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When a Director’s Advocate Isn’t Enough: Why Complex Problems Call for a Financial Strategist

28 July 2025 by
When a Director’s Advocate Isn’t Enough: Why Complex Problems Call for a Financial Strategist
Cameron Whinnett

Running a business is hard. When things start going wrong, it can be overwhelming, especially when it feels like every decision carries risk. That’s where a Director’s Advocate steps in: someone who’s on your side, helping you manage financial distress, navigate obligations, and avoid common traps that catch many business owners off guard.

But sometimes, the problems are deeper. More complex. And surface-level fixes just won’t cut it. That’s when you need more than advocacy, you need strategy.


Complex Problems


When you’re facing significant change, distress, or opportunity, and there’s a lot riding on the outcome, it’s not enough to just survive - you need to rethink, restructure, and rebuild.

Complex Problems Require a Higher Level of Support - from a Financial Strategist

Some examples of where a Financial Strategist steps in include:

  • Trade-on Voluntary Administrations – where the business continues to operate during administration, requiring a careful balance of cashflow, creditor management, and legal obligations.
  • Business Model Changes – shifting from a labour-heavy service model to a scalable, value-based offer often requires restructuring, marketing repositioning, and financial modelling.
  • Advisory Board Engagements – complex businesses need regular strategic oversight and accountability. That’s what advisory boards bring, and a Financial Strategist can either lead or support this function.

Real-World Example


We recently sat down with a director of a small services business. On the surface, things seemed manageable - she was working hard and clients were happy enough. But under the hood, it was a different story.

In that first meeting, we uncovered three critical problems:

  1. The business was selling on cost, not value. Prices were being set based on hours worked, with little regard for the outcome or the peace of mind the service delivered. Client's were questioning the cost because it was the only thing being sold. 

  2. The director was doing everything. From admin and client management to service delivery and marketing - there was no room to step back and grow the business. Burnout wasn’t just likely, it was inevitable.

  3. She didn’t see the real value of what she was selling. Her service wasn’t just manual help—it was project management, intermediary expertise, and emotional support during a major life transition. Her clients weren’t paying for hours, they were paying for certainty in a stressful time.

This business supports elderly people and their families through the difficult process of transitioning into aged care accommodation. That means dealing with real estate agents, families, contractors, and time-sensitive decisions, she was managing the whole process, but pricing it like it was simple labour.

Bringing in the Financial Strategist


As Director’s Advocates, we can spot when the problems are bigger than they seem. In this case, we brought in our founder and Financial Strategist, Cameron Whinnett, to work through:

  • Restructuring the business model – moving away from time-based billing to a value-based offering that reflects the real outcomes clients receive.

  • Building a referral network – positioning the business as a trusted partner to real estate agents, aged care providers, and professionals who often need to help families manage this transition.

  • Reframing the business identity – from a service provider to a project manager and advocate for the elderly and their families, ensuring clients get peace of mind, not just effort.

We’re now setting up the right structure, support systems, and financial oversight to help this business expand without the owner burning out or compromising quality.

When It’s Time to Call in a Financial Strategist


Director’s Advocacy helps you stabilise the ship, but when you need to rebuild it, you need someone who can:

  • Develop strategy and structure for growth or turnaround.
  • Support big decisions—like trading through administration or shifting your core offer.
  • Provide accountability and oversight through advisory boards or hands-on support.

Whether you’re facing financial distress, planning a major change, or seeing cracks in your current model, don’t wait for it to fall apart. If the issues feel too complex for a quick fix, it’s time to bring in a Financial Strategist.

Facing a Similar Challenge?

Book a Strategy Call with us

We’re here to back you and your business, at every stage. If you need help navigating financial distress, complex decisions, or business model transformation, reach out. You don’t have to face it alone.



When a Director’s Advocate Isn’t Enough: Why Complex Problems Call for a Financial Strategist
Cameron Whinnett 28 July 2025
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