Celebrating Wins and Learning from Challenges
- bryan6708
- Oct 10
- 5 min read
How to Build a Team That’s Aligned, Motivated, and Invested in Your Business’s Success
Introduction: Celebrate. Evaluate. Improve. Repeat.
In every business I’ve built—from our scheduled charter air service to property management to online educational programs—one core truth stands out:
Winning teams celebrate wins—and learn from every challenge.
This isn’t about trophies or pizza parties (although those can be great, too).
It’s about building a culture where your team is clear on what success looks like, knows how to track progress, and understands how they personally contribute to the company’s performance.
That kind of culture doesn’t happen by accident.
It happens through systems, structure, and transparency.
In fact, one of the most transformational things we ever did in our business was practice open-book management—and yes, that meant showing our financials to the entire team. Even our entry-level hires.
Sound risky? It wasn’t.
It was one of the most effective leadership tools I’ve ever used—and it created a team culture that was aligned, energized, and invested in results.
Part 1: Why Celebration Isn’t Optional
Entrepreneurs are often forward-thinkers.
We’re great at spotting what needs fixing, tweaking, or optimizing.
But if we’re not careful, that mindset can backfire. If your team only ever hears what’s wrong, they’ll start to tune out—or worse, burn out.
Celebration creates motivation.
It reinforces the behaviors you want repeated.
It shows your team what matters most.
And it helps you stay connected to the progress being made—so you don’t fall into the trap of chasing the next thing without appreciating the one you just conquered.
🛠 Systems for Celebrating Wins:
Weekly win shoutouts – Simple round-robin in team meetings
Monthly milestones – Visual dashboards showing progress
Team celebrations – Lunch, bonuses, or extra time off for key accomplishments
“Bright spots” board – Wins posted publicly, so everyone sees the momentum
📌 This doesn't have to cost money. It just has to be consistent.
Part 2: Align Your Team Around the Numbers That Matter
Want to take the celebration a step further?
Teach your team to read the numbers.
In our scheduled charter air service aviation business, many of our employees had never seen a financial statement.
We changed that.
We taught classes.
We walked through the reports line by line.
We explained what a profit and loss statement meant, what a balance sheet showed, and how the company’s success directly connected to its performance.
When people understand the financials, they stop seeing tasks—and start seeing impact.
🧮 Teach These Core Concepts:
Revenue – Where it comes from, how it grows, how to protect it
Expenses – What drives costs, and what can reduce them
Profit – What’s left, and what happens when it grows
Cash flow – How timing impacts the business
Even if you run a small service business, sharing even basic financials can change how your team shows up.
Part 3: Profit Sharing Builds Ownership
After we taught the team what profit meant, we shared it.
Not all of it. But a portion.
Tied directly to goals and performance.
We created a system where:
We set clear targets
When those were met, the business hit its profit goals
And when that happened, the team got a cut
Suddenly, the whole business was pulling in the same direction.
There was no more “us vs. them.” It was everyone watching the same scoreboard. This created valuable team alignment.
🧾 A Simple Profit-Sharing Model:
Set baseline performance targets
Share a % of profits above the baseline
Tie payouts to team-level performance—not just individuals
Communicate it monthly or quarterly so it stays top of mind
📌 This isn’t just about money—it’s about meaning. When people feel included in the wins, they’re more likely to help you win again.
Part 4: Make Challenges a Training Ground—Not a Punishment
Celebrating wins is half the formula.
The other half? Learning from challenges—without blame.
Mistakes are going to happen.
Projects will go sideways.
Team members will occasionally drop the ball.
The question isn’t “Did something go wrong?” It’s “What corrections can we make to prevent this from happening again?”
In my own businesses, we’ve always treated setbacks as:
Opportunities to improve a system
A chance to Identify gaps in communication or training
Feedback for refining how we work
Not reasons to panic.
🛠 A Simple Post-Mortem Framework:
After any big initiative (or failure), ask:
What went well?
What didn’t go as planned?
What did we learn?
What should we change for next time?
You can do this as a team meeting, or even as a 15-minute write-up.
Just make it a habit.
📌 Problems handled transparently build trust. And trust builds stronger teams.
Part 5: Build Feedback Loops Into Your Culture
You can’t celebrate or improve what you can’t see.
That’s why feedback loops are critical—not just from the top down, but bottom-up too.
💬 Create Regular Feedback Moments:
Weekly 1:1s – Check in with team leads or direct reports
Anonymous surveys – Especially after major initiatives
“Bright Spot + Pain Point” check-ins – One win + one challenge per week
Dashboard reviews – Walk through the numbers as a team
The more you normalize feedback, the more adaptable—and aligned—your business becomes.
Part 6: Build a Rhythm for Review and Reflection
It’s easy to lose sight of the bigger picture.
You’re busy. Your team is busy.
But if you never look up from the to-do list, you miss the trend lines that matter.
Review is where insight lives.
Every 90 days, sit down and ask:
What did we accomplish this quarter?
Where did we fall short—and why?
What did we learn?
What’s next?
It’s not always comfortable. But it makes you better.
📌 In my Mastermind, I teach entrepreneurs how to run these reviews without the overwhelm—just focused, actionable insights that move you forward.
Part 7: Anchor Your Culture in Ownership and Growth
Ultimately, what keeps people engaged—and your business growing—is a culture that rewards:
Initiative
Collaboration
Results
Improvement
You don’t have to be perfect. You just need to be intentional.
Celebrate wins with real context.
Learn from challenges with clear systems.
And lead with transparency that builds trust.
Conclusion: A Culture That Wins, Learns, and Grows
Want a business that scales?
Start with a culture that celebrates wins, learns from losses, and shares success.
Here’s your blueprint:
✅ Create consistent systems to celebrate wins
✅ Teach your team how the business really works
✅ Share financial literacy and build ownership
✅ Learn from challenges—without blame
✅ Build real feedback loops that improve performance
✅ Review progress quarterly
✅ Reinforce your values through your systems
Businesses don’t grow by accident. Neither do great teams.
They grow when you treat celebration and learning as core business functions—not just nice-to-haves.
Reflection Prompt:
What’s one win you can celebrate with your team this week—and one lesson you’ve learned that made you better?
Reply and let me know what’s working in your culture.
🎧 Podcast Spotlight: Well Aware Podcast with Conrad Ruiz
I recently joined Conrad Ruiz on the Well Aware Podcast to share my journey from growing up in an Alaska tourism family to building and selling my own company to Alaska Airlines. Along the way, we explored the pivots, lessons, and systems that shaped my path as an entrepreneur.
In this conversation, I talk about the importance of continuous learning, leveraging external resources, and creating systems that free you from the grind of day-to-day operations. We also discuss my latest venture—a course designed to help entrepreneurs build successful businesses without sacrificing the life they want to live.
🎙️ Listen here: Living the Business Dream with Ral West
P.S. Want help building a system-driven business with a team that’s truly aligned?
Watch my free training video here: https://www.ralwest.com/six-principles
Or check out my Mastermind, designed to teach entrepreneurs like you to build scalable systems and make confident decisions, so you are not sacrificing your life to build a successful business. https://www.ralwest.com/mastermind
Subscribe to my YouTube channel for insights on business systems, leadership, and entrepreneurial freedom: https://www.youtube.com/@RalWest
What was your biggest takeaway from this week's newsletter?
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