72% of organizational strategies fail due to issues related to people and culture—not because they were bad strategies but because execution wasn’t aligned with how people actually work.

While we may not always realize it, the impact of this failure is significant—especially in our ability to create the change our organizations were designed to make.

​​Many organizations are still trying to execute strategy with outdated ways of working—rigid structures, slow decision-making, and leadership models that don’t match the realities of today’s workforce. But the future of organizations will be built by those who evolve—not by those who cling to tools and structures that no longer serve them.

I’ve worked inside organizations full of brilliant, mission-driven people—people who were passionate about the work but constantly frustrated by how hard execution felt. I’ve seen the same cycle play out repeatedly: a big, ambitious strategic plan gets developed, but when it’s time to make it real, the people side of the plan doesn’t hold up.

Behind the strategy are real people—overextended teams, unclear leadership, outdated systems—trying to carry something that was never designed with them in mind.

Strategy Isn’t Failing—Our Systems for People Are

In the social impact world, the stakes are already high. 

We aren’t just trying to increase market share—we’re trying to expand equity, deepen community trust, and solve problems that aren’t easy or linear. 

Our organizations are led by people who care deeply and give generously, and yet many of us are still running into the same wall: a brilliant plan that no one is quite sure how to bring to life.

If we want strategies to stick, we must invest in something deeper: alignment that begins with people. At the end of the day, strategy is a human practice, and execution is a leadership choice.

This essay isn’t a teardown of strategy. It’s a call to reimagine how we support the people who carry it. It’s an invitation to rethink our tools—re-onboarding, team development, leadership expectations, culture design—not as isolated tactics, but as an integrated plan for execution that feels real and shared.

It’s also a challenge to how we think about capacity. Too often, capacity-building is underfunded, fragmented, or reserved for the few. But sustainable strategy demands we move beyond scarcity. We need to stretch further, re-purpose more intentionally, and design for the whole organization, not just a few roles at the top.

Because strategy isn’t just about where we’re going—it’s about how we get there and who we become in the process. And that starts with aligning our systems to what we value: our people, our mission, and the communities we serve.

Strategy Development is Necessary—Then It Becomes Hard to Execute

Strategic plan development is necessary but insufficient.

We spend a lot of time focusing on a strategy’s inputs—the vision, the metrics, the goals—but not nearly enough time on the people responsible for executing it.

Think about it. A strategy of stakeholder engagement, research, and planning is built over months (sometimes years!). By the time it’s ready, leadership has shifted, priorities have evolved, and teams are already operating under whatever informal system they’ve built.

And then what happens?

 The rollout, the announcement, and the slide deck. 

But without intentional execution alignment and acknowledgment of the shifts since planning started, teams aren’t prepared to shift how they work, leaders don’t have the right tools to drive accountability, and culture doesn’t reinforce the priorities set in the plan. 

Instead, execution becomes a slow, painful process of forcing a strategy into a system not built to support it. 

This isn’t just frustrating—it’s predictable. 

In most cases, execution isn’t failing because the plan was bad. 

It’s failing because we never built a plan for how people, leadership, and culture will support and sustain the strategy.

Most organizations go straight from “We need everyone to know and be clear about the plan” to:

• Why aren’t they executing the plan?
• Why can’t they just focus on the work?
• Why does it feel like something is missing?

So, we work harder using the same tools and approaches to align the team, but it still fails. 

Why? One answer I keep coming back to.

Strategy Alignment Isn’t Just About Execution—It’s About Transformation

Most people hear “strategy alignment” and assume it means ensuring everyone understands the plan. Get people clear on the vision. Create a slide deck. Maybe do a town hall or two. Then cross your fingers and hope execution follows. 

What’s missing isn’t clarity on the plan. 

What’s missing is capacity, alignment, and ownership to actually move the work forward. And that doesn’t come from memorizing goals—it comes from transforming the organization’s operations. Alignment is not just about execution; it’s about reshaping the culture, leadership norms, and people systems so the strategy can take root and thrive. Otherwise, we’re just layering new priorities over outdated working methods.

Let me give you a real-life parallel. Imagine trying to train for a marathon using a 5K plan. You can visualize the race, set goals, and even buy the gear. But if you don’t adjust your training regimen—if you don’t shift your routines, mindset, nutrition, or recovery—you’re going to burn out or break down halfway through. The goal isn’t the problem. 

The system that supports you isn’t built for the distance. The same is true in organizations. You can have a bold strategy, but if you’re still operating with short-distance practices, the strategy will break under the weight of what it’s asking your people to do.

Strategy success is not just about aligning people to the plan—it’s about transforming the conditions under which they work. 

That’s leadership development. That’s cultural clarity. That’s system design. 

Because you can’t execute a bold strategy in a structure that wasn’t built for bold moves. You need to rewire how decisions get made, how teams collaborate, and how power is shared. 

That’s a transformation plan.

Why People, Culture, and Leadership Are the Heart of Strategy

According to a 2023 Gartner study, only 38% of employees say they have clarity on how their work connects to organizational strategy. And even fewer feel empowered to act on it. Why? 

Because we haven’t built the connective tissue between the plan and the people. That’s not a messaging problem—it’s a leadership and culture gap.

I think of it like this: strategy is the house you want to build. People are the builders. Culture is the soil you’re building on. Leadership is the scaffolding that holds it all up when the weather gets rough. You can have the best blueprint in the world, but if your soil is unstable, your tools are rusty, or your team isn’t equipped—it won’t stand. The strength of your strategy depends on what surrounds and supports it.

And yet, I’ve watched organizations invest in a new strategic direction and leave everything else untouched. The same people in the same roles with the same pressures are now expected to do something radically different. That’s not alignment—that’s a recipe for burnout. It’s not that people resist change. It’s that they’re being asked to change without the leadership, support, and culture that makes that change feel possible.

We also underestimate how deeply culture shapes decision-making. If the strategy says “collaborate across teams,” but the culture rewards siloed ownership, collaboration won’t happen. If the strategy calls for bold experimentation, but leaders are afraid to fail, innovation stalls. The culture has to be designed to reinforce the priorities in the plan—not contradict them.

Leadership is no different. I’ve seen middle managers expected to “drive execution” without being trained on what that means. They’re handed a plan and told to make it happen without support in leading change, coaching their teams, or navigating tensions. That’s not fair, and it’s not effective. If we want strategy to be more than a set of goals, we must build leadership behaviors that match the work we’re asking people to do.

At the end of the day, strategy isn’t about perfect plans—it’s about people having what they need to make meaningful changes. And the organizations that get that right don’t separate strategy from culture, leadership, and talent. They build it all together, with the understanding that the strategy will only go as far as the people who carry it.

Strategy Can’t Be a Luxury for the Few—It Has to Be Built for Everyone

In the social impact space, we often separate the work. 

Culture work goes to HR. 

Leadership work goes to the executive team. 

Strategy lives with consultants or the planning committee. 

Equity work goes to the DEI team—if one exists. 

These silos aren’t intentional. They’re the product of limited budgets, capacity constraints, and an understandable instinct to do the most we can with what we have. But what starts as practical often becomes problematic. Because when strategy isn’t built for everyone, it can’t be carried by everyone.

I’ve seen it too many times. A foundation rolls out a new strategy, but only senior leadership goes through a development process. 

A nonprofit invests in DEI training for staff but leaves out the board—the very people making governance decisions that shape the work.

A coalition builds a brilliant strategic plan, but the community engagement team isn’t included in conversations about implementation. Not out of malice, but out of fragmentation. And in that fragmentation, the strategy starts to drift.

We end up building strategies that are technically sound but structurally unsupported. Some people are equipped, others are overwhelmed. Some understand the “why,” others are just told the “what.” And over time, that uneven investment creates fault lines—between teams, between departments, and between the plan and the people it’s 

This is why a full-organization people plan matters. We can’t just invest in “leadership” and leave everyone else guessing. We can’t just train staff without bringing managers along. We can’t have one department swimming upstream while the rest of the org keeps flowing in the same old direction. 

Everyone deserves to be part of the plan. Everyone needs access to development, context, and support.

A report by Bridgespan found that over 60% of nonprofit leaders cite “lack of staff capacity” as one of their biggest barriers to strategy execution. But that lack isn’t always about headcount—it’s about uneven investment. When we invest deeply in a few people and leave others without support, we create capacity gaps that show up as delays, dropped balls, or resistance.

Think of it like a relay race. You wouldn’t train only the first runner and expect the rest to finish strong. You’d build strength across the entire team, create a handoff strategy, and ensure everyone knew the goal and their role in reaching it. Strategy is no different. If you only invest in a slice of the team, you’ll see drop-offs. And not because people don’t care—but because they weren’t set up to carry the baton.

The best strategies aren’t just brilliant. They’re inclusive. They’re built for the real humans who must execute them—across roles, departments, and lived experiences. And they make room for everyone to grow, not just a select few. That’s what builds trust. That’s what builds power. And that’s how you turn a strategy into something that actually moves.

Capacity Isn’t Just a Budget Line—It’s a Design Decision

When people talk about strategy failure, they often point to a lack of capacity. Not enough time. Not enough staff. Not enough funding to support the work. And that’s not wrong. But it’s only part of the story. Because capacity isn’t just about having more resources—it’s about how we design and distribute the resources we already have.

In the social impact sector, this shows up all the time. Funders want scale, innovation, and impact—but only want to pay for programs, not the internal infrastructure required to deliver them. Leadership development, team training, and systems design are labeled as “indirect costs” instead of being recognized as strategic levers. According to the National Committee for Responsive Philanthropy, only 20% of philanthropic dollars are unrestricted, and even less are dedicated to internal capacity-building.

So what happens? Capacity building gets siloed. A grant pays for DEI work in one department, but doesn’t cover cross-org leadership training. A funder supports strategic planning but won’t invest in the culture shifts required to implement it. Coaching is offered to the executive team but not to the middle managers responsible for day-to-day execution. We end up with well-meaning efforts that only touch pieces of the organization—while the rest of the team keeps operating under outdated assumptions.

This isn’t just a funding problem. It’s a design problem. Because even when dollars are available, we often stretch them to fit into the same narrow patterns—supporting one group, one function, one initiative—without stepping back to ask: What does our whole organization need to align, grow, and carry this strategy together?

The result is what I call “pocket development”: building capacity in isolated corners of the org, without building connection across roles, teams, or leadership layers. It’s why so many organizations invest in great individual leaders but still struggle to shift culture. It’s why teams get trained but still feel disconnected from strategy. We keep layering new tools onto old systems and wondering why things don’t stick.

A 2022 study by The Bridgespan Group found that over 60% of nonprofit leaders cite lack of staff capacity as a top barrier to achieving strategic goals. But when you dig deeper, it’s not just that people are stretched—it’s that the right people aren’t being supported in the right ways. It’s not just about more people. It’s about more alignment.

Here’s the opportunity: even within constrained budgets, we can stretch further if we think differently. What if we planned for re-onboarding as a strategy execution tool, not just an HR function? What if we integrated leadership development into team cadences instead of outsourcing it? What if we prioritized cohesion—ensuring that every part of the organization has access to context, clarity, and capacity—not just the parts with funding attached?

Because capacity isn’t just about what we can afford. It’s about what we choose to prioritize. And at this moment—when the work is harder, the stakes are higher, and burnout is real—we need to stop building strategy for the few and start designing execution for the many. That’s not just good design. That’s equity. That’s sustainability. And that’s what will separate the organizations that stall from the ones that move with clarity, power, and shared purpose.

To get there, you need a whole-scale people plan—one that includes three key components: an Annual Re-Onboarding Plan, a People-Culture-Leadership (PCL) Plan, and a deep belief that people are not just the means to execute the strategy—they’re the reason for it.

The Annual Re-Onboarding Plan: How to Make This Work

Most organizations think onboarding is a one-time thing: something you do when someone’s new, then move on. But in fast-moving, mission-driven environments, that’s not enough. Priorities shift. Strategies evolve. Teams change. And if we don’t create intentional space to reconnect people to the work, we lose alignment faster than we realize. That’s where an Annual Re-Onboarding Plan comes in—not as a nice-to-have, but as a core execution tool.

Annual re-onboarding is the structured, organization-wide process of realigning your team to the strategy, the culture, and the work ahead. It’s not a refresher—it’s a recalibration. It gives people a chance to pause, regroup, and reengage with what matters most. Especially in organizations where change is constant, re-onboarding is how you rebuild shared language, expectations, and clarity around execution.

According to Gallup, only 41% of employees strongly agree that they know what their organization stands for and what makes it different. That number drops even lower the longer someone stays in an organization. Why? Because clarity fades. People fill in gaps with their own interpretations. And when that happens across departments, misalignment creeps in. What re-onboarding does is bring everyone back to the same page—before those small gaps become major drifts.

I worked with a nonprofit where staff had been with the organization for years, but they were struggling with execution after a new strategic plan was rolled out. It wasn’t that they didn’t care—they just hadn’t had the chance to re-anchor in the new priorities. Once we designed a re-onboarding process, complete with team sessions, role clarity conversations, and decision-making refreshers, the energy changed. Staff felt reconnected, leaders felt more confident, and the strategy finally started moving.

This isn’t just about productivity—it’s about people feeling seen, supported, and resourced. Annual re-onboarding gives space for questions. It makes room for learning. It acknowledges that even experienced staff need a moment to ask, “What’s changed? What’s expected of me now? And how do I do this well?” That’s not a sign of weakness—it’s a sign of a healthy, evolving organization.

Think of it like a pit stop in a race. Even the best drivers need to pause, refuel, and check their tires. If they don’t, performance suffers—even if they know the track well. Re-onboarding is the pit stop that keeps your people from running on empty. It’s the checkpoint that protects your strategy from slowly falling out of sync with reality.

And here’s the thing: this doesn’t have to be complicated. A good re-onboarding plan includes a few core elements—shared strategy touchpoints, role clarity conversations, leadership messaging, and time to reflect on what’s working and what needs to shift. When done well, it becomes a cultural rhythm: something your people expect, value, and rely on to stay aligned.

The most successful organizations don’t assume alignment—they build it into their calendar. Re-onboarding isn’t an extra—it’s the maintenance plan for your strategy. And in a world that changes quickly, that kind of maintenance isn’t optional. It’s essential.

This is where an Annual Re-Onboarding Plan becomes critical. 

Rather than assuming alignment will happen naturally, organizations must proactively realign, retrain, and reinforce execution priorities every year.

A well-designed Annual Re-Onboarding Plan provides a structured opportunity for teams to re-engage with the strategy, clarify role expectations, and ensure leaders at every level are reinforcing the right priorities. Think of it like recalibrating a compass before embarking on a journey. 

Without realignment, even the best strategies drift over time as team members interpret priorities differently, new hires come on board, and day-to-day pressures shift focus away from long-term goals. The plan serves as an intentional checkpoint to ensure the strategy stays relevant, the team stays connected, and the execution stays on track.

One of the biggest mistakes organizations make is assuming that onboarding is just for new employees. But in reality, even long-standing team members need structured alignment to keep up with evolving priorities. This is especially true in mission-driven organizations where external forces—such as policy changes, funding shifts, or community needs—can rapidly reshape how work gets done. 

Annual re-onboarding ensures that every team member, regardless of tenure, is given the tools, clarity, and support needed to execute effectively. It also provides a space to evaluate what’s working, address gaps, and adapt systems to meet the organization’s current reality.

Organizations with structured annual alignment plans outperform their peers by 32% in strategy execution. (Harvard Business Review, 2023) This means that simply taking the time once a year to realign can dramatically increase your team’s ability to execute successfully. 

The best organizations don’t just set a strategy and hope for the best—they build in dedicated time to make sure their people are always equipped to execute it.

The People-Culture-Leadership (PCL) Plan: Your Strategy’s Operating System

Too many organizations build bold strategic plans but leave the people, culture, and leadership systems untouched. They create a vision for the future, but expect that future to emerge from outdated operating norms. That’s like installing new software on an old operating system—it might boot up, but it’s going to glitch. The People-Culture-Leadership (PCL) Plan is how we upgrade the system to match the work.

A PCL Plan isn’t a side project. It’s not a team retreat or a one-off training. It’s the intentional alignment of three essential pillars: how people are supported and developed, how culture shows up in the day-to-day, and how leadership is defined, distributed, and held accountable. It connects the human infrastructure of your organization directly to the strategy you’re trying to execute.

Here’s what I’ve seen over and over: organizations invest in talent development, but it’s disconnected from their strategic goals. They do DEI work, but it doesn’t shape how decisions get made. They train leaders, but don’t shift the leadership expectations required for the future. So people keep operating based on what used to work, even as the strategy demands something new. A PCL Plan closes that gap—by making sure people development, cultural behaviors, and leadership practices are all reinforcing the work ahead, not resisting it.

According to Deloitte’s 2023 Global Human Capital Trends report, 93% of organizations say they know they need to redesign for adaptability—but only 23% have a plan to do it. That’s the gap. We know the strategy needs something different, but we haven’t built the structures to support it. A PCL Plan is that structure. It starts by asking: What does this strategy actually require from our people? What behaviors need to be reinforced? Where are we underinvesting in the very capabilities this plan depends on?

Let me give you an example. One client I worked with had a strategy focused on deeper cross-functional collaboration and shared accountability. But they still evaluated managers based on individual team performance, had no shared metrics between departments, and never clarified what collaboration was supposed to look like. Once we built a PCL Plan—revising leadership expectations, updating performance systems, and naming the cultural behaviors that would drive shared success—the collaboration finally took off. Not because people suddenly got better at working together, but because the organization finally supported them in doing so.

A strong PCL Plan doesn’t just help strategy get done—it makes the work more human. It centers people in the process, not as a resource to extract, but as co-creators of the future. It says: if we’re going to ask people to lead, adapt, and stretch, we’re also going to invest in their growth, design systems that help them thrive, and build a culture that makes that work possible.

And this isn’t just about leaders at the top. A true PCL Plan reaches across the organization. It redefines leadership at every level. It builds role clarity from the frontline to the boardroom. It makes sure culture isn’t just written in values statements, but embedded in how meetings are run, how decisions are made, and how feedback flows. When that alignment is in place, strategy stops being a document—and starts being a living, breathing practice.

The most effective organizations don’t separate strategy from people work. They understand that how you get the work done matters just as much as what the work is. The PCL Plan is the connective tissue. It makes sure your people, your culture, and your leaders are not just reacting to strategy—they’re carrying it. And when that happens? Strategy stops being fragile. It becomes durable, adaptable, and deeply alive in the organization.

We’re Not Just Aligning People to Strategy—We’re Aligning Because People Matter

Let me say something clearly: if we are only aligning people to strategy so we can “get the work done,” we’ve already missed the point. Alignment isn’t just about execution. It’s not about squeezing more productivity out of teams. It’s not about perfecting plans so we can hit our metrics faster. It’s about creating the kind of organizations where people are seen, supported, and equipped to do meaningful work—and where that work actually serves real communities with care and integrity.

We are people serving people. That’s the heartbeat of every mission-driven organization. And yet, in the name of strategy, we sometimes lose sight of the human beings at the center of all of it. The staff who are showing up tired but still hopeful. The leaders navigating change without a roadmap. The communities who are trusting us to do right by them. Strategy isn’t just a direction—it’s a promise. And how we treat people in the process is part of whether we keep that promise or not.

One client said to me recently, “We don’t need another strategy to chase. We need to feel proud of how we’re showing up inside the one we already have.” That’s it. That’s the work. Yes, alignment creates clarity. Yes, it helps with performance. But more than anything, it gives people a sense of integrity—knowing they’re part of something where the internal experience matches the external mission.

And this is especially important in social impact work. Because the stakes are higher. The work is personal. The boundaries between self and service are thinner. So when we talk about aligning leadership, talent, and culture, we have to remember—we’re not just building structures for efficiency. We’re building communities of care. We’re making sure that the people doing the work don’t get lost in the work.

This is why alignment has to be more than technical. It has to be relational. It has to ask: What do our people need to feel supported? What kind of leadership will make space for growth and voice? What kind of culture makes it safe to bring your full self to the work, even on the hard days? Because when people feel that, they don’t just execute—they invest. They stay. They lead. And they help shape strategy in ways no plan ever could.

So no, we’re not aligning people just to move the plan forward. We’re aligning because people matter. Because they are the plan. Because every outcome we’re chasing is made possible by the hands, hearts, and minds of real people who said yes to this work. And if we don’t honor that first, no strategy is ever going to be enough.

The Tools Aren’t the Problem—It’s How We’ve Been Using Them

The tools we need to align people and strategy already exist. Re-onboarding. Leadership development. Team training. Communication rhythms. Strategic execution systems. These aren’t new ideas. But the way most organizations use them is stuck in an old mindset—one that treats alignment like a checkbox, execution like compliance, and people like parts in a machine.

We don’t need shiny new frameworks. We need to reimagine the tools we already have—through a lens of care, sustainability, and collective ownership. Because when we use outdated tools in outdated ways, we get predictable outcomes: burned-out teams, stalled strategy, and a culture that can’t keep up with the goals we’ve set.

Re-onboarding becomes powerful when it’s not just for new hires, but a rhythm for reconnecting the whole team. Leadership development becomes transformational when it’s not just for the “high potentials,” but built into how we expect everyone to show up and grow. Team engagement isn’t about surveys—it’s about embedding reflection, adaptation, and feedback into how the work actually gets done.

And that’s what this is really about: updating the way we think about execution—not to chase perfection, but to do justice to the mission we’ve committed to. We can’t talk about equity and transformation while only investing in some teams. We can’t talk about bold goals and then default to the same old leadership playbook. If we’re going to build something different, we need to operate differently.

The future of mission-driven work won’t be built with old defaults. It will be built by organizations who are brave enough to pause, recalibrate, and reimagine how they work—not because they’re chasing efficiency, but because they care about people. The people on their teams. The people they serve. The communities that trust them to get this right.

Because that’s what it comes down to: the tools are only as powerful as the values behind them. If we use them to control and extract, they’ll fail. But if we use them to honor, equip, and align our people with purpose—we won’t just execute strategy. We’ll build organizations that are truly ready for the future.