Clarity Before Change - What I Look For First When I Step Into a Portfolio

There’s a moment that comes very early on when you step into a portfolio, often within the first few days, where you can feel whether the organisation is genuinely in control or simply comfortable.

It’s rarely about the numbers.

Loss ratios, premium growth, claims trends and dashboards all matter, of course. But they’re not where I start. In fact, they can be actively misleading in the early stages. Well-presented numbers can mask uncertainty just as easily as poor ones can exaggerate it.

What I look for first is how decisions are really being made.

Not how they’re documented. Not how they’re described in frameworks or policies. But how they actually play out in practice - at renewal, at referral, in claims settlement discussions and when something falls just outside appetite but feels commercially tempting.

After stepping into many portfolios, often during periods of transition, leadership change, acquisition or heightened scrutiny, I’ve noticed the same pattern repeat.

Portfolios that are performing sustainably tend to have one thing in common: clarity. Clarity about who decides, what gets escalated and why. Clarity about which trade-offs are acceptable and which are not. And clarity about when a decision should feel uncomfortable, because discomfort is often a sign that risk appetite is being tested properly.

By contrast, portfolios that later drift rarely start with obvious problems. They usually feel calm. Too calm.

Referrals are technically within authority. Exceptions are small and well-intentioned. Legacy decisions quietly roll forward because “nothing bad has happened yet”. And escalation becomes something reserved for crises, rather than a normal part of decision-making.

In those environments, governance still exists but it has subtly shifted its role. Instead of acting as a control mechanism, it becomes a reassurance mechanism. Its job becomes explaining why decisions are acceptable, rather than challenging whether they are.

That’s why, when I step into a portfolio, I don’t begin by changing strategy, restructuring teams or rewriting frameworks. The first priority is always stability.

Stability comes from understanding where judgement lives in the system.

I want to see how often decisions are challenged and by whom. I want to understand what prompts escalation in practice, not in theory. I look closely at how exceptions are handled, how renewals are reviewed and how claims outcomes feed back into underwriting behaviour.

Most importantly, I pay attention to the spaces between formal processes. The informal conversations. The “this feels close” moments. The decisions that don’t quite warrant a meeting but quietly shape the portfolio over time.

Because portfolios don’t usually fail due to a lack of information. They fail because small, unchallenged decisions compound. And once that compounding starts, it’s very hard to unwind.

The purpose of those first weeks isn’t to move quickly. It’s to see clearly. And clarity, done properly, creates momentum without noise.

That’s the foundation everything else rests on.

What I Look For Next

Once that initial clarity starts to emerge, the next phase is about understanding how the portfolio actually behaves under mild pressure, not in a crisis but in the everyday moments where judgement is quietly exercised.

This is where patterns become visible.

I look closely at decision rights first. Not the org chart version but the lived one. Who truly has the authority to say yes? Who feels comfortable saying no? And who absorbs risk by default because escalation feels awkward or time-consuming? In many organisations, authority exists on paper but accountability is blurred in practice. Decisions drift sideways, not up.

Closely linked to this is escalation behaviour. I’m less interested in whether escalation pathways exist and more interested in how often they are actually used. Healthy portfolios escalate early and routinely, not because something has gone wrong but because something feels close. When escalation only happens after outcomes deteriorate, it’s already too late.

Exceptions are the next signal.

Every portfolio has them and they are not inherently bad. In fact, some of the strongest portfolios I’ve worked with are commercially flexible and deliberately so. The issue is not the presence of exceptions but the absence of visibility. When exceptions aren’t tracked, discussed and periodically reviewed, they stop being conscious decisions and start becoming precedent.

Renewals are where this shows up most clearly.

I look at how renewal decisions are framed and challenged. Are they treated as fresh underwriting decisions or as exercises in defending the past? Are changes in risk profile genuinely reassessed or quietly smoothed over because the account feels familiar? Renewal discipline tells you far more about portfolio health than new business volumes ever will.

Claims behaviour provides another critical lens.

Not at the level of individual outcomes but in how feedback flows (or doesn’t) back into underwriting and pricing. When claims are seen as an operational function rather than a learning loop, the portfolio loses one of its most powerful early warning systems.

Across all of this, I pay attention to language.

Phrases like “it’s within authority”, “we’ve always done it this way” or “it’s only a small exception” are rarely problematic in isolation. But when they become default explanations, they signal that judgement is being replaced by comfort.

By this point, I’m not trying to fix anything.

The aim is to build a clear, shared picture of how the portfolio actually functions - where it is robust, where it is tolerant by design and where it is tolerant by accident. Only then does it make sense to talk about change.

Without that shared understanding, even well-intentioned interventions create noise. With it, small adjustments can have an outsized impact.

And that distinction matters more than most organisations realise.

Early Warning Signs I Take Seriously

By this stage, certain signals tend to stand out. They’re rarely dramatic and they’re often rationalised away as temporary or immaterial. But in my experience, these are the indicators that tell you whether a portfolio is quietly drifting or genuinely under control.

One of the most common is the absence of healthy disagreement.

When underwriting and claims teams consistently agree, when referrals are resolved quickly without debate and when committee discussions feel efficient but unchallenging, it can look like alignment. Sometimes it is. Often, it’s something else: people have learned what not to question.

Another early warning sign is authority creep.

This happens when decision-making thresholds are technically unchanged but behaviour shifts. Underwriters become more comfortable stretching judgement because prior decisions went unchallenged. Managers stop escalating because outcomes have been acceptable so far. Over time, the centre of gravity moves - quietly, incrementally and without a single rule ever being broken.

I also pay close attention to how performance is explained.

Strong portfolios can talk candidly about both good and bad results. Weaker ones lean heavily on narratives that smooth discomfort: market conditions, timing issues, one-off events. Context matters but when explanation consistently replaces examination, learning slows.

Legacy risk is another recurring theme.

Accounts, structures or wordings that predate current leadership often carry an implicit immunity. They’re renewed because they’ve always been renewed. They’re accepted because changing them would be awkward. These risks are rarely reviewed holistically, yet they often represent the largest accumulations of unexamined exposure.

Finally, I look at how quickly uncertainty is surfaced.

In well-controlled portfolios, uncertainty appears early and is openly discussed. In drifting portfolios, it appears later - usually once metrics move or losses crystallise. The difference isn’t competence; it’s confidence. Confidence to say, “I’m not comfortable with this yet,” before outcomes make the conversation unavoidable.

None of these signals mean something has failed. But taken together, they tell you whether the portfolio is being actively steered or simply allowed to continue on momentum.

What Good Looks Like After 90 Days

The goal of stepping into a portfolio is not to leave a personal imprint. It’s to leave behind clarity, confidence and continuity.

After around 90 days, the most effective outcomes are often subtle but powerful.

Decision rights are clearer, not because they’ve been rewritten but because they’re being used consistently. Escalation feels normal rather than exceptional. Exceptions are still possible but they’re visible, deliberate and periodically revisited.

There is a shared understanding across underwriting, claims and leadership of where the portfolio is robust, where it is deliberately tolerant and where it is under review. That shared picture reduces noise. It also reduces defensiveness because challenge is no longer personal; it’s structural.

Reporting becomes more useful, not more voluminous. Executive and board conversations focus less on explaining outcomes and more on testing assumptions. Reinsurers, auditors and other stakeholders' sense this quickly - confidence follows clarity.

Importantly, momentum is preserved.

This isn’t about pausing the business or freezing decisions. It’s about creating enough stability that future change can be made deliberately, rather than reactively. Strategy discussions become grounded. System improvements make sense. Capability uplift becomes targeted.

Most importantly, the organisation is no longer dependent on the person who stepped in.

The portfolio can be handed over cleanly (to a permanent leader, an existing executive or a refreshed team), without loss of control or confidence. That handover is the real measure of success.

Strong portfolios don’t need constant intervention. They need clear judgement, early challenge and governance that supports decision-making rather than explaining it after the fact.

When those foundations are in place, performance tends to follow.

Quietly. Consistently. And without surprises.