a·gen·tic a·gil·i·ty

Why Outsourcing DevOps Fails—and How Real Engineering Excellence Starts With Your Team

TL;DR; Outsourcing DevOps often leads to vendor lock-in, legacy systems, and teams that cannot maintain or evolve their own tools. Real engineering excellence comes from building internal capability through partnership, where experts mentor and guide your team to modernize workflows and systems themselves. Invest in developing your engineers’ skills and mindset so your organization can achieve sustainable progress and avoid costly dependencies.

Published on
3 minute read
Image
https://nkdagility.com/resources/Q69amJJ8iJY
Subscribe

One of the most common—and frankly, most damaging—mistakes I see organizations make when they set out to “do DevOps” or pursue engineering excellence is this: they outsource the whole thing to a vendor. It’s a pattern I’ve seen repeated across industries and continents, and it almost always leads to the same set of problems.

Let’s be clear: outsourcing your DevOps transformation is the least likely way to achieve a positive, sustainable outcome for your business. Why? Because you’re not just buying a set of tools or a shiny new pipeline. You’re buying a black box—one that your own engineers don’t understand, can’t maintain, and will inevitably become dependent on. This is the very definition of vendor lock-in, and it’s a trap that’s both expensive and difficult to escape.

Here’s what typically happens:

  • The vendor builds something bespoke, tailored to their own way of working.
  • Your engineers inherit a system they don’t understand.
  • Every time you need a change, you’re back at the vendor’s door—paying for every tweak, every upgrade, every fix.
  • Over time, you fall behind. You’re stuck on old versions, unable to move forward without another costly engagement.

This is exactly how organizations end up with legacy systems that are impossible to modernize. It’s how you get stuck on .NET 3.5, or find yourself still using TFVC or Subversion when the rest of the world has moved on to distributed source control like Git.

So, what’s the alternative? Partnership, not outsourcing.

You need someone who will come in and work alongside your people—not to do the work for them, but to help them do it themselves. This is the approach I take with every organization I work with. I’m not there to rack up billable hours making changes in your system. In fact, I often don’t even have credentials to your environment. My job is to help your engineers:

  • Rebuild their workflows for a modern engineering context
  • Refactor and break down legacy systems into manageable pieces
  • Understand the theory and philosophy behind modern practices
  • Tackle real-world problems as they arise, together

Let me give you a concrete example. I’m currently working with a customer who’s still on TFVC and SDN, with codebases scattered across .NET 3 and 3.5. The challenge isn’t just technical—it’s about mindset, workflow, and incremental progress. How do you even begin to upgrade? Where do you start? What’s the smallest, safest piece you can bite off and deliver value?

Moving from a server-based source control system like TFVC to a distributed system like Git isn’t just a migration. It’s a fundamental shift in how you manage code, branching, releases, and even what you put in your repository. Every decision has downstream implications for your product, your process, and your people.

This is why you need a partner who can:

  • Teach: Explain not just the “how” but the “why” behind each change
  • Mentor: Guide your teams through the inevitable bumps in the road
  • Coach: Help your people build confidence and competence
  • Transform: Enable your organization to own its engineering excellence

My background is in software engineering, not just coaching and training. I’m a Microsoft MVP in DevOps and GitHub, and I’ve spent years as a DevOps consultant, building pipelines, modernizing practices, and—most importantly—helping teams build the capability to do it themselves.

If you want to achieve true engineering excellence, you need to do it on your terms, at your pace, with expert guidance—not by handing the keys to a vendor. Let’s work together to build the skills, the mindset, and the practices that will set your organization up for long-term success.

Ready to move beyond vendor lock-in and start your journey to engineering excellence? Let’s talk.

Huge mistake that organizations make when they’re trying to move towards having a DevOps strategy, having engineering excellence, having that better suite of modern engineering practices within their organization is they outsource it to a vendor.

That is probably the least likely way to result in a positive outcome for your business because you’re giving the engineers in your business a bunch of new stuff that they don’t understand very well, that they perhaps don’t understand at all. Black boxes that this vendor’s created, and you’re probably going to end up with a lot of vendor lock-in. And you’re going to need that vendor to come back and redo things on a regular cadence, and it’s going to be very expensive, and you’re probably going to find that there’s going to be a long time between those things, right? It’s why you end up on old versions of your product in the first place.

So instead of a vendor, you need somebody, somebodies, who are going to come in and help you change that mindset within your organization, start moving people towards engineering excellence. Helping your people rebuild their workflows in a way that makes sense in a modern engineering context. Have them help your people fix their problems.

That’s something that I do with most organizations that I work with. I’m coming in and I’m helping their people do it. I often don’t even have credentials in their system, right? I’m not making changes for them. I’m helping them make changes. I’m encouraging them to refactor the things that they’re working on. I’m encouraging them to break it down. We’re talking about the theory and philosophies on why would you want to move in this direction, and then I’m helping them implement those things as they start hitting problems in the actual technology.

Just working with a customer at the moment that’s on TFVC and we need to move them to git. They have SDN and TFVC and they need to go to a modern source control system, a distributed source control.

They’re on, they have stuff on .NET 3, yeah, .NET 3.5. They have stuff on old versions of everything. And how do you tackle that upgrade? How do you even get started? How do you make that progression towards the smallest piece you can bite off and figure out how to do that first? What are the implications of making certain changes?

There’s a massive implication of moving from a server-based source control system like TFVC or Subversion and then adapting over to a distributed source control system like git, which has a lot of implications of branching strategy. It has implications of what you put in your source code. It has implications of how do you manage your product towards production. It has loads of implications down the line that are part of modernizing your engineering practices.

And that requires partnership, not a vendor. A vendor is going to do the stuff for you. And your people aren’t going to learn anything. You need a partner who can teach, mentor, coach, and engineering transformational experience within your organization.

That’s something that we can help you with. My background is software engineering, not coaching and training, software engineering. I’m a Microsoft MVP in DevOps and GitHub. I have engineering experience in building out DevOps pipelines. I was a DevOps consultant for many years and helping teams get better at building out these modern engineering practices and the implications of these modern engineering practices for their existing practices and building a strategy to get between them is where I bring my expertise.

And let’s get you to engineering excellence on your terms, at your pace, with expert guidance.

Smart Classifications

Each classification [Concepts, Categories, & Tags] was assigned using AI-powered semantic analysis and scored across relevance, depth, and alignment. Final decisions? Still human. Always traceable. Hover to see how it applies.

Subscribe

Connect with Martin Hinshelwood

If you've made it this far, it's worth connecting with our principal consultant and coach, Martin Hinshelwood, for a 30-minute 'ask me anything' call.

Our Happy Clients​

We partner with businesses across diverse industries, including finance, insurance, healthcare, pharmaceuticals, technology, engineering, transportation, hospitality, entertainment, legal, government, and military sectors.​

CR2

Big Data for Humans Logo

Big Data for Humans

Slicedbread Logo

Slicedbread

Higher Education Statistics Agency Logo

Higher Education Statistics Agency

NIT A/S

Schlumberger Logo

Schlumberger

Alignment Healthcare Logo

Alignment Healthcare

ALS Life Sciences Logo

ALS Life Sciences

Illumina Logo

Illumina

Teleplan Logo

Teleplan

Milliman Logo

Milliman

Qualco Logo

Qualco

Slaughter and May Logo

Slaughter and May

Philips Logo

Philips

Lockheed Martin Logo

Lockheed Martin

Trayport Logo

Trayport

Boxit Document Solutions Logo

Boxit Document Solutions

DFDS Logo

DFDS

Royal Air Force Logo

Royal Air Force

Washington Department of Enterprise Services Logo

Washington Department of Enterprise Services

Washington Department of Transport Logo

Washington Department of Transport

Nottingham County Council Logo

Nottingham County Council

New Hampshire Supreme Court Logo

New Hampshire Supreme Court

Department of Work and Pensions (UK) Logo

Department of Work and Pensions (UK)

Capita Secure Information Solutions Ltd Logo

Capita Secure Information Solutions Ltd

Genus Breeding Ltd Logo

Genus Breeding Ltd

YearUp.org Logo

YearUp.org

Slicedbread Logo

Slicedbread

Sage Logo

Sage

Brandes Investment Partners L.P. Logo

Brandes Investment Partners L.P.