How to Get Executive Alignment on Strategic Initiatives

Ah, executive alignment—the white whale of the PMO. You’ve got a rock-solid strategic initiative, a roadmap with more dependencies than a triple-A video game launch, and a vision that could (theoretically) change the game. But there’s a problem: your senior leaders aren’t fully on board.

Regardless of their reasons, you need them to align, commit, and champion the initiative. That’s where Human-Centered Design (HCD) can help. (Yes, even if they don’t realize they’re engaging in it.)

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Executives are fluent in two languages: business impact and risk mitigation. If you start by pitching the benefits of “co-creation” or “iterative ideation,” you’ve already lost them. Instead, flip the script:

? "We need to engage in a human-centered design process to deeply understand the problem."

? "Our initiative needs executive alignment because misalignment leads to delayed decisions, wasted resources, and low adoption rates. We’re proposing a structured approach to ensure we’re solving the right problem from day one."

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One of the biggest mistakes a PMO can make is treating executive alignment like a single decision point. It’s not. It’s a series of micro-decisions that need to happen over time.

Instead of asking for a sweeping "yes," run a small-scale prototype of alignment:

??????????-???????? 1: Run a short framing session with a few key execs to refine the problem statement. (Not a 2-hour workshop—think 20 minutes in their language.)

??????????-???????? 2: Gather quick feedback on strategic assumptions before bringing a fully baked plan to the table.

??????????-???????? 3: Provide a tangible example of misalignment (past project failure, market competitor success) and frame it as an avoidable risk.

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Executives don’t care about your methodology. They care about their goals, their legacy, and their ability to steer the organization toward success. So, position Human-Centered Design as a tool for them—not for you.

?????????????? ????: "We need to involve more stakeholders in this process."

??????: "We want to ensure you have the right insights to make high-confidence decisions faster."

?????????????? ????: "We’re leveraging design thinking to reframe the problem."

??????: "We want to reduce blind spots and surface risks earlier so we don’t have to course-correct later."

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The best way to overcome skepticism is to let them experience it. Find a quick win where a human-centered approach leads to an undeniable result—faster decision-making, clearer priorities, reduced risk.

? Run a rapid research sprint (days, not weeks) and bring in surprising insights that change the conversation.

? Use low-fidelity prototypes to show tangible alternatives instead of debating hypotheticals.

? Capture and share direct quotes from key stakeholders to humanize the challenge.

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There’s always one. One executive who’s open to new ways of working (or at least willing to experiment). Bring them in early, arm them with quick wins, and let them be the internal champion. When other leaders see one of their peers backing the approach, skepticism starts to dissolve. (???????? ????????????????: ????’?? ?????? ???????? ?????? ???????????? ????????????.)

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The goal isn’t just to get alignment on this initiative—it’s to make human-centered approaches a normal part of how strategic initiatives are shaped and launched.

Bill Strickland, a nonprofit rock star and GOI Peace Award winner and my former boss, once said that ?????????????? ???????????? ???? ???????? ?????????? ???? ??????????????—you may not see the change at first, but with enough persistence, you will make a significant change to the landscape. This is exactly how a PMO leader must think about executive alignment.

If executives aren’t aligned on what projects to prioritize, business ROI suffers and risk skyrockets. It takes continuous effort, strategic engagement, and well-placed wins to shape how leadership sees decision-making, strategic investment, and long-term impact. Just because alignment isn’t immediate doesn’t mean it isn’t happening—the shift is happening beneath the surface.

? Shift from big, formal asks to ongoing, iterative engagement.

? Frame design methods as strategic risk management tools.

? Create a culture where small tests lead to big decisions.

When done right, you won’t have to convince them next time. They’ll be the ones asking for it.

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Where are you seeing the biggest roadblocks to executive alignment? Drop them in the comments—I’d love to hear how your PMO is tackling this challenge.