Lessons Learned #1: The Leadership Tension Between Pivoting and Persevering
Over the past decade of coaching entrepreneurial leaders, I’ve seen one truth again and again: success comes from knowing when to persevere and when to pivot. It’s a constant tension. Great leaders stay committed to their strategies, but they’re also wise enough to recognize when change is needed. That’s why we always remind teams at the beginning of every session: “We reserve the right to get smarter.”
While this tension exists in every area of life, it’s especially critical in business. Leaders face a high volume of decisions, and a few are mission-critical. Knowing when to hold firm and when to adapt can mean the difference between thriving and merely surviving in an ever-changing marketplace.
Persistence is powerful as no great business was built on a whim or without enduring challenging seasons. But clinging too tightly to outdated decisions, even those that, in hindsight, were clearly wrong, can lead to stagnation.
So how do you know when to stick with a decision and when to change course? The answer lies in building smart habits: ones that help you stay objective, gather insights, and make better decisions.
How to Know When to Persevere or Pivot: Habits That Help
I’ve had a front-row seat to hundreds of “aha” moments, when a team realized they needed to pivot or recommit to a course of action. These insights rarely come out of thin air. Rather, they most often come from consistent practices that sharpen your awareness and decision-making.
Here are the disciplines I’ve seen work best:
1. Gain Initial Clarity (Even if It’s Not Perfect)
Get your best thinking down on paper. Even if your long-term vision, annual growth plan, or quarterly priorities aren’t perfect, documenting them is essential. Writing them out forces clarity, and gives you something to improve over time.
2. Challenge, Confirm and Sharpen Your Thinking
Great leaders don’t operate in a vacuum. They build mechanisms that challenge their assumptions and bring in fresh perspectives:
Weekly & Monthly Scorecards: Objective data doesn’t lie. It reveals trends before gut instinct catches up.
Market Intelligence: Stay close to your customers, suppliers, and competitors. What shifts are they seeing?
Candid Internal Feedback: Create a culture where honest input is safe, and expected. Don’t just allow feedback, actively invite it.
Clarity Breaks: Block 45–60 minutes each week or month to unplug, reflect, and think strategically without distraction.
3. Use Outside Sounding Boards
Sometimes, perspective from outside your business is what helps you truly “get smarter.”
Peer Forums: Join a group of fellow business owners where you can learn from peers and be fully candid. Peers with a similar role often spot issues before you do.
Executive Coaching: A good coach will ask hard questions and help you process tough decisions. They’ll also challenge you to either pivot, or stay the course, and help you make the right decision no matter how difficult.
4. Build a Great Meeting Rhythm
Meetings get a bad rap, but it’s not the meetings, rather it’s how they are used. When done right, your meeting cadence becomes an engine of continual clarity, alignment, and decision-making.
Each meeting format has a different purpose:
Daily Stand-Up (12 min): Quick pulse check to stay connected as a team.
Weekly Tactical (90 min): Review KPIs, progress on priorities, and resolve urgent issues.
Monthly Strategic (2–4 hours): Step back to evaluate strategy, discuss trends, and tackle really big problems, challenges and opportunities.
Quarterly Planning (Full Day): Reflect on the past 90 days, identify unresolved issues, and align on priorities. These sessions are ideal for asking, “Do we pivot or persevere?”
Annual Planning (2 Days): Go deep on strategy, vision, and long-term goals. Confirm, or revise, your direction based on internal and external realities and what has changed over the prior 12 months.
Without a strong meeting rhythm, you and your leadership team are like a group in a canoe barreling down whitewater rapids with no ability to steer, and are instead just reacting. The right meeting cadence gives you paddles, a map, and a plan allowing you to take control of your business back.
Final Thoughts
This blog post goes to the heart of one of the most challenging tensions a leader faces - knowing when to persevere and when to pivot. When you come to the realization that a pivot away from a previously made decision is needed, framing the decision as “We reserve the right to get smarter” helps you make and declare that change, but also helps your team accept why pivoting is the right course of action. Leaders don’t have crystal balls where they can perfectly see the future. But when you receive new information that implies a change of course, leaders need to have the courage and humility to ‘get smarter’ for the greater good of their team and company.
