Why Small Wins Matter More Than Big Speeches

Sunday Morning Coffee

I love a good motivational speech. I've given a few. I've sat through quite a few more. You know the kind.

Believe in yourself.

Never give up.

Your past doesn't define your future.

Dream big.

Keep pushing.

There's nothing inherently wrong with any of that. Sometimes people genuinely need encouragement. The right words, delivered at the right moment, can matter, but I've spent enough years working with incarcerated students, people returning home from prison, struggling organizations, and exhausted staff to have learned something: People rarely change because we give them a great speech.

They change because something happens that gives them evidence that change might actually be possible. Usually, that something is surprisingly small.

Hope Needs Evidence

Imagine you've struggled academically for most of your life. Maybe school was never a place where you felt particularly successful. You fell behind early. You learned to avoid situations that exposed what you didn't know. Eventually, "I'm just not good at school" became part of the story you told about yourself.

Then someone stands in front of you and says: You can do anything you put your mind to! Nice sentiment, but you have decades of evidence suggesting otherwise. One speech isn't going to erase that. Then something different happens.

You solve a math problem you couldn't solve last week.

You finish a book.

You pass a practice test.

You earn your first certification.

You help another student understand something.

Suddenly, there's a tiny crack in the old story.

Maybe I'm not bad at this.

That's a small win, and small wins are powerful because they don't ask people to believe something without evidence. They become the evidence.

We Sometimes Set the Finish Line Too Far Away

Education is full of big goals:

Earn the diploma.

Complete the degree.

Finish the apprenticeship.

Earn the credential.

Graduate.

Get the job.

Those are important goals, but imagine standing at the beginning of that journey when the finish line feels impossibly far away. A student functioning several grade levels below the GED standard doesn't experience "earn your GED" as a small, manageable goal. A person entering a workforce program after years of unemployment may not experience "get a career" that way either. Sometimes the goal is so big that it reinforces the belief that success belongs to somebody else.

That's why good educators and coaches create shorter distances between success points.

Let's get through this lesson.

Let's master this skill.

Let's finish this application.

Let's practice this interview question.

Let's show up again tomorrow.

Then we acknowledge what happened. You did that. And then we build from there.

Small Doesn't Mean Insignificant

We sometimes overlook small wins because they don't look impressive in reports. A student who finally raises their hand isn't a credential. Someone who attends class every day for two weeks isn't a graduation. A participant who makes their own phone call instead of asking their case manager to do it isn't a job placement. A staff member who brings up a problem in a meeting isn't organizational transformation.

But those moments may be exactly where transformation begins.

The student raising their hand may be developing confidence, the participant making the phone call may be developing self-advocacy, and the staff member speaking up may be beginning to trust leadership. Consider that the person who’s shown up for two weeks may be practicing consistency after years of instability.

If we're only looking for the big outcome, we can miss the behavior changes that make the big outcome possible.

This Matters for Staff, Too

Small wins aren't just for students. They're incredibly important for people doing difficult work. Correctional educators can spend months teaching students who are transferred without warning. Reentry professionals work with people facing barriers they cannot solve. Correctional leaders deal with staffing shortages, security concerns, budget limitations, and systems that sometimes seem designed to resist change. Nonprofit staff tackle enormous social problems with decidedly non-enormous budgets. When you're doing work like this, the gap between where things are and where you want them to be can become exhausting.

That's when leaders often reach for inspiration.

We remind everyone of the mission.

We talk about resilience.

We tell people their work matters.

Again, those things aren't wrong, but exhausted people don't always need another speech about the mountain.

Sometimes they need evidence that they're moving.

Show them the student who advanced two grade levels.

The participant who kept a job for 90 days.

The partnership that finally came together.

The process that used to take three weeks and now takes three days.

The classroom where attendance improved.

The problem the team solved.

Progress creates energy. People are much more willing to keep climbing when they can see that they've already moved.

Leaders Should Engineer Wins

I think one of the most overlooked responsibilities of leadership is creating conditions where people can experience meaningful progress, not fake wins, lowering expectations, or putting balloons around mediocre performance and declaring victory.

Real wins.

If you're launching a major organizational change, don't wait a year to determine whether anything is working. What can the team accomplish in 30 days? If you're redesigning an education program, what early indicator would tell teachers they're moving in the right direction? If you're coaching someone toward employment, what milestones come before the job offer? If a student has a long academic journey ahead, how will they know they're getting better?

Big goals give us direction.

Small wins give us momentum.

We need both.

Celebrate Progress Without Confusing It With the Destination

There's an important distinction here. Celebrating a small win doesn't mean pretending we've arrived. A student improving their reading level still has work ahead, someone completing a workforce program may still need employment, and a facility reducing class cancellations for one month hasn't solved every operational problem. We can say two things at the same time:

You did it!

And:

We're not finished.

In fact, acknowledging progress often makes people more willing to continue. It's hard to keep working toward a goal when nothing you do ever seems to count until you reach the very end.

Maybe We Need Fewer Speeches

There will always be a place for inspiration. Words matter, of course they do. Great leaders help people imagine possibilities they may not yet be able to see, great teachers encourage students when the work gets hard, and great coaches remind people that setbacks don't have to become endings.

But inspiration works best when we pair it with opportunity. Give people something achievable to work toward. Let them experience progress. Name it when it happens. Then give them the next challenge. Because eventually, those little wins begin stacking on top of one another. One completed assignment, one difficult conversation, one week of showing up, one certification, one good decision, one problem solved independently…until the person looks back and realizes something remarkable: They're not standing where they started.

No speech could prove that.

They proved it to themselves.

And sometimes that's how the biggest changes begin.

Not with a standing ovation.

With one small win that makes the next one seem possible.

Cheers to you on this October morning. I hope you have a month full of fall leaves, meandering road trips, hot coffee in cool, crisp, October air, and inspiration to build big dreams. ☕