The alignment illusion: why agreeing on strategy doesn't mean agreeing on what it means

Our Leading Through Chaos dinners bring together CEOs from across industries to share the realities of leadership at the top, candidly and openly. Our most recent dinner with CEOs from a range of industries including luxury clothing, commodity trading, airport management, retail and intelligence analysis software affirmed that chaos is still a good premise for beginning the conversation. 

The ‘alignment illusion’ is one of several recurring themes that surface when leaders speak openly about the pressures they're carrying and the tensions they're navigating. 

The first ‘story’ that emerged on the evening centred around the strategy-to-execution gap.

The board meeting ended well... the strategy was approved, everyone nodded and the exec team left feeling aligned. Six months later, when it came time to execute, they discovered something uncomfortable: they'd all agreed to the strategy, but they'd agreed to fundamentally different things. 

This pattern came up repeatedly at the dinner. A member captured it perfectly: "The strategy was agreed. What it meant clearly wasn't." Another added: "We thought we were aligned, until we actually needed to act." 

This gap between apparent agreement and actual alignment emerged as a consistent challenge around the table, regardless of industry or ownership structure. 

How agreement masks misalignment 

People aren't being dishonest when strategy gets approved. One CEO captured the real issue: "We were making decisions logically, just against completely different incentives." 

The pattern played out repeatedly in the stories shared. Debt-funded shareholders needing covenant protection, PE investors eyeing exit timelines, institutional holders wanting predictable growth and executive teams needing capability investment. When everyone agrees to pursue "profitable growth" as the strategic goal, they genuinely mean it. They simply mean completely different things. 

Cut costs now and invest later. Invest now and accept compressed margins. Grow the top line and let efficiency follow. Optimise current operations. Transform the business model. All of these are rational responses to "profitable growth" depending on your incentive structure and time horizon. The strategy documents don't force a choice between them. They allow everyone to leave the room aligned on words whilst remaining fundamentally misaligned on what those words require in practice. 

When misalignment surfaces 

Misalignment discovered during strategy conversations is uncomfortable but manageable. You can hash it out, make trade-offs explicit and move forward with genuine consensus. Misalignment discovered during execution is a different matter entirely. 

By that point you've burned months, deployed budget, hired people and built momentum towards something half your stakeholders never actually wanted. The CEOs around the table shared variations on this theme: shareholders systematically blocking investment proposals despite having agreed the business needed to transform and boards making decisions that fundamentally contradicted strategies they had recently approved. 

Another business leader captured a pattern several others recognised: "We changed the structure, but the behaviour stayed exactly the same." The reorganisation happens, the boxes move on the org chart, the all-hands email goes out. But because the underlying incentive conflicts were never resolved, the old patterns reassert themselves within weeks. 

What true alignment requires 

The leaders who had successfully navigated this weren't working from better strategy frameworks or clearer vision statements. They had faced into the conflicts those documents usually obscure. 

Attendees who'd broken through the alignment illusion offered practical approaches that had worked: 

• Testing alignment before you need it proved essential. Rather than asking "do you agree with this strategy?" the question that matters is "what does this mean you'll do differently tomorrow?" When your CFO, Chief Product Officer and Head of Sales give three completely different answers, you've avoided a difficult conversation rather than achieved alignment. 
• Making trade-offs explicit changed the dynamic. Getting specific about the choices: we can protect short-term margins or we can invest in capability, but we cannot do both. Which matters more for the next 18 months? The debate becomes difficult, but it becomes honest. Once genuinely resolved, execution can accelerate. 
• Naming incentive conflicts openly helped. Several leaders talked about the shift that happens when someone simply states what everyone knows but nobody is saying. When the real constraints and pressures driving different stakeholders get put on the table, teams can align around plans that are achievable rather than aspirational. 
• Getting specific about what stops mattered as much as what starts. Multiple CEOs emphasised this. New strategies always detail what you'll begin doing. Alignment requires being equally explicit about what you'll stop, de-prioritise or accept will fail. Otherwise, you're adding to an already impossible list whilst pretending you're making strategic choices. 

The cost of deferred conflict 

As the conversation continued, it became clear this was a shared challenge. Nearly every attendee had a version of this story: leaders often recognise misalignment early but hope that momentum will force resolution before the conflict becomes critical. It rarely works that way. Deferred conflict doesn't disappear; it compounds. Every week of false alignment makes the eventual reckoning more expensive and more destructive to relationships and trust. 

The leaders who had successfully broken through the alignment illusion described a consistent approach. They got uncomfortable earlier rather than deferring difficult conversations, and they spent more time in the strategy discussion rather than rushing to execution. They asked what people actually meant rather than accepting what they said, acknowledging that different stakeholders have legitimately different incentives and being direct about how to navigate that reality. 

The strategy-to-execution gap isn't primarily a capability problem. It's an alignment problem; alignment on what the vision requires people to do, stop doing and trade off against each other. 

Join the conversation 

We have had the privilege of hosting a rich mix of CEOs in a private dining environment, under Chatham House Rule, creating a kitchen type conversation with a trusted friend (if you can imagine that!). 

The Leading Through Chaos dinners take place every quarter, bringing together CEOs from across diverse industries and backgrounds. This relies on great references from previous attendees and CEOs making time for a unique peer-to-peer event. 

The alignment illusion is one of several recurring themes that surface when leaders speak openly about the pressures they're carrying and the tensions they're navigating.  

We will be sharing more stories as we capture them! 

For CFOs and COOs navigating these alignment challenges from the enterprise leadership perspective, our Inner Circle Community explores how Finance and Operations leaders are driving strategic cohesion whilst balancing cost discipline with value creation. 

Both Communities meet quarterly for intimate, peer-to-peer conversations. If you're interested in joining future sessions, get in touch with our team. 

Close your strategy-execution gap 

At Sullivan & Stanley, we work with leadership teams to make alignment visible and actionable through. If this resonates with challenges you're navigating, let's talk.