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Digital Transformation in Professional Services: What Consultants See That You Don't with Winnie Barnwell

Release Date: 05/26/2026

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Wicked Problems Podcast

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Digital Transformation in Professional Services: What Consultants See That You Don't with Winnie Barnwell

Wicked Problems Podcast

Is your firm spending money on new software when the real problem is hiding in plain sight, inside the processes, handovers, and habits your team has quietly built around a broken system? In this episode, Toby Corballis is joined by Winnie Barnwell, a digital transformation consultant and project and change manager who works primarily with law firms and professional services businesses. Winnie brings a structured, diagnostic approach to operational improvement, helping organisations understand not just what is going wrong, but why, and what to do about it in a way that actually sticks....

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More Episodes

Is your firm spending money on new software when the real problem is hiding in plain sight, inside the processes, handovers, and habits your team has quietly built around a broken system?

In this episode, Toby Corballis is joined by Winnie Barnwell, a digital transformation consultant and project and change manager who works primarily with law firms and professional services businesses. Winnie brings a structured, diagnostic approach to operational improvement, helping organisations understand not just what is going wrong, but why, and what to do about it in a way that actually sticks.

Winnie's work sits at the intersection of workflow design, system implementation, and change management. She is frequently brought in when a firm knows something is not working but lacks the clarity to define the problem, let alone fix it. Her focus is always on getting the process right before reaching for the technology.

What We Cover

Why clients almost always misdiagnose their own problems, and what the real root cause usually turns out to be
How discovery sessions and probing questions surface the issues that sit beneath the symptoms
The law firm losing 18 hours a week on admin, and why the answer had nothing to do with changing their software
Why a consultant does not need to know your specific CRM, and what they actually need to understand instead
The cost of delay: how to quantify the financial impact of an unresolved problem and use it to prioritise
Cross-pollinating methods across industries, and when bringing in a specialist really does make sense
Translation as a core consulting skill, from C-suite to accounts, and why speaking the right language to the right person is everything
Building solutions that work for everyone, including the people who are not comfortable with technology
What a consultant's working week actually looks like, from discovery through to Friday playback sessions

Whether you are a practice manager trying to make sense of a system that never quite does what it should, a leader considering a costly technology migration, or a consultant looking to sharpen your diagnostic process, this conversation will give you a clearer framework for finding the real problem and making change that lasts.

Chapters

00:00 — Episode begins

00:15 — Introduction

01:41 — What Winnie does: digital transformation and workflow consultancy

02:41 — The discovery process: diagnosing root causes, not symptoms

04:06 — Do consultants need to know your software?

07:04 — Case study: the law firm losing 18 hours a week

09:00 — When the fix is organisational, not technological

11:45 — The cost of delay: quantifying unresolved problems

14:59 — Cross-pollinating methods across industries

17:18 — Translation as a consulting skill

20:28 — Building anti-discriminatory solutions