The breakfast table erupted into chaos over the weekend. My youngest wanted pancakes, the middle one demanded waffles, and somehow—through a series of trades, compromises, and creative problem-solving that would make a Fortune 500 CEO take notes—they all walked away happy with French toast.
As I watched this unfold, coffee in hand, it hit me: my five kids might be the best negotiation coaches I've ever had.
5 Powerful Negotiation Lessons You Can Learn from Kids
1. The Power of Pure Persistence
My ten-year-old doesn't like hearing "no."
Not in a disrespectful way, but in a way that every entrepreneur should study. When she wants extra screen time, she doesn't just ask once and sulk. She comes prepared with reasons, alternatives, and if those don't work, she'll circle back an hour later with a completely different angle.
Last week, she wanted to stay up past bedtime to finish a book. First attempt: "But Dad, reading is educational!" When that didn't work, she returned with: "What if I wake up 30 minutes early tomorrow to help with breakfast?" By the third round, she'd recruited her siblings to vouch for her character.
She got the extra reading time.
In business, we often give up after the first "no." We hear rejection and retreat. But watching my kids has reminded me that persistence—respectful, creative persistence—often wins the day. That deal that seems impossible? Maybe it just needs a fourth conversation with a different approach.
2. Starting From Yes
Here's something fascinating about kids: they always assume the answer will be yes. They begin every negotiation from a place of possibility, not limitation. "When we go to Disney World..." not "If we go."
This mindset shift is powerful. In my real estate ventures, I've learned to frame discussions around positive outcomes. Instead of "If we can make this partnership work," I start with "When we finalize this partnership, here's what success looks like..."
3. The Art of the Package Deal
Kids are masters at bundling. "If I clean my room AND do my homework without being asked, can I have a friend over?" They instinctively understand that value isn't about one thing: it's about the total package.
I've taken this lesson into my business negotiations. When discussing terms with investors or partners, I don't focus on one variable. Like my kids trading vegetables for dessert privileges, I look for creative combinations that give everyone something they value.
4. Reading the Room
My fourteen-year-old daughter has an uncanny ability to read the room. She knows when I'm stressed from work, when her mom has had a long day, and she times her requests accordingly.
Emotional intelligence is something we often overlook in professional negotiations. We get so focused on our agenda that we miss the human element. Timing, empathy, and understanding the other party's state of mind can be just as important as the terms themselves.
5. Playing the Long Game
My oldest, who's now twenty three, learned to play the long game. Instead of asking for a car outright, he spent six months demonstrating responsibility: getting a part-time job, saving money, researching insurance costs, and maintaining excellent grades.
By the time he formally asked about the car, he'd already negotiated without saying a word. His actions had built trust and demonstrated maturity. The conversation wasn't about whether he deserved a car—it was about what kind and when.
In business and endurance sports, I've learned that the best negotiations often happen before you sit down at the table. Your reputation, track record, and relationships do half the work for you.
The Bottom Line
Every morning, I wake up to five little negotiators who challenge me, push boundaries, and find creative solutions to get what they want. They don't have MBAs or years of business experience, but they have something equally valuable: authenticity, creativity, and an unshakeable belief that there's always a way forward.
As I prepare for my next Ironman or structure my next real estate deal, I carry these lessons with me. Success in negotiation isn't just about leverage or logic—it's about persistence, creativity, emotional intelligence, and sometimes, the wisdom to see the world through younger eyes.
My kids may not realize it, but they're preparing me for every boardroom, every starting line, and every opportunity that comes my way. And honestly? I wouldn't trade these daily training sessions for any MBA program in the world.
The next time you're facing a tough negotiation, ask yourself: How would a kid approach this? You might be surprised by the breakthrough that follows.
I'd love to hear from you: What negotiation wisdom have you learned from unexpected places—kids, sports, even failures? Share your story below, and let's learn from each other.