Questions to ask when updating your enterprise software

The essential questions you need to ask before, during, and after an enterprise software update to maximise potential and minimise costs for your business.

Tasmin Lofthouse working from a cafe

Tasmin Lofthouse

Questions to ask when updating your enterprise software


Jun 22, 2023

Last Edited

Oct 19, 2023

Read Time

6 mins



In the past two years alone, an ‘adapt-or-die’ mentality swept through the world of business as organisations quickly adapted to remote or hybrid work environments.

The ability to adapt has become a foundation for any successful enterprise. If your enterprise plans to stand strong in the face of change, you need robust and adaptable software.

In this article, I’ll share the essential questions you need to ask before, during, and after your internal software update. These questions will help you maximise the benefits of your internal software and ensure it is scalable for whatever changes may lie on the horizon.

The importance of updating enterprise software

Old, outdated software can be hazardous to business performance — team members will struggle to effectively perform tasks, processes will be glitchy or convoluted, and new features will be nowhere to be seen. If it sounds like I’m describing your enterprise software, you could benefit from an update.

Upgrading enterprise software to a modern solution will make sure your software is scalable and future-ready. It will run faster, be more secure, and be easier to adapt. Team members will be able to perform tasks faster (and better) than before, and the costs of using outdated software will become a thing of the past.

But, updating your software isn’t always a straightforward line from A to B. There are a lot of variables you need to consider before making a change.

Common challenges businesses face when updating enterprise software

Before diving in the essential questions for your enterprise software update, let’s address the potential roadblocks you might encounter along the way.

Chances are your existing software has been built to meet very specific needs. It is crucial these custom features are integrated into the new system. This could require your development team to build complex customisations.

Updating internal software is a joint effort. Getting buy-in from stakeholders and end-users will help keep your software update aligned with internal priorities and needs. Failure to do so will result in low adoption rates and a waste of resources.

Another common challenge faced by organisations when updating enterprise software is a lack of resources to train and onboard staff onto the new system. If they don’t know how to effectively use the system it will lead to low productivity, poor task performance, and increased costs. Proper training will maximise productivity and make sure your team knows how to use the software to its full potential.

Not having someone to take responsibility for the software update project can cause bottlenecks. Make sure there is a responsible person overseeing the software update so they can set realistic timelines, drive adoption, and make sure the software aligns with enterprise goals and needs.

Ask the right questions before, during, and after the software update process to address these challenges.

Questions to ask before updating enterprise software

Before you even begin the process of updating your enterprise software, there are several questions you should ask your internal team (the people who will be using the software) and your chosen software development partner (the people who will be setting up the software).

Asking questions at this stage will help you overcome common challenges before they arise and give you a chance to confirm if your chosen partner is right for you. These questions will also help you create the best possible plan for developing your software by providing a clear insight into your software requirements.

Ask your team about their current user experience & future goals

Before changing your enterprise software, it is essential to gather feedback from your team about their experience with the current software. After all, they are the ones who use it every day.

Observe how they currently use the software and delve into their user experience to uncover pain points and frustrations. Take note of the time it takes them to complete tasks too. Exploring their current user experience will help you identify any missing features and areas for improvement.

As well as asking about their current experience, ask your team about their future software goals and needs. Discover what they would most like the new software to do so you can ensure this is built into your software development plan.

Questions you might want to ask at this stage include:

  • How long does it take you to complete tasks using the current software?

  • What is your biggest frustration with the current software?

  • What features are missing from the current software that you would like to see in the new software?

Ask your software partner about compatibility & scalability

As well as speaking with end-users, direct questions towards your chosen software partner.

Before updating your enterprise software, it is crucial that the new software is compatible and scalable. Your new software should work seamlessly with your existing systems and integrations, perform all the necessary functions, and be easy to adapt and scale as your business grows.

Ensure compatibility and scalability by asking your software partner the following questions:

  • How will the new software integrate with our existing systems?

  • Can the new software perform all of the functions our current software handles?

  • Will the new software be secure, reliable, and testable?

  • How easy is it to change or add new features to the new software?

Evaluate if you have any software preferences

And there’s even some questions you need to answer yourself like whether you have any software preferences.

Different solutions come with different benefits so it’s important to understand your software needs and preferences before finding a technical partner.

Determine what technologies you plan to use so you can make sure your chosen software partner is skilled in those areas.

Other questions you might want to ask yourself at this stage are:

  • Do we have any team members who specialise in a specific technology already?

  • How comfortable are we working with new technologies and being on the cutting edge of tech?

The answers to these questions will help you identify your software preferences, if any! Don’t worry if you don’t have a preference — your software partner should be able to help you find a solution that perfectly aligns with your needs.

Questions to ask during the update process

Keep momentum going with your enterprise software update by asking questions. Asking the right questions at this stage can help keep the project on schedule and pre-empt any potential issues.

Maintain transparent, ongoing discussions with your software partner so you can stay informed about the development process and any impacts it may have on your business.

Ask your software partner about the project timeline

Planning ahead and understanding the project will ensure a smooth transition to the new software. Key milestones keep the project on track, allowing you to set expectations and align the go-live date.

For larger software development projects, consider a phased roll out so your team can start using the software while waiting for extra features to be added. Asking your software partner about the timeline can help you effectively integrate the new system into your processes.

Here are some questions you can ask your software partner about the timeline:

  • What is the estimated timeline for the project, including any key milestones?

  • Are there any specific requirements or information we need to provide to keep the project on schedule?

  • When is the expected go-live date for the new software?

  • What is the process for onboarding employees onto the new software, and how long will it take?

  • Is it possible to roll out the new software incrementally?

    • If yes, whats the minimum viable product (MVP) that we can launch with?

Ask your software partner about potential downtime

Ideally, there won’t be any downtime. But when transitioning from one system to another, it can happen.

Ask your software partner about potential downtime when updating your enterprise software. Make sure any planned downtime happens during a time period that will have the least impact on your business.

Some questions you may want to ask your software partner about downtime are:

  • Will there be any downtime during the software update?

  • What will the downtime look like? Who will it effect?

  • How long is the expected downtime, if any?

  • When is the best time to schedule any necessary downtime to minimise the impact on our business?

  • What steps will be taken to minimise downtime?

  • How will we be notified of any planned downtime, and what support will be provided during this time?

By asking about downtime, you can be prepared for it.

Questions to ask after the update

After the software has been updated, assess performance and make sure it meets your expectations. Asking questions at this stage will make for a smooth transition by giving you a chance to address concerns or highlight areas for improvement.

Ask your team for feedback

Check in with your team and get their opinions and feedback on the software. I recommend doing this several times — get their first impressions on the designs, when they first use the software, then check in with them again after they have been using it for a while.

Getting feedback earlier is always better, so even if you don’t have a fully functional product you can still get feedback on the experience.

Ask your team:

  • What are your first impressions of the updated designs/new software?

  • What do you like about it?

  • What don’t you like about it?

  • How does it compare to the old software?

  • How easily can you use the software to complete your intended actions?

  • Is there anything you would change about the software?

Asking your team for their feedback helps you get a well-rounded understanding of whether it meets their expectations and if any improvements can be made.

Ask your software partner for training & support

Your software partner should offer software training as standard (we do).

Make sure they provide training and support after implementation. Ask your software partner to provide training documents for your team and to be on hand for ad hoc support to iron out any potential issues with the software. Use this time to ask them questions about how to get the most out of the software.

Some questions you could ask your software partner at this stage are:

  • What training options are available to help our team effectively learn and adapt to the new software?

  • Who should we contact if any technical issues or questions arise during daily use?

  • How frequently is the software updated?

  • How do we add new features or change elements of the software?

  • Are there any best practice tips you can provide to help us maximise the potential of this software?

I recommend getting training added to the project scope at the start of the new software implementation. But, this step offers a great final opportunity to make sure adequate training and support will be provided.

Final thoughts — ask all the questions to get the best results with your enterprise software

Updating enterprise software can be a complex process. But, by asking the right questions, you can address any challenges and ensure a smooth transition.

Keep your team involved with the process by asking questions that dive deeper into their needs and challenges, making sure the new software meets their requirements.

Your software partner also plays a crucial role in helping you make the most of your software update. By inquiring about scalability, timelines, software features, and training, you can make sure the software aligns with your business goals.

Approaching your enterprise software upgrade with a curious mindset means you can optimise the implementation, maximise the potential of your new software, and drive value for your business.

Reach out to us to take the next steps towards optimising your internal software and driving value for your enterprise.

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