Episodi

  • Nattering Nabobs of Information: Using AI is Playing the Odds
    Oct 19 2026
    AI can get you to the wrong conclusion really, really fast. How much are you willing to gamble on its answers?

    In this episode of Nattering Nabobs of Information, the Nabobs talk about “playing the odds” with AI. It looks like magic, but fundamentally it’s math — and a convincing answer still needs checking before you put it to work.

    We natter about:

    -- Why good information and sound workflows matter before you turn AI loose.

    -- How an off-target answer can become the foundation for more wrong answers.

    -- Why “human at the helm” is a better way to think about responsibility than “human in the loop.”

    Along the way: a health insurance letter that got the facts right but failed the person receiving it, governance tools with the cart and horse in the wrong order, and a whole new meaning for “steering committee.”

    Where have you seen AI help — or go really wrong really quick? Tell us in the comments, and subscribe for more nattering about putting information to work.

    Talk to Steve
    Steve Weissman helps organizations get control of their information so it’s trustworthy, findable, defensible, and actually useful to the business. If information governance, compliance, content management, or getting your information ready for AI is keeping you up at night, Steve is the guy to talk to.
    Email: Sweissman@HollyGroup.com
    Phone: 617-383-4655

    Talk to Bryant
    Bryant Duhon helps businesses turn what they know into useful marketing content that earns attention, builds trust, and gives customers a reason to stick around. If you need help with newsletters, content strategy, or simply figuring out what the hell to say to your customers, get in touch.
    Email: Bryant@SimplyUsefulMarketing.co
    Phone: 301-275-7496

    © Steve Weissman • All Rights Reserved • www. hollygroup.com • 617-383-4655

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    14 min
  • Nattering Nabobs of Information: In Data, as in Dating, Trust but Verify
    Oct 6 2026

    Bad dates and bad data can both leave you wondering why you trusted them in the first place.

    In the first episode of Nattering Nabobs of Information, Bryant Duhon and Steve Weissman connect online dating, marketing, and information governance through a shared problem: figuring out who and what you can trust — and living up to the trust other people put in you.

    Bryant brings lessons from the online dating salt mines. Steve brings the information governance perspective and, mercifully, considerably less recent dating experience.

    Together, they tackle:

    * Why your business needs to look like its profile photo.
    * What earns trust between the first click and a lasting customer relationship.
    * How to make the case for information governance beyond “something bad might happen.”
    * Where AI fits into the conversation about trustworthy information.

    If you’re trying to earn customers’ confidence or help colleagues trust the information they work with, there’s something here for you.

    There are also questionable dating analogies, a Little League lesson, and instructions for not boiling the entire elephant.

    Watch the conversation, then tell us in the comments:
    --- What makes you lose trust in a business? ---

    Talk to Bryant
    Bryant Duhon helps businesses turn what they know into useful marketing content that earns attention, builds trust, and gives customers a reason to stick around. If you need help with newsletters, content strategy, or simply figuring out what the hell to say to your customers, get in touch.
    Email: Bryant@SimplyUsefulMarketing.co
    Phone: 301-275-7496

    Talk to Steve
    Steve Weissman helps organizations get control of their information so it’s trustworthy, findable, defensible, and actually useful to the business. If information governance, compliance, content management, or getting your information ready for AI is keeping you up at night, Steve is the guy to talk to.
    Email: Sweissman@HollyGroup.com
    Phone: 617-383-4655

    © Steve Weissman • All Rights Reserved • www. hollygroup.com • 617-383-4655

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    27 min
  • Communities of Practice: The Multiplier That Drives Governance Adoption
    Sep 30 2026

    Most governance initiatives don’t stall because of technology — they stall because people aren’t aligned behind the effort. For many, the solution is to create a communities of practice that changed the trajectory of their programs.

    Have a listen and learn how leaders like you have structured their communities, sparked participation, and created the kind of cross‑functional momentum that makes governance stick.

    * See our page on LinkedIn! * https://www.linkedin.com/company/infogovroundtable

    Your hosts:
    • Steve Weissman - steve@hollygroup.com
    • Jesse Wilkins - jesse.wilkins@opensitysolutions.com
    • Donda Young - dlyoung@heliasconsulting.com

    © Steve Weissman • All Rights Reserved • www. hollygroup.com • 617-383-4655

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    55 min
  • How to Write Policies That Encourage Compliance - Community Roundtable
    Jul 28 2026

    Many organizational policies are written as a series of imperatives: do this, don't do that, always, never. While well-intentioned, this approach often leaves capable professionals feeling like children who have to be controlled rather than trusted. The result? Policies that are read reluctantly, followed inconsistently, and viewed as obstacles rather than guidelines.

    This installment of our IG Community Roundtable explores the connection between policy tone and staff behavior, and explains how respectful, positively framed policies can encourage questions without fear of reprimand.

    * See our page on LinkedIn! * https://www.linkedin.com/company/infogovroundtable

    Your hosts:
    • Steve Weissman - steve@hollygroup.com
    • Jesse Wilkins - jesse.wilkins@opensitysolutions.com
    • Donda Young - dlyoung@heliasconsulting.com

    Book mentioned in this video: by Lewis Eisen
    How to Write Rules That People Want to Follow, 3rd Edition: A guide to writing respectful policies and directives

    https://www.amazon.com/Write-Rules-That-People-Follow-dp-1988749069/dp/1988749069/ref=dp_ob_title_bk

    © Steve Weissman • All Rights Reserved • www. hollygroup.com • 617-383-4655

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    58 min
  • A Governance "Ask Us Anything!" - Community Roundtable
    Jun 2 2026

    This IG Community Roundtable is an “Ask Us Anything” session in which the conversation was driven entirely by YOU.

    Think of it as nearly an hour of free consulting with three top resources – plus a bit of peer review – and you get the idea. Watch, learn, and enjoy!

    * See our page on LinkedIn! * https://www.linkedin.com/company/infogovroundtable

    Your hosts:
    • Steve Weissman - steve@hollygroup.com
    • Jesse Wilkins - jesse.wilkins@opensitysolutions.com
    • Donda Young - dlyoung@heliasconsulting.com

    © Steve Weissman • All Rights Reserved • www. hollygroup.com • 617-383-4655

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    51 min
  • The Three Sides of the Information Inventory Coin - Community Roundtable
    May 18 2026

    If you’re reading this, then your to-do list probably includes tasks like updating your retention schedule, reducing paper, cleaning up your data stores, protecting privacy, boosting findability, etc.

    But you can’t do any of these things without first knowing what information you have and where it’s stored – which is why you need to start by conducting an information inventory and drawing a data map.

    This edition of the IG Community Roundtable will explores why this screamingly obvious bit of advice is so often (in our experience) given short-shrift, why the work is more than worth the psychic pain it can cause, and how to ease that pain for the people whose cooperation and input you need.

    * See our page on LinkedIn! * https://www.linkedin.com/company/infogovroundtable

    Your hosts:
    • Steve Weissman - steve@hollygroup.com
    • Jesse Wilkins - jesse.wilkins@opensitysolutions.com
    • Donda Young - dlyoung@heliasconsulting.com

    © Steve Weissman • All Rights Reserved • www. hollygroup.com • 617-383-4655

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    54 min
  • Citation vs. Provenance, and Their Criticality to AI Success (with John Martin)
    May 13 2026

    If you’re exploring, piloting, or implementing AI, take note of this critical distinction when it comes to ingesting and leveraging information:

    • Citation: the information exists, and I can tell you where to find it
    • Provenance: the information exists, and I can tell you where to find it, where it originated, and when it arrived

    Understanding the difference is foundational to getting practical value from AI, most instances of which cite their data sources but say nothing about whether those sources, or that data, is at all reliable.

    Join me and John Martin, Founder & CEO of RedFile Technologies, in this edition of Speaking Of, in which we discuss the meaning and ramifications of a LinkedIn post he wrote on the subject.*

    You really don’t want to miss it.

    – Steve Weissman - steve@hollygroup.com
    – John Martin - john_martin@redfile.ai

    *Citation alert! "Why Citation Is Not Provenance" https://www.linkedin.com/pulse/why-citation-provenance-john-martin-obske/?trackingId=iTtM6kVT2Y1me1APTa5xrA%3D%3D)

    © Steve Weissman • All Rights Reserved • www. hollygroup.com • 617-383-4655

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    35 min
  • When Policy Documents Contain the Wrong Content (with Lewis Eisen)
    May 7 2026

    Creating policy documents takes an awful lot of effort. But are we making it harder on ourselves than we need to? Lewis Eisen of Perfect Policies says “yes,” and you need to hear why.

    Spoiler: it’s because the people who should be focused on approving the policies spend too much time wordsmithing the user version – a job better left to those on the operational front lines.

    Have a watch and you’ll agree that it’s 30 minutes of pure gold.

    And if that’s not enough, there’s a free e-book in it for you as well! (See below.)

    --

    The article that sparked this conversation:

    https://www.linkedin.com/pulse/policies-organizational-legislation-lewis-eisen-jd-cip-ken9e/

    --

    Highlights:

    3:51 On whether people should even be reading policies

    5:56 On separating docs that communicate policies from those where the policies are formed

    6:53 On “marketing” your policies to facilitate compliance

    9:03 On separating oversight and operations

    11:48 On AI as an example

    12:56 On trusting the specialists you’ve hired

    16:34 On policies’ true intention

    18:00 On culture change

    24:50 On working through mission, then values, and then strategy

    28:38 On Lewis’ free new book “Why Are Your Rules Yelling At Me?”

    --

    Get Lewis’ new book – downloadable for free!

    “Why Are Your Rules Yelling At Me?”

    https://lewiseisen.com/yelling

    --

    Steve Weissman - steve@hollygroup.com

    Lewis Eisen - lewis@perfectpolicies.com

    © Steve Weissman • All Rights Reserved • www. hollygroup.com • 617-383-4655

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    30 min