Boulders vs. Pebbles
Why Prioritization and Commitment Drive Results
In my last post, I wrote about building an evidence-based culture. Evidence will give you a map that shows you where you are, where you could go, and what’s possible. But a map alone won’t get you to your destination.
What drives results is the ability to prioritize and commit. Success comes from identifying the biggest obstacle or opportunity—the boulder—and then having the fortitude to put disproportionate energy into moving it.
Too many companies, and too many people, spend their days chasing pebbles. The small, noisy issues that feel urgent but don’t materially change the trajectory of the business. Meetings fill with pebble-chasing. Energy spreads thin. People stay busy, but progress stalls.
Whether you’re running a company, leading a team, or managing your own desk, the truth is the same: you have to simplify and focus on what matters if you want to move forward.
Boulders vs. Pebbles
As leaders, our job is to create a path to success where our teams can run as fast as possible. Loose pebbles on the trail can slow you down. They can trip you up. But they’re nothing compared to the impact of the massive boulder sitting right in the middle of the path.
Being a successful leader, at any level, isn’t about clearing every pebble. It’s about identifying the boulder - that single problem or opportunity that has the greatest impact - and committing to move it. Moving boulders requires three things:
Identifying the challenge or opportunity.
Measuring the current or potential impact.
Focusing relentlessly on removing it, even when pebbles distract you along the way.
Focus isn’t proven by intent; it’s proven by what survives distraction.
You’ll stumble on pebbles, you’ll face noise and urgency, but if your energy stays fixed on the boulder, you create movement that pulls the whole organization forward. Once that boulder moves, momentum takes over.
The Trap of Pebbles
On paper, everything looks important. Pipeline creation, expansion revenue, churn reduction, enablement, pricing adjustments, new markets. Every initiative sounds worthy.
But when you treat everything as a priority, energy spreads thin. Teams confuse activity with progress. Leaders mistake urgency for impact.
Why do pebbles pull us in?
Urgency – Pebbles scream the loudest. They pop up in dashboards, customer escalations, and Slack threads.
Visibility – Pebbles are easy to measure. Counting tasks feels more tangible than assessing real change.Comfort – Pebbles are safe. They give the illusion of progress without requiring tough choices or real sacrifice.
The cost is the same at every level:
For companies, strategy fractures and resources spread too thin.
For teams, focus blurs and accountability fades.
For individuals, effort increases but impact stalls.
The pattern is always the same: lots of work, lots of effort, lots of discussion, and the feeling that progress is just out of reach.
The Power of Boulders
A boulder is the single challenge or opportunity that, if solved, changes the trajectory of your business, your team, or your own performance.
What makes it powerful isn’t just its size—it’s that moving it requires a bet. A conscious decision about where success will be most impacted.
And like any good bet, it’s not just about data or instinct. It’s about both.
Data shows you where the friction is—what’s underperforming, where deals stall, which customers are thriving or leaving.
Judgment tells you where to focus and why. It’s the conviction to choose one path and commit, even when other options seem equally valid.
I’ve seen both sides of that bet.
At DocuSign, CEO Keith Krach made a bold decision to focus the company on transactions. His belief was that usage—above revenue, retention, or innovation—was the key to achieving what he called “escape velocity.” He made a bet on moving that boulder, and it worked. Aligning every team around transactions created momentum that ultimately made DocuSign the verb for eSignature.
At Convoy, the vision was equally ambitious: to transform the over-the-road trucking industry. The challenge wasn’t ideas—it was prioritization. Was Convoy built for carriers and drivers, for shippers, or for brokers? Each direction had promise, and each came with thousands of pebbles to chase. But by trying to move all three boulders at once, focus fragmented. Despite incredible talent, the company couldn’t pick the one path that would sustain growth.
Two companies. Two outcomes. The difference wasn’t effort or intelligence. It was prioritization and commitment.
A Framework for Moving Boulders
Every organization and every individual has dozens of things they could focus on. The difference between movement and momentum is whether you can identify, prioritize, and commit to the one that matters most.
1. Define the Endpoint
Before you start moving anything, define what success looks like. What are you trying to achieve—at the company, team, or individual level?
If you can’t describe your endpoint in a simple, measurable way, you’re not ready to prioritize. Without clarity and metrics, you’ll confuse motion for progress.
When the endpoint is clear and measurable, the path becomes clearer too. You can see which challenges truly stand in the way and which are just noise. The boulders reveal themselves.
2. Identify the Boulder
Use evidence to find the challenge or opportunity that, if solved, will most change your trajectory toward that endpoint. The boulder isn’t always obvious—it often hides beneath symptoms like low conversion rates, churn, or misalignment.
Look past the noise and ask: If we solved this one thing, what else would get easier?
3. Name It
Make the boulder explicit. Give it a name everyone can repeat in a single sentence.
“We’re going to improve product activation.”
“We’re going to close the renewal gap.”
“We’re going to increase first-meeting conversion.”
Naming creates clarity. Clarity creates focus.
4. Communicate It
Naming the boulder is just the start. Real alignment comes from clearly communicating why it matters, and why other things won’t get attention right now.
If you want teams to commit, they need to understand the “so what.” Why this focus? What impact will it create? What are we intentionally not doing because this matters more?
When people see the connection between effort and outcome, and the purpose behind the tradeoffs, alignment becomes natural. The organization stops spreading energy thin and starts pulling in one direction.
Clarity on the “why” turns intention into momentum.
5. Commit to It
Commitment means saying no to other good ideas, at least for now. It means resisting the pull of pebbles when they pop up in meetings or Slack threads. It means staying the course when results take longer than expected.
Momentum builds through consistency, not constant resets.
6. Measure, Communicate, and Adjust
You can’t move what you don’t measure. Keep score in a visible, consistent way so progress is real, not assumed.
Celebrate progress as the boulder starts to move—small wins matter. They show that focus is working. But just as important is the honesty to admit when it’s not. If the data shows the impact isn’t what you expected, don’t defend it. Adjust it.
Measurement isn’t about judgment; it’s about truth. It’s how leaders stay grounded in reality and ensure their focus is delivering the intended impact.
Closing: Move the Boulder
Evidence will show you the map. Prioritization defines the path. But commitment—real, disciplined commitment—is what gets you to the destination.
The challenge isn’t in focusing; it’s in choosing what to focus on. It’s in having the courage to make a bet based on impact, to say “this matters most,” and then the fortitude to say no to everything else.
That’s what separates motion from progress.
Every company, every leader, and every salesperson faces the same choice: chase pebbles or move boulders.
The great ones don’t confuse activity with impact. They use evidence to choose wisely, conviction to commit deeply, and discipline to stay the course when distractions inevitably appear.
Because real progress—the kind that changes the trajectory of a business, a team, or a career—always comes down to the same thing:
the courage to pick your boulder and the discipline to move it.