Finding Your Sweet Spot: Why MSPs Must Navigate the Pumpkin Plan and the Innovator’s Dilemma

July 08, 2025

The IT channel is at a crossroads. Over the past decade, many of us have found our groove using strategies inspired by The Pumpkin Plan by Mike Michalowicz— a business methodology that teaches us to focus on what we do best, nurture our ideal clients, and build stronger, more profitable businesses through specialization. 

And it worked well. MSPs who've embraced this focused approach have seen solid results: streamlined operations, satisfied clients, and improved bottom lines. There's real value in knowing exactly who you serve and how you serve them best.

But here's where things get complex. The IT channel is evolving rapidly, especially with AI and new regulations creating new possibilities and shifting client expectations. This brings us face-to-face with what Clayton Christensen called The Innovator's Dilemma in his eponymous book — the challenge of staying innovative while maintaining what already works well.

The reality is, we don't have to choose between focus and innovation — but balancing them isn't always straightforward. The most successful MSPs are finding ways to honor both philosophies, creating businesses that are both efficient and adaptable. Let's explore how to navigate this balance effectively.

The Pumpkin Plan: A Popular Foundation for Success

Think of The Pumpkin Plan as your business's roadmap for prioritizing clients toward growing your business. Just like prize-winning pumpkin farmers who focus all their energy on growing one amazing pumpkin, this approach teaches us to:

  • Seed, Weed, and Feed: Identify your dream clients, gracefully part ways with those who don't fit, and pour your energy into delivering exceptional value to the ones who matter most.
  • Embrace Specialization: Rather than trying to be everything to everyone, become the go-to expert in your chosen niche.
  • Optimize Everything: Streamline your processes and positioning around your core offering to maximize both profitability and client satisfaction.

Take an MSP that decides to focus exclusively on serving law firms. By narrowing their focus, they are able to raise their prices, reduce complexity, and build stronger relationships within their chosen market. It's a clear demonstration of how focused growth can work.

The Innovation Imperative: Staying Relevant

While The Pumpkin Plan gives us a solid foundation, The Innovator's Dilemma reminds us to keep our eyes on the horizon. Clayton Christensen's insights show us that even successful companies can miss important shifts if they become too comfortable with the status quo.

For MSPs, this presents both challenges and opportunities. The rise of AI-powered tools, predictive maintenance, and automated solutions is changing client expectations. When we see MSPs using AI-driven analytics to deliver faster solutions, we're witnessing significant shifts in how services can be delivered.

Importantly to this concept is that "disruptive" doesn’t mean “new” as much as it means "accessible”. Often the most disruptive market newcomers are those offering a lower performance product, but at a price that accesses a new, larger market.

Finding Common Ground: Bridging the Innovator and the Pumpkin Farmer

Here's the thing about these two philosophies — while they might seem contradictory, they can actually work together when approached thoughtfully. Let's look at how they complement each other:

Client Relationships: Deep Roots, New Branches

The Pumpkin Plan teaches us to build deep, meaningful relationships with our ideal clients. The innovative mindset encourages us to anticipate their future needs rather than trapping yourself in the status quo. When you combine these approaches, you get something powerful: the ability to serve your best clients with cutting-edge solutions they didn't even know they needed yet.

Instead of waiting for your clients to ask for new solutions, you can proactively introduce these capabilities because you've taken the time to understand their business.

Service Development: Excellence Plus Evolution

Your core services should absolutely be optimized and systematized — that's non-negotiable. But innovation gives you the opportunity to enhance those services with new technologies and important services as they become more accessible.

The key is to treat new tech not as a separate offering, but as a means to make your existing services even more valuable. Imagine offering framework-based security planning alongside your traditional IT support or using AI chatbots to provide 24/7 client assistance while your human team focuses on complex problem-solving.

We didn’t pull those examples out of thin air, of course. Let’s explore how this interplay between innovation and optimization affects two of the most discussed emergent services in IT:

Exhibit A: Artificial Intelligence

While Artificial Intelligence (and Machine Learning) can be a divisive topic, it’s not going anywhere. Being in the IT channel, you’ve seen the trend as vendors and developers race to add AI to their feature set.

AI isn't here to replace what you do, but it is changing how services can be delivered. Forward-thinking MSPs are discovering practical applications:

  • Automation That Actually Helps: AI-driven tools can handle routine tasks like ticket triage and basic troubleshooting, freeing up your team to focus on strategic work that really moves the needle for clients.
  • Predictive Power: Instead of just fixing problems after they happen, you can now predict and prevent them. Imagine the value you provide when you can tell a client their server is likely to fail next month — and have a solution ready.
  • Competitive Positioning: While some MSPs are still evaluating AI adoption, others are using it to deliver faster response times and more proactive solutions.

Most importantly, it’s wise to consider getting ahead of the demand curve. The more end-users see marketing about the power of AI — regardless of where that marketing is coming from — the more they will seek it out.

Exhibit B: Compliance

Take another example. Compliance is rapidly emerging as one of the most in-demand offerings in the managed services space, driven by a surge in regulatory requirements and heightened client expectations across industries.

For MSPs whose existing clients have minimal compliance requirements, the Pumpkin Plan methodology might suggest ignoring the compliance trend altogether, focusing instead on established, profitable services. However, this approach carries significant risks:

  • Missed Market Shifts: Regulatory changes can rapidly affect entire industries, and clients who don’t need compliance support today may require it tomorrow as laws evolve.
  • Vulnerability to Competitors: MSPs that fail to offer compliance services risk losing clients to competitors who provide comprehensive, future-proof solutions.
  • Barrier to Growth: Over-specialization may limit an MSP’s ability to attract clients in regulated sectors like healthcare, finance, or legal, where compliance is non-negotiable.

To put it simply, while rigorous application of the Pumpkin Plan may suggest ignoring compliance if it’s not a current client need, this mindset risks leaving MSPs unprepared for regulatory shifts and market evolution.

And that's when the Innovator’s Dilemma rears its head again. Large, incumbent companies lose footing when solutions arise that give smaller players an advantage. For example, the affordability and simplicity of a compliance management tool like Blacksmith Infosec makes it easy for smaller MSPs to offer Compliance-as-a-Service without significant cost or resources. That makes such a tool disruptive by nature — especially to entrenched MSPs who fail to operationalize compliance before it’s too late.

The Path Forward

The IT channel is evolving, and the companies that adapt thoughtfully will be well-positioned for the future. We're at a point where we can combine the wisdom of focused growth with the capabilities of emerging technology, though doing so requires careful planning and execution.

This isn't about choosing between tradition and innovation; it's about finding ways to integrate both effectively. Your clients need partners who understand their business and can help them navigate increasingly complex technology. By balancing focus with innovation, you're positioning yourself to meet both current needs and future demands.

The opportunities are real, the tools are becoming more accessible, and client expectations continue to evolve. The question isn't whether you should embrace this evolution — it's how strategically you can approach it to benefit both your business and your clients.

The future belongs to MSPs who can be both focused and flexible. It's a challenging balance to strike, but one that's increasingly necessary in today's market.

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