With AI reshaping the Microsoft 365 landscape and low-code adoption at an all-time high, enterprises are under pressure to modernize workflows, whilst remaining in control of their systems.
This month, we’re in conversation with Cloudwell Senior Developer Mike Ostrander. With over 20 years of experience working with Microsoft’s collaboration tools, he specializes in building and maintaining enterprise-grade solutions across the Microsoft ecosystem.
Here he shares how IT leaders can balance innovation with governance, the secret to successful cloud migration, why you should nurture your citizen developers, and why starting small can drive big results.
Kelvin Helmholtz (KH): Tell us how you became involved in the Microsoft space.
Mike Ostrander (MO): Roughly 20 years ago, I volunteered to build an intranet site for my department. My organization, at the time, was part of Microsoft’s early adoption program, transitioning from WSS 3.0 to the upcoming MOSS 2007.
From the very beginning, Microsoft’s collaboration tools have been central to my IT journey. In the early days of SharePoint, the platform quietly demanded a wide range of skills, which led me down paths ranging from infrastructure to web development and everything in between.
KH: Enterprise adoption of low-code tools like Power Platform is accelerating but scaling them responsibly is a major concern. What does successful scale look like to you, and how does Cloudwell help clients strike the right balance between agility and governance?
MO: While the technical approach may differ, the fundamentals remain the same. With features like Git integration, pipeline deployments, dedicated environments, Power Fx, and deep ties to the Microsoft 365 security framework, the challenge is not so much with the platform itself but with its broad user reach.
Low-code initiatives often begin with enthusiastic power users, but as adoption grows, organizations struggle to maintain solutions that weren’t built with scale in mind. Fortunately, many of these applications can be stabilized and matured through iterative improvements—with minimal disruption to the business.
When it comes to agility, it’s about aligning risk tolerance with organizational goals. Increasing scale also increases operational and labor costs. Do you need dedicated environments and pipelines? Not always. Each approach—from a simple SharePoint list to a multi-environment Dataverse solution—comes with its own risks and mitigation strategies. Reconcile that with the classification of each tool (operational, business critical, mission critical). What is the impact of an outage? What does mitigation look like? How does that align with current SLA’s? Each tool should be scaled accordingly.
KH: Many enterprises are still burdened by manual or outdated processes. What types of legacy workflows do you see as “low-hanging fruit” for automation, and how do you modernize them without disrupting the business?
MO: It can be tempting to look for the least critical business process as a low risk starting point to modernize a process. What I find often leads to a successful outcome, is to find a high impact business critical process in need of improvement, review pain points with the business and identify a small piece of functionality within this process to start with. In this way, you are demonstrating high impact/high visibility improvements while minimizing disruption.
KH: AI is rapidly reshaping the Microsoft 365 ecosystem. How are you helping enterprise customers integrate AI and Copilot into their automation strategies, and what are the practical challenges that come with it?
MO: The most important step isn’t immediate adoption, but thoughtful planning and preparation to ensure long-term success. AI represents a dramatic and unconventional shift from traditional software.
We certainly work with clients that are ready to jump in the deep end, but for those that aren’t, we help align their information architecture, security landscape, and governance framework so they’re positioned to hit the ground running.
KH: Enterprise migrations often carry significant risk and complexity. Can you share an example of a migration project you’ve led, what the business drivers were, and how Cloudwell delivered a successful outcome?
MO: Migrations are complex, but experience has taught me that thorough planning is the key to success. I recently led a SharePoint migration for an international pharmaceutical organization—a project that had been stalled for years. With support for SharePoint 2016 nearing its end, the business needed to accelerate the effort.
Cloudwell was brought in to lead a global migration involving hundreds of sites owned by teams across multiple regions—all within a tight five-month timeline. We began by finalizing the information architecture and governance model, then partnered with marketing to roll out a communication and training strategy.
Each site was reviewed and classified with a clear migration method, feedback loop, timeline, and cutover plan. Site owners were empowered to make informed decisions based on the detailed guidance we provided.
The result: a smooth, on-time migration that allowed the organization to close a long-standing chapter.
KH: A lot of companies start small with Power Apps. How do you help organizations shift from building isolated apps to implementing a broader Power Platform strategy that supports enterprise-wide transformation?
MO: I highly recommend moving PowerApps development into a dedicated power platform environment. Utilize solutions to containerize the various aspects of your app (connections, reusable components, related flows, environment variables etc).
When ready, export to a managed solution and import to your production environment (or better yet, use pipelines for this). By using managed solutions, you are preventing potentially untested changes from being made in production.
Ideally you would also use a separate test environment for proper testing, but if you’re starting from scratch, it can be beneficial to get familiar with the process before ramping up to a full-blown software development lifecycle process.
KH: With more citizen developers in the mix, how do you advise enterprise clients on setting up guardrails, like environment strategy, DLP policies, and app lifecycle management, without crushing innovation?
MO: Work with your citizen developers. At the end of the day, these folks are providing value to your organization. The last thing you want to do is crush innovation. Start small and allow citizen developers to become familiar with the new process and overcome technical challenges without excessive impact to their productivity. Listen to feedback thoughtfully and address concerns when possible.
KH: Having worked across industries, from healthcare to finance to the public sector, what challenges tend to repeat themselves? And where do you see industry-specific needs demanding tailored solutions?
MO: In mission-driven sectors like government and healthcare, the core focus is on serving people. Revenue generation exists, but primarily to sustain or expand services. This creates a unique environment where success is measured by impact, accessibility, and compliance rather than growth metrics.
As an IT professional, this means working within strict regulatory frameworks, prioritizing accessibility, and designing solutions that support long-term stability and public trust.
In contrast, commercial sectors like finance or retail are often driven by efficiency, scalability, and competitive advantage. Here, automation and modernization are tied directly to ROI, and there’s typically more flexibility to experiment with emerging technologies.
These differences shape everything—from how projects are scoped and funded to how solutions are deployed and maintained. Success depends on understanding both the technical landscape and the organizational mission behind it.
KH: What trends or technologies are you most excited about on the horizon and how is Cloudwell positioning itself to help enterprise customers stay ahead in an evolving digital workplace?
MO: I recognize there’s a ton of innovation happening with Copilot, but what really excites me is the evolution of Microsoft’s low code tools. Power Platform has matured to the point where nearly everything needed for a proper enterprise SDLC is available.
Having worked on both custom development and low-code projects, I’ve seen firsthand how low-code allows you to skip the boilerplate and focus directly on usability, functionality, and reliability. While this doesn’t always lead to faster development times, I’ve found the maintainability factor to be excellent.
Organizations appreciate the transparency and sustainability of Power Platform tools—there’s less reliance on external expertise and more ownership over the solution. It’s a win for agility and long-term success.
That being said, there are times when technical requirements are simply too complex for low code. In those cases, we turn to other tools in the MS ecosystem such as SPFx and Azure services.
If you’re looking to modernize your workflows, scale your Power Platform adoption, or you have a migration project that’s stalling, reach out to our experienced team.