To me, good strategy is not about simply being clever or writing impressive sounding positioning statements. It’s about deeply understanding how people feel before everyone else does, and then turning that feeling into a brand, idea, product, or movement.

Most of the bigger cultural shifts we experience, for example the post-pandemic rise of working from home, start as a feeling people can’t quite explain yet (frustration with commuting, disillusionment, feeling burnt out etc.), something lots of people are sensing privately before it becomes obvious. Good strategists notice those feelings early on, before they become a huge conversation.

That’s why it’s important if you want to be a top notch strategist, to continuously develop your skills. There’s no end goal with this – you simply cannot know it all. The goal is to stay curious, train your brain to spot subtle patterns before they become widely known, and to hone your ability to empathise with and understand people.

So on that note, here is my two cents on how to improve and develop your strategy skills.

1. Too many average insights make work weaker

Don’t collect loads of average observations. The more average ideas you add, the less powerful the final idea becomes. Instead, find the one really emotionally true insight. For example, an average insight might be that “People want convenience, quality, sustainability and affordability.”

True, yes, but a little…stark and obvious? A more powerful, empathetic insight might be that “People are exhausted and want life to feel softer.” Instantly, the word “softer” opens up space for more creative thinking.

2. Make predictions about brands you follow

I love this habit and regularly try to practise it myself. Though admittedly, I’m often wrong! (That’s okay, by the way – the important thing here is getting the reps in.) The goal isn’t to predict the future perfectly. It’s to train yourself to spot patterns, think strategically and back up your opinions with reasoning rather than gut instinct.

Some thought starters:

• What problem is this brand actually trying to solve, and who for?

• Why do I think they’ve made this move?

• Do I think it will work?

• What are they likely to do next?

• What’s the biggest risk they’re taking?

• If I were on their team, what would I do differently?

• What do I think are the smartest next moves for them?

Then comes the most important part: check back in 3–6 months and compare the outcome with your predictions. Did they launch the thing you expected? Did customers respond the way you thought they would? Did they pivot? Why?

This is where the learning happens. Every prediction, whether it’s right or wrong, helps sharpen your strategic thinking. Over time, you’ll start noticing patterns faster, making stronger recommendations and developing instincts you can actually trust.

3. Study outcomes, not outputs

It’s easy to admire the work. The new logo. The campaign. The website. The product launch. But strategists should be far more interested in what happened after. The whole point of strategy is to create change. So instead of asking, “Do I like it?”, ask, “Did it work?”

Get into the habit of writing down your observations:

• Did sales increase?

• Did awareness grow?

• Did customers actually understand the message?

• Did they attract a different audience?

• Did they pivot six months later?

• What signals suggest it was successful (or not)?

• If it didn’t work, why do I think that was?

The more you connect strategic decisions with real-world outcomes, the better you’ll become at spotting what genuinely drives results, and what just looks good in a case study.

4. Great brands make people feel “that’s literally me”

The best brands don’t invent feelings, they uncover ones that already exist.

As a strategist, your job isn’t to create emotions out of thin air. It’s to notice the hidden tensions, frustrations and desires people already have, then put words to them.

A question I come back to again and again is:

“What’s already true here that nobody has properly articulated yet?”

Take Airbnb. They didn’t invent the desire to travel in a more personal, authentic way. People were already tired of generic hotels, tourist traps and feeling like outsiders in the places they visited.

Airbnb simply gave that feeling a name: “Belong Anywhere.”

That’s why it resonated. People didn’t think, “What an original idea.” They thought, “Yes. That’s exactly how I feel.”

The most powerful brand ideas often have this effect. They make people feel seen. Like someone has finally put into words something they’ve always felt but could never quite explain..

5. Talk to real people, not just ChatGPT

AI is brilliant for speeding up research, spotting patterns and helping you think through ideas. But it shouldn’t be your only source of insight.

Real understanding comes from talking to people. Watching what they do, not just what they say. Hearing the emotion behind their words. Noticing the contradictions. Picking up on the little details that never make it into a research report.

AI-generated research can flatten these nuances because it’s built on patterns, not lived experiences.

If you want to become a better strategist, spend less time asking AI what people think and more time asking people what they think.

Interview customers. Read reviews. Lurk in Reddit threads. Watch how people use products. Listen to sales calls. Read support tickets. Pay attention to the language people naturally use. That’s where the gold is.

Strategy isn’t about collecting information, it’s about understanding humans. And humans are wonderfully messy, contradictory and surprising. That’s something no AI can fully replace..

6. Strong feelings matter more than being liked

One of the biggest mistakes brands make is trying to appeal to everyone. The trouble is, if everyone feels a little positive about you, nobody feels much at all.

The brands we remember tend to make us feel something. They surprise us, challenge us, delight us, frustrate us or even divide opinion. Not because they’re trying to be controversial for the sake of it, but because they’ve chosen a distinct point of view instead of the safest one.

As strategists, we should pay attention to strong reactions. If something makes people uncomfortable, emotional, fascinated or fiercely opinionated, it’s often a signal that there’s a deeper cultural tension underneath. And that’s where the interesting work lives. Not every brand should be polarising, but every great brand should be memorable.

7. Every strategy has a viable opposite

A useful test for any strategy is this:

Could another smart team make a convincing case for doing the exact opposite?

If the answer is yes, you’re probably looking at a genuine strategic choice.

I recently worked with a healthy frozen food brand where we consciously decided not to compete on health, even though every other brand in the category was. Instead, we focused on freshness, provenance and reframing the freezer as the place where food quality is preserved, not compromised.

Competing on health would have been a completely viable strategy. That’s exactly the point. A good strategy isn’t the only possible answer; it’s one deliberate choice among several believable ones.

If the opposite of your strategy sounds ridiculous or impossible, you’ve probably just stated a truism. Strategy isn’t about choosing the right answer. It’s about choosing one of several believable paths and having the confidence to leave the others behind.

8. Build a library of patterns

Strong strategists often create mental categories in their heads. Over time you stop seeing individual brands and start seeing recurring human problems. Don’t be the person that consumes interesting things only to forget them. Keep a working document – I have an ever growing one in Notion! Here are a few examples of what I mean...

• Category is crowded → create contrast.

• Product is misunderstood → educate.

• Audience feels overwhelmed → make their decisions easier.

• Audience feels ignored → make them feel seen.

• Toddlers get attached to objects that make them feel safe.

• People complain about subscription services but forget to cancel them.

• Nobody says they seek status, but many buying decisions are status-driven.

9. Articulate your thinking to people

Explain the world to people AND yourself. When you notice something interesting, don't stop at: "That's cool." Ask: "Why is that cool?" Then, "what's the idea underneath it?" Then, "what could this be transferred to?” Now you've got a transferable insight you can use in dozenssss of categories.

To wrap up

Great strategy comes from noticing emotional truths before everyone else does, and having the courage to clearly name them. Don’t hoard ideas. Use them immediately. Talk about them. Write about them. Test them in conversation, because ideas get sharper through use, not storage.

Strategy isn’t about creating clever ideas; it’s about recognising truths before everyone else does.