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The Hard Thing About a CMS Upgrade: Getting Approval

March 28, 2024
Chase Richards

You already know why you need to upgrade your CMS. You’ve been on this one forever, and half the pages are hacked-together and need a dev ticket to update. It takes forever to respond to requests, a bunch of ticketsare blocked forever, and you’re always fighting fires because half its moving parts are still made of wood.

The problem isn’t always technical. Sometimes you findyourself in a situation where everything depends on an antiquated system somewhere that nobody can touch. But in most cases, it’s just about going through the process.

We’re old hands at that, and if you need some advice withplanning your upgrade or delivering the migration, get in touch and we'll lead you through it

The hardest thing about an already hard thing

Managers and developers are roughly the same shape and size, but there the similarities end. Unless you’re lucky enough to have a budget holder with a dev background, it’s not going to be a case of putting forward a logical argument and a project plan.

Most of the time what you’re suggesting will tie up resources, and presents management with a large commitment offering (on the face of it) intangible benefits.

What follows is not a guide on how to do a cost / benefits analysis for your CMS upgrade, but rather an exercise in political story-telling, from someone who’s worked both sides of the conversation.

1.      Make sure it actually IS a top priority

Tough love out of the way first: it’s important to youand to your developers, and the website stakeholders who depend on you. But try to get a picture of the bigger organizational priorities first.

Look for things like:

* Is there a big resource/tech freeze going on?

* Is the company undergoing a merger / acquisition/major PR disaster?

* Is the website a major Marketing/Sales funnel, or does it function more as support material for the Sales Team?

* Could we get along fine, but it’s just a bit rubbish?

2.      Timing is Everything. And Time is Money. And There is no Money.

As a manager, I never failed to get requests for major new tech purchases, new resources, or major unfunded projects the moment the budgets had just been signed off.

Yes, I know it’s important. But if I ping Finance now and say I need to add a big line item, the authorities will never find enough of me to make a positive ID.

Know when the budgets for the next quarter/year are being worked out – not when they get signed off, when the initial conversation sand first drafts start happening.

MAKE SURE not only your manager knows about your CMS upgrade project, but that all the managers of all website stakeholders know about it. If someone knows they won’t get their request done next quarter without that website upgrade thing, they’re more likely to mention or support it in budget discussions.

3.      Show them the money

The person you’re trying to sell this to has to probably has to sell it to someone else. Practice taking your detailed analysis and proposal and summarizing it in 2-3 very brief slides, with 1 or 2 ideas on each of them.Use pictures and small words, but most of all, use money.

Don’t lead with the security concerns or the drag-and-drop editor or the burning plastic smell from the server room when you do deployments. Lead with how much we’re going to save or make.

Here’s how to do this (simplified):

* Work out what types of website activity makes the money, and which of these are blocked by the CMS upgrade

* Find a dollar value for them that you know people generally agree on

* Imagine you get these dollars 20-30% faster

* Sprinkle in the SEO/Conversion benefits of faster page loads and lower bounce rates

* Speculate that you may not need that agency or contractor who keeps things from falling over anymore. Right under the bus.

4.      Pinpoint the exact moment it All Goes To Hell

If your CMS version is really old and nearing End-of-Life ,you have an easier story to tell. In most cases this means glaring security holes, broken functionality, and rapidly degrading performance.

The trick is putting this in a way that terrifies people. Give examples of security breaches due to not upgrading software. Be sure to mention it to the PR team and anyone you run into from Legal.

Explain that this upgrade is essential before X date, and it’s going to take at least this long, so we’d better get cracking.

5.      Give them 3 doors to choose from

Pitching something as a choice between Basic, Better and Best serves two important functions in persuasion:

·        It reduces the tendency to see it as a “yes or no” decision, and rather a choice between alternatives

·        It gives your manager a sense that you’ve reallythought things through and are prepared to compromise on everything you want,and be considerate of their other priorities.


If you need help making the case to management for why youshould upgrade your CMS, we provide a free CMS audit and business case serviceto new clients.

Pop us a message, and we’ll help you get it done