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Q&A with Penelope Barr

Exclusive Trusted Magazine Q&A with Penelope Barr, Agilist, Technologist, Innovator & Speaker.

How could you describe your career path in a few words? 

I’m described as a renaissance woman, effectively running the diverse tracks of my life. My abiding traits are curiosity, pragmatism, creativity in thoughts and deeds, as I seek to overcome any blockers with the question ‘how do we make this possible?’  

For the past few years, I’ve been running a portfolio career, I call ‘6:3:3’. I work 6 months of the year (as an interim executive), write a book or create a product in 3 months, and travel for 3 months. Over the past 2 years, I’ve also built an Accountability Community for job seekers and business-builders, based on agile techniques.  

What’s included in my current career portfolio? I’m an Agilist, Advisor, Author, Speaker. And a Technologist, Innovator, Product-developer, People-leader, Transformation-expert, Change-agent, Everyday Experimenter and Community-builder. 

My career began developing a Seniors Card product, after which my global career commenced with moving to Tokyo. I’ve since lived and worked in 8 countries.  Over 18 years, I acquired deep expertise in global financial services, working at the forefront of most digital product development and organisational-transformation.  I’m a Board Director who’s worked in Legaltech, Proptech, Medtech and Government, furthered my academic career and created several side-hustles. As a result, I speak startup and big-end of town.   

I encountered agile two decades ago in the UK. This way of working was eye-opening and enhanced my journey in helping enterprises transition, optimise growth and minimise waste. I’m grateful to have benefited from the evolution of agile over the years and its power to transform. My objective is to continue working at the intersection of the transformation of organisations, teams and individuals, to achieve my 6:3:3 goal and coaching others in doing so.  

How do you think agile practices have transformed companies over the past two years? 

Agile has matured since the development of the Agile Manifesto in 2001, from focusing on software development to enterprise-wide initiatives. The past couple of years have seen further maturation of the approach to agile transformations. With countless examples of success and failure available, organisations can learn and adapt, heightening the chance of success, no longer having to jump in blind. More agile transformations means a deepening of the pool of expertise from which organisations can draw and general capability uplift within organisations. The upside of normalising agile ways of working is being able to move beyond the rudimentary. Agile ceremonies and concepts are becoming standard.  With the increasing unbiquity of agile, however, has come more informed questions about the agile approach, value-creation and measurement. A greater proportion of an organisation’s people being familiar agile places the onus on those whose roles are to govern and deliver a transformation. Methods and outcomes are potentially challenged by more knowledgeable stakeholders. With the democratisation of agile approaches comes less tolerance for the factional squabbles that have been a hallmark of agile delivery since its inception.  A united focus on speed-to-value via enterprise-wide objectives alignment and desired success metrics is required for successful transformation. Embracing the benefits of agile and customising the tools and techniques to achieve discreet goals, will benefit all organisations willing to adopt this powerful way of working.  

What successful cases of agile transformations have you had the opportunity to observe that have particularly stood out to you? 

Undertaking an agile transformation is always ambitious and exciting! So many possibilities for change, particularly time saved, optimised process flow and greater portfolio clarity. However, there’s no guarantee of success. Agile transformations are widely reported to have between 50-80% chance of failure. Despite these confronting statistics, when agile works, it works abundantly. The State of Agile 2023 report declares that ‘building a strong agile culture yields an increased commercial performance of 277%’  

What are the differentiating factors between successful transformations and those that fail? An integral component is aligning ‘why’ ie what’s the impetus for change; with ‘how’, demonstrated in fit-for-purpose ways of working. Ensuring a shared rationale is a key. To derive the most benefit from transformations, ‘Success’ needs to be appropriately defined, ie aligned to internal drivers or market demands for change. At the outset, these preconditions for success may not be well-understood, therefore I’m  most impressed by those driven by experimentation, a data-driven approach to change.  Gathering evidence of what’s more likely to work may elongate the change cycle, but is likely to yield more aligned, sustaining results.  When enterprise-wide agile transformations were the mode of operating du jour, there was a tendency to mimic the Spotify model or ING’s approach, for example. While these may have some applicability, applying another organisation’s entire model is never going to work.  So, take the time to experiment, to customise an approach for you and your organisation, to give yourself the best chance of success.  

Will agile practices continue to generate interest? What challenges do you see in the context of deploying these practices? 

The past decade has seen several enterprise-wide transformations globally, with varying degrees of success. Having been involved in the strategy and execution of 8 transformations, at scale, I’ve seen the good and bad, and am left with questions. I sense I’m not alone. Perhaps we've seen the end of thinking about agile-at-scale? Enterprise transformations are all-consuming, requiring huge inputs of time, finances and people.  Working ‘big’, is the antithesis of agile which breaks down initiatives into the smallest possible increment. Deliver working software frequently…, with a preference to the shorter timescale. 


Rather than managing change at scale, I advocate experiment-driven transformation. A core principle of Agile is embracing experimentation to drive innovation. How? Experimentation is powerful in driving continuous improvement. Agile empowers teams to challenge the status quo, venture into uncharted territory and take well-calculated risks. To test and learn, work out what works, in their ecosystem. Iterating rapidly through small experiments delivers key insights, feedback and mitigates uncertainty. By cultivating a culture of experimentation, promoting innovation, where conscious risk-taking is celebrated, and harnessing the power of diverse teams, possibility is pioneered in enterprises. 


The ever-changing business landscape demands adaptability, with Innovation a direct response to this dynamism. An Agile team, with its experimental mindset, can swiftly adjust and adapt strategies, ensuring initiatives remain aligned with evolving needs and market dynamics and become one of the best ways for organisations to meet their goals.  



Penelope Barr bio

With 25+ years’ leading local and global technology, agile, product, innovation and transformation businesses, I’m motivated by solving complex problems. I strive to continuously improve how we continuously improve; while working with individuals, teams, startups and enterprises change how we change. 

I run a portfolio career, as an Agilist, Advisor, Author, Speaker. And a Technologist, Innovator, Product-developer, People-leader, Transformation-expert, Change-agent, Everyday Experimenter and Community-builder. 

As an Award-winning intrapreneur I use a genuinely creative approach to generating business value and driving excellence. I’ve been at the forefront of most major changes in digital, technology, innovation, product and data across fintech, legaltech, proptech, climatetech and enterprises.  


A connector of people, ideas, opportunity and things, I turn good ideas into great business 

and bring a kitbag to create products, generate revenue, improve savings or return on assets. I apply analytical insight, thorough planning, rapid implementation and deliver in highly ambiguous situations. 


In short, I’m passionate about living up to my philosophy: if we unlock ourselves, we can unlock opportunity with fit-for-purpose mindsets, toolsets and skillsets. From experiencing everything I can through food and travel in my personal life, to dreaming big and aiming high at work, I am passionate about making the most of the time I have been given. 

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