Worst “Kate” Scenario

When my kids were younger, they had a phrase for me.

Whenever we were planning something—a travel ball weekend, a gymnastics meet, a birthday party, or a vacation, I would start asking “what if ” questions.

• What if the flight was delayed?
• What if one of the kids gets sick during the tournament or meet?
• What if a glove, bat, or set of grips is inadvertently left behind?
• What if the meet runs late and we miss dinner?
• What if the hotel is too noisy and the team’s starting pitcher doesn’t get the needed rest?
• What if there is traffic and it looks like we’ll arrive late?
• What if it rains all week while we are at the beach house?
• What if someone forgets their medication, uniform socks, or inhaler?

While everyone else was picturing the fun parts, my brain immediately went to the places where things could fall apart. They called it Worst “Kate” Scenario mode.

Apparently, this was my superpower.

To them, it sounded negative.

But here’s the funny part: those weekends filled with all kinds of logistical gymnastics usually worked out pretty darn well. I can’t remember any major meltdowns.

The travel baseball and softball tournaments.
The gymnastics meets.
The multi-family beach weeks.
The college visit trips.
The birthday parties.
The massive errand days prior to all of these things.

Most were memorable and smooth—not because everything magically went right, but because I had already thought about where things might go wrong.

Extra snacks packed.
Backup reservations.
Alternate routes mapped.
Plan B… and sometimes Plan C.

(Sidebar: Well, there was one major meltdown in more than 16 years of chaos. One time, the coach picked up multiple girls from our house to drive them to a tournament 5 hours away. My husband was flying in from a business trip, arriving home after midnight, and planned to leave early the next day to see the tournament. One of my kids (who shall remain nameless) piled into the coach’s van and headed off to South Carolina. Upon arrival, that child of mine realized she had left her entire suitcase sitting in our foyer. No jammies, no uniform, no underwear. The kid at least remembered her bat bag, so if she could find a spare uniform, she could still make it on the field, but admitting she forgot her stuff to the coach was a fate worse than death. Lucky for her, she has the best Dad in the business, and he got up at 2:00 AM and drove the suitcase down to meet her.)

What my kids called Worst Kate Scenario was really just anticipating risk and removing it before it became a problem.

And honestly, this is exactly how I approach sales.

Salespeople are, by nature, optimistic. That optimism is important. It keeps us prospecting, pushing forward, and believing the next opportunity will work out.

But too much optimism can actually derail a deal.

Most deals don’t fall apart because the customer suddenly changes their mind.

They fall apart because of issues that weren’t anticipated early enough:

• A stakeholder who wasn’t included
• A stakeholder departure
• A process bottleneck that slows approval
• Implementation concerns that show up late
• A new priority that takes precedence
• Operational risks that make the customer nervous
• The fear of making a mistake wasn’t uncovered or worked through

When those issues arise at the end of the sales cycle, they feel like surprises, leading to indecision that stalls deals.

But most of the time, they aren’t surprises at all.

They’re simply risks that weren’t surfaced early enough.

The job of a great salesperson isn’t just to close a deal.

It’s about thinking through the worst-case scenarios before the customer encounters one that sidetracks a deal and creates a bad customer experience.

It’s the sales rep’s job to recognize where the client will face challenges and help them navigate around them.

• Where might they get stuck?
• What concerns will surface internally?
• Where could our team struggle during implementation?
• Does the customer have the right expectations about this project to ensure my company does its best work?

Then you work through those issues during the sales process, not after the contract is signed.

There’s another side effect of this mindset. Part of the “Worst Kate Scenario” mentality is that I get nervous about deals that feel too easy.

When everything seems effortless, my brain starts whispering:

“You’re probably missing something.”

So, I dig deeper.

And more often than not, that’s where we uncover additional challenges the customer hasn’t fully articulated yet—and where real value gets created.

I’m still doing Worst Kate Scenario mode with my kids, and they still don’t like it. But just as with sales, even if I’m just advising, my questions can steer them out of trouble. 

• What if the moving company arrives late and misses the scheduled dock time?
• What will you do if you can’t get the internet installed by your first work day?
• What’s your plan to get two people’s clothes into a one-person closet?
• Does the venue have a rain plan that can accommodate all the guests?
• How long will alterations take on that dress?
• What if the violinist doesn’t show up for the ceremony?

But in sales—and in life—Worst “Kate” Scenario mode has saved more deals, projects, and family weekends than I can count.

Sometimes the best way to make things go right…

is to start by asking what could go wrong.