Develop leadership skills
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“What did you fail at today?” That’s the question Sara Blakely’s father asked her every evening at dinner. The founder of Spanx and Sneex learned early that trying and failing were worth celebrating, not hiding. For parents looking to raise resilient, capable leaders, both leadership and an entrepreneurial mindset start with everyday interactions — not business plans, startup funding or a title.
Leadership and entrepreneurial thinking are more connected than people assume. Both come down to spotting opportunities where others see problems, building resilience, staying curious, and taking action without being asked to. In an age where anxiety, over-scheduling and screen time shape so much of childhood, this combined mindset may be one of the most valuable things parents can hand their kids.
Research backs this up. Early exposure to entrepreneurship, whether through education or the home environment, significantly boosts entrepreneurial intention while building the critical thinking, problem-solving and creativity that leadership requires in any field. Parental influence matters here, often before formal education even begins.
In The Anxious Generation, Jonathan Haidt argues that overparenting and excessive screen time are driving declines in youth mental health. Instead of building independence and emotional strength, many parents hover and manage while childhood becomes increasingly virtual. Haidt’s prescription is more freedom, more real-world experience and more room to learn from failure — which happens to be the same foundation that builds both leaders and entrepreneurs.
Here’s how to build both at home. No business plan and no title required.
1. Leadership Begins With Asking Different Questions
“How was school today?” is a perfectly fine question to ask. However, you might want to consider alternatives like, “What problem did you solve today?” or “What would you change if you could?”
Leaders and entrepreneurs often share an important habit: they identify points of friction and imagine improved systems. Parents can create a family tradition of brainstorming solutions for everyday challenges, such as a slow cafeteria line, a confusing homework platform, or an unsatisfactory school lunch.
The same habit works outside the house. During a walk, a shopping trip or a vacation, ask what your teen would improve about the experience. One WIT teen turned her frustration with the costs of school lunches into a business that pays off school lunch debt, instead of just complaining about the issue like everyone else did. That’s leadership and entrepreneurship in the same instinct: noticing a problem nobody’s fixing, and deciding to be the one who does.
Try this: Start a “Problem Solver of the Week” tradition at family dinners. Each person names a problem they noticed and floats a possible fix. Keep a running family log — you might be surprised when your teen decides to act on one.
The goal isn’t a company. It’s helping teens see themselves as capable of creating change, which is what eventually makes someone worth following.
2. Leadership Means Treating Failure As Valuable Data
Children who never fail don’t learn how to recover — and recovery, not perfection, is what leadership actually requires under pressure.
At WIT — Whatever It Takes, the organization I founded in 2009, teens pitch projects that sometimes flop, then regroup and come back stronger. One student launched an in-person tutoring compny that got zero sign-ups. She pivoted to an online tutoring club and gained traction within two weeks. The pivot, not the original idea, was the real leadership move.
Parents can borrow the structure: a weekly “Fail Forward Friday,” where everyone shares what went wrong and what they learned from it. Embracing setbacks and celebrating the willingness to try again builds the resilience necessary for effective leadership.
Try this: Create a “Fail Forward Resume” with your teen. This resume is the opposite of a traditional one; it focuses on setbacks they’ve experienced and the lessons each setback taught them. Review it together every few months and observe how many challenges they have learned to handle with ease over time.
Recovering from setbacks isn’t just a minor detail in leadership; it’s a significant part of the role.
3. Leadership Is Built Through Real Responsibility
Leadership is ownership before it’s anything else, and ownership is built through real responsibility, not simulated responsibility.
Allowing a teenager to plan the family dinner menu, research a vacation within a real budget, or organize a garage sale helps them build confidence by making decisions that truly matter. A Junior Achievement survey revealed that 66% of teens aged 13 to 17 are likely to start a business as adults; however, most have never had the opportunity to practice making important decisions and dealing with the outcomes.
Developmental psychologists note that teens with regular real responsibilities tend to build stronger executive functioning skills — the same mental muscles that support both entrepreneurial thinking and leadership under pressure.
Try this: Hand your teen a “Family CEO” role for one project — planning a vacation on a real budget, running a garage sale — with full decision-making authority and clear parameters. Resist stepping in unless they ask.
This is the incremental version of what a title eventually asks for anyway: the ability to own an outcome, not just complete an assignment.
4. Leadership Needs Room For Unstructured Problem-Solving
Unstructured time builds negotiation skills, creativity, and adaptability — three things no leadership seminar can install after the fact. Haidt argues that free play, without an adult managing every interaction, is where kids actually learn to collaborate, improvise, and self-regulate.
If the instinct as a parent is to step in and direct, try pausing instead. Letting a teen sit with a hard problem, without rescuing them from it, is where the growth actually happens.
Many teen entrepreneurs develop their best ideas during exactly this kind of unstructured time, when nobody’s managing their attention for them. It’s also where leadership actually gets rehearsed: deciding what to do next without someone assigning the next step.
Try this: Establish a “No-Solution Zone.” When your teenager presents a problem, listen attentively without jumping in to provide a solution. Instead, ask questions like, “What have you tried?” or “What are you considering?” Pay attention to your own balance between offering solutions and exploring their thoughts, and make an effort to shift towards more exploration.
Leadership And Entrepreneurship Are The Same Mindset
The world today’s teens are entering is fast-changing, uncertain, and increasingly shaped by AI. Giving them practice with this mindset — seeing problems as opportunities, knowing how to start something without being told to, and recovering from setbacks in public — may prepare them better than test scores or a title ever will.
Promoting this mindset at home encourages adaptability to change, builds confidence in making calculated risks, improves problem-solving skills that can be applied in many areas, and fosters a sense of ownership that ultimately develops a valuable leader.
Parents play a bigger role in this than most realize. In her book Raising An Entrepreneur, Margot Machol Bisnow interviewed 70 successful entrepreneurs and their mothers and found that parental support of a child’s authentic passions and strengths, more than pushing traditional markers of success, was the real foundation. When parents encourage curiosity and self-directed problem-solving, they raise kids who treat problems as opportunities and setbacks as data — the same instincts that eventually get called leadership.
Entrepreneurship-specific training, as we do at WIT – Whatever It Takes, has more than doubled from one generation to the next, which says something about how seriously this is being taken. But the most important lesson here doesn’t require a business plan, a title, or venture capital. It’s simply encouraging a teen to start—to take the first small step toward solving a problem they actually care about, and to keep going when it doesn’t work the first time. That instinct is what leadership is built from, long before anyone hands over the name for it.