, but it also is accountability. We want to make sure that they know we're what we said we were gonna do, we are working on it, and here's what we've done.

SPEAKER_01 15:54

So and the mini milestones make you more efficient because you're not having to go back and think, what haven't I done or what have I done? So now you're more efficient, you're saving time, you're putting time back on your plate while you get these initiatives done because you're not searching for where you left off. You know exactly where you left off because it's documented.

SPEAKER_00 16:10

If y'all can't tell, we're a big fan of the milestones, breaking things down so they are accomplishable. And make sure you share that. You share what you accomplished. You also can share where you're stuck or where things aren't where you thought it would be. There's a lot of benefits to having it and the, you know, the clarity that it brings, the motivation that it brings. So, well, thank you all for listening in today. I think for for my, you know, what we want you to take away with this is the best leaders are strategic by not just planning well, but being able to adjust well along the way.

SPEAKER_01 16:46

And they build habits around the adjustments that they make.

SPEAKER_00 16:50

Yes. So if you've been with us through this series, you now have a foundation for thinking more strategically about your business.

SPEAKER_01 16:57

And hopefully a clear understanding that strategy isn't about doing more. It's about doing the right things consistently. But that wraps our series three of the Delegation Download Podcast. We will be joined next time by a special guest who will give us all of her lessons learned on her strategic mapping process. Thank you for joining us for this episode of the Strategy Sessions, mapping the business you actually want. If this conversation sparks something for you, we created the strategic mapping starter guide to help you take the first step. It's not a full business plan template, it's a clarity tool, a way to pause, zoom out, and think strategically before you make your next move. You can download it by using the link in the show notes. And if you're ready to go deeper to build a fully aligned strategic map with real structure ownership and execution, book a clarity call with Ashley. And remember, you've got this. Thanks for listening to the Delegation Download Podcast.

SPEAKER_00 17:48

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