SMB Community Podcast

A key focus of the episode is on practical approaches to conducting pre-sales assessments for prospective managed service clients, particularly those with existing MSP relationships and under 100 employees. Hosts discussed that frontline assessment methods often prioritize observational “walk-arounds” and targeted questioning rather than the deployment of specialized tools, except in cases where complexity or asset uncertainty warrants additional rigor. The conversation emphasized that visible signs of technological investment (or lack thereof) and management engagement provide valuable risk indicators to help MSPs assess prospect suitability and potential client alignment.

Supporting details included recommendations against using automated network scanning tools as a default during the sales process, especially for smaller prospects. Instead, initial technology and business process understanding should be driven by reviewing company websites, social media, and conducting direct observation and informal dialogue with staff. For more complex environments or where asset counts are ambiguous, tools such as Galactic Advisors, RapidFire Tools, or Lansweeper were suggested, but only after careful consideration of the actual information gap. MSPs were advised to leverage preexisting documentation and probe for differences with prior MSPs, focusing on gaps in service, dissatisfaction, or unaddressed needs.

Secondary topics included the necessity of formal Master Service Agreements (MSAs) and the operational risks of long-running unwritten arrangements. The hosts reported that customer pushback on contracts is rare; those unwilling to sign can be managed through premium pricing or operational discretion. The use of digital document management and auto-renew online agreements was cited as a means to streamline governance and ensure that contractual terms keep pace with operational changes. The conversation also addressed best practices for Quarterly or Technology Business Reviews (QBRs/TBRs)—advocating for business-oriented, forward-looking discussions rather than technical or ticket-driven reporting, and highlighting risk in overinvesting staff time in meeting preparation.

The episode concluded with a practical case study on recurring revenue management, highlighting a systematic approach to price increases after extended periods without adjustment. The case demonstrated that fears of customer attrition due to price adjustments are often overstated, particularly when supported by transparent communication and a graduated rollout to well-aligned clients. The discussion reiterated the importance for MSPs to maintain accountability, regularly review contractual agreements, manage operational costs, and structure client engagements to reduce risk exposure while improving alignment with organizational goals.

Title:   How do you complete an assessment for a prospect?

Topics/Events

Question Of The Week: How do you complete an assessment for a prospect? 

What to do if you don’t have agreements in place, but you’ve worked with recurring clients for years. 

QBRs – what questions should you be asking during your regular QBRs with your clients

CMMC third-party audits are paused. The channel opportunity isn’t. ChannelE2E https://share.google/4vXDd5G3ysgflU6PU

STORY:  Reviewing a MSP’s current agreements, James realized the MSP hadn’t had a price increase for over 5 years. 

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A significant development discussed in the SMB Community Podcast episode highlights the evolving Microsoft Partner Program. Microsoft has updated its partner program at the start of its fiscal year, introducing new opportunities and incentives. Notable changes include the loosening of Agent365 licensing, allowing its addition to Business Premium licenses and other tiers, and offering a 25% discount on Windows 365 licenses for both new and existing customers. Additionally, Copilot for Business is now available with a 15% discount for the upcoming year through the partner program. These updates present potential financial benefits and strategic advantages for MSPs engaging with Microsoft's offerings.

The episode also touches upon the increased adoption of onboarding fees among MSPs. While some MSPs prefer to integrate initial setup costs into project-based work, a growing percentage now charge explicit onboarding fees. One discussed model involves charging a fee equivalent to one month's recurring service cost, with some offering waivers for multi-year agreements. Another creative approach noted is using the onboarding fee to fund sales commissions, providing sales representatives with negotiation leverage. This trend suggests a shift in how MSPs are structuring their client acquisition and initial service delivery processes.

Further discussions in the podcast address the broader labor shortage in the technology sector, which is reportedly more significant than concerns surrounding AI's impact on jobs. The shortage particularly affects highly educated IT professionals, including those with degrees and senior engineering expertise, with an estimated 50,000 jobs at risk. This situation presents opportunities for existing industry professionals to advance and for AI or new entrants to fill entry-level roles. Concurrently, there is a recognized need for enhanced business acumen and financial literacy among IT professionals to better understand client business needs and articulate the return on investment for technology solutions.

For MSPs and IT service providers, the updated Microsoft Partner Program offers tangible financial incentives and opportunities for service expansion, particularly with the introduction of the Copilot specialization. The increasing prevalence of onboarding fees warrants a review of client acquisition strategies, balancing revenue generation with potential client apprehension. The persistent labor shortage underscores the importance of continuous training and upskilling, with a particular emphasis on developing business and financial literacy alongside technical expertise. Finally, the discussion on mergers highlights the critical importance of cultural alignment and clear, written agreements regarding governance and exit strategies, as poorly managed mergers can significantly diminish business value.

Is it worth it to become a certified Microsoft Partner?   

Labor shortage link: https://www.linkedin.com/news/story/record-labor-shortage-may-pose-larger-threat-than-ai-8379017/

 

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The episode addressed the heightened challenges MSPs and IT service providers face in client acquisition, with specific reference to a recent Kaseya report indicating that twice as many MSPs describe obtaining new clients as more difficult compared to the previous year. This shift is attributed, in part, to changes in marketing efficacy and the increased reliance on referrals rather than structured marketing strategies. These findings emphasize the need for a consistent, proactive marketing approach—moving beyond informal networks—to counteract periods of slow business and ensure stable revenue.

Discussion highlighted that many MSPs lack a formalized marketing plan and treat the absence of active marketing as a matter of pride, despite clear evidence that consistent marketing activities are essential for growth and resilience. According to James Kernan, "marketing is the oxygen of your business," and its absence correlates directly with reduced new business opportunities. Strategies such as recurring in-person or online engagement with clients, regular assessment of marketing practices, and leveraging written marketing plans were identified as actionable recommendations for sustaining pipeline health.

A secondary focus examined operational risk and opportunity related to "shadow AI"—unauthorized or unmanaged use of AI tools by clients’ staff. Amy Babinchak detailed three core risks: accidental exposure of confidential data, violation of contracts or regulatory requirements, and a lack of auditable records for actions taken by shadow AI tools. The discussion identified practical risk mitigation steps, including staff education, policy development, and implementation of monitoring tools, all of which represent billable opportunities for MSPs while reducing downstream liability in the event of a breach.

For technology service providers and decision-makers, the episode underscores the operational imperative of formal, consistent marketing—even during slow periods—as well as the need for vigilant governance over emerging technology risk vectors such as shadow AI. By proactively engaging clients through both marketing and risk education, MSPs can better protect their businesses while expanding stable, recurring revenue streams rooted in demonstrable expertise and accountable service delivery.

Title:   How do I get more business when it’s slow?

M&A Topic: Why is an elevator pitch for my business important?

Article: Why is finding new clients harder? Double the number of MSPs in Kasaya reported said so. https://www.kaseya.com/blog/msp-growth-challenges-2026/

QBR Talk: Talk to your clients about Shadow AI https://www.thirdtier.net/2026/06/25/speak-to-your-client-about-shadow-ai/

Tales from the field: A fictional tale about the Trunk Slammer from Hell. 

https://www.reddit.com/r/msp/comments/1u82vnh/i_got_obsoleted_by_ai_so_i_wrote_you_all_a_bofh/

UPCOMING CHANNEL EVENTS

Mastermind LIVE in Omaha NEJuly 30-31st

Register: 

https://kernanconsulting-mastermind.mykajabi.com/mastermind-event

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The episode prioritizes the operational and exit-planning risks associated with MSPs lacking formal contracts. According to Amy , approximately half of MSP business owners operate without managed service agreements (MSAs), a decision that frequently results in reduced business valuation during sale negotiations. Both James and Amy emphasized that the absence of documented agreements is commonly flagged by buyers as a significant risk, often resulting in a devaluation of the acquired customer relationships. This exposes small and mid-sized providers to continuity risks, particularly where customer retention and service transferability are not contractually secured.

Further details outlined by Amy indicate that reluctance to implement contracts stems from concerns about client reactions, particularly in longstanding relationships. She observed that auto-renewal clauses and periodic, non-intrusive contract updates can streamline compliance and reduce friction. A personal account highlighted that, out of numerous customers, only one refused to sign an agreement, and this isolated case did not lead to client loss but necessitated risk pricing adjustments. James Kernan advised that contract clarity—covering terms, automated payments, and built-in annual price adjustments—should be positioned as a value to both parties, reinforcing operational stability and predictability.

Adjacent topics addressed contemporary service risks such as the proliferation of shadow AI applications and exposure to business email compromise. Amy reported discovering over 150 unmonitored AI-powered apps at client sites, emphasizing these as vectors for data exfiltration and compliance gaps. The Guards Cybersecurity Statistics report was cited, identifying business email compromise and social engineering as persistent attack methods, while underscoring that modern threat actors often bypass traditional privilege escalation in favor of capturing identity credentials and tokens. The operational focus for MSPs was advised to shift toward email, AI governance, and identity protection rather than legacy device vulnerabilities.

For MSPs and IT service providers, the main takeaways involve reassessment of contractual practices and a heightened approach to governance and risk management. Documented client agreements are necessary not only for valuation at exit but also for protection against operational disruptions and liability. Simultaneously, providers are urged to implement discovery and control mechanisms for AI use and to refresh security postures in line with current attack methods. The importance of establishing relationships with specialized advisors, attorneys, and alternative financing partners was also articulated, illustrating the multi-layered risk landscape that management teams must navigate for business resilience.

Show title: “How to Start a MSP”

1. How to Start a MSP- Resources: www.itspu.com

2.    New article from Third Tier: Taming Shadow IT before it tames you https://www.thirdtier.net/2026/06/21/taming-shadow-ai-before-it-tames-you/

3.    Guardz released a new cyber security statistics report: https://guardz.com/blog/security-awareness-statistics-msps-cant-ignore/

4.    Thoughts about whether an MSA is needed? Send them through the website: www.smbcommunitypodcast.com

5.    Anthropic Partner Program - https://www.anthropic.com/news/services-track-partner-hub

 

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The conversation focused on the practice of providing managed service pricing to customers during an initial meeting. One concept discussed was that MSPs are encountering prospects who increasingly expect immediate, transparent pricing, with many decision-makers opting to make choices after a single round of vendor meetings. The discussion explored how this shift contrasts with traditional industry advice that recommends withholding pricing until after an in-depth assessment and value-building process. Several points were raised, including the observation that coming prepared—with thorough research on the prospect and a clear pricing structure—can facilitate business wins, especially in competitive settings where prospects expect streamlined proposals.

A key theme that emerged was the importance of preparation ahead of initial client meetings. The discussion clarified that researching client backgrounds, conducting preliminary discoveries, and leveraging prior experience with similarly sized environments enable MSPs to present informed, realistic pricing. The conversation addressed that exceptions remain: in complex environments or when the client lacks clear infrastructure visibility, an assessment may still be necessary prior to quoting. However, these situations are reportedly less common, as clients often provide substantial upfront context during pre-meeting calls.

Secondary topics included practical guidance for financing large product orders, navigating out-of-state project requirements, and managing margin compression. The discussion explored options for financing substantial hardware purchases, highlighting leasing through distributors or manufacturers, encouraging clients to handle their own financing where possible, and considering purchase order (PO) financing to reduce resource strain. For out-of-state projects, building a professional network through peer groups or leveraging distributor partner networks was recommended. Regarding margin management, participants suggested standardizing service stacks, packaging recurring solutions, and reviewing contracts to ensure annual rate adjustments. The use of value-added services, such as cybersecurity and compliance, was recommended to offset margin thinning.

The discussion outlined several implications for MSPs and IT leaders. Responsive, transparent pricing aligns with current buyer expectations but requires robust preparation and established pricing models to maintain accountability and ensure fair risk allocation. For hardware procurement, shifting financial responsibility to clients or utilizing external financing tools can preserve operating capital and mitigate margin erosion. Resilient operational models—incorporating peer collaboration, flexible service packaging, and annual price reviews—enable firms to adapt to ongoing industry pressures including rising costs and tightening margins. MSPs are advised to prioritize accountability in client communications, vendor negotiations, and conflict resolution policies to reduce operational risk and protect organizational wellbeing.

Title:       Should you give a proposal at the first meeting?

MSP Question of the week:   Should you give Managed Services pricing to your prospect on the first meeting?

Topics/Events

Apple Price hike is not welcome news:  https://www.linkedin.com/news/story/apple-hikes-prices-we-know-this-is-not-welcome-news-8956946/
https://www.linkedin.com/news/story/apples-price-hikes-reflect-ai-eras-growing-price-tag-8305905/    

20% price increase ipads, macbooks, iMacs – iPhone unchanged

How do you finance larger product orders?   Lease, PO financing w/ distributor – don’t tell mfr

What if you have a project in another state for a current client ?  How do you deliver?

With margins thinning, how can I increase my overall margin?

Tales from the field:  How do you deal with an irate customer?

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