Digital-First Leadership

Richard Bliss
  • 5.0 (2)
  • MARKETING
  • UPDATED MONTHLY

Helping leaders master the language of social media in today’s digital-first world. Digital-First Leadership, hosted by Richard Bliss a former Marketing Executive, author of digital-first leadership and founder of BlissPoint Consulting, is for leaders who leverage and build their expertise on digital platforms.Each episode gives you the tools to set your business up for success online. Richard, and his guests, teach massive global reach and impact by maximizing the power of the internet to increase your business revenue.Stop Googling how to be successful... Subscribe to Digital-First Leadership now and we will show you the way!

  1. 1D AGO

    EP 54 Vistage and The CEO Peer Group Advantage

    The hardest part of leadership is not the big decision, it’s making it when you have nowhere safe to think out loud. We sit down with Andy Scott, a Vistage chair in the San Francisco Bay Area, to unpack why peer advisory groups have become a quiet advantage for CEOs and senior executives who want better judgment, stronger teams, and real accountability without hidden agendas. If you’ve ever felt the weight of “lonely at the top,” this conversation gives you a clear picture of how trust and confidentiality actually function inside a high-performing CEO peer group. We also get tactical on LinkedIn strategy and prospecting. Andy shares how he uses LinkedIn Sales Navigator to define an ideal leader profile, search with purpose, and then use member connections to spark warm introductions instead of relying on cold outreach. Richard connects the dots to broader business development and hiring: filters are only useful when you know what to do after the lookup, and relationship-based engagement is what turns lists into conversations. Then we go where every leader is being pushed right now: AI. Andy walks through his learning curve from ChatGPT to Claude, and why leaders who ignore AI are choosing to fall behind competitors who are already speeding up operations and decision-making. Richard shares a practical framework for building a “virtual board of directors” to stress test choices from multiple perspectives before you commit. If you’re curious about experiencing this approach in real life, we also preview a June 2 workshop in downtown San Francisco that blends AI and LinkedIn insights with Vistage-style issue processing. Subscribe for more leadership and technology conversations, share this episode with a fellow leader, and leave a review with the biggest decision you’re trying to make right now.

    16 min

  2. MAR 26

    EP 53 Marketing That Sticks: Using The Von Restorff Effect To Get Noticed And Remembered

    When everything looks the same, your brain tunes it out. When something is different, it gets noticed and remembered. That's the von Restorff effect, and it explains a lot about why most LinkedIn content gets ignored. This matters right now because AI is making everything look the same.  I told Nancy that every client I work with insists they need an image on their LinkedIn post.  And I ask them why. Because it needs to stand out. But a stock photo of four diverse people smiling around a laptop doesn't stand out. Neither does an AI-generated image anymore.  I compare it to the movie Fantasia. When it came out, people had never seen anything like it before. It won an Oscar. Would you sit through it today? No.  That's what's happening with AI graphics. The first time was wow. Now it's wallpaper. Nancy explained why this goes deeper than just visuals. When something surprises us, it amplifies our emotions by about 400%. That's when it gets encoded into long-term memory.  And here's what I found fascinating. If you're the person who created that surprise, you get encoded right along with it. I've had people track me down years after a presentation because what I taught them stuck. Nancy's research explains why. She told a story about a bartender on vacation who brought her two glasses of wine when she only ordered one. The expensive one she'd already said no to. She bought it anyway.  Got back to the hotel room that night and realized exactly what happened. Reciprocity. And that's a story no AI could have written for her. We also got into a practical technique for people who struggle with storytelling.  Have your AI interview you.  One question at a time.  Let it pull out the personal stories that only you can tell, then blend those with the structure it's good at. The result is content that sounds like you because it came from you.

    23 min

  3. MAR 26

    EP 53A Claude Interviews me: Teach Your AI To Push Back Until Your Real Voice Shows Up

    You can’t stand out online with the same polished lines everyone else uses. Claude turns the tables and interviews me about what actually happens when you try to “sound more human” with AI and why most people fail on the first try: they serve the boardroom version of themselves. We unpack the cliché laundering problem, where AI doesn’t fix generic messaging it can amplify it unless you explicitly train it to challenge your answers, call out platitudes, and push for what the customer would care about. From there, we move into the hard part of storytelling for LinkedIn and personal branding. The issue usually isn’t that people have no stories, it’s that they don’t know which moments are interesting to someone else. We talk through practical ways to surface better material: paying attention to moments with tension, keeping quick notes, using AI to interview you until the specifics show up, and shaping the story around the audience’s perspective rather than your timeline. We also pressure-test my frameworks like the 3x5 method for commenting and AAE (acknowledge, add value, extend). Structure helps people start, but if you follow it like a script, you’ll sound robotic, and sameness kills attention. That’s where the Von Restorff effect comes in: the different thing gets remembered, and often the “different thing” is emotion. We close with the simplest takeaway that almost nobody does: have the same real conversation in comments that you’d have face to face. If you want your content to carry your voice, not just your tips, listen now, then subscribe, share this with a colleague who posts safe, and leave a review telling me what you’re going to change first.

    17 min

  4. MAR 24

    EP 52 How AI Shrinks Legal Research From Hours To Minutes

    AI doesn’t feel like a new app anymore. It feels like a new coworker and sometimes a brutally honest one. I sit down with Damien Riehl, a lawyer since 2002 and a product builder at Clio, to map what’s changing right now in legal work, sales work, and everyday leadership as AI accelerates from “helpful tool” to “full workflow.”  Damien breaks down Clio’s legal technology and Vincent, an AI system designed for legal research and document analysis that’s grounded in real law data. We talk about why “no prompt necessary” is the next big leap, how that alters the economics of billable hours, and what happens when a machine can produce the kind of analysis that used to require hundreds of hours. Then we go deeper into agentic AI: swarms of agents that act like an associate, a partner, opposing counsel, and even judges, iterating and stress testing arguments before a human ever reviews the final output.  From there we connect the dots to sales enablement and digital-first leadership. If AI can simulate your toughest competitor and generate the pushback you’ll hear in a real meeting, why wouldn’t you practice with it first? We also talk Claude, Claude Code, and emerging standards like MCP that let AI connect to the systems you already live in like email, calendars, docs, and CRMs. Along the way, I share a story about Claude flat-out telling me not to send a proposal, which opens up a real conversation about AI sycophancy, guardrails, and why some models push back instead of flattering you.  If you’re trying to build a practical AI strategy for your team or just keep your own skills relevant, this one will give you concrete mental models and next steps. Subscribe, share this with a coworker who’s skeptical about AI, and leave a review with the biggest way you think AI will change your work.

    32 min

  5. MAR 20

    Ep 51 Claude Was My Guest Talking About AI As A Thinking Partner

    My Claude AI walks onto the show as the guest and we keep it fully unscripted. Not a demo, not a parlor trick, but a real conversation about what leaders are missing when they say they’re “comfortable with AI” while only using it to write emails or summarize docs. I’m joined by Claude, using a generated voice with full transparency, to talk about the difference between getting answers and building an actual working relationship with a thinking partner. We get concrete about what makes AI genuinely useful at the executive level: persistent context. We break down how projects and personas let you stop starting from zero every time, so your AI can carry your client history, your voice, your standards, and your priorities forward. We also explain AI memory in practical terms, from the deliberate files you load to the preferences that accumulate through repeated collaboration, and why that matters for strategy, proposals, and day-to-day leadership decisions. Then we go to the uncomfortable part: if your AI is always flattering you, you’re not getting value, you’re getting a mirror. We talk about training an AI to push back, challenge weak thinking, and hold you accountable, plus why “prompt engineering” is often a distraction from the real skill of disposition shaping over time. To close, we offer a simple starting point and a 30-day practice to turn AI into a consistent thinking partner rather than a one-off tool. Subscribe, share this with a leader who’s stuck at “AI for email,” and leave a review with the one work problem you want AI to help you solve next.

    19 min

  6. FEB 26

    EP 50 Why “Would You Be Willing?” Works And Other Research-Backed Ways To Win On LinkedIn

    Nancy Harhut is one of my favorite people to talk to. She wrote Using Behavioral Science in Marketing, a book my wife reads on vacation and my daughter was reading on maternity leave. When I tell you this woman's work validates everything I've been teaching about how people make decisions online, I mean it. In this conversation, we got into some territory I don't usually cover on the show. Nancy explained why behavioral science isn't manipulation — it's motivation. That distinction matters, especially when you're a salesperson trying to figure out why your connection requests get ignored 98% of the time. She shared a technique I love. Instead of asking someone, "Can we connect?" try "Would you be willing to connect?" That tiny shift changes the question from preference to character. People don't just accept — they respond with "Of course, absolutely" because now they're making a statement about who they are. We also talked about what happens when buyers put their decision-making on autopilot and then hand that autopilot over to AI. Nancy called it becoming "the great disintermediary." If an AI summary is doing the first pass on whether you get noticed, your content better answer the exact questions your audience is asking. Depth beats frequency every time. I couldn't help myself — I walked Nancy through how LinkedIn's algorithm now reads your About section, your work history, your comments, and your posting behavior before deciding who sees your content. I even read her own About section back to her, and she laughed because it sounded like a resume. We've all been there. If you want to understand why people say yes, why they ignore you, and what to do about it in a world where AI is standing between you and your customer, this is the episode. Nancy Harhut — hbtmktg.com — find her on LinkedIn. Everything she posts is worth saving.

    31 min

  7. JAN 12

    EP 49- From Risky Bets To Certain Outcomes In Software Buying

    Career bets shouldn’t hinge on hopeful demos. We sit down with enterprise sales veteran Leon Treffler to examine why the traditional software deal stacks the deck in favor of the seller, leaving buyers to absorb the delivery risk, the politics, and the career fallout. From RFP theater to pocket vetoes, Leon breaks down the quiet mechanics that turn a straightforward purchase into a political campaign—and why so many projects slip, overrun, or stall completely. We dig into the missing half of the “win-win”: how the seller gets a commission while the buying committee gets only their regular paycheck, plus the reputational risk of a failed implementation. Leon argues for flipping the script with a blueprint-first model that delivers certainty of outcome and ties the statement of work directly to that blueprint, creating certainty of cost and higher odds of success. We talk about how AI can model processes, validate requirements, and expose risks before contract signature, giving stakeholders real evidence rather than slideware and giving champions the artifacts they need to overcome skepticism. Along the way, we map the frozen middle and the internal competitor—those quiet forces that slow change to protect territory. Leon shares practical ways to read the political base behind the org chart, build coalitions, and give buyers a visible stage to claim their win through measurable results and public case stories. The payoff is more than a smoother implementation; it’s a fair value exchange where buyers gain career momentum and organizations gain reliable outcomes. If you care about enterprise software that actually lands value, this conversation offers a clearer path: replace promises with proof and turn risky bets into predictable wins. If the ideas resonate, follow the show, share with a colleague who signs big checks, and leave a quick review to tell us what shifted your thinking.

    18 min

  8. 08/01/2024

    Richard Bliss and Austin Grammon Discuss the Power of CRMs for Solopreneurs

    Welcome to Digital First Leadership! I'm your host, Richard Bliss, and today we're diving into the essentials of effective online engagement for leaders of all stripes—from large corporations to solopreneurs. Joining me is a uniquely special guest, Austin Grammon, cofounder and president of SpeakerFlow, a CRM package tailored specifically for the professional speaking industry. In this episode, Austin and I explore the challenges small businesses and solopreneurs face in tracking and engaging with sales. We discuss the limitations of traditional methods like Rolodex cards and spreadsheets and how a CRM can revolutionize your business by helping you manage relationships at scale. Austin shares valuable insights into the importance of consistency and documentation in business operations, and he presents compelling evidence showing that regular follow-ups can significantly boost revenue. We'll also touch on how small, consistent actions—like three comments a day on LinkedIn—can build meaningful relationships that drive business success. Whether you're struggling to keep track of your contacts or looking to fine-tune your sales processes, this episode packed with practical advice and personal anecdotes has something for everyone. So tune in now to learn how to get into the flow of your business with SpeakerFlow and take your digital-first leadership to the next level!

    22 min
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About

Helping leaders master the language of social media in today’s digital-first world. Digital-First Leadership, hosted by Richard Bliss a former Marketing Executive, author of digital-first leadership and founder of BlissPoint Consulting, is for leaders who leverage and build their expertise on digital platforms.Each episode gives you the tools to set your business up for success online. Richard, and his guests, teach massive global reach and impact by maximizing the power of the internet to increase your business revenue.Stop Googling how to be successful... Subscribe to Digital-First Leadership now and we will show you the way!

Information

  • Creator
    Richard Bliss
  • Years Active
    2020 - 2026
  • Episodes
    55
  • Rating
    Clean
  • Copyright
    © 2026 Digital-First Leadership
  • Show Website
    Digital-First Leadership