Best Practices

11 Digital Transformation Questions to Ask for Success

Jonathan Friedman
April 7, 2021
11 Digital Transformation Questions to Ask for Success

Are you noticing a drop in productivity across your organization? Perhaps you are experiencing inefficiency with manual processes. No matter why you are thinking about undertaking a transformation, it would be best to ask the right digital transformation questions to ensure the switch is a success. According to McKinsey, only 16% of companies say their digital transformation has succeeded in improving performance for the long term.

Keep reading to learn what digital transformation assessment questions to ask at each step of the way.

11 digital transformation questions to ask for success

1. What is the goal?

The first digital transformation question to ask is in regards to your organization's goals. Consider what you want from the transformation and how you want it to help you and your team.

Most organizations want to digitize their operating models, and digital tools can help with that. Some less common reasons include interacting with partners digitally or releasing new products and services.

You can have multiple goals for the transformation. Before you start, you should get clear on those goals and document them in a charter. That way, everyone involved can understand how they align with the company's strategy.

2. Whom will the change affect?

When outlining what questions to ask about digital transformation, don't forget to ask whom the change will affect. Most digital transformations will involve a few departments or business units.

In some cases, your transformation may affect all employees and teams. No scenario is best or most successful. However, understanding whom the change will affect means you can better prepare the employees in question.

Once you've identified whom the change will impact, senior managers must create a sense of urgency in making transformational changes. That doesn't mean making the employees think their jobs are on the line. Instead, it should be a rallying cry for the company's importance as a whole - the company's survival long-term, if you will.

3. What technology will you use?

Next, you should ask what technology your organization will use for each part of your digital transformation. You can use simpler technologies, like hard drive storage and digital file systems.

Your organization can also opt to use more sophisticated technologies. Artificial intelligence (AI) and the Internet of Things (IoT) tend to result in more successful digital transformation within organizations.

Advanced neural engine machine learning techniques can also help your digital transformation be a success. If these more sophisticated options are right for your organization, they can help you ease the transition.

However, you should choose the technology that will work best for your company. If all you need is a digital filing system, stick with that. You can use something like AI to help categorize it for an even easier transition.

No matter what technology you use, consider how it will impact the switch. You should make sure everyone can use the technology necessary for their roles.

4. How many technologies will you use?

In some cases, you may decide to use multiple technologies for your digital transformation. You can start with one and add more as you need them, but you may want to start with more.

It may surprise you, but using more technologies doesn't always lead to more failures. Of course, there is a higher risk of something going wrong. However, if you choose the right technology and tools, it can be successful.

Traditional web tools are some of the most common ones to use in your digital transformation. Whether you need to build a massive cloud network or program a unique software update, you can use as many technologies as you need.

Consider what makes sense for your organization. You can get input from employees in all departments that the technology will affect.

Now, the decision will be yours and that of the others leading the project. Still, getting input from others can ensure you have accountability with the project. If you talk about the technologies you'll use, you can give yourself the motivation to stick with them.

5. Who will lead the digital transformation?

Next, your list of digital transformation questions should cover who will be in charge of the project. We advise that you identify the working team, an executive sponsor, and a project leader. An executive sponsor should be someone from the c-suite that can help block and tackle, and communicate progress to peers. Then, a project leader should be someone who's compensation is tied to the transformation's success. This project leader will be driving the day-to-day.

Consider what roles you will need to fill in the digital transformation. While you can't have every employee work on the project, you should have a diverse team of employees. These employees should be brought in early as well, to help with the strategy. Additionally, senior leadership should encourage the working team to think out-of-the-box and challenge the old way of thinking.

The more functional areas you can represent, the better you can prepare for your transformation. Each member of the leadership team can report back to their team on project updates and information.

Your leadership team can also assist others in training and coordinating the transformation when you're ready for that step. Then, you won't have to spend as much time going around answering questions or fixing problems.

6. How can employees and partners use new technology?

Having employees from different products and functional areas working together can help you answer this question more efficiently. It would be best if you thought about how employees and business partners can use the new technology. If possible, digital self-serve technology that allows multiple use cases can help ease the transition.

Think about how each department affected by the change will use the new system. If the change is complex, you also need to account for some downtime as people learn how to use it.

Your digital transformation doesn't have to be easy at first. However, it has to be comfortable enough for people to learn to use it efficiently. If they can, then you will have a successful digital transformation.

7. Will the change make information easier to access?

Depending on the goals you have, you may want to ask this next digital transformation question. The change ideally should be more comfortable after everyone gets used to it. Perhaps your current system is time-consuming, so digitizing it will make you more productive.

If the change helps a few departments the most, you may want to start with those areas. You may decide not to include specific departments that don't need the new system.

Perhaps the accounting department already uses accounting software. Your employees may not need a new digital system for tracking invoices and bills.

As you ask this question, you can determine what departments to include at what time. If you want to have the whole organization, you may want to pilot the new system with one group.

You can use that team to pilot the new system for real work. However, you can easily track and catch issues. Then, you can fix those issues before they affect the entire company.

8. What is the communication plan?

Establish a clear communication plan that outlines who should be communicated to, how they should be communicated with, and when they should be communicated with. Your plan should include employees, but you may also want to communicate with clients, partners, or contractors. Think about the transformation and every stakeholder.

As you start to implement the digital transformation, you need to have open lines of communication. Start by talking to employees before the change begins. You can leverage your clearly defined change story for why the company is undergoing a digital transformation. Then, you can provide updates after you meet with others leading the project.

9. When should the transformation take place?

Hopefully, you already have an answer to the digital transformation questions regarding whom it will affect and how many people it will involve. Answering those questions is essential before you can schedule the switch.

You need to schedule your digital transformation so that it doesn't disrupt standard workflow. Avoiding disruptions is especially crucial for customer-facing positions, like sales, account management, or customer success.

If your transition affects all departments, consider spacing out the change between those departments. You can transfer one area of the business each day and do so before or after hours.

And if something does go wrong at the start, other departments can still work. It will take longer to make your digital transformation, but it can help everything be successful.

10. How flexible can we be during the transformation?

For your digital transformation to be successful, you need to be agile and flexible. As you plan out the new system, you will almost certainly encounter issues. Give your organization as much time as possible to acclimate to the new system. If you can't take any time to train people beforehand, you'll need to be even more flexible.

While some digital transformations are straightforward, others are more complicated. If you're using multiple complex technologies, you'll need to account for potential problems.

Your leadership team should make themselves available for questions and problems from the start. Other employees can then have multiple people to go to with questions, saving you and everyone else time.

11. What training will be necessary?

Lastly, it would be best if you considered what training you would need. Think about how different the new system is from your current one. Consider if any employees may already have the experience to help them with the switch.

If possible, everyone should have a training session on the new system before using it. You can use that training session(s) to ensure each employee feels comfortable using the technology.

Manage your digital transformation with TrueNxus

TrueNxus understands digital transformation. Our platform is built to enable your entire organization through your digital transformation initiatives. It has everything that you need to change the way your company operates.

In any digital transformation, you need help with:

Here's a look at some of TrueNxus's features:

1. Multiple views

Personalized views illustration

With any digital transformation, people require different ways to visualize work across time. Not only that, but each individual specializes in a specific domain, and as such, each thinks about work differently. To ensure successful planning and execution, you need software that provides personalized views that make sense to everyone involved in the change. These views need to be in sync as well.

TrueNxus provides you with the following views:


Plan screenshot

A list is a table that allows you to manage your cross-functional projects easily. You can organize your project work into groups such as workstreams or any logical way to categorize tasks.


Product roadmap or project timeline screenshot

With TrueNxus's Timeline, a Gantt-chart like view, you can visualize your project plans across time. It lets you understand how all of the work fits together. You can make updates to the project plans through an interactive interface.

3. Automated project status reports

Automated project status reports illustration

We understand that each cross-functional team member is busy balancing multiple priorities, from your day-to-day responsibilities to various programs and projects. Therefore, TrueNxus successfully executes monitoring and controlling projects by automatically analyzing the project's health in real-time, giving senior leadership and the team the insights they need to make decisions and move the ball forward.

4. My Work

View all of your work in one place

Another essential thing for everyone involved in a digital transformation is understanding what you're on the hook for delivering. With TrueNxus, you can view every task and every dependency vital to you, across every project, in one location, ensuring success.

5. Dependencies


Additionally, we know that you don't want to let your colleagues down or be let down. You can ensure the successful delivery of programs and projects through collaboration and documenting task dependencies. By doing so, you can be accountable when others are reliant on you. You can understand dependent tasks, change implications, and adjust course as needed.

6. Automated notifications

Automated workflows - notifications

No matter your role in any digital transformation, you can also successfully execute work by leveraging software to notify when changes occur. With TrueNxus's 20+ out-of-the-box automated notifications, you will have the transparency you need to stay in-the-know.


Cross-functional team collaboration - comments

Additionally, the entire cross-functional team can ensure project plans are successful by collaborating directly in the app. With TrueNxus, you can communicate with colleagues, clients, consultants, and contractors in one place.

8. Project charter

Charter illustration

Lastly, you can leverage OKR and create a project charter. You can ensure the successful execution of projects by documenting and aligning the project's objectives, benefits, and risks from the very beginning. TrueNxus is the only software that has a project charter directly in the app.


When you decide to digitize your organization, you need to ask the right digital transformation questions. Asking questions about digital transformation early on can help you avoid problems later.

Additionally, you'll want software so that you can manage the transformation.

We at TrueNxus want to be a part of your digital transformation, to make this process easier and smoother for you and your entire organization. Contact our sales team and let us help you get started in your transformation.