The World’s Toughest Negotiator

Multi-billion dealers, political leaders, or even kidnappers don’t hold a candle to our 2-year-old when it comes to negotiations.

Caleb Tan
A Parent Is Born
Published in
3 min readSep 27, 2018

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When you think of the world’s toughest negotiators, you think of multi-billion deals, political leaders, or even kidnappers. These people are tough negotiators, but the toughest negotiator in my life (so far) is my 2-year-old daughter.

I am a believer of respectful parenting because children deserve the same respect as adults. They may have lesser life experience and often need our guidance but they should not be belittled.

A big part of respectful parenting focuses on consensus. This means that as parents, we don’t force our children to do anything against their will. Except for life-threatening scenarios, we strive our best to guide them in making decisions instead of dictating every move they make.

As I try to balance between respecting my daughter’s decisions and doing what I want, I find myself negotiating with her multiple times a day, every single day. Here’s our typical conversation:

Me: Arielle, would you go wear your shoes, please? We’re going to school.

A: No

Me: Do you want to go to school?

A: Aiyah (which means yes)

Me: You’ll have to wear your shoes before going out, can you wear them, please?

A: No want! Nooooooooooo!

The conversation would continue with her showing her displeasure until I stop asking her to wear shoes. Here’s why I think it is so hard “negotiating” with her.

  1. She has the luxury of time and we don’t
  2. She has limited vocabulary and I don’t always understand her words

I would bribe her with her favorite food in the past (I still do, sometimes) but I know that is not getting to the root of the problem. There’s a fine thread between bribery and negotiation, and what I wanted is for her to wear her shoes, on her own accord.

Cracking the code

In many negotiation situations, the more you understand your opponent, the more likely you’re going to win. It is the same for her and only recently, I (think I) discovered why she doesn’t want to wear her shoes.

It turns out that most of the time, I would have pre-selected a pair of shoes that I thought were most suitable for her outfit. (She has a whole cupboard of shoes by the way.) That didn’t go well with her because she wanted to choose her shoes on her own but couldn’t express her thoughts. All she could say was “Noooooooo”.

So instead of pre-selecting her shoes now, I invite her to choose the shoes she wanted to wear for the day. These teeny weeny life decisions may seem small to us but it is a big deal to our children because they feel empowered with the ability to make their own choices.

Successful negotiators look for win-win outcomes instead of a win-lose scenario. The same principles apply here when I negotiate with my daughter. She wins because she gets to choose what she wants to wear and I win because I save so much time preparing her for school.

The bottom line is to truly dig deeper to understand her real needs and wants. There is never a one-size-fits-all approach to negotiation so the only way to deal with the “World’s Toughest Negotiator” is to keep trying and never give up.

About the author

Caleb is a millennial dad to two beautiful daughters and enjoys exploring issues around technology, health, and parenting. In his free time, he daydreams about what the future holds for humanity.

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Caleb Tan
A Parent Is Born

Public health professional with an interest in health tech and employee wellbeing | 🇸🇬