The Digital Diaries Hosted by Peter Woods

Peter Woods
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The Digital Diaries is a podcast about navigating modern work, creativity, and identity in a rapidly changing digital world. Hosted by Peter Woods, the show features conversations with builders, creators, technologists, and leaders who are shaping — and questioning — how technology influences culture, careers, and human behaviour. Each episode explores themes like creativity in the age of AI, leadership in the digital era, personal branding, entrepreneurship, and the tension between building and critiquing. This isn’t a hype-driven tech podcast. It’s a reflective space for people who want to

  1. 1d ago

    #51 | The Human Side of AI: Why Better Tools Don’t Fix Broken Collaboration with Rujuta Singh

    Episode Summary What happens when the smartest people in the room still can’t make a decision? In this episode of The Digital Diaries, Peter Woods speaks with Rujuta Singh, founder of Solve Together, about the hidden human challenges behind business transformation, AI adoption, and organisational change. Rujuta shares how her experience leading complex transformations across global organisations led her to question why teams could spend months discussing the same problems without moving forward. The answer wasn’t better technology. It was better collaboration. Together, they explore why clarity and alignment are the foundations of successful transformation, why most AI strategies fail because organisations start with tools instead of problems, and how companies can use structured experimentation to move from ideas to working prototypes in weeks rather than months. From leadership meetings and AI implementation to recruitment technology and the future of work, this conversation examines the gap between what organisations say they want from technology and what they actually need from people. Key Topics Discussed Why smart teams still get stuckThe hidden cost of unclear goals and misalignmentWhy meetings often create the illusion of progress without decisionsThe difference between having expertise in the room and actually using itWhy transformation failures are often collaboration failuresWhy diverse perspectives create better solutions — but require structureHow facilitation helps teams separate ideas from egosMoving from discussion-heavy meetings to outcome-driven collaborationThe “together alone” approach: giving people space to think independently before group discussionWhy quieter voices often hold the insights organisations needWhy buying ChatGPT, Copilot, or other AI tools does not equal an AI strategyThe importance of understanding business problems before selecting technologyHow structured experimentation can help companies test AI solutions safelyThe risks of AI-driven recruitment systemsWhy organisations need AI confidence at leadership levelHow executives can better understand AI capabilities before making investment decisionsThe missing ingredient in transformation: humansDesigning better meetingsAI adoption: start with the problem, not the toolThe future of work and AI Key Takeaways ✅ Transformation succeeds when people have clarity on what they are solving and alignment on why it matters. ✅ The best technology strategy starts with a business problem, not a software purchase. ✅ Meetings should be designed around outcomes, not conversations. ✅ AI adoption requires experimentation, learning, and human validation. ✅ Leaders don’t need to become AI engineers — but they do need enough understanding to make better decisions.

    41 min

  2. 6d ago

    #50 - Partner Success in AI with Joanne John

    Episode Overview Partner programmes are the invisible infrastructure behind most enterprise software revenue, yet they rarely get airtime. In this episode, Pete talks to Joanne John, who spent over nine years at Salesforce moving from incident management through partner operations into transformational change leadership, about what partner success actually means, how AI is reshaping partner programmes without replacing the trust at theircore, and the real mechanics behind a major attrition-risk reduction programme she led.Key Takeaways • Partner success is ultimately measured by customeroutcomes, not just deal size; a poorly fitted solution damages trust even whenthe deal closes. •   According to Joanne, roughly 70 to 80% ofpartner-related escalations at Salesforce traced back to communicationbreakdown rather than product or delivery failure. •   AI's role in partner programmes is in surfacing betterdata for decisions (referral fee structures, certification value, partner motivations), not in replacing the relationship-building that still drives trust. •   Leading cross-functionally without direct authority depends on transparency and finding a genuine win-win, not positional power. •      One simple structural fix, mandating partner involvement within 24 hours of an escalation, was, according to Joanne, the central driver behind a measured year-over-year improvement in partner-related account risk. 🌐 Connect with Joanne John on LinkedIn

    37 min

  3. Jun 22

    #49 | David Homan: Building Trust at Scale in the Age of AI

    Episode overviewDavid Homan has spent more than a decade building a private community of over two thousand connectors, founders, family offices and impact investors. In this conversation with PeteWoods, he explains why he eventually decided the analogue version of his work needed an AI engine behind it — and how that became SOAR Connect, his relationship intelligence platform currently in beta. It is a wide-ranging conversation about the things technology has quietly broken about human connection: the way contact data evaporates after every conference, why most introductions are wasted, and why the people who built the social platforms we use every day are themselves the loudest critics of how cold those platforms have become. David also tells the story of taking the phone call, at 28, that wiped out the fourteen-million-dollar endowment of the foundation he ran at the time — a call from a fund managernamed Bernie Madoff. The fallout from that single moment, and the way most of his network walked away rather than helped, became the real beginning of everything he has built since. There is also a vacuum cleaner, a ballet at the Joffrey, an encounter with Steven Spielberg, and a genuinely useful reframe of the well-worn phrase “give without expectation of return.” For anyone trying to figure out how to use AI thoughtfully in the parts of work that are most human relationships, trust, asks, follow-up, this episode is worth your time.

    39 min

  4. Jun 15

    #48 | Joshua Gould on Running thebigword, AI as Speed Not Strategy, and the Discipline of Managed Risk

    Episode OverviewJoshua Gould is Group CEO of thebigword, one of the world's largest language service providers, handling around 50,000 assignments a day across translation, interpreting and localisation. He took the company through a majority private equity sale, stayed on to run it, and has spent the last few years rebuilding the business around AI orchestration, automated workflows and the WordSynk platform. In this conversation, Josh walks through the journey from a £44-a-week room and a sales job at Coors Brewers to running a tech-enabled language group across more than 80 countries. He's refreshingly blunt on what AI actually does inside a real operation, why "AI strategy" is the wrong starting question, and how the unsexy work of fixing broken processes is what compounds. If you're a leader being told to "have an AI strategy in 90 days", this one is for you. Key Learnings Why AI is "like taking speed" and what that means for broken processesHow thebigword drove operations from 20% of revenue down to 9% (and why that doubles profit)The questionnaire Josh would send to every department head on day one of an AI mandateWhy companies that called themselves "internet businesses" all failed, and what that tells us about today's "AI businesses"The difference between data-informed and data-driven decisionsManaged risk over blind gambling: how to size AI bets when token costs are unpredictableWhy a zip manufacturer is suddenly more attractive to buyers than a flashy tech business Resources mentioned: thebigword: https://www.thebigword.comWordSynk platformJoshua Gould on LinkedIn

    42 min

  5. Jun 9

    47 | The Hidden Risks in Every Ad You Run with Pamela Slea, CEO Boltive

    Episode OverviewOne in eight ads running across the internet today containsmalware. Most marketing teams have no idea. In this episode, Pete talks to Pamela Slea, CEO of Boltive and a two-decade veteran of ad tech, about the invisible security and privacy risks baked into modern digital advertising and why AI is making the problem dramatically worse.   Pamela has led at Google, YouTube, AppNexus, Index Exchange,and InMobi. Her contrarian view: compliance is no longer a quarterly checkbox. It needs to be always-on, agentic, and built into production not just policy.  What We Cover   •       WhyAI is a double-edged sword in ad tech -- accelerating both innovation and th capabilities of bad actors •       The 1 in 8 ads contain malware' statistic and why CMOs are not reacting with theurgency it demands •       The shift from periodic compliance audits to continuous, agentic monitoring •       Why the regulatory spotlight is moving from web cookies to in-app and connected TV environments •       What streaming companies are being forced to confront about cross-device data and consent flows •       Who actually owns responsibility for ad security today -- and why the answer has changed •       How AI-generated sales outreach is forcing a return to relationship-led selling •       The biggest mistake advertisers will regret not having fixed in the next 12 months The same AI tools accelerating legitimate softwaredevelopment are being used by the people building malware. Security solutions from two years ago may already be obsolete. The threat landscape is not static it is moving at the same pace as the technology.   Brands can have a perfectly designed consent managementplatform that completely breaks in production -- because a new partner was added to the page, the CMP loads too slowly, or a third-party script fires before consent is collected. Regulators do not care about intent. They care about what the consumer actually experienced.   Historically, ad security and privacy compliance weretreated as periodic audits. The expectation from regulators -- and from the market is now continuous monitoring. This is not just best practice; in many jurisdictions, it is becoming a legal requirement.   As advertising budgets move heavily into streaming,regulators are following the money. The CTV ecosystem involves multiple data handoffs -- OEMs, content partners, ad servers -- and consent signals can break at any one of those touch points. Streaming companies are now actively seekingexternal validation that their privacy posture matches what is actually happening in their systems.   The traditional view was that the publisher owns thewebsite, so the publisher owns the liability. Litigation in both the US and Europe is shifting that. If your ad tech pixels or tags are on someone else's page and they behave improperly, the brand may now find itself on the hook.   Pamela notes that the volume of AI-generated cold outreachhas become so overwhelming that senior buyers are increasingly only engaging with people they already know. Some CEOs are now explicitly hiring salespeople based on their existing relationships rather than their process skills. Key Insights From This EpisodeBad actors are keeping pace with the best AI toolsPrivacy intent and production reality are two different thingsThe compliance model is shifting from quarterly to always-onConnected TV is the new frontier for privacy riskResponsibility for ad security is no longer the publisher's problem aloneAI-saturated outreach is driving a return to relationship-led sales

    37 min

  6. Jun 1

    #46 | Why Your Marketing Strategy Isn't Working — and What Behavioural Science Says to Do Instead

    Rich Smith has spent 30 years as a CMO inside financial services, healthcare, and mortgage — managing $100M+ budgets and leading companies through crisis, hyper-growth, and turnaround. He is the founder of Rich M. Smith Growth Studio and host of The Revenue Science Podcast. In this episode, Rich and Pete pull apart why most companies jump straight to tactics without a strategy behind them, what behavioural science actually means in practice, and how marketing leaders consistently lose the boardroom by speaking the wrong language. They also cover the AIG Bank crisis playbook, the future of AI search, and why distribution is the most underrated factor in sustainable growth. Key Learnings Tactics without strategy is just noise. Most CEOs are asking "should we do more on social media?" before they have a repeatable strategy. Without intentional architecture, even a win can't be scaled — because you don't know why it worked. If you can't use a superlative, go back to the drawing board. First, fastest, only, cheapest, proprietary — if you can't describe what you do with a word like that, you are part of the sea of sameness. Customers cannot tell who is telling the truth until they buy. Capture the heart before the mind. People make decisions emotionally and rationalise them later. Leading with ROI charts and features at the top of the funnel is a guaranteed way to lose attention before you've earned it. The boardroom disconnect is a marketing leadership failure. Talking about MQLs and engagement metrics in front of a CEO is speaking the wrong language. Reframe website traffic as "demand capture potential" and watch the conversation change. You never fail your way out of a crisis — you succeed your way through it. During the 2008 AIG crisis, Rich proposed launching a direct-to-consumer online bank and kept the AIG brand. The logic: a sophisticated depositor understands FDIC insurance. An unknown brand would have taken years to build trust they simply didn't have. Intent data has a longer lead time than most marketers expect. At Jornaya, Rich found that consumers begin active shopping behaviour far earlier than credit triggers or late-stage signals suggest. Most businesses are reacting far too late. Alignment decays — you have to apply energy to maintain it. Ask a CEO what the company's top priorities are, then ask a leadership team member the same question. The answers will not match. The further from the original plan, the worse the matching gets. Connect with Rich on LinkedIn 🌐 http://www.richmsmith.com

    50 min

  7. May 27

    #45 | From Luxury Watches to Agentic AI: The Future of Sales

    Episode Overview Michael Kalinichenko has earned six promotions across a decade in SaaS, leading high-performing sales teams atIntercom, Zendesk, and Rieke — all while maintaining under 10% voluntary attrition across seven years of management. Before tech, he was selling Swiss-made luxury watches in one of the most relationship-driven, paper-based industries imaginable.   In this conversation, Michael and Pete trace the arc from manual relationship selling to the age of agentic AI — and find that the most durable competitive edge in sales has nothing to do withsoftware. They cover the hidden spectrum of AI adoption across European markets, why the world's most advanced LLMs carry a Western cultural bias that EMEA sellers must account for, and how to lead a team through constant disruption without letting uncertainty become anxiety. Connect with Michael on LinkedInBook mentioned — The Choice: by Dr Edith Eger

    37 min

  8. May 25

    #44 | Why ERP Implementations Fail (And It's Not the Software) | Kevin Patrick

    EPISODE OVERVIEW Kevin Patrick has spent over 30 years in operations, manufacturing and enterprise technology. He has led more than 120 SAP Business One deployments, launched a brand new Acumatica practice that generated $2 million in revenue within 17 months, and earned Softengine the Acumatica Rookie of the Year award at the 2025 Summit. Today, through his company Trinity One Consulting, he works as a fractional CEO, EOS integrator and certified Dream Manager, blending operational rigour with a deeply human approach to workplace performance. This conversation explores the pattern Kevin noticed across hundreds of ERP projects: the system is almost never what breaks. It is the people asked to use it who were never consulted, never brought in and never cared for. From that insight, Kevin found the Dream Manager methodology, developed by Matthew Kelly and delivered through Floyd Consulting, a programme that helps employees define and pursue personal goals across 12 life categories, with the aim of reigniting engagement, reducing turnover and driving business results from the inside out. Pete and Kevin also go deep on AI adoption, the EOS framework, the cost of employee disengagement and what it really takes to build a podcast audience worth having. KEY LEARNINGS 1. The four red flags that signal an ERP implementation is heading sideways Kevin identifies the warning signs he looks for from day one: only managers in the room with no frontline workers, bad or incomplete data, no testing plan and no genuine employee buy-in. Any one of these is a problem. More than one and the project is in trouble before it starts. 2. Frontline workers are stakeholders, not afterthoughts When management runs an implementation and then arrives on the floor six months later to say "here's your new system," they communicate something powerful without saying a word: your opinion does not matter. Kevin builds subject matter experts from the floor into every project from the outset. 3. Employee disengagement is measurable and expensive The cost of replacing a consultant or manager typically runs to 20,000 to 30,000 euros in recruitment fees alone, before you factor in ramp-up time, lost tribal knowledge and the customers who follow the departing consultant to their next employer. The Dream Manager programme addresses the root cause, not the symptom. 4. The Dream Manager works across 12 life categories Developed by Matthew Kelly, the programme structures monthly one-to-one meetings across areas including physical wellbeing, financial health, legacy and relationships. Participants often report coming to work in noticeably better spirits within three to six months, with downstream improvements in customer satisfaction, output and retention. 5. AI is a force multiplier for the operational consultant Kevin was sceptical of AI until about 18 months ago. Now his entire practice runs on it. He has built a custom Dream Manager tracking application, an EOS management tool and automated his outbound sales pipeline, all without being a technical developer. His view: the fear of AI taking jobs is holding back the people it could help most. 6. Authenticity wins audiences faster than polish Kevin's two biggest podcast episodes by a wide margin are his addiction recovery story and a raw episode he calls The Reckoning, in which he admitted to his audience that he was still in the middle of the journey, not beyond it. Audiences can hear when someone is performing. They stay when someone is telling the truth.

    47 min
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The Digital Diaries is a podcast about navigating modern work, creativity, and identity in a rapidly changing digital world. Hosted by Peter Woods, the show features conversations with builders, creators, technologists, and leaders who are shaping — and questioning — how technology influences culture, careers, and human behaviour. Each episode explores themes like creativity in the age of AI, leadership in the digital era, personal branding, entrepreneurship, and the tension between building and critiquing. This isn’t a hype-driven tech podcast. It’s a reflective space for people who want to

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