Making Strategy Stick in the Real World

A conversation with a Nate Richardson, the Strategy & Operations Director at Papermill Agency Turning strategy into execution is easy to say, hard to do. For Nate Richardson, Strategy & Operations Director at Papermill Agency, success lies in marrying creativity with commercial rigor — ensuring strategic ideas survive the real-world pressures of budget, alignment, and shifting priorities.

In this edition of Exec Edge, Nate unpacks where strategy often breaks down, what real alignment looks like in cross-functional teams, and how to pivot when the narrative — or the numbers — no longer line up.

Below is our full Q&A, lightly edited for clarity and flow.

What does “successful execution” actually look like in your organization — and how do you measure it? In an integrated communications agency like ours, success looks different across service streams. A digital campaign and a media campaign will have vastly different KPIs.

We measure hard metrics like conversions, but we also track qualitative indicators like sentiment, key message inclusion, and overall client satisfaction.

Coming from a PR and earned media background, we’ve moved away from outdated metrics like Advertising Value Equivalency and developed our own tools — including a Media Sentiment Report that gives clients a more holistic and commercially relevant view of outcomes.

Where do most strategies break down when moving from PowerPoint to implementation? The breakdown usually starts with budget alignment.

You can sell in a powerful idea or campaign — but if it’s not financially and operationally feasible, it won’t translate into execution. Budget becomes the great divide between concept and completion.

Ideas can scale, yes — but they also need to be grounded from the start in reality.

How do you ensure alignment across teams without creating rigid top-down plans? By fostering a culture of shared leadership.

In a cross-disciplinary environment like marketing, we bring heads of media, digital, brand, and events to the same table. Everyone contributes to the vision.

We don’t force a single “project leader” structure. When people feel empowered and clear on how their work contributes to the whole, alignment happens organically, not through rigid delegation.

What mechanisms or cadences do you rely on to keep strategy and execution in sync over time? Accurate scoping is the foundation — getting a clear picture of what’s needed to stay on time, on budget, and on brief.

Upfront strategy work is critical: insight, research, trends. But that can’t be the end of the line. We rely on project management tools to monitor milestones and flag when we’re veering off track.

As we often tell clients:

“If strategy were a 100-metre race, it’s how you get off the blocks and how you finish that really matter. No one remembers the middle.”

Can you share a time when you had to adjust or abandon a strategy mid-execution? What triggered the pivot? In media, transparency is everything.

We’ve seen strong strategies fall apart when clients weren’t willing to publicly share key information. A unique story can quickly become generic — and when we can’t get the right facts, the right spokesperson, or the right visual, we’re limited in what we can achieve.

In those cases, we pivot: instead of chasing Tier One earned media, we shift to owned channels, advertorials, or social content. The strategy remains — but it morphs into a format that still delivers value.

What role should the strategy function play after the strategy is set? Strategy isn’t just about direction — it’s about delivery and iteration.

The strategist should act not only as the architect but also as the builder and the crew. Strategy continues to evolve through the project. It shifts, segues, simmers, and sparks.

That’s why we build in reflection loops: What worked? What didn’t? What surprised us? It’s in this continuous learning cycle that strategy stops being a deck — and starts driving real impact.