The 7 Stages of Software Grief

Captain! Time to jump ship!

The 7 Stages of Software Grief

You know that ache you feel, way down deep, every time you click the icon to open the most dreaded application ever? It’s called Software Grief.

Yep! It’s that agony of having to work with this awful piece of software, having your team cry to you about it every chance they get, then reminding yourself of how much money you spent on it.


A quick story

Last week I found myself at the conference table with two company directors. It was the proverbial “come to Jesus” meeting about a piece of management software.

No one in the company had a positive thing to say about this software.

It was slow

It didn’t make calculations correctly

The user experience was horrible

Their support was terrible

I could tell just by using it for five minutes that the back-end programming they were using wasn’t modern and wouldn’t be well supported in the future.

The talk began about how we can work around its shortcomings and ‘make the best of things’. Typically this means developing workarounds that slow everyone down and cause a lot of double entry.

I just spoke up. “I may not be popular for saying this, but we need to find a replacement.”

“Does anyone disagree?”

There were a few raised eyebrows, but no one spoke up.


How many of you feel like having this conversation? How many software applications do you use in your business that you absolutely hate?

Hate is a strong word, and it’s well deserved!

After 9 years of doing systems support and administration, I haven’t found one thing that brings out more complaints, frustration, and pure hatred in people than bad software…like really really bad software.

It could be old, clunky slow and have the worst user interface. But it may be brand new, clunky, slow and have a bad user interface. I’ve seen both.

I still get shivers roll down my spine when I see a demo for a new piece of software and it still looks like it was made in 2001.

A lot of software companies either don’t realize how fast the market is changing around them, or they are fearful of change because it means they have to rewrite all of their code.

OK…enough about the software company’s problem. You have a problem with their software and it’s time to fix it.


There are 7 stages to getting over this software grief

  1. Realization
  2. Denial
  3. Panic
  4. Mindset Shift
  5. Research
  6. Convincing
  7. Moving on



You will likely find this to be a slow process that happens over time. When you first buy new software, you usually really like it for quite a while. You did some research up front and it accomplished a task. As the months or years pass on, the software becomes aged, it runs more slowly, and you discover that you need more features than it offers.

If you are the unfortunate one who just purchased a brand new piece of software, or subscribed to a software service, and right out of the gate you are having problems, I know your pain all too well.

Don’t worry. It will all get better right?



You’re surely telling yourself, “The software company will get its act together and build in those features that I really need.” They may have just had a huge influx of users so they can finally afford to update their code and interface (that’s techie speak for how it looks).

Chances are, no.

You can tell very quickly what a company’s development mindset is by the way the customer service team reacts to your requests. If you get a cold message about it going into their queue of feature requests and “someone will look into it”, chances are that nothing is going to relieve your software grief. If, on the other hand you get a bright and joyful response thanking you for your creative feedback and they give you a definite answer on how your request is going to be handled, you’ve got a better shot here.

The last thing you want to do is panic.



OK, you didn’t listen and you are panicking anyway.

You have hundreds, if not thousands of dollars invested in the setup and ongoing cost of the software. You have a team that is shoehorned into it and built their own workarounds and processes for dealing with it. How dare you think about disrupting that organized chaos!

Ok, take a quick breath —

Unless you are operating in a totally obscure business category, there are likely dozens of other software companies out there competing for your attention. They know who their competition is, and they know who the market leaders are. Most importantly, they know the data that goes along with your business and how it should be maintained.

Now is the time to take your first action. Export or backup your data!

Claw and search through your existing application and find some way of getting your information out of there. If they are even halfway decent, they hopefully provided some way of getting information out to a CSV (kind of like a spreadsheet) that has columns and rows of your raw data.

If you can get this data in your hands you have a tremendous chance of making it out of this in one piece.

I can see the panic is starting to subside a little bit.


Mindset Shift

This is probably the hardest stage for most people. This is the conscious decision to make a change, that will bring your team out of the slump they are in, and allow productivity to finally move forward.

You can’t go down with the ship! By continuing to stay on board with horrible software that your team hates, the productivity and loss of moral is much greater than the cost in switching.

You make need to take a few nights to yourself to think all of this over. It can be a huge decision. If you have some key stakeholders that use this software within your team, you need to consider how you are going to communicate this change with them first.

If the change is so radical that it may affect how your team does their job, you may need to consider updating your employee handbook to reflect the expectation you have. (you have an employee handbook right?)

Now where do we start to actually get the ball rolling?



It’s time to get the core team together. You need to go through your current software with a fine tooth comb and write down what is working, and what isn’t.

  • How is their customer service? Do they respond on time? Do they care?
  • What is the user experience like? Is it suffering from bad software design?
  • Is it too complicated? Are simple processes a daunting task?
  • Is it buggy? Are you plagued with crashes, slowness, and inaccuracies?


Now it’s time to build your wishlist. Prepare your notes on what you are looking for in your new software, what it needs to do, and are your GO/NO GO requirements.

Now that you are clear about what you want, and what to avoid. It’s time to find some alternatives. Here are three places to start your research.

  • Capterra
  • Software Advice
  • Getapp


Get a demo. Be completely open with the sales person about what software you are using know and why you don’t like it. Make them give you creative examples on how to solve those problems with their software.

Now present the alternatives to your team.



Are you a good salesman? I certainly hope so.

Getting a team to make change is not for the faint of heart. It’s essential to get everyone on board.

You may get really lucky and they have been wanting this switch for years, but were too afraid to bring it up to you. Let’s hope that’s not the case too much. We want your team to have open

channels of communication with you at all times — but that’s a different blog post.

The best way to start this meeting is to identify the problems. Make them feel the pain of the current software so that they are already craving a solution.

Now you can give them a breath of fresh air by talking about or showing the new user interface, the improved features, and great support experience.

Get some feedback. Let them talk openly and ask questions. If they asks something you don’t know, write it down to follow up on with your sales person.

Ok, now look around the table, because I think you are ready now.

Final question… “Is everyone on board?”


Moving On

Now it’s finally happening! How good is this feeling?

You trusted yourself and your team to be strong enough to work through this change. Even if your team is 1 other person, what you have accomplished is HUGE!

Now let’s make sure you don’t make any mistakes that would get you back in the same position you were with the old piece of junk.

  1. Ask questions! Ask too many questions. It’s better that all expectations and hiccups come during the sales & implementation stage rather than when your team is a year into it.
  2. Document and record everything. It’s quite common for a sales engineer to promise a feature and the implementation team not able to deliver. If you have your conversations (yes your sales calls) and demos recorded, you will have something to reference back to and show the implementation team.
  3. Let your team be involved with the development process. They may have some insight into how certain areas should be organized, or how workflows should be modified.
  4. Don’t throw in the towel. If you do run into some bumps, push the sales team or implementation team to work through it. Make them do the heavy lifting, that’s why you are paying them.


Going through a software shift can be a stressful and time consuming process, but the benefits far outweigh the headaches you and your team will have to struggle through if you keep working with horrible software.

If you need any one on one help, you can work with me here.


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