How Do You Turn Long-Term Strategy into Near-Term Action?

A few weeks ago at the Jump Offsite in Napa, I spent some time with senior leaders of strategy and innovation. One theme came up again and again: “I’m clear on our company’s long-term strategy, but my teams struggle to put it into action.”

The specifics varied—some wrestled with helping teams prioritize, others were overwhelmed with fighting daily fires. But the underlying question was the same: How do I ensure my team’s day-to-day actions drive our long-term strategy?

Set Challenges, Not Plans

Too often, long-term strategy gets packaged into 50-page decks that are skimmed, shelved, and forgotten. If you find yourself crafting or reviewing one of these tomes, chances are you’re detailing a plan, not setting a strategy.

Detailing a plan sets you up to micromanage. And it trains your team to wait for instructions rather than take initiative. Not only does this lead to burnout all around, but it is the number one way strategies stall out. Meanwhile, the future approaches rapidly, another year slips away, and your company grows vulnerable to disruption and delay.

Instead, leaders should translate long-term strategy into 3-5 challenges that inspire and empower their team. President John F. Kennedy used this kind of challenge to focus America’s space efforts in 1961. His seminal congressional speech had one clear takeaway: put a man on the moon and bring him back to Earth by the end of the decade. This unmistakable challenge rallied engineers, contractors, and citizens in a single direction. Challenges help leaders stay focused on the horizon, while trusting their teams to navigate the way there.

While strategic challenges are simpler and more effective than 50-page decks, they aren’t necessarily easier to write. Here are a few tips to keep in mind:

1. Orient: Write strategic challenges as outcomes, not activities.
2. Inspire: Use language that resonates with your team.
3. Empower: Get the right people in the right seats.

Let’s unpack each.

Orient: Write challenges as outcomes, not activities

To set effective challenges, clarify the outcomes you must deliver to make progress toward your long-term strategy. Outcomes make the destination clear, while inviting ownership from your team.

When setting out to create the first digital reader, Jeff Bezos set a challenge for his team: “Any book, in any language, ever in print should be available in less than 60 seconds.” Bezos didn’t tell engineers which wireless protocol to adopt or what battery chemistry to use. He just named the finish line. At launch, the Kindle offered 88,000 titles, and that number has grown to more than six million today.

Clear outcomes provide a common scoreboard. For Amazon, “under 60 seconds” was a binary measure. Engineers could test whether a feature moved the customer experience closer or further from that goal. If we measure activities alone, we get a read on energy expended but not progress toward the strategic challenge at hand.

Pursuing outcomes also helps you refine the challenge over time. Before Bezos set the 60-second challenge, he started broader: build a business selling digital books, music, and video that destroys the old business. When early tests revealed promise in digital books, Bezos revised the challenge. Holding teams accountable to outcomes encourages near-term action—and learning—that directly drives long-term strategy.

Inspire: Use language that resonates with your team

Writing challenges as outcomes is a great start, but often not enough to activate a team. Most of us default to writing strategy at an abstract level (e.g., transform AI operations, expand our audience, win in a new market, etc.). This boardroom jargon is a fast track for confusion and de-prioritization. Instead, try connecting your strategy to what matters to your consumer.

When Fran Horowitz set out to turn around the 133-year-old Abercrombie & Fitch brand, she boiled a multi-year transformation into a single image: The Long Weekend. Consumer research had uncovered that’s what shoppers in their mid-to-late twenties look forward to most. Decisions across A&F, from denim fits to store layouts, were redesigned “to make every day feel like the start of a long weekend.” Employees suddenly had a gut-level filter to guide their decisions. The payoff: eleven straight quarters of growth and a record $1.2 billion in Q2 2025 sales.

Most people are hard-wired to care about people, so helping your employees envision their impact on real people is the fastest way to inspire them. It isn’t the only way, though. Patagonia, for example, connects their strategic moves to impact on the environment. You need to figure out what your employees care about. Writing challenges that resonate for your team is as much an exercise in building empathy as it is in strategy. When you connect strategic challenges to real-world impact, your team sees a common goal that they’re excited to chase.

Empower: Get the right people in the right seats

Once you have a clear and resonant challenge, you need to assemble the team. For innovation, that often means getting past organizational titles. Consider who is best suited to deliver on the strategic challenge at hand. What kind of perspective, attitude, or aptitude does the challenge call for?

Satya Nadella knew Microsoft’s cloud transformation started with its own systems. IT needed a leader who could set a new vision, not just manage servers, so he tapped Kurt DelBene. With 25 years of experience building Office and other flagship products, DelBene ran IT like a product shop. Every system had a clear owner and a vision tied to company goals. Microsoft employees became “Customer Zero,” the first users and critics of new tools. That user-focused approach turned internal platforms into proof points for external customers and powered the rapid growth of Azure and Microsoft Cloud.

When a challenge serves as a beacon and filter for talent, the right fits surface, as do the wrong ones. With that clarity, you can coach, reassign, or hire accordingly, just as Nadella did with DelBene. Some people will opt out on their own, and that’s fine. If someone isn’t eager to tackle the challenge at hand, everyone benefits from finding a better fit. You want all teams playing to their strengths. When challenges have committed owners, near-term decisions accelerate progress toward the long-term.

Getting Started

As a senior leader, your strategic challenges set the direction for the entire organization. They should be grounded in the 5-to-7-year vision and focused on what’s most important. But challenges are helpful across all levels. Managers and directors should ask themselves what portion they’re responsible for: what sub-challenges will you own? That’s how long-term strategy turns into daily action. Use the following activities to get started today:

• List your annual outcomes: What are 3-5 things you must deliver in the next year to move the needle on the long-term strategy? If it reads like a to-do list, rewrite it as outcomes.
• Run a strategy pop-quiz: Ask 10 random employees where your company is headed over the next five years. If fewer than eight answer correctly, the strategic challenges aren’t sticky yet.
• Do a team audit: Do you have the right people in the right seats? If the answer is no, make reassigning ownership a top priority for the next year.

Don’t wait to get moving on your strategy; you’ll only lose more time in reaction mode. Name the strategic challenges, make them sticky, and hold your team accountable. Then, get out of the way and let your team shine.