How to Use Your Cherwell Replacement to Drive Transformational Change

How to Use Your Cherwell Replacement to Drive Transformational Change

Written by: Erika Flora PMP, PgMP, ITIL Expert, CSM

It may not seem like a Cherwell replacement effort falls into the category of initiatives that can fundamentally change the trajectory of your organization, your teams, how you serve your customers, and even your own career, but it does, and it can. Yet, many leaders are not seeing this opportunity for what it could be, as it requires challenging assumptions and looking at the situation in reverse, with a people and process lens rather than one focused first on the technology.

As with any change in technology, this can be something to dread, or it can be the start of a transformation that will change everything.

How Most Leaders Look at the Cherwell Replacement Problem

What I’ve seen a lot of leaders do in the months since Ivanti announced Cherwell’s end-of-life date is ask their teams to research alternative ITSM products, read through Gartner’s magic quadrant, and ask peers at other companies what their experiences have been with different platforms. They then typically have their teams draft a report informing leadership of the different tools’ functionality – paired against the team’s requirements – with an overview of cost and recommendation on which one to buy.

While this approach isn’t necessarily wrong, it’s not likely to result in long-term success or growth for the organization. Why? Because it’s predicated on a fundamentally limiting question: What would be a good replacement for Cherwell? Starting this process with a technology question rather than asking what the organization is looking to achieve on a larger scale will leave you with, 1. more of the same and, 2. a sorely missed opportunity.

The Best Leaders Start by Asking Bigger, Better Questions

Alternatively, this moment can be used as a springboard to tackle nagging challenges within your organization, automate work that’s currently sucking the life out of your teams (or interactions with customers), and create something new and better – the transformative work that is pretty cool to be a part of.

Here’s a quick story that may help as you look at your own timeline and decision to replace Cherwell:

Early on in my career, I led a seemingly innocuous project to replace a variety of tools (in this case, a combination of Excel spreadsheets, Microsoft Project schedules, scattered documentation, and information that was stored in employees' heads) with a true enterprise project management platform. This project ended up changing the way the entire organization operated from the moment the platform went live.

It was so successful that, beyond dramatically improving the work life of everyone who used it, it put previously-unavailable information into the hands of those who needed it, and changed the path of my own life. The critical point here is that this never would have happened if I had started with the question, “What’s a better version of our existing toolset?”

Instead, I started by considering what we as a company were struggling with and trying to achieve, then seeking answers to questions like:

  • How do we get dramatically better at how we’re managing projects and make it so anyone in the organization has visibility into what work they need to complete and by when?
  • How can we give leaders visibility into what’s going on with our 150+ highly complex, interdependent projects so they can catch issues quickly and give them the support they need?
  • How do we give our leaders information that will help them answer questions for the board of directors, better forecast when we’ll be able to submit approvals for drug candidates to the FDA, and tell investors when we’ll be able to recoup revenue for the company’s research and development efforts?

Asking more transformation-minded questions that are squarely framed on bringing real benefit to the larger organization will get you closer to something that will challenge the status quo, drive a much better result, and make you a hero.

Use This Moment to Think about Your Biggest Hopes and Dreams

The current imperative to replace Cherwell presents a unique opportunity to tackle these challenges, reimagine what’s possible (especially since ITSM technology has come a tremendously long way in the years since your team likely purchased Cherwell), and figure out a way to make things drastically better.

If you can work on answering questions like the ones below, you’ll get closer to solving these larger challenges and meeting bigger goals. Now is the perfect time for this kind of exploration. Think of it as a we-get-to moment rather than a we-have-to moment:

  • What could we streamline and automate (or reimagine entirely) that our executives would be really excited about?
  • What are some of the big themes in our digital vision that we could work to address?
  • What technology-driven successes and/or trends are we seeing in our industry that we could lean into and be at the forefront of?
  • What, if we could pull it off, would wow our customers?

Take a minute to really think about what else you (and those around you) want. Maybe it’s to consolidate several disparate toolsets into a single, seamless, omni-channel platform for customers to buy products and services. Maybe it’s to help improve the speed at which products move from “concept to cash.” Maybe it’s to attract top-tier candidates with the ability to build innovative products and work with cutting-edge technology. Write down your hopes and dreams in question format starting with “How do we…” and figure out how this seemingly small Cherwell replacement project can be so much more - one that drives lasting change and new ways of working across the organization.

How to Find a Partner That Will Help You Succeed

If you want to transform quickly, you’ll need some help. Even when I led transformation efforts as an employee, I always brought in solid consultants who were not only experts on the specific technology but were true thought leaders as well. I found they helped our team get our questions answered quickly, pushed us to think beyond our current state, and dramatically shortened our learning curve. In doing so, it freed up our time to work with our internal stakeholders and run faster with the project. Here are three key characteristics I looked for when selecting a partner. I always tried to work with people who:?

Challenge Assumptions

It may sound counterintuitive, but you want a partner who isn’t afraid to tell you when something’s a bad idea (even when you’re sure it’s a great idea) or that a functionality decision will paint you into a corner – someone who will give you a wealth of bright ideas and options to consider, and ultimately help you and your team improve.

With any ITSM solution, you also want a team with solid ITIL chops (the framework both Cherwell and ServiceNow are based on) and industry expertise. I’ve seen way too many customers have a poor implementation because their implementation team didn’t understand the bigger context of what the organization was trying to do or of best practices – something like this typically starts when you’re working with people who have never sat on your side of the table before.

Understand the People and Process Side of Change

Organizational change requires more than just replacing technology. The best transformations also reimagine how we work and how we communicate – the people and process side of change. Understanding Organizational Change Management (OCM) is critical as you will be changing the way people do their jobs – maybe even the way they think about their jobs – and they need to be brought along for the ride for the change to stick. While the implementation project itself will help you tailor the solution to the needs of the organization, adding OCM helps prepare your people for the solution. You want a partner who has experience in both.

Ultimately, the goal is to come away from this project with new – and challenged – ideas and perspectives. Undertaking a highly complex transformation that’s visible and impactful across a large part of the organization, especially one that is new to you, can lead to significant repercussions (including wasted time, money, and reputational damage) if not executed correctly. You only have one opportunity to get it right, so it’s crucial to collaborate with a partner who is as committed to your success as you are. Here are some questions you can ask to help identify a good partner:

  • What expertise does your team have with ITSM and Enterprise Service Management outside of the platform?
  • How many staff members come from industry and have implemented this product as customers, either on the business side or in IT (for example, if I’m looking at a HR product, who will I work with that has actually worked in HR before)?
  • What’s the mission of the organization and do you have Advisors on staff? What will their level of involvement be on this project?
  • How do you leverage OCM to help ensure our people are equipped and excited for this change??

Hold My Hand and Help Me Define a Plan

As a customer, I was quite demanding, especially when it came to learning. My aim was to gain more knowledge from each interaction with our consultants, ensuring our team could handle things once the platform was up and running. I did a lot of reading on my own and arrived at every meeting armed with a lengthy list of questions. I’m sure it was really annoying for the consultants we hired, but they never let on.

Instead, they patiently addressed my questions and explained the why behind it all. They had been there before, figured it out, and I got to learn from them (not the other way around). I walked away from every conversation smarter and was able to communicate the why to my leaders, as well. They also helped me craft a plan for the essential things that needed to happen in the short-term to get us live quickly as part of Phase I and figure out a longer-term roadmap for rolling out additional functionality (Phase II and beyond) when it made sense to do so as the organization matured and changed.

While having a team of technically strong folks on a project is important, having a world-class team of experts who go beyond writing down what you ask of them and essentially acting as glorified technical order takers is invaluable. Great ServiceNow partners meet you where you are on your journey, explain technical topics in simple business terms, add value to every conversation, and speak your language.

Here are some questions that will help you identify solid technical experts who are also good hand-holders:

  • What’s your team’s approach to training, engaging with, and enabling my team? What does that actually look like day-to-day?
  • How much does the team I’ll be getting understand the toolset I’m currently using as well as the one I’m going to, so nothing gets missed and we can move quickly?
  • What has your team already built that will help us automate what we’re trying to do?
  • How will your team ensure we have a successful project from the perspective of people, process, and technology?

In addition to asking the questions above of potential partners, I highly recommend speaking with non-salespeople at the organization, researching what their people write about, and investigating who they are and what they care about. Look for organizations whose executives are involved in the sales and implementation process and ask to meet the people involved on the implementation team. Don’t just make a purchase based on how much you like a salesperson. Sales teams are notoriously charming, but you won’t interact with them at all once you start to implement the work.


Your impending Cherwell replacement effort can be much more transformative than you may realize. Success from the outset ultimately comes down to asking the right questions – of yourself, your teams, and any partners you may work with. Getting it right is unbelievably cool, and I hope some of these questions help ensure that you do.


Why Beyond20?

As a Cherwell partner for the last decade (and now a ServiceNow Elite partner), our team has helped hundreds of Cherwell customers implement, maintain, and improve their systems. We’ve also led some of the world’s most complex implementations and have deep technical expertise on all things Cherwell. With that said, at our core, we are a company that cares deeply about digital transformation and improving the people, process, and technology side of work, in that order. We are great at answering your hardest questions, providing a unique outside perspective, and can help you build a roadmap to make your technology modernization (and Cherwell replacement) efforts wildly successful and drive positive, lasting change across your organization.

If you're ready to start your transformation from Cherwell to ServiceNow, we're here for you. Get in touch and let us know how we can help.


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