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Stopping the Losing Streak

Sometimes all it takes is a fresh perspective to start winning again.

October 15, 2025

A, an executive at a mid-size company, came to me for a one-session breakthrough coaching call. She shared a list of challenges—internal tension, stalled growth, and her own motivation slipping. Her division was doing okay, not great, and she felt stuck and worn down.

 

As she talked, I kept picturing a sports team—pick your favorite: football, baseball, soccer, axe throwing—that’s trapped in a losing streak. The players are talented. The effort is there. But when losing becomes the norm, it starts to feel expected. Each game feels like a repeat of the last.

 

Here’s what we did to turn it around.

 

1. Stopped the losing streak.
We began by changing how she saw what was happening. I asked, “What if the losses were really a way to say you need to change some ways you’re doing things to create even more success?” She paused and said she had never thought of it that way.

 

But think about it. When a team is stuck, the coach changes the lineup or the plays. They don’t abandon the game; they adjust how they’re playing it. She could do the same.

 

2. Identified her next win.
Instead of trying to fix everything, she chose to sit in on several calls between her salespeople and their top clients. Her goal wouldn’t be to critique—it was to listen with fresh eyes and ears, and to look for opportunities to make positive changes.

 

Just like a coach reviewing game film, she wanted to see what was really happening on the field before making adjustments.

 

3. Created a new game plan.
We wrapped up the session by outlining how she would build on what she learns from those calls. Her plan included identifying what was working, where clients were truly responding, and what might need a new approach or play.

The goal isn’t to reinvent the business; it is to make small, smart shifts that reignite winning momentum.

What if this week, you looked at your own approach and made one smart change to start your next winning streak? 

Doug

You’re one action away. Starting today.

Create Your Next Winning Streak

My one-session Breakthrough Call is a great way to create your own new winning streak—whether at work or in life. It helps you clarify what’s next, spark fresh ideas, and make the right next move with focus and confidence. Learn more at dougfleener.com/coaching or just reply to this email.

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Frequently Asked Questions About Changing Losing Streaks

1. What does it mean to “stop the losing streak” in business or life?
It means interrupting the patterns or habits that keep producing the same disappointing results. Instead of pushing harder, you pause, ask better questions, and make small, intentional changes that shift your direction and mindset.

2. How can a What If question change how I see things?
What If questions open new perspectives by challenging default thinking. They create space between reaction and choice—helping you see opportunities instead of only problems.

3. What is a Breakthrough Coaching Call?
A Breakthrough Call is a focused one-on-one session designed to help you gain clarity, identify your next win, and create a simple plan to move forward—whether in your business, leadership role, or personal life.

4. Do I need to be struggling to benefit from a Breakthrough Call?
Not at all. Many clients use a Breakthrough Call when they’re already doing well but want to sharpen focus, find new momentum, or set up their next winning streak.

5. How can I start creating my own winning streak right now?
Start by pausing to look at your approach. Ask yourself, What if I made one smart change this week to create even more success? That mindset—combined with consistent small adjustments—builds confidence and lasting progress.

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