“Execution > Excitement” – Turning Strategy into an Action Plan

In this episode of The Strategy Sessions series, Ashley Carlson and Nichole Hughes tackle one of the biggest reasons strategic plans fail: execution.

While planning often feels productive and inspiring, true business growth happens when ideas are translated into consistent action. Ashley and Nichole explore why so many businesses create great plans but struggle to implement them once day-to-day operations take over.

The conversation breaks down the importance of quarterly planning, turning priorities into actionable projects, and creating operational structures that support follow-through. They share practical frameworks for breaking large initiatives into milestones, assigning ownership, setting timelines, and establishing accountability systems to keep projects moving forward.

Ashley and Nichole also discuss the value of weekly check-ins, cross-team visibility, and making strategic adjustments based on data rather than emotion. If you've ever felt like your business is great at planning but struggles to execute, this episode will help you bridge the gap between strategy and results.

✨ Takeaways

• Execution breakdowns rarely happen during planning. They happen when day-to-day responsibilities take priority.
• Quarterly planning creates focus and helps teams prioritize what matters most right now.
• Large goals become more manageable when broken into milestones and mini-projects.
• Clear ownership prevents confusion and keeps projects moving forward.
• Defined success metrics help teams measure progress and outcomes.
• Realistic timelines should account for capacity, workload, and business realities.
• Visibility creates accountability and helps teams stay aligned.
• Weekly check-ins encourage collaboration, transparency, and problem-solving.
• Strategic adjustments should be driven by data, not emotions.
• Consistent execution happens when vision is supported by structure.

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Transcript

SPEAKER_01 0:01

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

SPEAKER_00 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. 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 actions. Because growth doesn't happen by accident. It happens when vision meets structure. Whether you're planning for your next quarter or the next five years, this series will help you think bigger, lead better, and execute smarter. Today we're talking about something that I think a lot of people think they're really, really good at, but it's actually where most plans fall apart, and that's the execution part.

SPEAKER_01 0:50

Yes, because I think planning feels really productive. You walk away from a planning session feeling clear, motivated, and probably pretty inspired. But the execution is definitely where you find out if your strategy works in real life.

SPEAKER_00 1:05

Yeah, absolutely. And I think we see it a lot and we've seen it here elevate too. It's especially in that like growing phase of business, you're not lacking any ideas. You've got all of the ideas. You're lacking a way to turn those ideas into consistent action. And I think that that's a it's a really hard thing to like look at and really, you know, dive deeper into. So actually, I'm curious when you think about clients that we worked with here at Elevate or just from our own experience, where do you see that execution breakdown happening most?

SPEAKER_01 1:38

Yeah, I think honestly, it's rarely the strategy itself. When I do strategic mapping with clients, and even when we do our own, the plan is beautiful. We're all inspired, we're all very excited. But most of the time, what happens is that the breakdown happens after, right? When we all get back to the day-to-day. So things, the day-to-day operations, things come up, right? It could be fires, it could be just general client work, emails, uh, you know, all of that. And just suddenly the strategy that we put together, the initiatives, the priorities, they all just kind of get pushed back to when you have time. So I think we we both know, we all know, all the listeners probably know the answer to that is that that time just never quite happens.

SPEAKER_00 2:25

Yeah, that's right. And I think that that's where the misconception is is people assume that they've taken the time to plan and then execution will just naturally happen and it'll flow and everything will get done. But execution itself needs actual structure as well.

SPEAKER_01 2:40

Right. Yeah. I think with strategy, it has to come with operational structure. It has to come with dedication to the plan. So it doesn't just sit there. So I think that if we were to make this really practical, one of the biggest shifts that we help clients make is to yes, think annually, but really then the next step from there, instead of just think annually, now move on. We want to start focusing on the next, the next focus should be executing quarterly. So annual plans matter. They give you direction. They have, it's important for you to kind of reflect on year over year, adjust your goals and vision and all those things, but usually they are too big to manage the day-to-day. So that next phase of looking at things in a quarterly basis is a really important step.

SPEAKER_00 3:29

Why do you think that the quarterly basis works so much better than looking at it from an annual basis?

SPEAKER_01 3:35

Yeah, I think it it forces focus. It forces us to look at, you know, the next 90 days and be really honest with what actually matters right now. Because I think when you look at the full year, you're really, and in the way that we map it out visually, it all looks very attainable and it all feels equally important. But when you're able to break things down in a quarter and really think about what matters now, you have a clear runway. We're not going to guess what's coming up next. We actually know what success looks like by the end of the next quarter. It also allows us to, when we look at a quarterly basis, it allows us to look at things like vacations or um different things that we have coming up as a business, as the people who are in this business. So we're able to really say, in reality, what can we get done in this quarter given what we know is going on? And also accounting for the things that we mentioned earlier, the day-to-day, the fires, the emails, the things that come up. So we can be a little more intentional with what we place into that quarter.

SPEAKER_00 4:37

Yeah, I think that that makes a huge difference in what you're looking at, right? Because I've we've there's been times where we have done it as well, but we've seen teams with annual goals, but no quarterly breakdowns. So those check-ins just aren't aligned properly. And everyone's working hard. It's not that nobody's not working, it's just that they're not necessarily working together at the same time on the same thing, which leads to some misalignment.

SPEAKER_01 5:00

Yeah. Yeah. I think that effort isn't necessarily the issue that people face. We all, like I said, we're all, we all leave it very excited when we have this plan mapped out. So the effort isn't the problem, but alignment of what to focus on next usually is the problem.

SPEAKER_00 5:16

Now let's talk about the step that I think sometimes gets skipped. It's turning those priorities, those things that you've mapped out for each quarter into actual projects. Because saying something along the lines of client experience, like you were talking about in the last episode, sounds great, but it's not actionable. So, how do you turn that thought of we want to improve client experience into an actual project?

SPEAKER_01 5:39

Yeah, and I think that's really important because it gives what we do also, and I'm sure you can speak to this in your own process, is we have found that it's really important to have, let's just say we choose, like you said, that a one Q1 priority is improve client experience. If that is the general, and you just take a bunch of notes of what that might look like. That weekly update, let's just say, if you look back on how much, like, did I get anything done? You might have gotten a lot done on that project, but it just still sits open because it's very ambiguous. So we have realized that it's really important to break down that client experience into what we call milestones, subtasks, whatever it might be. So it might be, let's just say, subtask one, milestone one is redesigning the onboarding process. Another one is standardizing maybe communication templates, email templates. Another one might be updating our feedback system or response time, things like that. So there's different milestones. So that way, let's just say it's a month-long project. Now we've got four things that week over week we know exactly what we're going to work on. We can hit complete on something. I know we talked about it before, but that sense of completion is really important because you are excited to get to work because you're making a difference. But if it is, like I said, this ambiguous project that the deadline just keeps getting pushed, it feels like you're dragging your feet and not accomplishing anything when in reality you are. You just haven't set it up with milestones that are can be accomplished throughout the journey, right? We want to see the progress. We want to see it isn't all just about the finish line. It's about the progress and all of that. So breaking it down into mini projects, milestones, whatever subtask that it looks like for you, I think is really important. So you want it to be attainable, like things that people can execute on a week-to-week basis. And I know you do that really well in our clickup system with your projects. I love the way that I feel like you are the one who figured it out the fastest as far as breaking it down and having mini due dates and all of that. Maybe you can speak to how that has helped you.

SPEAKER_00 7:43

Yeah, I think having that, the mini milestones is a good distinction. And it's also a great way to track your progress because I know that in the past, before we started implementing these mini milestones, we would have like bigger milestones, but there was still so much within those bigger milestones that was getting missed. And I was like, I know I worked on it, but I don't really know where I'm at. And so I think breaking it down and getting into the nitty-gritty is really where you determine what your mini milestones are going to be within that project. Sometimes your your first step is evaluating where everything is at right now and doing an audit of your current process because I think you cannot start to improve something without identifying exactly how things are working right now and what there within that, those steps that you have currently needs to be fixed or improved or just completely removed. And then from there, it just it's a slow process of doing one thing at a time and making sure that the right people are in that project with you because that is a big part of any project. Even if you are leading the project, you're still most likely going to be tagging people in to help review or create SOPs or help update this platform or whatever the case may be, but making sure that they also have dates where they know that they are, they have that ownership and they have the responsibility to continue to keep the momentum moving forward. But the milestones for me have been a huge, a huge lift as well. Like I know it sounds weird to be like, I have all these extra steps within this project that I'm doing, but it's a huge lift because I know that I'm getting things done and I can see that. I am checking, I know we always say, like, you're not just checking things off a list, but I am legitimately checking things off my list to get this project to its full completion, which feels good knowing that I have completed things because when you're not able to see that progress, it nothing's changing operationally because you're still like, I don't know where I'm at. We don't know, we gotta look back at this, we've got to see where this is. But having those steps and being able to physically see the progress is huge in that execution stage.

SPEAKER_01 9:51

Yeah, I think that when what this made me think of is like that satisfaction of we all know like crossing something off your to-do list. It and also not only that, but think about just something as simple as a to-do list to know what if you have, let's say, an hour to get work done on this larger milestone initiative, for example, you know, because of that breakdown, you know what to focus on next. And it just becomes more clear. You're not wasting a bunch of time trying to remember where you left off because you've done that pre-work of coming up with the layout, if you will, of what those milestones will look like. So I also want to talk about just maybe like a simple framework that execution can really be. It doesn't need to be super complicated, but I think that when you are coming up with the projects for these milestones, for these goals that you've established, you want to make sure that each of these projects have a couple of things, four things, I think. So one is an owner. You just mentioned it. And something that I we do really well now is making sure that the larger project, if you will, is owned by one person. And even if you need to bring in others to accomplish the milestones, like we've talked about, those can have other co-owners. But the the project as a whole is owned by one person. Uh, there is a defined outcome, right? We talk about it a lot as far as what does success look like? What does the what does the end goal look like? The timeline, how, what does this look like timing-wise? How critical is it to get done on a different date if something else is depending on it, especially? And a success metric. So I think overall on the larger scale, being able to say, like we just talked about an example of client experience, what is the success of that look like? It could look like, hey, we're gonna start, you know, tracking our, or we have been tracking our, you know, client feedback, right? Ratings one to five. We want to see an increase be based on all of these improvements that we're making. In the end, we want to see an increase in our rating scale, for example. So I think that those four things are so important to establish because it it really defines the what success looks like as far as timing, outcome, all of that, and metrics, and then also who's gonna own it needs to be clear. Like I said, even if you're bringing in other people that way, there's just one person who kind of is speaking the language for all of it. And I think if any of these pieces are missing, the project could stall. There could be confusion, lack of clarity, which we all know just leads to problems.

SPEAKER_00 12:21

Yeah, absolutely. Now, out of these four, fun question, which do you see is typically the one that's missing the most?

SPEAKER_01 12:28

Yeah, I think I think it's ownership. And we've been guilty of it before. And it's not that I don't think for us ownership is lacking necessarily, but I think that it is unclear where we just have too many cooks in the kitchen type of feeling. So if it's a, you know, oh, the team, the this team will handle it, yes, I think that it does need to like the team might get pulled into, like we said, the the mini milestones, the subtasks, but there does need to be one clear owner who is holding the team accountable, who can be the owner of the timeline and knows all the things. Cause when you have too many cooks in the kitchen, that does tend to get get a bit messy having no one person responsible.

SPEAKER_00 13:08

Absolutely. I'd love to dig a little bit deeper into timelines because this I think is a place where unfortunately, and we have done it too, but people unintentionally set themselves up for failure or not to succeed the way that they had expected to, because sometimes I feel like we create the timelines based on like a case-by-case scenario and not real capacity, like you were talking about earlier. You know, we've got, we still have the day-to-day operations, people have vacations and all of those things come into play. So I want to dig a little bit deeper and get into why timelines are so important and like how to set them up successfully.

SPEAKER_01 13:43

Yeah. I think the question that we always come back to is what else is on that person's plate? Who is owning it? So we have gotten a lot better at being honest ourselves because I think I think we always asked each other those questions, but we actually ran into the issue that the individual was not being honest with themselves. And so we have gotten into a better practice of being honest about that. We so during our quarterly planning calls, so we mentioned we're talking about quarterly planning here, right? And so we do quarterly planning calls and to review the last quarter and plan for the next one. And so at each of those, we kind of look back and say, what went well? Did we overcommit? If we did, why? And we're able to identify the why so that way we could do better the next quarter. And also when we do plan for the next quarter, we we now look at what's what's on your plate? What do we have going on? Like I mentioned earlier, are there vacations? Is your workload bigger than we originally planned when we uh said what was going to be worked on in this quarter? Let's shift. Or who can you bring in on this project to help you get it done? That way you're not owning the whole thing as far as execution on all the topics. So I think that being able to every quarter looking at, you know, breaking those bigger projects into phases, like we talked about the milestones, that's a good approach. And picking potentially in advance who is the co-owner of that phase, if you will, identifying what depends on what. So where are the hard dependencies? Sometimes certain things don't have to happen in a, you know, like the next step doesn't depend on the prior step, but sometimes it does. So making sure that's very clear because those are the definite hard deadlines. And also building in buffer time. We have gotten better at that, I think, where we understand that sicknesses happen, uh, different, different things that deter our attention, time and energy do happen. And so being a little bit more gracious with that, and we also have established a process that, hey, if everything does go according to plan, then I'll just get it done faster or what we originally thought and just move on to the next project. Like we make it clear that if things do go according to plan, uh, I already know what I'm gonna pull in next and focus on next. If it doesn't, I've already pre-built in the time for, you know, operational things to come up, life to come up, whatever that might be.

SPEAKER_00 16:04

Yeah, and I think it's a huge shift. It's such a leadership, leadership shift. Those are two hard words to put together. Because it's not just assigning work. You're not just saying like this, you need to do this, you need to do this, but you're actually thinking about the bigger picture, not just for the business, but for the individual as a person. Because, like you were saying, if you're still working with clients, your client may have something coming up in that quarter that you know was going to take a lot of your energy and a lot of your time. And so you also need to be considerate of that because it all affects one another, right? If you're spending too much time here, then you're not spending time here. If you're spending too much time here, you're not spending time here. So it has to be balanced out so that everything can flow and you can still make progress around the board.

SPEAKER_01 16:48

Yeah, absolutely. And I think another piece that we haven't yet talked about as far as making this all successful is visibility. So I being making sure that this plan, this strategic plan, is visible to everybody is really important to getting it executed.

SPEAKER_00 17:06

Yeah. What does that look like in practice for business owners?

SPEAKER_01 17:11

So for I don't think it has to be anything complicated. I think making sure that you have a project management tool in place. And I always, I mean, I've said it before, whatever tool you're gonna use is the right one. There, I'm not gonna say that there is one right one out there for everyone, whichever one works best for you, and that you're actually going to it, you and your team will be in there using. Having some sort of shared dashboard. So we created, for example, a view that filters and shows very easily what are our current focuses and where has progress been made. We've made it very easy for everyone to be able to put in comments every week as far as what's been done, why it might be stalled, or I sent this in for Jane to review, just waiting on her feedback. So everybody has visibility and accountability. All of us, at least in our business and in a lot that I have worked with for strategic mapping in general, accountability is a huge piece. So being able to uh know that someone is waiting on updates for you or there's visibility to what you're doing, it does make us prioritize our time and execute a bit better, me included. So, and then a weekly, some sort of weekly tracking or reporting. And so I think for us, it is we meet live to talk through this because we've tried a document before. And for us personally, it didn't work as efficiently as we wanted. And so we do a live meeting every week, but we also do uh weekly updates in Slack. So we have a beginning of week and end of week type of format that we use. So I think that the visibility to the plan overall, how things are progressing, maybe raising a flag when we're we need, hey, I need help on this, or I've been staring at this too long, or I really need second opinions, whatever that might be. So opportunities every week to show where we're at, have that accountability, and also collaboration where needed. So I think that the format of what how you do all of what I just said doesn't matter as much as just in general, the visibility and the accountability there. Everyone needs to know what's being worked on, who owns it, and where does it stand in order to keep the needle moving.

SPEAKER_00 19:19

Yeah, because otherwise you're relying on memory, which memories can sometimes be deceiving. So we definitely want to make sure that we're not doing that because that doesn't scale. You're not able to track that, you're not able to look back on it because it's living up here and nobody else can see it. So that's a very important thing to remember. I want to dive a little bit deeper into the weekly leadership check-ins that you were mentioning, because I think a lot of people will hear that and they assume it's micromanaging and that you're constantly asking question after question after question. And I just want to be very clear about what are weekly check-ins in and how you can use them with your own team as well.

SPEAKER_01 19:58

Yeah. And I think you could speak to it too as far as how it feels as a team member. For me, what my goal is is that it's actually the opposite of micromanagement. It's about alignment, not control. I want to create a space to ask each other, all of us to ask and share what move forward this week, what's stuck truthfully. Most of the time when things are stuck, it's because of me. And so it is a place where I can be called out when that I am being the bottleneck. And sometimes I just need to be live to answer said questions. And so suddenly during that weekly check-in, we are now unstuck. So that's the goal. And also to be able to have each person share where they need support. So I think that for me, these meetings are about connection and like I said before, accountability and the live time to share in with each other where we're at. And I we've said it before about micromanaging. If you're sensing that you are doing that as a leader, that you're at, you're constantly asking, hey, where are we at? Where are we at? And following up and you feel that tendency to be a micromanager, you might want to do something like this: a weekly meeting where this is where they are going to report on where they're at, where they need where they might be waiting on you or someone else, or where the stuck points are, where they need feedback. If you preset in those connection times, it doesn't feel micromanage-y. It feels like collaboration on a project. We're trying to get this done together. And I'm here for you to answer any questions you have every Monday or whatever it might be. That doesn't feel micromanage-y, that feels collaborative.

SPEAKER_00 21:35

Yeah. And from my perspective as a team member who does the weekly check-ins, for me, it's a lot of accountability. Um, and I'm able to say, for instance, like at the end of quarter one, I finished three initiatives in one week. I was like, I'm getting them all done. We're not moving these into quarter two. But then last week, for instance, I didn't make any progress on my initiatives because I had a lot of client workload stuff that I needed to take care of that was more time sensitive. And so That just it keeps it keeps me accountable. Like I know that there are things on my plate that need to be done, but I'm also being transparent as to why it wasn't completed. There were other people that stepped in and were, you know, said, Hey, can I help you with this? So again, that collaboration, that team mentality definitely helps keep things moving forward. Even when that individual is stuck, there's somebody else that may be able to step in and say, hey, I can help. Let me raise my hand. It also allows me to see into what other people are working on. I mean, we're in a remote environment. I don't know what everybody is doing on a day-to-day basis outside of looking at our dashboard and saying, oh, this is what they're working on. But in those check-ins, I get a little bit of insight as to what progress they've made on these things or what things that they're blocked on. So it's just a really great way for transparency, open communication, and accountability across the board because there have been times where other team members have said, hey, I'm stuck on this and I don't know where to go. And I'm like, hey, let me take a look at it, put another set of eyes on it, like you were saying earlier, and give some feedback. Do I always have feedback? No, because sometimes I'm like, this looks great. I don't know what you're thinking. Like you should just move forward with this. But you do get, you go cross-eyed when you stare at a doc for too long and you get this tunnel vision. So sometimes you just need a fresh set of eyes to say, this is great. Let's move forward with it. So that's what the weekly check-ins do for me.

SPEAKER_01 23:24

Yeah, I think a word that came up to mind for me is perspective. So, like you said, there was one week where you got a lot done internally with our initiatives, but then there was another week where you, you know, we all do it at the end of the week. We realize, oh my gosh, I didn't get to this. And it's okay, but because we have these preset shareouts, if you will, the you're able to fill us in and give us perspective on why. And that again leads to less micromanaging because I'm able to know that heading into this meeting, I'm gonna understand what progress you made and/or if you got stuck, why. And this now gives us all perspective also on each other's work to know she's got a lot going on and really needs some support. I'll come in and help, or whatever it might be. And to your point, too, another way to look at the perspective is sometimes you where you are stuck, it just requires someone else's brain. It just might take someone else's past work experience or the the way they look at things differently to get you unstuck. So clearly we're a high, we're very passionate about our weekly check-ins to avoid micromanaging and to encourage accountability and collaboration. So, one of the last things that I want to talk about when it comes to how to make these strategic plans successful in action is adjusting, being willing to adjust and pivot because no plans stay perfect. I tell clients all the time when I lead their quarterly planning, is they not even when we get there in advance. I let them know by the time we meet next quarter, some of these that we said is going to be accomplished in the next quarter, they probably won't be, but I'm gonna guide you through it. There's is a big difference between adjusting strategically every quarter versus just constantly reacting. Yeah. Do you have examples that you could share of the differences? Yeah. So I think that strategic adjustments in these quarterly plannings, for example, could look like we've now reviewed the data. So that's a big piece is looking at metrics dashboards every quarter. So it's not just looking at the projects and the initiatives and what got done and what didn't, but it's also looking at the data. So it could be, for example, something like we tried Google Ads last quarter, and here's how that turned out metrics-wise. It did or it did not work. Now we can make a shift heading into the next quarter. So that's a strategic adjustment. A reactive adjustment might be like, this is just not, I just feel like it's not working or it feels too hard. So let's just change all of it. So one of those is strategic leadership, and the other is dressed as is panic dressed as pivoting. Yeah, absolutely.

SPEAKER_00 26:09

It's like everything's on fire. We have to stop everything just at this very moment. And I think it's an important distinction to have is when you are looking at things, data drives a lot of information. So making sure that you have those metrics where you can track the data, making sure that you're documenting, whether you're documenting monthly or quarterly, making sure that you are documenting this information somehow so that you can look back to make those strategic adjustments and not just be like, well, it's not working. We're done. Right.

SPEAKER_01 26:39

So at the end of the day, a strategy without accountability is just optimism.

SPEAKER_00 26:45

It is. And optimism does not create consistent results. Structure does. So here's what we want you to think about as you leave this conversation today. Where in your business are things getting stuck between planning and execution?

SPEAKER_01 26:58

Because that gap that you're experiencing is not a time issue. It's a structure issue. Thanks 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 a 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 using the link in the show notes. And if you're ready to go deeper to build a fully lined, aligned strategic map with real structure, ownership, and execution, please book a clarity call. And remember, you've got this. Thanks for listening to the Delegation Download Podcast. Don't forget to subscribe, leave a review, and follow us at Elevate VB Solutions for more tips to help you lead smarter and live better.