Answers Are Cheap, Judgement Is Everything: Strategy Leaders on the Job’s Reinvention

Photo by Eugene Zhyvchik on Unsplash.​

Strategy used to earn its keep by finding the answer; the magic of the job, after all, was seeing what others missed. But today, AI can generate 5,000 possible answers before your stomach grumbles for lunch, and that’s erring on the conservative side of estimations.

Almost overnight, the role mutated from deciding 'what' to deciding ‘which’. Which answers are just noise? Which area does a brand have permission to enter? Which plan is worth investing in, and which needs binned altogether?

We spoke to strategists across the US and LATAM to find out from the source itself how the role is evolving. And perhaps most importantly, in an evermore automated world, what remains human?

Stephanie Berenson

Head of brand strategy at TBWA\Chiat\Day LA​

One major change is the emergence of the multi-hyphenate strategist. For a while, strategic roles were becoming quite fragmented (social strategy, brand strategy, cultural strategy, comms planning, experience design). While the need for experts will never go away, today’s most valuable strategists are dynamic. They are leaning into an expanded skillset and building custom tools and capabilities that allow them to do more than ever before. Shrinking budgets demanded this change of us, but technology recently made it possible to do it without losing strategic rigour and integrity.

AI is the tool at the centre of most of this change. At its best, it solves the blank page
problem. It's a thought partner and a baseline to beat. More importantly, AI is transforming how strategists scale qualitative and behavioural insight, speeding up the loop between experimentation and feedback. And this is worth being excited about. I believe human discernment is the most critical strategic skill in this new world. AI should never be a replacement for taste and a real-life understanding of business realities. More and more I'm seeing strategists let these fundamental skills atrophy, and the result is the dreaded AI slop that takes a brand nowhere.

Beyond just how strategists work, what we are working towards is also changing. Much
of strategy used to be about messaging and product differentiation. Now it's world-building, creating expanded universes with an aesthetic you can live inside. Think Bad Bunny, Jacquemus, and Marty Supreme. The best brands aren’t running campaigns; they’re building cultures. It takes a different strategic sensibility to do this, and again, taste is critical.

Most people think strategy is heading somewhere dark. I'm more optimistic. I think it feels like the dotcom boom – chaotic, yes, but wide open. The Wild West for anyone willing to reinvent their own practice.

Crystal Anderson

Partner and chief strategy officer at 3Headed Monster​

The digital and physical streets are where culture and trends are actually born, and that’s where creative strategists need to be. While finding and connecting with a human truth remains core to the job, finding and connecting with culture has become the new mandate to maintain or gain relevance.

True disruption will never be born out of traditional research methodologies. By nature, they produce insights obtained through forced and rational thinking and are already behind by the time they are reported, let alone implemented. The same can be said for the once most precious commodity, customer data. Data can provide a valuable base, but strategists must stop looking in the rearview mirror to move forward. Culture doesn’t start in a focus group or a recorded transaction. It starts on the streets of communities you most likely are not in. You need to get there, and the fastest way is by diving into the digital street corners of Reddit, Substack and TikTok, where real-time conversations are happening and influence is being made.

No human can absorb all of that at once, and that's where AI becomes a strategist's best friend. AI helps you get in on more conversations, faster. But it's still up to human strategists with problem-solving brains and empathetic hearts to crack the code and find the tiny opening in culture where a brand has permission to not only exist but also co-create.

Laura Janness

Founder and chief strategy officer at Orchard​

Orchard finds that qualitative and quantitative research remains indispensable; you simply cannot unlock a marketing budget today without proving your work will move the needle. However, the legacy approach of treating research as a dry, linear step is dead.

To stay on top of today's hyper-short cultural cycles, our essential new habit is collapsing the distance between strategy and execution. We pair strategy and creative teams from day one to co-create stimulus, experiment with unorthodox recruiting, and ask weirder, better questions. This agile, collaborative loop allows us to react to cultural peaks in real-time, transforming raw data into immediate, actionable creative expression.

Yet, in an increasingly automated world flooded with AI-generated insights, technology can only synthesise what already exists. What remains distinctly human about great strategy is radical listening. True strategy isn't just about parsing data points; it’s about hearing the unsaid, capturing human contradiction, and finding the emotional truth beneath the noise. Machines can find patterns, but only humans can find meaning.

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Caroline Seklir

​Head of strategy at Yard NYC

The industry is always evolving, but I think in this world of AI-generated content and brand stunts, foundational brand strategy is only becoming more important. And when it comes to foundational strategy, AI is at best an entry-level strategist. It can write something that sounds good but says nothing – and that's exactly the trap strategists spend their careers learning to avoid. And it doesn't know what's happening in the world today, whereas I am finding the best work from futurists and those noticing cultural patterns is Substack. It's become a quicker, more intuitive resource for observing culture.

John Graham

Head of strategy at Cartwright​

Strategy has always been a balance between the internal and external. Experience versus research. Gut versus data. The intuitive versus the empirical. This moment, however, is tipping the scales – hard – toward the external.

AI has its own gravitational pull. It's always there – looming in the bookmarks – offering a supercharged shortcut to the answer. The temptation to start there is real and completely understandable.

We say resist.

We believe the thinking should never begin in AI. We push our strategists to live inside the problem first. To sit with their own instincts, their own taste, their own discomfort. To map its contours before reaching for any external help. Only then do we welcome in AI – and with it, every thought ever thought.

This isn't just about protecting original thinking. It's about what separates great strategy from strategy that gets implemented: conviction. Conviction is what attracts champions, pushes the thinking further and builds genuine belief across an organisation. It can only come from the inside out. And it can't be borrowed from a machine.

Elliott Bastien

Head of strategy at LOLA USA

In the world of AI, we as strategists have a new world of abundance: information, research, analysis, and answers. We face a new challenge of shedding the fat and identifying what matters.

Strategy is the bridge between endless information and meaning, and it is more vital than ever. But identifying meaning requires judgement and rigour. AI is confident but not always correct. Treat its output as a hypothesis, not a conclusion, and ask it to challenge its own recommendations first.

The fastest route to a bad strategy is solving the wrong problem brilliantly. Spend more time exploring alternative problem definitions than generating solutions.

As answers become abundant, competitive advantage comes from asking better questions. Use AI as a thought partner to challenge assumptions, reveal blind spots, and reframe the challenge.

Lastly, AI learns from existing patterns, which means it gravitates toward consensus. As average strategy becomes free, originality becomes more valuable. Start with AI's answer, then deliberately move away from it.

AI changes the tools of planning, not the fundamentals. It's not about knowing the most, but understanding what matters.

Suzy Mae Mattay

Strategy director at Battery

Legacy planning’s past AND future are simply understanding people. In a world where isolation is growing and trust is fading, we need new ideas that connect us.

As content cycles speed up, we can use technology to stay informed on trends, but we require human capacity to create new ideas. AI delivers a version of the past, not the future, so the tool can’t be used for fresh writing or new insight. It’s essential, though, for pulling data. And the new news is utilising AI fluency to play platforms against each other, double-checking the work, using one platform to prompt another, and generally knowing the benefits of each.

Strategists looking for cultural awareness must understand human creativity intimately. For example, this month I drove 100 miles to a new museum and bought tickets to six indie plays. The month before, I produced, performed, and sold out my own solo performance piece. Passive data aggregation doesn’t deliver anything new or ownable. To gauge the good from the bad, insight from slop, we need to know what taste is from the inside. The first step to understanding an audience's POV is having an informed one of your own.

Meghan Lorito

Group strategy director at R/GA​

Before AI, strategists spent time gathering and arranging information to provide clarity to the problem at hand. They often focused on the most obvious information first, which just confirms and validates our existing knowledge. The challenge with this is that we spent more time organising the problem than actually solving it.

We once could get away with longer lead times to great work, but today we can’t. Algorithms collapse time, and our ideas have to resonate instantly without context.

The solution isn’t more AI, it’s better ideas. The promise that AI brings to creativity isn’t creativity itself, but the space it affords us to experiment, make jumps, and be provocative. AI becomes our analytical partner, helping us track the most likely paths so that we can explore the least.

This means focusing more on the messy, brilliant intangibles that make a point of view feel fresh and interesting and less time inside the strategy comfort zone: research and frameworks. We should be getting more things wrong, with AI getting more things right. As the pipeline from ideation to consumption shortens, we have to execute quickly, with the right cultural message, and a strong signal of taste. Most of which, you can’t get from AI. Because generative thinking isn’t just reserved for machines, it was meant for humans.

Valerie Nguyen

Managing partner & chief strategy officer at Anomaly NY​

As a discipline that can get a bad rap for being more rational given effectiveness, data, etc., AI is not just a tool to help with many of those more rigorous aspects, but it’s also a push for strategy to embrace its most human and imaginative form.

One example is that the current age has revived what felt like a dying art of ethnographic research. When anybody can query Claude or crunch large data sets, there is a new premium on the power of being in a place, soaking up culture that escapes the 9x16 camera frame and spending time with and speaking to the people you ultimately want to connect with.

This also places importance on the more relational skillsets of strategists to teach, facilitate and inspire. In a world where all best practices are quickly commodified, it’s the leaps, twists and risks that set brands apart. Strategists must not just be armed with data and insights but know how to use them to help our clients get inspired, align on vision and make bold decisions.

Suzanne Hader

Managing director at Ready Set Rocket​

The fundamentals of planning are still intact. Deeply understanding your audience and their context is the job. What's changed is the speed and dynamism in how we get there. We're in a golden age for analysing niche consumer feedback – it's everywhere, good, bad and everything in between. And it’s allowing us to drive research much faster without sacrificing depth.

What's becoming essential is letting go of the static brand book. Brands today are vessels shaped as much by audience input as by the operating and creative teams behind them. Many audiences expect communication that reflects their mindset in a way that feels like a secret handshake — not a broadcast.

When it comes to culture's shorter cycles, the move is to pick your battles. Lean hard into the moments that give you the spikiest, most shockingly brand-amplifying ways to participate. Those moments both reward your existing audience and have the potential to cut through to those who don't know you yet.

And in an increasingly automated world, humans remain the ones with the best taste.

We make the unexpected feel beautiful and exhilarating instead of scary. People wouldn't pay what they pay for live DJ sets if Spotify could fully automate curation. Strategy lives in that gap between what machines can optimise and what only people can feel.

Mason Pereira​

Senior strategy director at Cactus​

Strategy itself isn’t changing. Our core frameworks (the 4Cs, category entry points, and comms matrices) are timeless and will never go out of style. What’s shifting is where the value sits within the strategic process.

In the past, ‘generating strategy’ was considered hard and therefore valuable. Thanks to AI, that part of the process is abundant and cheap. We can generate 15 great insights over the course of an hour. What’s scarce now is actually helping clients decide which of the 15 insights is truly the best for them.

The challenge is that our existing tools are inadequate for helping clients make this choice. It’s also why the next generation of strategy tools will be focused on “simulating outcomes", rather than generating strategic output.

At Cactus, we're shifting our focus to a single question: of all the strategic directions available, which one has the highest likelihood of working? We’re already building tools like synthetic consumer panels, living category models, and real-time culture simulations and seeing great results. The future isn’t just to generate strategy faster.

It’s to predict which direction works best before the work even runs.

Adam Reader

Global head of Go-To-Market at M+C Saatchi Consulting

Strategy has always been about understanding people, culture and behaviour. It has also always required judgement. The ability to interpret signals, make trade-offs and point a team in a clear direction has never been optional. What is changing is how much of the surrounding process still belongs to us.

AI is compressing the mechanics of planning. Audience research, cultural scans, comms frameworks and channel plans can now be generated in seconds. The risk is not that AI produces bad strategy. It is that it produces the same strategy.

You can see it playing out right now at the World Cup. Every major sportswear brand has arrived at the same answer. Bright pink boots. The logic is clear; pink aligns with wider fashion trends, signals confidence, and stands out on the field and on screen. A rational, well-founded strategic decision. The problem is, they all got there. What was meant to differentiate has flattened into uniformity.

When similar tools are trained on similar data, directions start to rhyme before they are even presented. The pathways get clearer. And narrower.

Which brings the focus back to something that has always been true. Strategy is not the process. It is the choice. What is changing is the intensity of that requirement. The signals are easier to access but harder to prioritise. The routes are clearer but less differentiated. The role shifts from building the plan to interrogating it, from outlining options to eliminating them, from tracking every cultural peak to deciding which ones are worth following.

In an increasingly automated process, what remains distinctly human is the willingness to make a call. Because strategy is not the route. It is the decision about where to go.

Mollie Partesotti

Co-founder, strategy at KDSP​

Strategy is changing, but the job is still the job.

What’s different is the speed and shape of the inputs. Culture moves in shorter bursts. Audiences are harder to group neatly. A strategist now has to read across social, commerce, entertainment, community, technology, and whatever else is shaping how people behave that week.

AI helps, definitely. It can sort, scan, summarise and pressure-test thinking quickly. But it also creates a new problem: too much of the work can start to feel detached from actual people.

That’s why simple research is becoming important again. Talking to real people, watching what they do, and asking questions. Not everything needs to be a dashboard or a 90-page trend report. Sometimes the most useful thing is hearing how someone explains their life in their own words.

The modern strategist needs to be fast, but not frantic. Curious, but not trend-drunk. Comfortable with tools, but not dependent on them. The skill is knowing which cultural signals matter and which are just noise.

What stays human is judgement. Taste. Empathy. The ability to spot when something is technically true but emotionally false.

AI can make strategy faster and more efficient. People still make it good.

Alissa Stakgold

President of strategy and creative services at Quigley-Simpson​

The best parts of legacy planning still matter because they were never really about decks, demographics, or clever language. They were about disciplined curiosity: understanding what people believe, what they fear, what they ignore, and what might cause them to reconsider.

What has changed is the speed and volume of information which strategists must process. Culture no longer moves in neat annual cycles. A brand can become relevant, irrelevant, praised, mocked, copied, and forgotten in a matter of days. While strategists have always been researchers, editors, anthropologists, and translators, AI has increased the importance of interpreting a constant stream of signals and turning them into clearer choices about where a brand should act, what it should say, and why it should matter. AI can surface patterns and accelerate analysis, but it cannot determine which insights truly matter. That still requires human judgement.

The new habit is not simply using better tools. It is learning to ask better questions. What is a durable trend versus a passing signal? What is attention versus affection? What is efficient but forgettable? What is culturally loud but commercially meaningless?

In an automated world, great strategy remains distinctly human because it depends on taste, empathy, scepticism, and restraint. Machines can produce options. They cannot yet understand why one idea feels true, generous, surprising, or necessary. That is still the strategist’s job.

Tania Wendt

SVP strategy and engagement at tms

The reality: AI is not a human, and it isn’t supposed to be. The things we value in strategy remain timeless disciplines and skills. Strategists utilise observation, tension mapping, cultural understanding, and human truth to cultivate creative opportunity. What is changing is the speed and breadth required to do it.

AI is accelerating the synthesis of signs and signals, expanding our view beyond channels. Things such as creators, entertainment, communities, commerce, and tech, which used to be strategy activations, are now inputs that shape it. So while AI is accelerating and expanding the possible, it is making strategists even more important because we decide what really matters versus what is simply visible or available.

We are doing the same job – creating direction and purpose – but our stimuli are always on and ever-changing. Great strategy depends on empathy, taste, intuition and the ability to identify or create meaning that exists before, which AI cannot match.

Monica Lorusso

EVP, strategy at Allen & Gerritsen (A&G)

The fundamentals of strategy haven't changed nearly as much as the tools have.
As strategists, we are still students of human behaviour. We study the psychology, biases, and motivations that shape decisions. We still ground ourselves in core marketing principles and the role brands play in people's lives. And we still need the ability to "read the room" – to recognise the tensions, emotions, and unspoken signals that data alone can't reveal.

What's changing is the scale and speed at which we can work.

AI has become a valuable sparring partner, helping us pressure-test ideas, explore alternative scenarios, and challenge our assumptions. New research technologies allow us to engage audiences more quickly and in more meaningful ways. And access to larger, richer datasets gives us greater confidence to move with precision.

As audiences fragment and culture accelerates, strategists must become more adaptive, connecting signals across social, commerce, entertainment, technology, and community.

The distinctly human part of strategy remains unchanged: making sense of the complex, identifying what matters, and turning information into insight that inspires action. Technology can accelerate the work, but judgement, empathy, and imagination remain our most valuable tools.

​David Klineberg​

President and partner at StayGold​

Legacy planning still earns its place in the discipline of asking why something matters to a person, not a monolith, and then pushing past the first answer until something real surfaces. That fundamental question hasn't changed. What's changed is how fast you can get to the starting line.

Which is also why critical thinking and pushback matter more now. Assume everyone has access to the same AI output, and everyone's already seen the generic, passable version of the answer. The job isn't generating ideas anymore; it's rejecting the ninety that are merely fine. AI can't tell you which idea is true to the brand or the moment.

That's wisdom, instinct and taste, and it still has to be applied by a person.

What remains distinctly human is the ability to connect dots in unexpected ways. To pull from something in yourself or that you notice in someone else. Nostalgia. An insecurity nobody says out loud. What you do when no one's watching. What exhilaration feels like. Experiencing loss. Falling in love the first time. That's the actual human experience, and it's what people recognise when they see it.

​Robert Cooney​

VP, client strategy, at DAC

Great strategy has always been rooted in empathy and human insight. AI can surface signals, but it can't tell us what matters. Brands are no longer just navigating just a few major cultural moments but potentially thousands of micro-moments across communities, creators, platforms, and fandoms – which can be difficult to identify and predict. When culture moved slowly, organisations could rely on deliberation. Today, they need to marry clear brand principles with a bias toward action. The strategist's role today is to continuously interpret culture, identify opportunities, and help organisations respond quickly and authentically. In that sense, strategy is evolving from a planning exercise into an active discipline of stewardship, judgement and participation.

Alicia Fisher

Head of strategy at Trade School​

Strategists are insatiably curious creatures who love to experiment, so evolving has always kind of been part of the job. What feels different right now is the pressure. Timelines are way faster, expectations broader, and the anxiety around what AI means for our work is legit.

It’s tempting to focus on whether or not we’re losing our craft. But I think if we let curiosity take the lead, while holding onto a few non-negotiables, we have more opportunities to make good strategy great than we've ever had before.

For example, keep conducting traditional research, but now, extend its use by building synthetic audiences that bring consumers deeper into our process. Keep writing sharp briefs, but now turn the one-pager into an interactive site teams can engage with.

Keep reading reports, tracking trends, and having a pulse on culture, but analyse it using an entire world of knowledge to connect the dots in unexpected ways and find unusual patterns.

The thing we can’t abandon is having real conversations. Calling a friend about a recent trend or chatting up a stranger at the store for a pitch makes a huge difference in our perspectives and keeps us from all sounding alike.