What a Sales Turnaround Has in Common with a Baseball Turnaround

For most of 2026, the Boston Red Sox have been among the worst teams in baseball. Sitting near the bottom of the AL East with one of the league’s highest strikeout rates (over 24% of plate appearances) and ranking near the bottom in runs scored, it wasn’t supposed to be this way. Roster issues and injuries to key contributors delivered negative momentum for nearly the entire first half of the season.

Then, starting on a recent road trip and continuing with a convincing four-game sweep of their long-time rival and nemesis, the New York Yankees, we could finally see the change. As of June 29, The Red Sox have won five consecutive games, starting pitchers have thrown 11 straight quality starts (min 6 innings and 3 or fewer runs allowed), and for the first time in 2026, there is positive momentum on the team and positive feelings from the fans.

Coaching

The Achilles’ heel for this Red Sox team has been offense: lack of hits, lack of key hits, lack of timely hits, lack of runs, and far too many strikeouts. Recently, that started changing. The team cut down on strikeouts, began putting the ball in play far more often, and started generating timely hits. While not publicly mentioned, the turnaround must be due to the new hitting coaches. Same team, same core players — nothing else changed except the results. The momentum has swung, and with injured stars due to return, there’s legitimate hope for a strong second half.

The Sales Version

If your sales team is unspectacular, missing quota, failing to fill the pipeline, watching win rates and deal sizes decline, with opportunities stalling midway through the sales cycle, and prospects ghosting, they are a lot like the Red Sox’s offensive woes early in 2026. If a baseball team can turn it around with a change in approach and better coaching, a sales team can do the exact same thing. Unfortunately, too often, they don’t.

Why?

High-Powered Fans (or the Lack Thereof)

There are plenty of reasons, but two big ones rarely get mentioned and stand out for me:

1. Fans aren’t screaming for the sales leader to be fired like Red Sox fans screamed for the Chief Baseball Officer to be fired. There’s no constant media pressure or viral outrage, so leadership can remain complacent and rely on hope instead of action. As you know, hope is not a strategy.
2. Fans aren’t demanding that the owners sell the business as Red Sox fans have been demanding for the past four years, so there’s no burning desire to make difficult changes.

Without that external heat, it’s easy to keep doing what you’ve always done — even when it’s clearly not working.

Sales Coaching in Action

Real coaching doesn’t have a scary “what if it doesn’t help?” downside. Research from Objective Management Group shows that consistent, daily sales coaching drives a 28% increase in sales. Combine that with effective coaching, and the bump jumps to 43%. Effective means more than a quick “how’s it going?” call or some quick encouragement like a Rob Schneider movie character yelling “YOU CAN DO IT!”

Effective sales coaching includes:

• Post-call debriefs
• Pre-call strategizing
• Role-playing
• Lessons learned
• Next steps
• Real accountability

What’s Not to Like?

Apparently, quite a bit — because only 7% of sales managers actually embrace this. I find the fact that more don’t embrace it cowardly, hilariously stupid, and I am brain-melting incredulous.

Many leaders are afraid of:

• Looking weak to their bosses asking for money to invest in outside expertise
• Engaging in Role-play themselves (or pushing their team to role-play)
• Their salespeople not learning from them
• Resistance from the team
• Failure

But the biggest challenge is egos. Egos so huge they can’t admit they might need help to turn things around.

Ego is important in all selling roles and it’s difficult to land a sales leadership role without a decent sized ego, but come on! When the ego that got you there gets in the way of getting the team there, it’s a problem.

Think about it like a dad coaching his kid’s Little League team. Yelling “just hit the ball!” from the sidelines doesn’t work. Red Sox hitters received guided batting practice on getting back to hitting basics. Stay inside the ball, drive it up the middle, and hit to the opposite field instead of trying to pull the ball and hit a home run on every swing. With 2 strikes, just put the ball in play.

Coaching salespeople uses the very same principles.

Two Ingredients for Real Change

• Change in Approach: The Red Sox new approach of putting the ball in play works in sales too. It means putting more opportunities into the pipeline and adopting a time-tested, milestone-centric, buyer-focused sales process like Baseline Selling. That helps you run the sales cycle (bases) properly.
• More Individual Coaching: The Red Sox hitting coaches did targeted work with each hitter. The image at the top of the article was taken 8 years ago, when my then 16-year-old son, received targeted coaching from former MLB DH Luke Scott. Sales coaching provides the same things: role-plays targeting specific milestones and/or a salesperson’s specific selling challenges demonstrate what good conversations should sound like. Debriefs uncover what went wrong and reinforce what works, and accountability builds positive momentum around change.

Putting the Ball in Play = Filling the Pipeline
Batting Practice = Role-Playing

The combination of a strong sales process and professional coaching creates the shift. Wouldn’t you love to see your team respond like the Red Sox when they swept the Yankees? (No offense to Yankee fans, those who hate the Red Sox, those who dislike baseball and those who dislike me.)

We can help. Whether it’s optimizing your current sales process, training your team on a predictable milestone-based approach, coaching your leaders to coach effectively, or supporting everything with unlimited sales debriefs (including our AI-powered options), please reach out. Let’s turn that negative momentum around.