Driving My Children’s Teachers Crazy

I believe in teaching my children to question nearly everything.

The correct answer to most questions in social studies, science and literature is “it depends.” Maths is about the only class where there is such a thing as an absolutely right answer. Since my younger daughter likes to argue with nearly everything, including inanimate objects, this can be a trying experience for her teachers.

I recently learned that by teaching her to question authority and question the status quo, we are driving some of them slightly mad.

They don’t find it particularly amusing that she questions science, social studies and the rest. She understands that the world is grey rather than black and white. She grasps that in politics, in rules, and in most things, there are endless opportunities for interpretation.

Her academically gifted teacher was on the receiving end of this once too often and told her to go back where she came from. Xena’s response — that this would be physically impossible and extremely painful for her mother — was not appreciated.

Another teacher told her to use smaller words so the other children could follow.

The bit I’d say differently now

Reading that back, I was enjoying it more than I should have been in one respect.

Teaching a child to question authority is genuinely valuable. Teaching her to tie her classmates in knots with vocabulary is a different thing wearing the same clothes, and I don’t think I was distinguishing between them clearly enough at the time.

One is intellectual independence. The other is just being unpleasant with a larger vocabulary.

Similarly, I was quicker to be amused by the teachers’ frustration than to notice they were managing thirty children and one of them was mine. Most of them were doing a hard job well. The instinct to question isn’t cost-free to the people on the receiving end, and part of the skill is learning when to deploy it.

What I’d keep entirely: the principle that children should understand the rules well enough to choose whether to follow them, rather than obeying because obedience is the only option they’ve been shown.

I usually let them get away with a creative interpretation once. Case in point: at Mellow Mushroom, Xena was licking beer cheese straight out of the container. I told her she had to use a utensil. So she put her straw in the cup and sucked it out. Bonus points for creativity, and I told her that if she ever did it again there’d be consequences — since a straw is technically a utensil, by some stretch of the word.

The question this raises about being the boss

Here’s the part that took me years to notice.

I was raising children to question authority. I am also, at work, the authority.

Those two things sit less comfortably together than I’d assumed. It is very easy to admire independent thinking in your children and find it inconvenient in your employees, and most owners don’t catch themselves doing it, because the internal experience isn’t “I want compliance.” It’s “they don’t have the full picture” or “I’ve already thought this through.”

Sometimes that’s true. Often it’s the same reflex the teachers had, arriving with better justification.

So it’s worth asking plainly: **when was the last time someone who works for you told you that you were wrong?**

If you can’t think of an instance, there are two possible explanations, and only one of them is that you’ve been right.

What questioning actually costs a business

Some honesty on both sides here, because “encourage dissent” is the kind of advice that sounds free and isn’t.

Questioning everything is genuinely expensive. A team that relitigates every decision moves slowly and exhausts itself. There are decisions that simply need making, and the right response to them is to get on with it. Anyone who has worked with a professional contrarian knows the cost is real.

And not questioning is far more expensive, but later. The failures that damage small businesses are rarely fast. They’re a bad direction held for two years because nobody wanted to be the one to say so. The cost is invisible until it’s enormous.

The resolution isn’t “question everything” or “trust the boss.” It’s being explicit about which mode you’re in:

  • Before a decision: challenge is wanted, and the more senior you are, the more you should actively ask for it.
  • After a decision: disagree and commit. Argue it hard beforehand, then row in the same direction.
  • Always: new information reopens anything. If the facts changed, the decision is back on the table and saying so is not disloyalty.

That distinction is what lets a business get the benefit of questioning without paying for it in paralysis. It also has to be said out loud, because in its absence people guess, and they usually guess that you want agreement.

What I was actually doing

Teaching children to understand rules well enough to choose is the same job as building a team that can think.

They understand the rules, so they can decide whether to follow them and know exactly where they stand. Those are the tools anyone needs to become what they want to be — and they’re the same tools that make someone worth employing rather than merely worth instructing.

It probably did drive their teachers a bit crazy. I suspect it’s occasionally driven me crazy too, and that’s the part I’ve earned.

If this resonates, you don’t have to figure it out alone.
We host small, thoughtful Round Table conversations inside Women’s Entrepreneur Network where women leaders talk through exactly this kind of challenge.
You’re welcome to join us.

Related Posts

Rest Is a Leadership Skill

Rest Is a Leadership Skill

Rest gets filed under self-care, which is why owners ignore it. Self-care sounds like something you do when there's spare capacity, and there is never spare capacity. Try a different frame. Your judgement is the product. Not your hours — your judgement. Pricing,...

Founders, Find Your Work-Life Balance: Tips That Actually Work

Founders, Find Your Work-Life Balance: Tips That Actually Work

Most work-life balance advice was written for people with jobs. That's not a small distinction. A job comes with an external boundary — contracted hours, someone else's deadlines, a defined scope, and a moment where the building closes. The advice assumes that...

Stop Glamorizing Burnout: A Healthier Approach

Stop Glamorizing Burnout: A Healthier Approach

Somewhere in the last fifteen years, being exhausted became a way of signalling that you matter. "I haven't had a day off since March." "I was up until two finishing it." "I don't really sleep." These get said with a particular inflection — ostensibly complaint,...

Balancing the Mental Load: Strategies for Business Owners

Balancing the Mental Load: Strategies for Business Owners

Mental load doesn't mean being busy. It has a more precise meaning, and the precision is what makes it useful. The concept comes from work on invisible domestic labour — Arlie Hochschild's research on the "second shift" in the late 1980s, and later Emma's...

Guilt-Free Parenting: Advice for Working Moms

Guilt-Free Parenting: Advice for Working Moms

Most advice about working mothers and guilt is written for employees. It talks about negotiating with your manager, using your leave, and asking for flexible hours. If you own the business, there's no manager to negotiate with, often no leave policy at all, and the...

Build a Business That Fits Your Life

Build a Business That Fits Your Life

In the venture capital world, "lifestyle business" is mildly insulting. It means a company that will never be very large — one built by someone who, the implication runs, lacked the ambition to build something bigger. For most people reading this, a lifestyle...

Find what you need

Lead Your Team

Delegation, hiring, difficult conversations, and becoming the boss you'd want to work for.

Build the Business

Pricing, launching, systems, and building something that doesn't depend on you.

Women in Leadership

Negotiation, the pay gap, and what the research actually says about women who lead.

Get Seen

Being visible without the cringe — podcasts, content, and being remembered.

Lead Yourself

Courage, your inner critic, time, and protecting what matters most.

You're Not Alone

The loneliness of leading, and why the best owners don't solve everything alone.