Is Your Strategic Plan Too Ambitious? Or Not Ambitious Enough?

You’re weighing a plan to enter a new market, launch a new offering, or create a new business division. You have benchmarks in mind and a rough sense of the cost. What you don’t know is whether your idea is ambitious enough to be worth it.

Your goal can miss the mark in more than one direction, says Sheena Iyengar, a professor at Columbia Business School and the author of Think Bigger: How to Innovate. “It could be too high, and you’d be setting yourself up for failure. It could be too low, and you’d be settling for mediocrity,” she says. “Or it could be just right—a bit of a stretch, but not so much that people give up because they see the futility of it.”

Choosing the right goal is one thing; making it happen within the realities of your organization is another, according to Donald Sull, a professor at the MIT Sloan School of Management, and a coauthor of The Upside of Turbulence: Seizing Opportunity in an Uncertain World. “If you just declare ambitious goals and expect the organization to achieve them, you’re somewhere between naive and delusional.”

How to Calibrate Your Strategy’s Ambition

Here are eight questions to help you assess how high you should aim.

1. Are you solving the right problem?

Before you can judge whether your plan is ambitious enough, you have to be clear on the problem it’s solving, says Iyengar. Say your goal is to double revenue. Don’t get stuck debating whether that number is too high or too low; instead, she recommends looking at what’s standing in the way of that growth in the first place. “Maybe the better question is: How do I deal with my labor shortage? How do I speed up everyday processes? How do I reduce daily costs?” she says. Once you know the problem, and what solving it would gain, you have a more concrete way to gauge your plan’s ambition.

2. Are you weighing more than one kind of solution?

The pull toward conservative goals runs deep in many organizations. The antidote, says Iyengar, is range. She suggests building at least three to five distinct alternatives into your plan: one that mirrors what competitors are doing and grabs the lowest-hanging fruit, one that’s more aggressive, and at least one that breaks from your usual playbook by, for instance, borrowing strategies from businesses outside your industry. There likely won’t be a clear winner and you’ll probably combine ideas into a hybrid solution. “But you need those very different options upfront, because they help you see the trade-offs more clearly.”

3. How is your plan funded?

The size of a plan’s ambition shows up in how it gets funded. “Organizations can achieve goals through incremental improvements—doing more of what they’ve always done a little faster, a little harder,” says Sull. “But truly ambitious goals, the 10x goals so popular in Silicon Valley, can’t be achieved incrementally.” For those, the capital must come from somewhere else. “You don’t need allocation, you need reallocation,” he says, meaning pulling money and people off of existing projects and redirecting them to new ones. The hard part is that money and talent are already committed. “People hoard talent,” he says, and “they fight tooth and nail to hold on to their budget.” So, consider your plan’s funding request: a modest ask might be a symptom of modest ambition—or a signal that you’ve not made a case for why it deserves a larger investment.

4. Is it staffed to succeed?

Talent is a resource too, and a strategic plan can fall short if it isn’t staffed with the right people. When a plan sticks close to what you already do, it can run on the skills you and your team have, according to Iyengar. With a bold plan, though, “you need people with different expertise and knowledge bases to help with the concreteness of implementation.” The catch is that your best people are always in demand, and they gravitate toward projects that stretch them. “Ambitious people want to do ambitious things,” says Sull. Look carefully at who’s on your plan. The staffing could tell you more than the numbers.

Setting the right level of ambition also means understanding what drives your team, says Iyengar. “Do you have accurate information, or a bunch of assumptions? Do you know what barriers your employees face? What slows them down? What incentivizes them?” Without that knowledge, you might misjudge how hard your team can be pushed.

5. Does your plan leave room for uncertainty?

The more uncertain the outcome, the more your plan should be built to adjust as you learn. “You’ve got to experiment, and experiment broadly,” says Sull. That said, “the fact that you’re experimenting doesn’t guarantee you win. Some will work and some won’t.” The way to experiment without going all in is to start small while aiming high. Iyengar points to Jeff Bezos, who launched Amazon with books, easy to ship and simple to scale. But his ambitions were far grander from the start. To pressure-test a decision, she suggests asking yourself two questions: “If this succeeds, what new options could it create? If it fails, what would it open, or shut down?” The answers should line up with your future vision, she says. “If it’s not giving you options, don’t do it.”

6. Is your time horizon holding you back?

Annual measurement cycles tend to work against ambition, says Sull. “If you’re asking people to innovate but setting annual targets, you’re going to push them toward incremental innovation rather than swinging for the fences.” He recommends a longer horizon instead, chunked into smaller, more tactical quarterly goals. A longer runway is also what lets you aim higher in the first place. Sull suggests working through your plan with a thought experiment: What would it take to double revenue, market share, or customers in the time you’ve set? Your answer will expose whether you’re thinking too small. After all, “there’s no incremental path from a billion dollars to two billion in three years,” he says.

7. How will you know if it’s working?

A strategic plan needs a way to show progress along the way, says Sull. As an example, he points to Burberry’s expansion into China under Angela Ahrendts, who ran the company from 2006 to 2014 and effectively tripled revenue during her tenure. Cracking the Chinese market wouldn’t happen overnight, so to keep investors on board, Burberry reported interim indicators, like comparable sales growth for that region, to demonstrate momentum. “You might have super ambitious three-year goals, but on a quarter-to-quarter basis, you’re showing steady progress,” he says. Those benchmarks only work if they’re measurable, adds Iyengar, “otherwise you can always pat yourself on the back no matter what outcome you have.”

8. How are you measuring your plan against competitors?

However bold your plan looks on its own, bear in mind that it’s competing against rivals making their own bets, and some of them have more room to take risks than you do. Your plan ought to take into account an honest read of the field, says Iyengar. “You have to know what your competitors are doing, what their strengths are, and what their constraints are, and then you have to know the same about yourself.” This helps inform how you move forward. “If you have major strengths and a major lack of constraints, obviously you shoot for the moon, and you’d better ride hard and fast.” For an outside perspective, Sull points to Silicon Valley, an ecosystem built around ambition. He suggests asking a startup leader in your field: “If you were the CEO of this company with these resources, what would you aspire to?”

Match Your Ambition to the Opportunity

Finding the right level of ambition for a strategic plan ought to be straightforward: figure out how much boldness the moment calls for, and how much your organization can handle. The trouble, says Iyengar, is that leaders tend to “get so caught up in the weeds, they just do what’s sitting in front of them,” which is why so many plans end up less ambitious than they could be.

The remedy, she says, is to lift your gaze and ask a broader question: “What could this company be?”

The same question applies to whatever you’re building. What could a new market, offering, or business unit become? And is your ambition big enough to match it?

Principles to Remember

Do

• Define the problem before you set the target. Otherwise, you risk aiming your ambition at the wrong thing.

• Consider how your plan is staffed. If your strongest, most varied talent isn’t on it, it could be a signal the plan isn’t much of a stretch.

• Maintain a margin for error and uncertainty. Your plan should include small, reversible steps, so you can adjust as you learn.

Don’t

• Weigh a single option in isolation; without bolder alternatives beside it, it’s difficult to tell if you’re thinking too small.

• Neglect your competitors. Your plan ought to account for their strengths, capabilities, and constraints alongside your own.

• Overlook your plan’s time horizon. Annual targets cap how aggressive a goal can be; stretch it over a few years, and you can aim higher.

Copyright 2026 Harvard Business School Publishing Corporation. Distributed by The New York Times Syndicate.

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