making your strategy stick

hard earned lessons of 12+ years inside

Having the ideas isn’t enough if they’re left to gather dust.

In your career as a strategist, it’s not just about writing a great strategy. It’s about making sure that the plan is championed, executed, and celebrated across every level of an organization. You aren’t a hero. You need people to hear you. Think of yourself as an advocate.

Early in your career, you might have believed that your job was solely to produce flawless strategies and big ideas. And to some extent, it is. A lot of the tactics I’ll name in this article you should apply to how you engage with your boss and across your organization.

A great idea without the muscle to push it forward is just another deck in a sad Google Drive folder. What separates the people with a solid book from the greenscreen bros is the ability to champion your work—transforming concepts from rough sketches into actual initiatives.

At different times, you’ll be in environments where the stakes are sky-high, whether you’re operating out of a sweaty startup office or maneuvering through the bureaucracy of a Fortune 50 giant. In each case, your ability to navigate internal politics, adapt your message, and push relentlessly for execution is what ultimately sets you apart.

Startups: the stakes are high

If you’ve ever worked at, consulted for, or been near a startup, you know it’s like riding a roller coaster: exhilarating, unpredictable, and not for the faint-hearted. In these environments, every decision has the potential to make or break the business.

Survival mode, 24/7
In a startup, every move is about survival.

The stakes are real, and every decision can mean the difference between going viral or vanishing. Founders have often thrown away the rulebook (and often times a career, savings, an education) to chase what they believe to be a game-changing vision, and you’re expected to catch that raw energy and channel it into a workable strategy.

Break it into pieces, make it relevant to the company at the time. Yeah, you want to be like Nike, sure. We’re pre-seed though!

Vision → execution
Startups don’t have the luxury of over-rotated, refined plans.

Whether you’re a consultant or hire #1, what you will get is an unfiltered, almost chaotic vision that needs immediate translation into clear, actionable steps. Your role is to distill this vision into something that teams can rally behind—quickly and effectively. Oftentimes, ‘strategy’ is a dirty word because it means words on a page instead of action.

The first version of your idea isn’t the final version - not until product-market-fit at least. A rigid plan is a death sentence here; agility and adaptability are your best friends. Do not live and die by the deck. Live and die by a vision.

Communicate, communicate, communicate
With every second counting, your communication needs to be sharp, concise, and impactful. Forget about long reports—what matters is getting your message across in a way that mobilizes action immediately.

Instead of a long deck, send a Slack message with the data and why it matters.

Fortune 50: Red tape, self-advocacy

If startups are about decisions made ASAP, Fortune 50s (insert any big company here) are about 2-week feedback cycles. Survival isn’t the primary concern, but maintaining momentum and relevance is an entirely different beast.

Navigating red tape
In a large corporation, brilliant ideas can get caught in an endless loop of approvals. Your challenge isn’t just about proving that your ideas are solid—it’s about ensuring it doesn’t get lost in the labyrinth of bureaucracy. Building internal alliances is key.

And if you’re working as a consultant, 80% of your role is about setting up your point of contact to look good. Keep in touch with them often. Grab a coffee! Shoot them a link that made you think of them!

It’s about the story
Large corporations can be environment saturated with data and competing agendas, clarity is critical. Your strategy needs to be broken down into digestible, persuasive elements that cut through the noise. Every stakeholder must understand not just the “what” but the “why” behind your plan. And you gotta do some 007 maneuvering to get who the players are.

Persistence pays off
Expect to follow up relentlessly. In a corporate environment, it’s not enough to deliver a great idea—you must also be there to see it through, adapting your pitch as necessary and ensuring that momentum is maintained long enough for change to take root.

A Strategist’s Core Toolkit

After twelve-plus years, I’ve learned that there are universal strategies that will help you champion your work effectively.

Endless empathy
Understanding your audience is non-negotiable. In startups, you’re dealing with founders who are laser-focused on survival. In large corporations, you’re engaging with executives who have to navigate endless layers of internal politics. Get in their shoes.
Spend time understanding the unique pressures and ambitions of your stakeholders. What keeps them up at night? What drives their decisions?

Create a simple map of your audience’s challenges and aspirations (both internal and external). This is your personal blueprint for how to get the message across. Refer to it often.

The ability to iterate
In each environment, the first draft is never the final draft. Embrace the chaos of change and use it to your advantage.

Build structured feedback sessions into your process. Whether it’s a quick chat over coffee or a formal review meeting, continuous feedback ensures your strategy remains relevant and effective. Soft sell people, read them in. Then they’ll advocate for you – don’t save it for a Don Draper reveal.

The delivery counts
Skip obfuscating. Your work must be communicated in a way that’s both compelling and crystal clear. A great narrative is your most powerful tool for ensuring your ideas not only get heard but acted upon.

Strip away the jargon and present your strategy in straightforward, relatable language. Use visuals and data points to back up your claims, but always aim for clarity over complexity. Every strategy has a story. Frame your work as a journey—highlight the challenges, the pivots, and the eventual breakthrough.

Make It Matter

Your career isn’t built on ideas alone: it’s built on your ability to bring those ideas to life. The best strategists aren’t just thinkers; they’re doers, advocates, and navigators. It’s not enough to write a brilliant strategy; you have to fight for it, sell it, and see it through execution. You have to make people believe in it as much as you do.

Championing your work means wearing two hats—one of the visionary, seeing what others don’t, and one of the advocate, ensuring that vision takes root. It requires persistence, adaptability, and a deep understanding of the people who hold the keys to execution. Every environment, from scrappy startups to corporate giants, presents different obstacles. In some cases, your challenge is speed—getting buy-in before the moment passes. In others, it’s endurance—navigating bureaucracy and sustaining momentum over months or years. In all cases, success isn’t just about having the right answer; it’s about making the answer obvious.

And while the details of execution matter, don’t lose sight of the bigger picture. A strategy that looks airtight in a deck but never leaves the meeting room is a failure. Words on a page don’t change businesses—action does. Your impact isn’t measured by how many brilliant presentations you deliver but by how many ideas turn into initiatives, campaigns, or products that create real results.

The difference between strategists who stagnate and those who move up isn’t just talent—it’s the ability to make things happen. The big moves in your career won’t come from a single breakthrough moment but from the small, consistent acts of pushing your ideas forward, rallying support, and ensuring execution.

Own your impact. Make every idea count.