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How to Build a Successful Digital Transformation Strategy

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Successful digital transformation means gaining consensus from your organization.

What Does Digital Transformation Mean to Your Organization?

Digital transformation has had a remarkable shelf life as a buzzword. We get it, it’s cringe, but you might as well get used to it because it’s here to say. Part of the cringe factor is the misuse or overuse or misuse of the term over the past year. A consensus definition of digital transformation remains elusive and fragmented at best. The only thing leaders unanimously agree on is that transformation is happening now, and, frankly, that is obvious. We’ve seen countless businesses get vacuumed up through the pandemic as they simply didn’t have the agility or the mindset to respond to their markets. Digital Transformation is here to stay. Embrace this cringeworthy buzzword, and build out a strategy that will bring transformation to your organization and keep you competitive in 2023 and beyond.

Because digital transformation is a relatively new concept, no map is tailored to businesses showing them how to ‘transform digitally.’ Meanwhile, software vendors are laughing all the way to the bank, taking advantage of the situation by positioning themselves as the answer to all your problems (before they even asked you what your concerns are!). While great for giving you a list of options (by default sorted by who’s marketing team pays the most) doesn’t give you the answer to what you genuinely need for digital transformation. How can they, when they don’t know your needs or overarching reasons for transformation?



One of the reasons we started Olive is that CIOs and IT leaders are aware of the need for digital transformation, but few know where to start. Moreover, fewer yet have taken the time to clarify what digital transformation means individually, what success looks like, what the benefits are and why it is crucial. So let’s clear a few things up.

What is Digital Transformation?

First things first, digital transformation isn’t just a fad that will blow over. On the contrary, it is a concept that is changing how business is done. The complication is that it looks different for every company and every industry, which is why we have not yet landed on a clear definition.

The Definition of Digital Transformation

McKinsey defines digital transformation as “an effort to enable existing business models by integrating advanced technologies.”

CIO.com quotes George Westerman, MIT principal research scientist and author of Leading Digital: Turning Technology Into Business Transformation; “Digital transformation marks a radical rethinking of how an organization uses technology, people and processes to fundamentally change business performance”

Salesforce.com argues that “Digital transformation is the process of using digital technologies to create new — or modify existing — business processes, culture, and customer experiences to meet changing business and market requirements.”

Often, digital transformation begins with the introduction of technology or software to solve a business problem. It’s where most people start – because it boils things down to individual issues. However, complete digital transformation goes much deeper.

At Olive, we define digital transformation as adopting the right technologies and processes that transform companies’ internal and external-facing operations to achieve an overarching business goal. Our definition examines entire departments and systems and reimagines them by infusing technology in place of inefficiency.

Digital Transformation Examples

An example for a retailer could mean the global introduction of a BOPIS (buy online pick up in-store) system that integrates with the current POS (Point of Sale) system to speed up sales, with the overarching goal of optimizing the customer experience.

For the healthcare industry, it could be leveraging Artificial Intelligence to help cut costs of ongoing health operations and impact the quality of care for patients.

For manufacturing, it may include stripping down entire systems to eliminate redundancies with the use of technology. For many verticals right now, CEOs are asking CIOs about their cloud migration strategy.

Digital transformation doesn’t just ‘happen’ when a new technology is purchased and implemented.

The most critical word in Olive’s definition of digital transformation is the word adoption.
A successful digital transformation will see game-changing digital solutions used with high adoption rates from your organization to solve business problems. Solutions either replace outdated and inefficient technology or processes or restructure entirely how crucial business results are achieved. But if your end-users are not bought into the technology, there’s a high chance they will reject it. Poorly adapted technology, no matter how renowned it is, is the wrong technology.

“But digital transformation is not just about tech; it’s about people!”

The key metric to measure the success of digital transformation is user adoption. Ensuring that you take your time to figure out who needs to be heard and include these stakeholders in the process will lead to high user adoption later. In addition, valuing the right voices creates a compounding benefit throughout the software buying process. With the correct input and validation, you guarantee a seamless implementation and high user adoption.

What are the Benefits of Digital Transformation?

Digital answers to traditional problems are borderline mandatory for many businesses. Either customers’ expectations make old-school methods redundant, or competitors are getting ahead with new digital solutions.

Despite being buzzwordy, digital transformation comes with some eye-watering benefits. Let’s take, for example, a retailer looking to drive transformation:

  • Improved customer experiences – E-commerce and digital sales mean customers no longer have to talk to people to buy products and services. Streamlined digital funnels bring more revenue with a lower cost per unit of sale for the business.
  • Boosted efficiency – Digital transformations pride themselves on dissolving bottlenecks, communication blockages, and inefficiencies. Automating redundant tasks and leveraging data to make better decisions faster results in time and money saved.
  • Advanced marketing efforts – Data collection and analytics are changing how marketing works. For example, campaigns can now be adjusted based on the preferences customers have previously expressed down to the individual level.
  • Increased productivity – Automation is replacing human effort with software that frees up hours per day. Staff can shed costly responsibilities and focus on income-generating work.
  • Enhanced agility – Nobody was perfectly ready when the pandemic hit, but those with better digital capabilities responded best. Incorporating agile software means companies are quicker to shift to market changes.
  • Employee engagement growth – Monotony, repetition, and redundancy are the parts of the jobs that employees hate, yet they are perfect fodder for automation and software. Introducing solutions that make employee lives easier contributes to staff retention, productivity, and morale.
  • Supply chain management improvement – ERPs and other management packages drastically improve the transparency of your supply chain. They allow systems, suppliers, and departments to communicate and iron out the kinks in your processes.
  • Competitive advantage – Every improvement you make to the customer experience that your competitors don’t make is a huge advantage. Customers judge providers based on how easy it is to navigate to the solution they are looking for. If your platform is cheaper and comparatively easier to use, you become the benchmark.
  • Greater profitability – Digital transformation is about making processes cheaper, faster, and more productive using technology. Reducing the cost of resources, improving productivity and growing revenue, increased profitability is an assured result.


What are the Risks of Not Planning Your Digital Transformation

Look, the reality is that the risks of not using digital solutions to improve operations are the missed competitive advantages others gain and how they make your business look. However, you should undoubtedly be aware of the risks of sloppy digital transformations. Buying something off the shelf without regard for your organization’s input results in implementation failures.

1. Disenfranchised employees = low user adoption.

Getting the buy-in of your team is the number one priority for software implementation. If your team hasn’t been part of the buying process, the software choices are unlikely to work for them.

Don’t tackle the process alone. Get their opinions throughout discovery, evaluation, and procurement processes. Implementation and high user adoption depend on it.


2. Incompatibility = implementation failure

Your business needs tools that play well with each other. Choosing tools that don’t integrate will cause headaches further down the line. For example, you don’t need your marketing department generating reports and solutions that sales can’t use or production can’t act on. Ensure each tool works together within your tech stack.

3. Prioritizing Vendor Features over YOUR Business Needs = low user adoption.

Software sales are riddled with bias toward the seller. Because so few buyers have assurance on what they need, they are willing to trust the people pitching to them. This is a mistake. Not the trust, but the relegation of your needs.

Learn, articulate, rank and prioritize your exact requirements throughout the process.


How to Build a Successful Digital Transformation Strategy

Transformations, by nature, are disruptive. The aim should always be to derive the most value from the process.

1. Set clear goals and objectives

WHY do you need to transform? What is to be gained through a digital transformation? Set clear objectives from the outset to steer the entire process. Doing this informs stakeholders on exactly what you are attempting to achieve, which increases their buy-in. Now you can ask them, “What do you need to achieve this?”

  • Laying out the goals guides the process but it also tells you exactly what you need to do to enact change.
  • What frameworks and systems are needed for change to occur?
  • What is the budget? What is the scale of the change?

Change scares and overwhelms people. Be prepared to define what is expected. Transparent collaboration with your key stakeholders can do a lot to mitigate your organization’s fears.

Companies who choose to partner with Olive on their digital transformation benefit from starting the process here. Olive guides you in your business transformation journey. We begin by building an understanding of your organization’s overarching goals. This sets the stage for your projects, and keeps all your evaluations and decisions in line with your goals. When your organization understands and is aligned with why there is a need for change, it’s less scary.

2. Identify the right stakeholders, and listen closely and diligently to their needs

Think about the stakeholders this transformation will affect and incorporate them into the process early. Stakeholder engagement is the critical piece of the puzzle that most businesses overlook.

Often, lazy CIOs or first-time transformation leaders think their ideas are brilliant, and maybe they are, but without identifying or listening to the right stakeholders, they flop. Has your business resisted changes suggested by the team down through the years? Will you need to address your culture and attitude to change?

Aligning the affected departments and stakeholders will streamline your process for assessing the needs, gathering requirements, discussing and evaluating the options.

Olive was built to facilitate and support this concept. A major roadblock in finding the right technology is understanding exactly what your stakeholders and collaborators need in their ideal solution. With Olive, it is painless to quickly capture feedback from around your organization, without the overhead of having to meet with everyone individually. Listening to these needs will give you a broader perspective on what your organization truly needs.

3. Adopt an agile process for gathering and ranking requirements to get better requirements

Laying down the direction and who will have consultative input gives you the materials to get started.

The next step is to assess the relevant internal and external structures and to understand what processes, tools, software, and systems need to be retired or replaced.

Once you have made decisions on where you need to change using technology, it is time to gather your software requirements.

Appoint a leader and a team if needed to collect the requirements. What do you need the software to do exactly? Interview the stakeholders. Shadow their processes. Host cross-functional meetings. Be clear and systematic. When you have compiled a list, ask the stakeholders to rank each one. Give the proper weight to individual stakeholder opinions. Revisit requirements as new information arises. Be agile.

Come away from this phase with a defined list of needs that represents the stakeholders and achieves your goals, but don’t get too attached, an agile process allows for these needs to be adjusted as your evaluation continues.

If your company is now fully or partially remote, this stage can be a total nightmare. Olive has made it a dream by facilitating seamless collaboration. Work with key stakeholders across your business to ensure all project requirements are collected and rated based on company-wide needs. Time saved doing this work in Olive, allows you to dive deep into each requirement and ask “is this important to our organization and the way we do business?”. 

4. Discover Vendors who meet your requirements

With your requirements in order, you should be ready to see what is on the market to satisfy your criteria. Be careful with who you trust for advice because so many vendors and platforms have a bias.

For example, G2, Capterra and Gartner all take payment from vendors to be featured prominently, so be prepared to scroll! The problem here is that when you search these sites, you are looking at reviews of other companies’ experiences based on their needs, not yours.

Compare the vendor’s features to the needs you have collated in collaboration with your organization. Select a shortlist of vendors based on how well they meet your requirements.

5. Take Demos with the Shortlist of Vendors

Conduct demos with the best 4 or 5 vendors that meet your priority criteria. Grill each one because they are used to making the same pitch time after time. That’s not good enough. You need a solution to work specifically for you. Are they pitching to your requirements, or are they trying to manipulate your requirements to fit their features?

Bring stakeholders who also have a vested interest and understand exactly how they serve your needs. After a hearty vendor evaluation process, you are well-positioned to make your decision.

Sales pitches at this stage of the process are a total waste of your time. With Olive, you can be sure that all vendors you invite to demo have already been qualified against your needs and requirements.

6. Implementation

Implementation can often be the scariest part so choosing a vendor willing to help is critical. Alternatively, you can choose to bring on an implementation partner. Ensure each stakeholder has received adequate training in the new software. Ask them how they feel about it after. Again, we cannot stress how critical the collective buy-in of the team is. They are the ones who make the transformation work. Ask them how it went, how it’s going, and listen to the feedback that comes through. Respond to their feedback, be transparent. If things are not going to plan, tell them. The only people that are able to help you avoid failure are the eventual end-users. Getting feedback on implementations through Olive’s platform helps you get that information quickly, so you can react to any hiccups that happen during implementation. Olive helps you to reduce the margin for error so that your implementation goes exactly as you had visualized in the very beginning.

Investing in support with your digital transformation strategy pays off in the long run

Successful digital transformation is about gaining consensus to find the right technology that will be adopted by your organization and transform business processes for the better.

With so many software advice websites putting the power in the hands of the sellers and vendors, lazy attempts at digital transformation carry considerable risk.

Investing in support pays off in the long run. Whether you hire a consultant, use a tool like Olive or both, getting support will ensure that you get that input from your people.

Olive is here to combat that risk and give the power back to you. Can you imagine how easy your decision would be, if ‘those websites’ showed you options based on your requirements, collated and ranked perfectly in consensus with your organization? That’s what Olive facilitates.

Olive is a digital transformation platform that helps IT consultants, CIOs and technology buyers shorten the technology evaluation process, and get buy-in from key stakeholders in the organization by automating the activities in the process. You can collaborate with your organization to gather, rank, and get feedback on requirements in Olive without exhausting spreadsheets, RFI RFQ templates, or meetings. We provide a library of potential requirements to reduce the chance of oversights.

Once you are satisfied with your requirements and criteria list, we filter responding vendors based on your needs. To ensure credibility and eliminate bias, Olive does not take money from any vendor. This means you only see vendors and solutions that answer your needs. In addition, Olive timestamps all communication through our platform which has shown greater due diligence than RFI or RFQ templates, or vendor management tools.

Olive helps you to reduce your risk exposure by providing an expert helping hand through automation. Our platform is set up to help you save time, effort, and cost of technology evaluations. Our process is freeing up resources for CIOS and IT leaders to focus on strategic digital transformation activities.

Either you successfully accelerate your digital transformation, or your competitors will. Olives Digital transformation platform and services will walk you through leading, scoping, and scaling your organization’s digital initiatives.



A roadmap for a digital transformation


Commentary, Digital Transformation
Bias, Business Software, Business Transformation, CIO, Collaboration, Digital Transformation, Digital Transformation Strategy

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