Unlock the full potential of your strategic planning process with Strategic Planning: Connecting Strategy to Execution. Agile Rising’s CEO, Chris Ruch, and Upwards Consulting CEO, Michelle Gilboy explore the impact of effective strategic planning in aligning your organizational goals with actionable execution and results.
Discover key components of well-facilitated strategic planning workshops and learn how to create outputs that directly translate into high-priority initiatives and OKRs. Whether you’re a business leader, portfolio manager, or Agile practitioner, this webinar provides you with practical tools and insights to drive real change and achieve measurable results with your strategic planning process.
If you would like to jump-start your annual strategic planning process or need help transitioning to an iterative strategic planning cadence, reach out to talk to us today at info@agilerising.com.
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Transcript:
Chris: Hello and welcome to Agile Rising’s webinar, “Strategic Planning: Connecting Strategy to Execution.” It’s great to have you join us. My name is Chris Ruch, CEO of Agile Rising, and I’ll be leading the conversation today about strategic planning. I’m joined by Michelle Gilboy.
Michelle: Thank you, Chris. I’m Michelle Gilboy, CEO of Upwards Consulting. Great to be here, and I’m looking forward to our conversation.
Chris: Michelle and I have worked together for the better part of a decade on various efforts, from strategic planning to organizational transformations. We’re here today to talk about why strategic planning is important and how executing on that strategy is equally important. This is a timely conversation, as many organizations are moving into their strategic planning phase of the year. We know a lot of strategic leaders are thinking about what comes next and what they’re going to focus on. Today’s conversation will involve picking Michelle’s brain about her experience leading strategic planning efforts and sharing Agile Rising’s experience helping customers with their strategic planning processes.
Michelle, can you talk a little bit about your background and your role in strategic planning? What makes you an expert in what we’re talking about here?
Michelle: I primarily led or was part of transformations. Often, as part of a transformation, it’s about getting clear and focused on what needs to be done and how to execute on it. Along the way, I’ve had the opportunity to build strategy myself, so I understand the challenge firsthand. I’ve also facilitated strategic planning and been responsible for executing strategies many times. I’ve had a lot of experience, both successes and challenges.
Chris: Before we jump in, for our participants and audience, we will have a question and answer period at the end of the presentation. Please use the Q&A functionality in Zoom, and we will go through those questions at the end of our conversation.
To dig into it, when we’re talking about strategic planning, there are a variety of different kinds of planning. To frame the conversation, how do you define strategic planning, and what makes it different from typical planning or budgeting that an organization might do?
Michelle: Great way to start. One thing I’ll level set on is what you see here, and then I’ll talk about strategic planning. I know when I enter organizations, “strategy” is used in different ways. When I’m talking about strategy today, it’s a unified set of choices that position you to win. The strategy itself should be focused on things we don’t control, like the customer. It’s a theory because, really, we’re trying to predict the future. We’re taking information about our customer, our competition, and our own organization, but we’re formulating a theory. We’re trying to figure out the unmet needs. And because it is a theory, you need to iterate on it. I’ve worked in organizations where they think they don’t need to change their strategy. Maybe you don’t, but it’s unlikely we’ve guessed the future perfectly.
That means as we translate that into strategic planning—the process by which we understand how to realize or advance that strategy—we need to figure out what to do next or in the near term. Strategic planning incorporates a lot of different pieces, like budgeting. But really, what we’re talking about is how do we move from strategy development to strategic planning? The best experiences I’ve had, they do strategy development separate from strategic planning. You need a smaller group of people to figure out where to head, and then you start to translate that. That’s where you make sure everybody’s involved and understands.
Chris: You hit on a couple of really important and key things there. For me, strategic planning is about the things that will make a big difference in the future of the organization. We’re not talking about the next feature to build or the next incremental improvement. It’s about the big things that will be different a year, three years, five years down the road. And that key point that it’s a theory—another way to think about it is that it’s a bet. You’re taking a risk and saying, “We’re going to try to bring a new product to market to satisfy a customer’s need, and we have a theory about how that’s going to work.” It’s either going to work or it’s not. So having that iterative nature, to be able to look at what is working and what isn’t, is key for effective strategic planning.
Michelle: One of the biggest distinctions is that, again going back to strategy, these are the things that we don’t control. It’s the future. So it’s about influence. When we look at our strategic planning, we’re talking about the things we do control: our resources, our skills, our money, our capacity.
Chris: You just hit on one of my favorite topics, which is capacity. That’s a good segue from what strategic planning is to how we connect that strategic planning and vision to execution. I’d love your thoughts on how we move from having a vision to actually aligning that to something achievable.
Michelle: There are a couple of things I’ll highlight here. When we’re talking about connecting strategy to execution, we’re all looking for clarity on direction and alignment. And when I’m talking about alignment, I don’t mean just nodding your head. I mean, “I’m aligned to what we’re doing. I want to show up here every day. I’m inspired.” And the last piece is commitment. “I am committed to this, and I’m working with other people that are committed.” Getting clear on those kinds of things—strategy plays a huge part in that direction, but the alignment and commitment are where strategic planning comes into play.
The thing that people struggle with is what… I forget, “The Four Disciplines of Execution,” I think, is the name of the book. They talk about the whirlwind. The whirlwind is our daily lives. We show up to work every day, and there is a whole host of things that we either think we have to do or are being asked to do. Strategy is about the one or two things we’re going to put massive attention on in addition to the whirlwind.
So the best thing we can do is emphasize focus. When I look at even really good strategy, it’s often too conceptual to action. You have to have a way to take these concepts and turn them into targets. I remember the story of NASA in the early ’60s. They had this vision that they wanted to be the world leader in space exploration. Meanwhile, in the early ’60s, we were not that, by a long shot. So how do you execute on that? Then you had Kennedy help target it: “We’re going to put a person on the moon by the end of this decade and return them safely home.” Those are things you can start to say, “Ah, I can execute on that.”
The best way I’ve seen, and there are a lot of good examples of this—Google is the one who kind of brought this back into fashion—is OKRs. Using a goal-setting system like OKRs, where you simply state your objective in short cycles so it feels tangible and real, and then define the key results… that is what I’ve seen time and time again really light people up.
Chris: OKRs have become very popular in the last few years, but they are not a magic bullet. They are a good tool for capturing the output of a good strategic planning process and making things actionable. But one of the things that I often see is that OKRs don’t necessarily drive the alignment, clarity, and prioritization that you mentioned. This is because organizations don’t have a good process for creating OKRs. Instead, it becomes a competitive thing: “You have your OKRs, I have my OKRs,” instead of us having shared OKRs.
Could you talk a little bit more about some of the specifics that you’ve seen work in driving alignment and clarity among leaders from different parts of the organization? How does that happen in the strategic planning process?
Michelle: There’s a translation, like I said, from strategy. And when I’m talking about strategy, the input into these conversations are the strategic choices that we made. How I test whether we have a good strategic choice is: if I see “better customer service” or “trusted advisor,” or “build awareness”—I usually do the test of, “Would you never want the opposite of that to be true?” So you never want, you never say, “Well, we don’t want better customer service.” That’s just a litmus test for me to know that we have at least a pretty good strategy. Because if you’re creating strategy, you’re making actual choices.
So, those choices—you need to be saying, “We’re doing this instead of this.” So I kind of start there. But if you… I assume that going into the strategic planning and the creation of the OKRs, we have a pretty good strategy. We understand the behavior shifts we want to see in our customers or in the market, the experiences we want them to have.
Our organizations have an operating rhythm to them, right? Yearly planning, quarterly planning. It’s just taking that kind of cycle and getting focused on what we’re doing now. What do I mean by that? I mean, okay, so strategy feeds our OKRs. That helps us understand where to focus. But then we need to take those, as a collective group of leaders… I think the worst examples I see happening is that you might have a leadership team of eight or ten people, and each one of them has their own list of OKRs. I’m not saying that’s a bad way to start; everybody has to think about how they want to contribute towards that strategy. But it really does take some coordination amongst your leaders to whittle that down into what to focus on.
What I find most important is that collaboration needs to happen. You need to get it down to a smaller list. And I kind of want to talk about who you’re including here, because I think it’s important, too. At the minimum, you have your leadership that is intimate and familiar with the strategy, starting to build those OKRs. But when it comes time to set those key results, don’t set your key results until the people who are going to develop your key results and who are actually going to do the work understand these objectives, understand the customer, understand what we’re trying to realize.
And then that’s where these conversations around, “Here’s what we’re trying to do.” And listen, if you’ve been the person or the people that develop these objectives, I think your first job is to say, “Here’s my draft, here’s what we came up with, but please make these better. Fight me on them.” Invite them into that conversation. And then from there, as a collective, everyone involved starts to lay out what these key results are.
My preference is getting into a bit of… we saw the slide with the operating rhythm. There should be a rhythm for leaders setting strategy, how often we’re revisiting it, taking a look and redefining it. Same thing with the OKRs: resetting those objectives and then inviting people in to set those key results.
Chris: It’s really… strategic planning is a process, and it’s an iterative process. It’s important that the right people are involved at the right time, especially as it’s moving from the vision—what are the things we want to achieve—to how we’re going to achieve that, which is itself an iterative, Agile development process, or creative process.
One of the keys for me for successful strategic planning is, one, having somebody own it. I think a lot of times that kind of… everybody having their own individual OKRs is because that’s the level of ownership. There’s not somebody crafting the overall OKRs; it’s each organization, each department, kind of doing their own. And the other is just not having good facilitation in those sessions. Well-facilitated strategic planning processes—and I don’t just mean a single workshop, I mean the whole series of workshops and planning sessions and feeding the vision down to the more detailed OKR creation—is really key.
Michelle: Something I’ll add here, and it’s emphasized a little bit in this slide, is that it is not uncommon… because we’ve talked about your strategy, your OKRs, your objectives and your key results… but in building your strategy, in setting your key results, there’s a whole host of assumptions that we are all making. I find bringing visibility to those assumptions is incredibly powerful. First of all, it helps us see that our strategy is a bit of a theory. We had to make some assumptions; maybe we didn’t have all the data. But it also helps then, as you’re setting up what you’re going to execute on… well, of these assumptions, are there any that are really risky that we need to test out? Because that then needs to become part of your work.
And then to your point, Chris, with the facilitation, it is truly a process. This isn’t a day-long thing. And also, with the facilitation, I think the other thing is, strategic planning can be really soulless. There’s no humanity to it if it’s not done well. I mean that in two ways. Number one, there’s not enough emphasis… we, of course, should be emphasizing the business, but also, who are the people that we’re impacting? What are the unmet needs?
And then, as humans, those of us showing up to do strategic planning, that facilitation is really key for a number of different reasons. First of all, it’s kind of awkward when you’re getting together with people that you don’t work with on a regular basis. So that facilitation of how to bring people together in a thoughtful way and make sure that, before we make any decisions, we creatively and collectively make decisions… that everybody has as much shared understanding as possible, and that we’re answering the right questions along the way. What are our big bets? What are we going to… if all else, we’re going to put extra emphasis on these bets and not these other things.
And then kind of walking us through: how do we take that and get more focused in on what are the… I actually love this technique. It’s called a pre-mortem. It’s from NASA. Some of us may be familiar with it. You can Google it; it’ll tell you how to facilitate it. But once we understand what the big bets are, I love doing a pre-mortem with a large group of people, because that then gets some of the things that you’re afraid of.
A pre-mortem, if you’re not familiar, is where you kind of look into the future, maybe a year from now, and you ask the question, “If everything’s gone wrong, what went wrong?” Your technical people are going to have a perspective, and your operations people… everybody’s going to bring their perspectives. I love getting those things out on the table because those are the kinds of things where you can start to proactively, as you’re doing your strategic planning, emphasize what is going to have the biggest impact on our success. And I like actually even doing that in advance of starting our planning. I like to just think really big, say, “What really scares us? What’s on your mind?”
Because that does help us understand: do we have the skills in our own organization? Do we need to build them? What are all the other things that are going on? Do we have the capacity? What technically… maybe we assume that the technology is where it is, and it really isn’t. It’s not available to us. So on and so forth. So getting those things out on the table before we start to walk ourselves towards what are the goals that we really need to see right now, that’ll help us advance. And then finally, just building out what are we actually going to do? How are we actually going to hit those goals?
Chris: Pre-mortems are a great approach to risk management. It helps you expose those things that are… “What’s going to cause this to fail? What’s going to cause it to not go well?” so that we can plan around that or mitigate it. It’s also a good way of trying to turn the… we tend to have perhaps elevated levels of… that our idea is going to work, or we’re excited about our own idea. Having a time and place to really think about alternative views and other ways of working…
Your other key there is, when we’re talking about strategic planning, and particularly Agile strategic planning, if we want an agile organization, business agility starts with the strategic planning process. If you have that group of people doing strategic planning that don’t normally work together, that’s kind of a symptom of a siloed organization that maybe hasn’t organized around the delivery of value, hasn’t organized around value streams, hasn’t organized in ways of trying to deliver on these strategic initiatives. So that’s a great place to start with trying to break down the silos. If you have a siloed leadership team that’s not working together on.
Chris: …If you have a siloed leadership team that’s not working together on a frequent, iterative basis, that’s going to flow throughout the whole rest of the organization. It’s going to be really hard to deliver with cross-functional teams and get out of those silos.
Michelle: We’re touching upon some of the common mistakes or problems I see when it comes to strategic planning. One of them is optimism. I call it “disconnected activity,” but it’s really optimism around our capacity. Silos are another problem, because they disconnect ideas and people from each other.
At the heart of it, anytime I’m sitting down with executives and we’re doing strategic development, one of the things we want to avoid is getting so focused on what we’re doing that opportunities pass us by. If you’re not continually learning, you get locked into executing on this plan, and you forget the learning and sharing piece. There are opportunities that are going to walk right past you. So, silos are a piece of this.
We’ve already talked about the lack of focus, how OKRs can help us, and how coordination and picking just a few of them—we’re talking three to five, not 20 or 30. Missing the customer, we kind of highlighted this. It’s critical to create empathy and help us understand that direction.
Two pieces that we haven’t talked about as closely are, number one, flawed measures. The way I think about measures and help people set those measures, both strategy and execution measures… First of all, it was new to me to even think about setting measures for my strategy. It’s very common to measure your execution, but I see it less common to measure your strategy. How do you even know… back to that theory, how do you even know? It’s a little bit harder to do, but the advice I follow is: what decisions do we need to make? That’s what measures should lead to. What kind of things should we be measuring that are going to help us make decisions or help change behaviors? That’s true for measuring strategy and execution.
And then the other one is that lack of commitment. We emphasize alignment, which is incredibly important, and bringing everybody along, but the commitment piece is critical to realizing what we’re doing. It’s a huge piece of the commitment. That means everybody has said, “All right, I’m passionate about this, or at least interested enough. I’m aligned with what we’re doing, and I’m going to do this. We’re going to make this commitment to one another.”
Chris: Commitment is something that we often think of as an execution aspect. “There’s a deadline, and things have to be done by the deadline, and we’ve committed to achieving the deadline.” You need commitments at that level, but you also need commitments to driving the outcomes. Not just doing the work, but achieving the outcomes. And having that feedback loop where you’re looking at the measures, you’re looking at the leading indicators, like the assumptions that we built into this. Are we proving those assumptions? Are we disproving those assumptions? So that we can decide if we’re going to continue to do this or not.
We do want to have some time for question and answers here, but I think it’s good to spend a little bit more time digging in on the horizons that we’re looking at for strategic planning, and some specifics around what goes into each one of those horizons, and the timing and cadence around a good facilitated strategic planning process.
Michelle: I use the time horizons… for organizations that would like to eliminate or flatten their organization or change the attitude towards hierarchy, I think the time horizon is a good backdrop to that. It’s not that hierarchy is necessarily, “These people are making these decisions, these people…” It’s also on the time horizon by which we do it.
To get specific and tie that to where you’re going, the time horizon helps us get better focus. We’re looking at setting the strategy itself, 24 to 60 months. Most people would say three to five years. I’ve actually altered that a bit. Things are changing more than ever. So, when I said three to five years 20 years ago when I was doing this… okay, but maybe your time horizon needs to change.
Anyway, all that to say, we’re looking at 24 to 60 months, and this is where we’re looking at our direction, our big assumptions, our offering, our message. Then that typically—often, not always—breaks down into some programs or projects that we’re going to focus on in the next, say, 12 to 20 months. So, like a year, year and a half. This is where we take that direction, we set those OKRs. Now, you may not need a time horizon for this 12 to 20 months. I don’t see a lot of examples of that. But there’s some flexibility here.
Typically, you see strategy on a three- to five-year, two- to five-year… your programs and projects help you emphasize what you’re doing in the next 12 months to advance towards that strategy. Then you create, if you’re working in… depending upon what fashion you’re working on, but some sort of backlog that says, “Okay, for the next quarter, what are we actually going to emphasize?” And that, again, for me, is: what are our objectives for these next three months, and what are the key results we need to see that are moving us towards that?
Michelle: …And then that helps… if I’m working on a team, that really helps me get clear on, “Okay, so for the next month…”
Chris: And I think that that focus on the next month, the next quarter, is really key. Because if you only do strategic planning once a year, it’s very difficult to keep that top of mind and keep people aligned and committed to it. But if you have that regular cadence of revisiting it, updating it, and adjusting it based on what you’re learning, it becomes much more powerful.
Michelle: Exactly. And I think that’s a good point to emphasize. It’s really… you know, we talked about the time horizons, and you’re absolutely right. I mean, the time horizon for your strategy can be three to five years. But I think what’s most important is that you revisit that every quarter. Take a look at it, dust it off. Has anything changed? Do we need to make any adjustments? And then, of course, the time horizon for the strategic planning is much shorter. It’s really in that three-month time horizon.
Chris: So, we do have some questions coming in. Let’s see… The first one is, “How do you get started with strategic planning if your organization has never done it before?”
Michelle: That’s a great question. I think the first step is to really get clear on what your goals are. What are you hoping to achieve with strategic planning? Once you have a good understanding of your goals, you can start to develop a plan. There are a lot of resources available to help you with this, including books, articles, and templates. You can also hire a consultant to help you get started.
Chris: I would add that it’s important to start small. Don’t try to do everything at once. Focus on a few key areas that you want to improve, and then gradually expand your efforts over time.
Michelle: Absolutely. And don’t be afraid to experiment. There’s no one-size-fits-all approach to strategic planning. What works for one organization may not work for another. So, be willing to try different things and see what works best for you.
Chris: Here’s another question: “How do you measure the success of your strategic planning efforts?”
Michelle: That’s another great question. There are a few different ways to measure the success of your strategic planning efforts. One way is to track your progress towards your goals. Another way is to measure the impact of your strategic plan on your business. For example, you can track things like revenue growth, customer satisfaction, and employee engagement.
Chris: I think it’s also important to get feedback from your employees. Ask them how they feel about the strategic planning process and whether they think it’s helping the organization achieve its goals.
Michelle: Yes, that’s a great point. Employee feedback is essential. You want to make sure that everyone is on board with the strategic plan and that they understand how their work contributes to the organization’s success.
Chris: We have time for one more question. “What are some common mistakes that organizations make when it comes to strategic planning?”
Michelle: One common mistake is not involving the right people in the process. Strategic planning should be a collaborative effort that involves people from all levels of the organization. Another mistake is not revisiting the strategic plan regularly. Your strategic plan should be a living document that is updated and revised as needed.
Chris: I would add that another common mistake is not aligning your strategic plan with your budget. Your strategic plan should be realistic and achievable, and it should be supported by your financial resources.
Michelle: Those are all great points. I think it’s also important to remember that strategic planning is not a one-time event. It’s an ongoing process that requires continuous attention and effort.