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Tech-Enabled — 12.18.2019

Five Steps to Kickstart Your Digital Transformation Journey

Austin Westerfeld, Business Development

It should come as no surprise that tech is going to be around for the long haul. From insurance, to real estate, to home appliances, companies across all industries are embracing digital experiences as their great differentiator. Embracing digital transformation can elevate all aspects of your business; it can improve your customer experience, gain internal efficiencies, attract the best talent, and provide visibility necessary to make the best decisions for your business.

Despite its competitive advantage, however, digital transformation can still seem like an intimidating task for a traditionally non-tech company. The most intimidating part can often be the first step: How do I get started on this transformation journey? As proud specialists in digital transformation, we can tell you that if you set the right foundation for your digital initiatives, you will set yourself and the rest of your team up for success. To build that foundation, simply follow these five steps.

1. Establish clear goals (and how to assess them)

Just like any long road trip starts with an end destination in mind, your digital transformation should start with a clearly defined goal that aligns with overall business objectives and goals. In order to achieve that alignment, involve key stakeholders in the process and give them the opportunity to see those dots being connected.

A good way to ease into the conversation with key stakeholders is to start small. Discuss the areas of your business that could use a digital makeover. Ask them what they think should be a priority and what should not. This can mean starting with something where people may not even notice the change, then explaining the efficiency around it in order to further grow.

As you set out to establish these goals, make sure that you’re aligning those goals to exactly how you want to assess your performance. If you get out in front of that conversation and set the stage for your own evaluative methods, it will help keep everyone bought in to the process. By getting their buy-in at this stage and setting expectations for assessing performance, you will ensure that even if you take a few unexpected pit stops along the way, you’re all still driving toward the same end destination.

2. Get everyone on board

After flushing out the goals of this digital initiative and establishing how it will benefit the business as a whole, it is time to rally the troops. From employees to the C-suite and everyone in between, there needs to be support and enthusiasm for this initiative. Digital transformation can be intimidating and, just like any organizational change, can result in some skepticism or pushback.

However, if you can anticipate these questions and over-communicate in the beginning, your digital transformation is much more likely to succeed. To achieve company-wide buy in, be sure to emphasize the goal that was agreed upon with all the key stakeholders and bring every conversation back to that goal. Similarly, tie everything back to business outcomes. By emphasizing how this will foster growth, improve efficiencies, and help everyone make more informed decisions, employees will be able to envision what the potential benefits could be for them in their own work.

3. Prioritize

Once everyone is rallied around your digital transformation initiative, it is time to corral your ideas into a prioritized list. Narrowing scope is important to make ideas more actionable and doable, and will help to maintain motivation by dividing the project into bite-sized pieced.

Prioritize these ideas based on impact and effort by balancing the business impact with the time and money it would take to actually bring that idea to life. This is where the concept of MVP will come in handy: what is the initial version that gets your product up and running and allows you to iterate, get feedback, and narrow in on your unique value? When creating this prioritized list, start with the ideas that are high impact and low effort. They will help you build the business case for digital and get you going quickly.

4. Secure budget and set expectations

Bring your digital transformation initiative to life will require time and resources. Asking for a longer timeline, more manpower, or an external partner means a cost to the company, even if these near-term expenditures will save time and money in the long run. To help alleviate the friction of these conversations, shift the conversation from viewing digital transformation as an cost to viewing it as an investment.

This does not mean overpromising on what you will deliver: set realistic expectations for everyone upfront. Do your research upfront and understand what a digital initiative means for your specific industry, how it could benefit the end users, what your competitors are doing, and what the greener pasture could be with this transformation. Then translate that research to realistic, actionable resource requests that show exactly how you plan to reach that greener pasture.

5. Assess performance and craft the right story

You’ve secured the stakeholder support, team buy-in, and resources to implement your digital transformation. However, as transformative as the process may be, you need to critically assess how this process has impacted the business. At the beginning of this journey, you established a goal. It is now time to look back at that goal and use the key performance indicators you set to gauge the success of your digital transformation.

Use these indicators to evangelize the digital initiative throughout the organization. When done correctly, your team should be able to feel the impacts that this digital transformation has had on their day-to-day work, but by tying it back to business impact you can be confident that you’re telling the right story and generating business value.


Digital transformation can elevate all aspects of your business. It can make your team better and your value clearer in the process. While digital transformation should not be intimidating, it should be approached with intention upfront in order to establish the right foundation.

After all, this digital initiative will require a significant investment and buy-in from the whole team, but when approached with these 5 steps in mind you can set goals, get team buy-in, secure budget, and evaluate your performance of your digital transformation journey.

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