How to make strategic planning stick: 3 tips for avoiding common pitfalls
Strategic planning sessions often feel like a breakthrough—big ideas are mapped out, goals are set, and your team leaves feeling energized and excited. Fast forward to a few weeks or months later and the situation can look a lot different—enthusiasm may have faded, execution might have even stalled. Either way, the strategy has failed to launch.
I’ve guided teams at startups and Fortune 50 companies through everything from strategic planning and innovation to product definition and roadmapping. Regardless of company size or industry, I’ve noticed that the issues blocking execution tend to follow familiar patterns. Each organization has its nuances, but the reasons I get called in are remarkably consistent.
Why? Because real change doesn’t come from a plan alone—it comes from people.
So, what are the common culprits blocking execution? And what can you do to avoid them and keep your team oriented to strategy daily?
In this article, I’ll cover the solutions to the deeper challenges that block successful execution so you can keep team momentum going long after the strategy has been set.
1. Start With a Clear, Shared Vision
Whether we’re talking about a product or an entire org, establishing a vision is important because it gives people a north star to rally around. I can’t tell you how many teams I’ve seen spiral out over this root cause. Without knowing what future you want to inhabit, it’s hard for teams to be excited or motivated to pursue it.
The Pitfall: Many organizations lack a compelling vision that unifies leadership and teams. Without it, strategy becomes reactive rather than purposeful.
The Fix: Before diving into detailed planning, align on a vision that’s clear, inspiring, and actionable. It needs to be something that team members can get excited about. Keep it simple, succinct, and memorable—this is what makes it repeatable.
A strong vision answers:
What impact do we want to have?
What are we striving for aspirationally?
Who do we serve?
What values drive our decisions?
I’ve seen too many leadership teams draft long, jargon-heavy vision statements that look good on a slide deck but fail to inspire action. A good vision isn’t just something that sounds impressive in a boardroom; it’s something that sticks. Without it, progress slows. People feel unmoored. Decision-making becomes inconsistent. Teams get stuck in loops of incremental change rather than meaningful progress.
💡 Facilitation Tip: Co-create a purpose statement with your teams. The key is to help the team understand why they exist, who they serve, and the unique value they contribute to the overall success of the org. Here’s a guide to help you do that together.
2. Create Buy-In + Ownership
Better work output = better human experience = better impact for the business and, ultimately, the customer. But when people feel like things are being done to them or they don’t feel empowered to chart their own path, execution suffers. To keep momentum going, your team needs to be motivated, and that’s fueled by their own will and desire.
The Pitfall: Teams often aren’t truly invested in the strategy because they weren’t part of shaping it. They see it as “leadership’s plan,” not their plan. I’ve watched so many teams stall out because they don’t feel like they have the autonomy to do things differently.
The Fix: Co-create a path toward that shared vision with your team. Give them a voice in setting priorities and defining how success is measured. Rather than telling them how to get the job done, define what success looks like, then let them determine the steps to get there. When people feel ownership, they engage more deeply.
💡 Facilitation Tip: Use interactive exercises where teams can contribute ideas and challenge assumptions. Make the process inclusive rather than top-down. To do that, you’ll need to create the space for them to define their own answers. Here are a few tips for shifting your role from their leader to their facilitator to encourage answers to emerge (rather than telling them the answers).
3. Define What Happens Next
Sometimes you’ve done everything right—from co-creating a vision to fueling team autonomy—and yet the plan can’t seem to get off the ground.
When I see teams struggling with this, it’s usually because they haven’t yet gotten practical and specific about what happens next. You have to get real about what needs to occur in the days, weeks, months, and years that follow. This establishes accountability and catalyzes ownership.
The Pitfall: If a strategic plan is too aspirational or lacks a clear sense of how to execute the work, momentum stalls out.
The Fix: Make the strategy actionable by defining:
What needs to happen in the next 3–5 years (here’s a Time Horizon exercise to help)
Who is accountable for immediate milestones + action items
What resources and capabilities are required
How progress will be measured and adjusted over time
💡 Facilitation Tip: Push teams to get specific—what do you want to be different a year from now? What needs to happen next quarter? Ensure the plan has tangible, time-bound steps with champions for each.
Plans + People = Progress
Strategic planning is not just about the big picture—it’s also about cultivating the right conditions for your team to hit the ground running. By addressing or getting ahead of these common pitfalls to execution, you can activate your teams in a way that builds trust, ownership, excitement, and momentum for the work. This is the secret sauce for progress.
Want help with that part? Send me a note and we’ll chat about what it might look like to partner (I’m currently booked through Spring, so think about reaching out even if you aren’t sure of your timing just yet).