I overthink everything. I’m not as sharp as I want to be. And I’m definitely a bit cynical. Oddly enough, these are the very things that make me good at strategy.
It’s easy to talk about strengths. But I’ve found the things that make me effective as a strategist don’t always show up on a strengths-finder quiz.
They’re quirks. Habits. Flaws, even. The kinds of things I’ve spent years trying to fix – only to realise they might actually be working for me.
So, in the spirit of honesty, here are three of my biggest weaknesses – and why I’ve stopped apologising for them.
One.I’m not as smart as I like to think I am
This isn’t false modesty. I just don’t get things instantly. It takes me a while to truly understand something – a system, a brand, a stakeholder dynamic. I need to listen, read, research, and test before I feel like I get it. But that’s exactly what strategy needs.
This slower pace forces me to ask better questions. It makes me more curious, more rigorous, and much more likely to uncover what others might overlook. I don’t show up with answers, I show up with a willingness to learn.
That also means I’m more comfortable with complexity. I don’t expect things to be simple, and I’m not afraid to sit with ambiguity while we work it out.
In strategy, humility beats cleverness every time.
Two.I overthink (pretty much everything)
I once read that only 30-50% of people have a constant internal monologue. It turns out that might not be a strictly accurate representation of the research (shocking, facts on social media turn out to be false), but either way, I’m definitely in that group – and a good chunk of my inner monologue is spent mentally circling client challenges, turning problems over in my head, replaying conversations, or imagining alternative outcomes.
Yes, it can be exhausting. But it also means I’m never stuck in one perspective. My mind naturally rehearses different scenarios. It looks for nuance. It wants to understand why something really happened – not just what appeared to happen.
This mental overactivity has its downsides. But in a strategic context, it makes me sharper. More empathetic. More able to anticipate ripple effects, see unintended consequences, or catch that one thing we’ve all missed.
What feels like overthinking is often just advanced pattern recognition.
Three.I’m cynical (or maybe just sceptical)
Cynicism gets a bad rap. But for me, it’s less about pessimism and more about healthy disbelief. I’m wired to challenge the status quo – to ask, “Is this really working?” or “Is this the most efficient way?”
That instinct stops me from being easily impressed. It makes me question surface-level wins or shiny new tools. And it keeps my focus on outcomes – not optics.
Being a bit cynical means I don’t fall in love with my own ideas. I don’t mind pulling apart what’s already working if I think we can make it better. It makes me push for clarity, alignment, and genuine impact.
Scepticism, at its best, is a commitment to better thinking.
Final thought
These aren’t traits I chose, they’re just how I’m wired. For a long time, I tried to sand down the edges: be more confident, think faster, feel less. But somewhere along the way, I realised these so-called “weaknesses” are also the source of my edge as a strategist.
- They slow me down just enough to see things others might miss.
- They keep me asking uncomfortable questions.
- They push me to dig deeper, listen harder, and get things right.
I’m rarely the smartest person in the room. But I might be the one still thinking about the problem three days later, and that tends to pay off.