What separates successful organizations from those that fall short? It often comes down to one thing: leadership.
In Episode 41 of The Strategy Gap, Jonathan Morgan, SVP of Operations at AchieveIt, and Joe Krause, SVP of Strategy Consulting, unpack the first and arguably most critical pillar from the 2025 State of Strategy Execution report: Alignment and Leadership.
Through real-world stories, survey-backed insights, and no-holds-barred commentary, the duo exposes why many strategic plans never make it past the kickoff—and how leaders can build trust, clarity, and momentum from day one.
Leaders Set the Tone—But Are They Saying Anything
Every strategic plan begins with a vision. But whether that vision sticks—or stalls—depends on how well leadership communicates it. And more often than not, that communication falls flat.
“One-third of teams said they’re not aligned with their organization’s overall strategic direction,” Jonathan shared, pointing to one of the standout stats from the report. “If you’re essentially playing tug of war and a third of your organization is pulling the other way, that’s a huge drag on performance.”
Joe illustrated this point with a story that strategy professionals will likely find all too familiar:
“I’ve been in kickoff meetings with 50 directors in the room. I pull the CEO aside beforehand and say, ‘This is your moment to set the tone. Tell them why we’re here and what you expect.’ But when it starts, the exec just says, ‘Here’s Joe and Jonathan. Take it away.’ And that’s it. No energy. No direction. No buy-in.”
It’s a painful missed opportunity. Leaders don’t need to give a rousing TED Talk—but they do need to communicate why the plan matters, what success looks like, and what they expect from the team. Without that, it’s no wonder many employees assume the new initiative will fizzle out in a few months.
Consistency Builds Credibility (and Trust)
Of course, a strong kickoff is just the beginning. If leaders want alignment, they need to maintain it—through consistent, visible engagement. According to Joe, that means going beyond one-time speeches and committing to an actual communication strategy.
“Figure out before the plan is launched what your communication strategy is going to be. Pick your points. Will there be monthly town halls? Will the CEO send a monthly note? Will the strategy lead share weekly updates? Write it down. Make a calendar.”
Why does this matter? Because as Joe bluntly put it, “Some people in your organization are just going to wait for this to go away.” Only through repetition and accountability can leaders prove the strategy is here to stay.
Jonathan agreed: “Good communication can fix the rest. If objectives aren’t clear or there’s poor time management or insufficient resources, that often comes down to prioritization. If people don’t hear that it’s important, they won’t treat it like it is.”
Vision Isn’t Fluff—It’s the Foundation
Let’s address a misconception: Vision statements are not optional. Done well, they can inspire and anchor execution. Done poorly—or ignored entirely—they become empty wall art.
Joe brought this to life with a great example from Warby Parker. Their vision statement reads:
“We believe that buying glasses should be easy and fun. It should leave you happy and good-looking, with money in your pocket. We also believe that everyone has the right to see.”
It’s not just words—it’s a litmus test for decision-making. “If you’re advocating for a new initiative,” Joe asked, “does it make buying glasses easier or more fun? Does it help customers save money? If not, why is it in the plan?”
He added that crafting a strong vision doesn’t have to be a months-long branding exercise. Sometimes, it’s as simple as asking in a room: What do we want to be when we grow up?
According to the report, 91% of strategy leaders say a lack of strategic vision is a key reason plans fail. That doesn’t necessarily mean the vision is missing—it might just be invisible to the rest of the team.
How and Why: The Secret to Structural Alignment
One of the most practical takeaways from the episode came from a simple but powerful framework that Jonathan and Joe use with clients: The “How and Why” Model.
“Think of your strategy like a tree,” Jonathan explained. “Start at the top and ask, ‘How will we accomplish this?’ Then break it into initiatives. From there, how do we track them? Metrics. Then how do we move those metrics? Tactics.”
And in reverse?
“Start at the bottom and ask, ‘Why am I doing this task?’ To move a metric. Why that metric? To support an initiative. Why that initiative? To move the company forward.”
This exercise not only clarifies the plan’s architecture—it also reveals who’s misaligned. If someone can’t trace their work back to strategy, or if a strategic goal lacks clear tactics, there’s a disconnect. Fixing that gap helps teams regain focus and feel a sense of purpose.
Don’t Just Set the Plan—Champion It
In a world where strategies change quickly, one truth remains: Execution lives or dies by leadership.
Joe summed it up with a challenge for listeners:
“Ask yourself: Would you be convinced by the way you talked about your plan? If not, that’s a problem. This is one of the easier things to fix. It just takes time and repetition.”
Jonathan echoed the sentiment: “You can’t expect people to prioritize the plan if leadership doesn’t. You have to show up for it—consistently.”
The bottom line? Strategy isn’t a side project. It’s the lifeblood of your organization’s future. And if you’re serious about execution, the tone you set at the top will either inspire your team—or silently give them permission to ignore it.
Final Thoughts
This episode makes one thing clear: leadership is the lever. A well-crafted vision, repeated messaging, and thoughtful structure can turn a static plan into a movement. But without intentional leadership, even the best strategies stall.
So whether you’re a CEO, strategy lead, or department head, it’s time to ask the hard questions:
- Are we aligned on where we’re going?
- Are we consistent in how we communicate it?
- And are we leading in a way that makes others want to follow?
If you can’t answer “yes” with confidence, this episode of The Strategy Gap is the perfect place to start.
🎧 Listen now to EP 041 – Alignment + Leadership, featuring Jonathan Morgan and Joe Krause, and get ready to lead your strategy forward.
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A podcast about the space between savvy strategy and practical execution, including everything that can go wrong on the way.
