After 20 years inside some of the world’s most iconic companies, the moment I stepped out, what both sides were missing became unmistakably clear. As an executive, pitches never stop. Everyone believes they’ve cracked your problem — they just need a moment of your time to prove it. Each conversation starts with the same confidence: that they’ve discovered a capability you were oblivious to, one that will unlock what your own organization somehow failed to see.
After two decades on the inside — 13 years at Moët Hennessy and Diageo, six at Maersk, and four at Google — I crossed the line for the first time. I went from the inside to the outside and it was a huge wake-up call.
On the inside, people are not blind to opportunity., but they are managing a dense web of commitments, history, habits, and risk. What looks like resistance or a gap from the outside often masks careful sequencing, resource constraints, and competing promises — all invisible unless you’ve lived them.
We talk endlessly about AI replacing jobs. But inside any organization, few people ever say: “Let’s cut 20% of my department because we’ve become 20% more effective.” Efficiency is easy to celebrate in principle; much harder to act on when it means reassigning people, reshaping budgets, or renegotiating board expectations. In many organizations, incentives quietly reward footprint growing larger teams, bigger budgets, broader scope. Those signals tend to carry more clout than focus or simplicity. This creates a subtle tension: the choices that would streamline work often sit at odds with what many cultures implicitly encourage to grow.
On The Inside: The Hidden Handcuffs that Really Hold Change Back
When I was on the inside, I contributed to the behavior where good ideas were met with 15 “buts.” Even when the strategy was right, many elements would complicate execution. A few of the core ones I would often encounter:
- Capacity: Whether financial, human, or cognitive; the bandwidth of people and systems determines what’s feasible.
- History: Every executive carries past scars — and skepticism — from previous initiatives.
- Timing: The corporate calendar defines what’s possible. The next board meeting, the next budget cycle, or a pending leadership change can shift even the best plan.
- Invisible Shields: Middle managers often protect their teams — for good and bad reasons — acting as unseen filters for decisions.
Priorities aren’t arbitrary; they’re promises. Each is linked to commitments — to people, partners, and the board. Asking executives to “add something” is rarely the right question. The real leverage comes from helping them cut or upgrade existing activities. As I would often ask: “if you had to reduce your activities by half, what would truly add value — and what would simply return by habit?”
Many things carry on year after year because they’ve become rituals of continuity: annual celebrations, gestures of support, the time invested in showing up as a present and available leader. These actions sustain trust but also absorb immense time. The human side of leadership — the quiet considerations for someone’s difficult moment or the energy spent creating a sense of stability — is rarely visible in board updates but deeply shapes organizational rhythm.
Then there are the well-known reflexes of internal life:
“It’s not my mandate.”
“We’ll revisit this after the next budget cycle.”
“Procurement will take months.”
“That’s not how we do it.”
These aren’t signs of apathy. They are survival mechanisms in systems that are already stretched.
When organizations stretch too far for too long, capacity doesn’t just constrain growth — it erodes it. I saw this during COVID, but the pattern didn’t stop there. The real question isn’t why these cuts happen. It’s why the full potential of people and systems wasn’t unlocked earlier — when there was still time to redirect rather than reduce.
I once played a key role in a large transformation where everything was formally aligned. The board had signed off. Budgets were approved. The CEO was publicly supportive. Even high-level KPIs signalled the shift.
Yet the organization didn’t believe the change was real. Every year, new priorities appeared, change fatigue was real and every year, old habits prevailed. Cultures, not communications, held the real power. Looking back, the turning points came much more from experiences than from messaging.
Telling teams what was expected of them, left them half engaged, but when new realities were illustrated and they were invited in by deeper context they saw new roles for themselves in this. We stopped convincing and started engaging.
We balanced external analysis expectations with the highest found rhythm of the organization lifting others alongside peers from within, managing both capacity, timing, and energy — and constantly found stories which fuelled belief. We accepted messiness as long as there was accountability. Change took longer to appear — but it stuck.
The Outsider’s Myopia: What Partners Miss
Now that I have joined the outside, I still feel the inside. This perspective—being the bridge between complexity and external expertise—uncovers the fundamental friction that slows nearly all external initiatives. On the inside, being at the core of heavy decision-making often meant not seeing the wood for the trees. The outside granted me a luxury of essential distance nearly impossible to maintain while in the dense web of organizational reality.
While consultancies bring impressive functional expertise, the work often travels in parallel tracks. The AI team brings in the marketing team, who involves HR or communications — and suddenly the conversation becomes a relay. When discussions blur across functions, new teams step in, or a long-standing relationship leader returns, and the thread can quietly slip.
It isn’t a lack of intelligence; it’s a structural reality. Large engagements are scoped for speed and senior access, not for the slow, embedded work of understanding how decisions actually move inside the organisation. This is why solutions can remain high-level: well conceived, but not always shaped to the organization’s timing, culture, or absorption capacity. The work makes sense in theory — but struggles to anchor once the consultants leave.
It’s not a lack of intelligence; it’s a lack of integration. Transformation doesn’t happen in functions — it happens in the seams between them. Yet ownership for those seams is often missing.
Recent research reinforces what many executives quietly know: it’s not the lack of intelligence holding teams back — it’s the cognitive load of navigating across functions. A Procter & Gamble field experiment involving more than 700 professionals showed that individuals working with AI improved performance by almost 40% because the system could surface perspectives they didn’t have the bandwidth to access.
The insight is simple, and deeply relevant: even the strongest teams struggle not from lack of ideas but from the friction created by silos. When cognitive load drops, cross-functional quality rises. You don’t need more people — you need clearer assembly.
So now on the outside I always focus on three areas I have seen missing before:
- When referencing other successes, clearly articulate what were the circumstances under which this worked (or didn’t work) because even the best work loses relevance if the underlying ask doesn’t relate.
- Which experiences have before shifted momentum and who was involved? Most blockages are personal before structural.
- Understand Incentives & Revenue Models. Let’s be transparent about everyone involved’s revenue models and reporting so we can honestly plan for mutual success. Too often one thing is said in sales pitches, but when delivery happens, the engrained business models of partners can in fact hamper progress.
The best partners understand that effective change is about interdependencies and sequencing, not just ideas. And not just about one skill.
Key Recommendations for Mobilizing the Inside and Outside to Work Together to Achieve Fluid Change
1. Focus on Assembly, Not Addition
As the problem is rarely missing pieces. It’s often the inability to connect and mobilize what already exists. So coming from the outside: Ask whether it’s more pieces to a new puzzle that are needed, or simply better assembly of the existing ones. Be curious about interdependencies and share the ownership of these.
2. Create Headspace
The most valuable question a partner can ask: “What can I do to give you headspace so you can work smarter and progress your initiatives?”
Creating space is not a soft skill; it’s the precondition for real progress. See if tasks can be carried on the outside to allow the key people to make better decisions for all.
3. Treat Partnerships Like Governance
Create a greater sense of shared accountability. Try holding monthly partner sessions that act like AGMs for collaboration. Use them to reframe situations, revisit dependencies, and build shared ownership. At first, people will attend to “look wise,” but over time, these sessions create a foundation of dependability and mutual understanding.
4. Listen and Adapt
In hierarchies where power is concentrated, flexibility becomes the differentiator. Success depends less on frameworks and more on comprehension — knowing when to adapt pace, tone, or focus. Be comfortable where ownership blurs and be curious about which other success criteria could exist. And be willing to give away celebrations to others — it is likely worth much more in the long run, when the opportunities which can be solved are bigger and wider.
Transformation Fails in the Gaps No One Sees — Not in the Ideas Everyone Debates
From the inside, every decision carries unseen weight. From the outside, every delay looks like complacency. Real progress comes when both sides see — and respect — the other’s constraints, capacity, and commitments.
Transformation doesn’t fail for lack of initiatives. It fails for lack of understanding what it truly takes to grow in motion.
The opinions expressed in Fortune.com commentary pieces are solely the views of their authors and do not necessarily reflect the opinions and beliefs of Fortune.
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