3 min read

Why are you like this? Tricky questions that need asking.

Why are you like this? Tricky questions that need asking.

"Why am I like this?!" is a bit of a catchphrase in my house. Usually, I’m bemoaning something I’ve stuffed up. Either I’ve messed up my admin, worked too many hours, overcommitted, or left the house at a time that makes a punctual arrival dicey.

It’s usually said with a laugh, but ‘why am I like this?!' is a more useful question than it first appears...if you take the time to answer it. 

Because here's the thing: you're probably like that for a good reason. Every habit, pattern and behaviour that annoys you develops in response to your experiences and environment for a useful purpose.

You're like this because you had to be.

We’re all lopsided

I've been thinking about this a bit this week as I prepare to move again. Like many vulnerable kids and teens, I moved a lot in my life. I’m now in my early 30s, and I’ve moved over 30 times.

It means I’m really good at packing, not accumulating too much stuff, and setting up new places. It also means I’m great with change. Tweaking, rearranging and staying flexible are my default. They had to be, right?

But like most well-developed skills, they have a shadow side. I’m not so good at... staying. Being present and sitting still. I have to actively cultivate these qualities through intention, mindfulness - and constant course correction - and I have a long way to go. I'm a runner. A mover. An escaper. A changer. And patterns of a lifetime are hard to break.

You might have the opposite experience - if you’ve had a lot of stability, you might need to try harder to stay open to new opportunities or seek new experiences.

This lopsidedness is common, normal and reasonable. Strategy will be harder if you’ve spent your career rewarded for technical proficiency and detail orientation. If you’ve always been in a liaison role, stepping back from the people to take a systems view might be tricky.

That’s cool; we’re contextual animals. We do what we’re required to and rewarded for. But we're not stuck. There's always a chance to take a fresh look if we're brave enough to ask the tricky questions.

Ask tricky questions

We should be asking ‘why am I like this?” or, in a team setting ‘why are WE like this?’ far more often. Rather than accepting things at face value, we need to dig deeper into why the same things keep happening and tackle the underlying forces instead of the symptoms.

Of course, questions like that don’t work when they contain blame, shame or regret. They definitely don’t work when they come with a sanctimonious pointed figure, and they ABSOLUTELY don't work when we say “Why are YOU like this?”.


Tricky questions only work when we use a tone of compassionate curiosity. When we’re curious about why we are the way we are, or why other things, people or teams are the way they are – genuinely curious and not judging – we ask better questions, and we have better insights.

Harness an innate curiosity about the world. Assume positive intent, listen before forming an opinion, and seek to understand differences, rather than eliminate them. Find the shared values and sense of purpose that rest inside conflicting opinions and perspectives, to create the foundation for collaborative change.

Ask tricky questions without ego or recrimination. Wonder, without attachment, how the world works and how we might start to improve it together. Accept a situation or story for what it is – even when it sucks – and use that as the starting point for what comes next. The best facilitators, leaders, communicators, strategists – and people – ask tricky questions with uncertain answers because they know you can’t work with what you can’t see.

Get messy

Don't be afraid to go places where strong feelings live. If you don't feel it, you can’t heal it. The path to progress is muddy, messy and twisted because meaningful change doesn’t often feel good.

Don't get so tangled up in your own sh*t, or make judgements, or decide the answer before you've asked the question. Unless we’re aware of what’s really going on, and we can accept it for what it is – even, no, especially when it’s butting up against shame, ego, fear, regret, anger, disappointment or anything else - we can’t work with it. Unless we can be compassionate with ourselves and others and recognise that every system works exactly as it was designed and was made that way for a good reason, we can't move forward. All we can do is perpetuate the status quo, stick bandaids on things and leave ourselves and others feeling hollow and unheard.

Don’t shy away from the tricky stuff. Don't take your own behaviour at face value. Don't feel paralysed by the habits of a lifetime. Don't rage and despair at the way things are or assume that everyone else is just an asshole and everything's broken.

Stay open, and go deep. Seize the messy stuff. Sit in it. And then (and ONLY THEN) you can work on how to solve it. 

So, why are you like this?

And how do you want to be?

Are you asking enough tricky questions?

Most importantly, what are you avoiding the answer to right now?

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