The Outside View

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This is the seventh edition of Enable Great Conversations; a series unpacking the leadership challenges behind technology decisions, exploring how clarity and confidence can be built through open conversation and experience.

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The best technology leaders actively seek out perspectives that make them uncomfortable. Not because they lack conviction, but because they understand that internal certainty can hide external blind spots.

Microsoft Ignite is running this week, reinforcing this point at an organisational level: the strongest companies don’t wait for the answers to arrive, they go looking for them in conversations with peers, at industry events, and through advisors who sit outside their own internal bubbles. They treat external perspective as a necessary check on their own thinking.

It's not about lacking confidence or a need for external validation. It's about recognising that the most challenging and dangerous decisions are often the ones that everyone internally agrees on.

Where Internal Perspective Falls Short

Organisations can spend months debating a platform decision internally, only to discover in a single external conversation that they were asking the wrong questions entirely.

This happens more than most leaders realise. Teams get locked into their own language, their own assumptions, their own history… and internal debates start to recycle the same viewpoints. The problem isn't a lack of intelligence or effort - it's that everyone is working from the same set of constraints and experiences.

Realised or not, leaders unintentionally optimise for the inside view. They ask "what do we think?" when the more valuable question is often "what are we missing?"

This pattern connects to themes we've explored in previous articles; The Activity Trap - where organisations generate momentum without external validation, Leadership Debt - where decisions get deferred because no one challenges the status quo, The Cloud First Plateau - where organisations stop looking outward at how maturity is evolving elsewhere, and finally The AI Illusion - where companies copy noise rather than learning from real outcomes.

In each case, the underlying issue is the same: internal perspective, however capable, has limits. Without external challenge, those limits can go unseen and become costly mistakes.

Why External Perspective Matters

There are a number of reasons why this matters more now than it used to.

Better questions emerge. External viewpoints often surface the thing no one internally thought to ask. I've seen this happen repeatedly - a leader described a challenge they've been wrestling with for weeks, and someone outside the organisation immediately positioned a question that reframed their entire decision process. It wasn’t that they were smarter, but it was the case that they weren’t carrying the same baggage.

It breaks the confidence loop. Leaders can be surrounded by people with similar views. Consensus can feel like validation, but it can also mask fragility. When everyone agrees, it's often worth asking whether you're aligned around the right answer, or just ‘aligned’. External challenge introduces healthy friction, the kind that strengthens decisions rather than undermining them.

Mental models update faster. The pace of change in Microsoft's ecosystem, cloud architecture, AI capabilities, security threats is a great example - no team can keep up through internal experience alone. External perspective such as this weeks’ event provide recognition from a wider sample. You learn what's working elsewhere, what's failing, and where the wider consensus is heading before you have to discover it yourself through trial and error.

Learning cycles compress. Experience is often gleaned through mistakes. That can be hugely valuable, but it’s also expensive. External perspective allows you to learn from others' mistakes. In fast-moving areas like AI, Security, and Cloud Governance, this compression matters. The cost of being 18 months behind is no longer just technical, it's strategic. Markets move quickly, while competitors adapt and gain ground.

The Role of Events and Conferences

Events like Ignite aren't valuable solely because of what gets announced. They're valuable because they educate, and surface what's working for organisations at similar stages of maturity. The announcements often matter less than the conversations in the wings - the informal exchanges where leaders admit what's not working, what they'd do differently, and where they're seeing unexpected challenges.

The question of whether attending these events is worth the time and cost comes down to intent.

If you're going for vendor pitches and product demos, you can get most of that online. If you're going to be "seen" or to collect swag, don't bother. But… if you're going to recalibrate your assumptions against the experiences of others, to pressure-test your strategy against emerging patterns, and to find the perspectives that your own teams can't generate - then yes, it's absolutely worth it.

The value comes from the conversations that happen when someone describes a problem you're facing and explains how they approached it. It's in discovering that the thing you thought was unique to your organisation is actually a pattern others are navigating too. It's in hearing what's emerging before it becomes common knowledge.

Events aren’t the only mechanism for accessing external perspective. Peer networks, advisory relationships, and structured conversations with people outside your sector can all serve the same function. What matters is the discipline of actively seeking viewpoints that challenge your internal consensus.

The Leadership Discipline

The strongest leaders aren’t the ones who know the most. They're the ones who refuse to lead from the inside alone.

They treat external perspective as a key component in the way they operate, not something they turn to only when they're stuck. They build it into their rhythm - regular conversations with peers, periodic engagement with advisors, and deliberate attendance at events where they know their thinking will be challenged.

It’s not a sign of weakness. It's a sign of maturity.

Weaker leaders avoid external challenge because they want to protect their position. Strong leaders actively seek it because they want to protect their decisions. They understand that conviction built on limited perspective is fragile, and that the best way to strengthen strategy is to stress-test it against reality that goes beyond their organisation's walls.

External perspective doesn't replace leadership. It strengthens it.

It prevents narrow thinking. It strengthens decision quality. It reduces noise, and it increases clarity. It accelerates alignment because teams gain confidence that decisions have been tested against more than internal opinion.

Most importantly, it brings organisational maturity into sharper focus. When you expose your thinking to external challenge, you quickly discover where your foundations are solid, and where they're not. You discover whether your data strategy holds up against what others are building, whether your AI approach is grounded or speculative, and whether your governance is genuine or simply designed to put a tick in the box…

Why This Matters Now

The technology landscape is moving faster than internal teams can track: AI capabilities are evolving monthly, cloud providers add features faster than most organisations can evaluate them, and security threats are becoming more sophisticated.

In this environment, internal perspective alone isn't sufficient. Internal teams are capable, but the pace of change makes it impossible for any single organisation to maintain comprehensive awareness through internal experience alone.

Leaders who recognise this are building external perspective and validation into their operating models, treating conversations with peers and advisors as strategic inputs not just social pleasantries.

At Enable Great, independence isn't just positioning - it's structural. We exist outside of your organisation's internal dynamics, vendor relationships, and historical decisions. That positioning isn't incidental - it's key. It's what allows us to ask the questions that internal teams can't (or won't!), to surface the assumptions that have become lost, and to bring perspective from adjacent sectors and from similar challenges experienced elsewhere.

Whether it comes from peers, industry events, or trusted advisors, external perspective is no longer optional. It's part of the way that modern leadership needs to work.

Uncomfortable Questions?

There are questions that every leader should be asking:

• When was the last time your thinking was truly challenged from outside your organisation? Not questioned internally by those who share your context, but intentionally challenged by someone with a completely different frame of reference?
• How often do you recalibrate your assumptions against the outside world? Do you actively seek opportunities for your strategy to be stress-tested, or do you wait for external forces to reveal the gaps?
• What would a fresh perspective reveal about the way your organisation makes decisions today? About the blind spots that internal consensus has rendered invisible?

The leaders who avoid external challenge aren't protecting their authority - they're limiting it. The ones who seek it out are building the kind of resilience that comes from knowing that their decisions can withstand scrutiny from multiple angles.

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Enable Great Conversations

The best decisions don't happen in isolation. They happen in conversation - with trusted peers, experienced advisors, and teams who know what it’s really like.

That's what Enable Great Conversations is about: a series exploring the real moments – the ambiguous ones, the uncomfortable ones, the ones that don’t fit neatly in a playbook - where leadership is tested, and clarity is found. Each release aims to capture a single insight, decision, or challenge that helps move organisations from noise to clarity.

There are many more of these moments worth unpacking and we’ll continue to explore them in the weeks and months ahead. We hope you’ll follow along, or join the conversation in the comments below, or follow along via the Enable Great page.