How to align effectively with visionary leaders as a Chief of Staff

As a Chief of Staff, you probably spend your days translating ambitious visions into concrete steps. You thrive on structure, clarity, and clear next actions. That’s likely why you got hired—your ability to make complicated things manageable.

But sometimes the very quality that makes your CEO or founder special—their ability to think big—creates friction for you. Visionaries naturally see opportunities everywhere. New ideas constantly flow, and this creativity is exactly why their businesses succeed. It’s the essence of their strength, not a flaw.

Still, it can cause practical issues. Maybe you've experienced something like this: you run a tight offsite, everyone leaves with clear goals, and then three days later your founder sends an excited Slack message about an entirely new direction. You wonder why you bothered spending all that time aligning everyone.

You’re not alone. It’s normal to feel frustrated when the ground shifts after carefully laying the foundation. But here's the key: visionary leaders aren’t doing this to frustrate you. It’s simply how their minds work—always scanning for opportunities, always spotting something new. Your job isn’t to fight that instinct; it's to channel it effectively.

The real reason "best practice" processes fall short

When a founder throws out new ideas, your first instinct might be to add more controls. You consider tightening up meetings, mandating frequent check-ins, or adding detailed approval processes. But here’s the catch: most visionaries don’t thrive with rigid constraints. If they did, they wouldn’t be visionary in the first place.

Visionary leaders usually built the company precisely because they were able to move quickly, adapt, and pursue bold ideas without bureaucratic roadblocks. They don’t reject structure because they're stubborn—they do it because structure often slows the creative pace they naturally work at.

Pushing too much process onto a visionary usually results in frustration rather than clarity. It’s not because they’re rebellious; it’s because their thinking doesn’t neatly follow predefined frameworks. Recognizing this lets you stop fighting it and start managing it differently.

A better way: create dedicated spaces for visionary thinking

Instead of trying to contain a visionary's natural impulses, intentionally build spaces for them. Rather than seeing visionary thinking as disruption, proactively make room for it:

1. Separate Vision from Execution:
   Schedule meetings specifically dedicated to exploration. Don’t try to mix visionary brainstorming and practical planning together—separate them. For example, once a month hold a session purely for exploring bold, future-focused ideas. No one commits to actions yet, and no detailed plans are required.

2. Follow-up with clear action meetings:
   After you've allowed room for creative thinking, schedule separate, practical meetings dedicated to turning selected ideas into concrete steps. Here’s where your operational expertise kicks in, translating those ambitious concepts into feasible actions aligned with your existing resources and strategy.

Doing this signals clearly: visionary thinking isn't a distraction; it’s essential, and we value it enough to give it its own dedicated space. It also sets clear expectations about when ideas can freely flow versus when decisions must be finalized.

How to communicate openly about this approach

Visionaries appreciate transparency. It helps to openly name this dynamic with your founder or CEO. Say something direct and clear like:

“I notice you often have great ideas right after we set our quarterly goals. Instead of trying to squeeze them into our planning meetings, let's set aside regular sessions where you can comfortably explore these ideas without pressure to decide immediately.”

This type of communication builds trust. You're not positioning yourself as the "process police," you're positioning yourself as someone who genuinely wants to help their ideas become successful. Most visionaries respond well when you explicitly make room for their strengths, rather than treating them like a barrier.

Why this approach builds real trust (not tension)

Your founder likely hired you precisely because you’re different from them. They might struggle with operational details, so they brought you on to help translate their vision into action. You were chosen exactly because you have the complementary strength of structured thinking.

The goal isn’t for either of you to change fundamentally. It’s about embracing the strengths each of you brings and building processes that intentionally harness those differences. Visionaries provide ambition and big-picture thinking; Chiefs of Staff provide clarity and practical steps.

When each of you respects and embraces these complementary strengths, real trust forms. You stop feeling frustrated by sudden shifts. Instead, you recognize them as opportunities to have meaningful conversations about what the company needs most, right now.

Your true role as Chief of Staff: the translator

The most valuable Chiefs of Staff don’t merely control or restrain visionary thinking. They translate it into something actionable.

Your superpower is translating high-level ambition into concrete steps your teams can follow. You're the bridge between big ideas and real-world execution. Your job isn’t to simply apply best practices or rigid frameworks—it’s to carefully observe your unique environment, adjust processes thoughtfully, and facilitate clear conversations about priorities.

When you view your role this way, you stop seeing visionary thinking as disruptive. Instead, you see it as vital energy your company needs, and your job becomes guiding that energy effectively rather than trying to contain it.

Ready to align better with visionary leaders?

If you’re struggling with how best to work with your visionary CEO or founder, let's connect. I regularly help Chiefs of Staff design practical approaches tailored to their team’s unique dynamics. No templates, no rigid processes—just practical frameworks built to match your reality.

Because your job isn’t to stop visionaries from dreaming big. Your job is to help those dreams actually come to life.

If you're interested in exploring practical ways to improve alignment and execution in your team, reach out. I'd love to help you find the right balance.