AssociationHelpNow

Raymond Dickey

AssociationHelpNow® delivers practical, real-world conversations for community association managers and board members who live this work every day. Each episode features candid discussions, expert interviews, and timely insights covering legal, insurance, operational, leadership, and communication challenges facing HOAs and condominiums. From livestream highlights to workshop takeaways, the show bridges the gap between theory and practice—helping listeners make smarter, more confident decisions in complex environments.Hosted by AssociationHelpNow® | Practical insights for managers and boards who live this every day.This content does not constitute professional advice and may have been edited.

  1. Psychology of Groupthink in HOA Boards – When Governance Turns Dysfunctional

    3 DAYS AGO

    Psychology of Groupthink in HOA Boards – When Governance Turns Dysfunctional

    What do high-control groups and dysfunctional HOA boards have in common? —————— YouTube: https://youtu.be/cIZ_4cK9VRY —————— More than most people are comfortable admitting. In this provocative but practical session, we explore the psychology behind groupthink, dominant personalities, loyalty pressure, and information control—and how these dynamics quietly impact HOA and condo board decision-making. This is not about comparing community associations to cults. It’s about recognizing human behavior patterns that can undermine leadership, increase liability, and damage trust within your community. In this session, we break down: • How groupthink forms in volunteer HOA and condo boards • The danger of strong personalities dominating decisions • Why dissenting voices disappear—and why that creates risk • How misplaced loyalty can override fiduciary duty • The warning signs of an insular or isolated board • Practical strategies to restore transparency, balance, and accountability Every board starts with good intentions. But without structure, awareness, and open dialogue, even well-meaning boards can drift into unhealthy governance patterns. If you are a community association manager or board member, this session will challenge your thinking—and give you practical tools to strengthen leadership and decision-making. It’s about behavior. PANELISTS Raymond Dickey • AssociationHelpNow® • www.AssociationHelpNow.com David Byrne, Esq. • Ansell Grimm & Aaron, PC • dbyrne@ansell.law • www.ansell.law Jennifer Hawk, CMCA, AMS • CAMS • jhawk@camsmgt.com • www.camsmgt.com Kristine Bates, CMCA, AMS, PCAM • Associa New York • kristine.bates@associa.us• www.associanewyork.com --- Hosted by AssociationHelpNow® | Practical insights for managers and boards who live this every day. This content does not constitute professional advice. --- #HOA #CommunityAssociations #HOAManagement #BoardGovernance #PropertyManagement #CondoBoards #Groupthink #Leadership #AssociationManagement #HOABoard #CAM #CommunityManagement #BoardMembers #Governance #HOALeadership

    1 hr
  2. RFPs That Protect

    26 MAR

    RFPs That Protect

    Every major HOA or condo project starts long before the contract is signed. ======= YouTube: https://youtu.be/PlAaUJTcYAU ======= It starts with the RFP—and when it’s done wrong, everything that follows can fall apart. In this practical, real-world session, we break down how to structure a Request for Proposal that protects your association, creates true “apples-to-apples” bidding, and reduces the risk of disputes, delays, and budget overruns. From scope of work and vendor instructions to insurance requirements, timelines, and change orders, this discussion highlights what boards and managers must get right before the first bid ever comes in. You’ll also hear why poorly written RFPs lead to confusion, legal exposure, and project failure—and how a well-structured process can defend board decisions when they’re challenged. WHAT YOU’LL LEARN • Why the success of your project depends on the RFP • How to define scope of work to eliminate disputes • Why “apples-to-apples” bidding is critical • The real risk of relying on AI instead of professionals • How timelines, delays, and accountability should be structured • What causes change orders—and how to minimize them • Why insurance requirements can dramatically impact pricing • The role of engineers, attorneys, and insurance advisors • How to properly evaluate vendors and qualifications • Payment structures, retainage, and lien protection strategies CEU INSTRUCTIONS To qualify for CAMICB CEUs, please follow the on-screen instructions that appear during the video. These instructions will be displayed within the first 10 minutes of the program, so please watch carefully. To receive CEU credit, you must use the “Question” feature and respond to all three CAMICB checkpoints during the program. If these steps are not completed, we will not be able to submit your participation to CAMICB for credit. Please allow up to five days to receive your CEU confirmation. PANEL Raymond Dickey • www.AssociationHelpNow.com Gregg V. Gerelli • Gerelli Insurance Agency, Inc. • gregg@gerelli-insurance.com • www.gerelli-insurance.com Cory Kravit, Esq. • Kovitz Shifrin Nesbit • ckravit@ksnlaw.com • www.ksnlaw.com John LaGumina, Esq. • The LaGumina Law Firm, PLLC • www.laguminalaw.com • jlagumina@laguminalaw.com David Byrne, Esq. • Ansell Grimm & Aaron, PC • dbyrne@ansell.law • www.ansell.law] David Chesky, R.S., P.R.A. • Falcon Engineering • dchesky@thefalcongroup.us • www.thefalcongroup.us WATCH / LISTEN YouTube Channel: www.youtube.com/@AHNData/videos Podcast: https://www.buzzsprout.com/2565449 Hosted by AssociationHelpNow® | Practical insights for managers and boards who live this every day. This content does not constitute professional advice. #HOA #CondoAssociation #PropertyManagement #CommunityA

    1hr 2min
  3. AI May Already Be Creating Legal Risk for Your Association

    25 MAR

    AI May Already Be Creating Legal Risk for Your Association

    AI is everywhere—but are community association boards and managers using it safely… or setting themselves up for lawsuits? ========================== YouTube Video Full LiveStream: https://youtu.be/3iRk4l4n56s ========================== In this eye-opening session, we break down the real-world risks of using AI in HOA and condo operations—from confidentiality breaches and copyright violations to insurance coverage gaps and potential negligence claims. You’ll hear how something as simple as copying text into AI or relying on it for decisions could expose your association to serious liability—including federal violations, data breaches, and even subpoenaed AI conversations. This is not theoretical. These issues are already happening. --- What You’ll Learn • Why using AI for board decisions can backfire in court • The hidden danger of entering confidential HOA data into AI tools • Open AI vs. closed AI—what boards MUST understand • How AI can accidentally copy copyrighted material (and cost you The  • Why “we didn’t know” won’t protect your association • Insurance gaps: when coverage may NOT apply • Why board members still carry full fiduciary responsibility • How AI use by vendors and managers can expose your association • Simple policies every board should adopt immediately --- Panel Raymond Dickey AssociationHelpNow® www.AssociationHelpNow.com Dawn Becker-Durnin, CIRMS Acrisure dbecker-durnin@acrisure.com www.acrisure.com Lori P. Hager, Esq. Kyberia Legal lori@kyberialegal.com www.kyberialegal.com --- Who Should Watch: HOA Managers, Condo Boards, Community Association Leaders, Insurance Professionals, and Anyone Using AI in Association Operations --- Hosted by AssociationHelpNow® | Practical insights for managers and boards who live this every day. This content does not constitute professional advice. --- #HOA #CondoBoards #PropertyManagement #AI #ArtificialIntelligence #HOAmanagement #CommunityAssociations #CyberRisk #HOAlegal #Insurance #DataPrivacy #BoardMembers #RiskManagement

    59 min
  4. Reserve Funding Isn’t a Math Problem

    22 MAR

    Reserve Funding Isn’t a Math Problem

    This interview was based on a recent LinkedIn post from Michelle Baldry. YouTube: https://youtu.be/IzXnCaRJ2sw In her post, Michelle Baldry, PE, PRA, RS as Chair of the Foundation for Community Association Research’s Best Practices shared insights from a national reserve funding survey that highlighted a key issue: many communities aren’t underfunded due to lack of awareness, but because of how difficult these decisions are to communicate and implement. LinkedIn Post: https://www.linkedin.com/posts/michelle-baldry_communityassociationresearch-hoa-reservefunding-activity-7432468970303033344-2kjj?utm_source=share&utm_medium=member_desktop&rcm=ACoAAA1xftoBOhA1qKbJiwA4J9SAeYTF83ToYHI Reserve funding isn’t a math problem, it’s a communication problem. In this discussion, we cover: - Why 64% say communication—not numbers—is the biggest challenge - What boards understand… but struggle to convey to homeowners - How reserve studies are evolving into risk mitigation tools - Why lenders and insurers are paying closer attention - Common mistakes when presenting funding plan Practical ways to position reserves so communities understand the long-term impact This video builds directly on Michelle’s original post, turning the data into real-world application for community association managers and board members. If you’ve ever had pushback on reserves, delayed funding decisions, or struggled to explain the “why” behind increases, this is worth your time. Panel: Michelle Baldry, PE, PRA, RS • Reserve Advisors, Inc. • mbaldry@reserveadvisors.com • www.reserveadvisors.com Raymond Dickey • www.AssociationHelpNow.com Hosted by AssociationHelpNow® | Practical insights for managers and boards who live this every day. This content does not constitute professional advice. #HOA #CondoLiving #CommunityAssociations #PropertyManagement #ReserveStudies #HOABoard #FinancialPlanning #RiskManagement #SpecialAssessments #AssociationManagement

    18 min
  5. HOA Collections Explained

    20 MAR

    HOA Collections Explained

    HOA Collections Explained: Liens, Foreclosure, Bankruptcy, Payment Plans, and Board Collection Mistakes Collecting assessments is not optional for HOA and condo boards. It is a fiduciary duty. But when collections are handled inconsistently or without the right legal process, associations can create serious risk, including selective enforcement claims, Fair Debt Collection issues, confidentiality problems, board liability, and unnecessary conflict with owners. ———————————- YouTube: https://youtu.be/f_DW7pZFeMs CAMICB CEU Video: Please register for CEU Video - “HOA Collections Explained” Apr 16, 2026 (1 hour video available all day) at: https://attendee.gotowebinar.com/register/5185089483040991574 ———————————- In this practical livestream recording, our panel breaks down how community association collections really work, including liens, foreclosure timelines, notice requirements, bankruptcy complications, payment plans, late fees, money judgments, suspension of privileges, and why written collection policies matter. The discussion also covers what boards can and cannot do when owners claim hardship, whether compassion can affect enforcement, how different states handle collection timelines, and why delaying action can damage association cash flow and increase legal exposure. This is a must-watch for HOA board members, condo board members, community association managers, and anyone responsible for protecting association finances while enforcing governing documents fairly and consistently. This recording is especially helpful if your community is dealing with delinquent owners, inconsistent enforcement, unpaid assessments, bankruptcy filings, lien questions, foreclosure concerns, or board uncertainty about how aggressive collections should be. PANEL: Raymond Dickey • www.AssociationHelpNow.com Dawn Becker-Durnin, CIRMS • Acrisure • dbecker-durnin@acrisure.com • www.acrisure.com David Byrne, Esq. • Ansell Grimm & Aaron, PC • dbyrne@ansell.law • www.ansell.law Adam Clarkson, Esq. • Clarkson McAlonis & O’Connor, P.C. • aclarkson@cmolawpc.com • www.cmolawpc.com Elliot M. Engstrom, Esq. • Sellers, Ayers, Dortch & Lyons, P.A • eengstrom@sellersayers.com • www.SellersAyers.com Gregg V. Gerelli • Gerelli Insurance Agency, Inc. • gregg@gerelli-insurance.com • www.gerelli-insurance.com Cory Kravit, Esq. • Kovitz Shifrin Nesbit • ckravit@ksnlaw.com • www.ksnlaw.com John LaGumina, Esq. • The LaGumina Law Firm, PLLC • jlagumina@laguminalaw.com • www.laguminalaw.com Hosted by AssociationHelpNow® | Practical insights for managers and boards who live this every day. This content does not constitute professional advice. #HOACollections #HOALiens #HOAForeclosure #HOABankruptcy #AssociationCollections #CondoCollections #CommunityAssociationLaw #HOABoard #CondoBoard #PropertyManagement #CommunityAssociationManager #HOAAssessments #DelinquentOwners #CollectionsPolicy #HOALaw #CondoLaw #AssociationHelpNow #BoardGovernance

    1hr 1min
  6. Massive Boulder Blast Update + Can Managers Be Friends With Board Members?

    17 MAR

    Massive Boulder Blast Update + Can Managers Be Friends With Board Members?

    A routine HOA-area blast turned into a nightmare when huge rocks crashed into homes, damaged association property, and triggered major insurance, liability, and communication issues. In this livestream recording, we revisit one of the most shocking HOA incidents discussed this year and break down what happened next. Were the homes repaired? Who ended up paying? What did the insurance process look like? What should managers and boards do immediately after a disaster like this? YouTube Video: https://youtu.be/gaXNpfrbMrw CEU Video - HOA Blast Update + Are Manager–Board Friendships Appropriate On-Demand 1 hour, All Day Apr 21, 2026 12:00 AM EDT at: https://attendee.gotowebinar.com/register/9164698152445669470 This session is especially valuable for HOA managers, condo board members, community association leaders, and anyone involved in property management, insurance claims, reserve planning, risk management, or resident communication. The discussion covers real-world lessons about emergency response, documentation, inspections, owner updates, disaster planning, and how fast a community can spiral if the wrong steps are taken. Then the conversation shifts to a topic that hits just as close to home: can HOA managers and board members really be friends? It sounds harmless, but this is where perception, favoritism concerns, gossip, influence, and professional boundaries can create serious problems. The panel discusses when being friendly crosses the line, how optics affect trust, and what managers should do to protect their neutrality and credibility. This recording includes practical takeaways on: HOA disaster response, community association insurance issues, claims handling, liability questions, owner communication, manager professionalism, board relationships, and avoiding hidden conflicts. Original livestream referenced in this program: “HOA Hit by 45 pound Rocks!” https://youtu.be/9UCgBm4-EsU Hosted by AssociationHelpNow® | Practical insights for managers and boards who live this every day. PANEL: Raymond Dickey • www.AssociationHelpNow.com Dawn Becker-Durnin, CIRMS • Acrisure • dbecker-durnin@acrisure.com • www.HOAInsuranceSC.com Chris Petrik, CMCA, AMS, PCAM • Bulle Rock Community Association • chris.Petrik@FSResidential.com • www.bullerockcommunity.com Chris Lozier, CMCA • Ponderosa Management LLC • clozier@pm-llc.com This content does not constitute professional advice. #HOA #HOADisaster #PropertyManagement #CommunityAssociation #CondoAssociation #HOAInsurance #InsuranceClaims #RiskManagement #DisasterPlanning #HOABoard #AssociationManagement #CommunityManagers #ProfessionalBoundaries #BoardMemberRelations #CondoManagement #HOALiability

    1hr 1min
  7. HOA Special Assessments: How to Communicate Them, Avoid Legal Mistakes, and Decide If Borrowing Is Smarter

    15 MAR

    HOA Special Assessments: How to Communicate Them, Avoid Legal Mistakes, and Decide If Borrowing Is Smarter

    Special assessments are one of the toughest challenges HOA and condo boards face. In this practical livestream, our panel explains how boards and managers can communicate a special assessment without creating panic, avoid procedural mistakes that often lead to disputes or litigation, and evaluate when borrowing may be the better option. The discussion covers owner communication, governing document requirements, voting procedures, collections, insurance considerations, reserve shortfalls, and lender perspectives. ——————————————— CAMICB CEU Video: Please register for CEU Video - Special Assessments - Sell, Structure or Borrow It on Apr 14, 2026 (1 hour video available all day) at: https://attendee.gotowebinar.com/register/1613926293455377495 ——————————————— If you are a community association manager, board member, or industry professional looking for guidance on special assessments, association loans, reserve funding, owner communication, fiduciary duty, or major repair funding decisions, this recording provides practical insight on structuring the process, explaining the need, and reducing owner backlash. PANEL: Raymond Dickey • www.AssociationHelpNow.com Deborah Gerelli, CIRMS • Gerelli Insurance Agency, Inc. • deborah@gerelli-insurance.com • www.gerelli-insurance.com Dawn Becker-Durnin, CIRMS • Acrisure • dbecker-durnin@acrisure.com • www.HOAInsuranceSC.com John LaGumina, Esq. • The LaGumina Law Firm, PLLC • jlagumina@laguminalaw.com • www.laguminalaw.com Cynthia Jones, Esq. • Sellers, Ayers, Dortch & Lyons, P.A. • cjones@sellersayers.com • www.sellersayers.com Thomas Engblom, PhD., PCAM • First Citizens Bank • thomas.engblom@firstcitizens.com • www.bankers.firstcitizens.com Sean A. O’Connor, Esq., CCAL • Clarkson McAlonis & O’Connor, P.C. • soconnor@cmolawpc.com • www.cmolawpc.com David Byrne, Esq. • Ansell Grimm & Aaron, PC • dbyrne@ansell.law • www.ansell.law Cory Kravit, Esq. • Kovitz Shifrin Nesbit • ckravit@ksnlaw.com • www.ksnlaw.com Hosted by AssociationHelpNow® | Practical insights for managers and boards who live this every day. This content does not constitute professional advice. #HOA #CondoAssociation #SpecialAssessments #HOABoard #PropertyManagement #CommunityAssociations #ReserveFunding #AssociationLoans #CondoBoard #HOALaw #CondoLaw #BoardGovernance #CapitalProjects #HOAManagers #FiduciaryDuty

    1hr 2min
  8. AI in HOAs - Powerful Tool or Legal Time Bomb

    13 MAR

    AI in HOAs - Powerful Tool or Legal Time Bomb

    Artificial Intelligence is already inside community associations. ---- This video is not eligible for CEUs ---- YouTube Video: https://youtu.be/kRXYzKmLAzc Managers are using it to draft emails. Boards are asking it to interpret bylaws. Vendors are embedding it into software platforms. But here’s the real question:  Are we using AI wisely — or creating new liability without realizing it? In this livestream, we’re breaking it down the way we always do — practical, real-world, and balanced. We’ll look at: • How AI can dramatically improve communication and efficiency • What happens when boards rely on AI instead of legal counsel • Confidentiality concerns most managers haven’t thought about • Deepfake fraud, cyber exposure, and vendor accountability • Whether associations should adopt an AI usage policy This is not a tech lecture. It’s a candid discussion about how managers and boards can use AI responsibly — without turning a helpful tool into a silent liability. If you manage or serve on a board, this conversation is no longer optional. AI is here. The question is whether we understand the risks that come with it. Panel: Cameron Leyh, CMCA, AMS • Ravenel Associates, Inc. • cleyh@ravenelassociates.com www.ravenelassociates.com Raymond Dickey • AssociationHelpNow.com Dawn Becker-Durnin, CIRMS • Acrisure • dbecker-durnin@acrisure.com • www.HOAInsuranceSC.com Valerie Garcia Giovanoli, Esq. • McCabe, Trotter & Beverly, P.C. • valerie.giovanoli@mccabetrotter.com • www.mccabetrotter.com Content does not represent professional advice.

    1hr 1min
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About

AssociationHelpNow® delivers practical, real-world conversations for community association managers and board members who live this work every day. Each episode features candid discussions, expert interviews, and timely insights covering legal, insurance, operational, leadership, and communication challenges facing HOAs and condominiums. From livestream highlights to workshop takeaways, the show bridges the gap between theory and practice—helping listeners make smarter, more confident decisions in complex environments.Hosted by AssociationHelpNow® | Practical insights for managers and boards who live this every day.This content does not constitute professional advice and may have been edited.

Information

  • Creator
    Raymond Dickey
  • Years Active
    2025 - 2026
  • Episodes
    27
  • Rating
    Clean
  • Copyright
    © 2026 AssociationHelpNow
  • Show Website
    AssociationHelpNow