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How to Avoid Digital Transformation Failure

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Choosing partners and solutions for your digital transformation, is a nightmare. Are outdated tools and processes to blame for digital transformation failures?

Here, we discuss how to avoid the common pitfalls when undertaking a digital transformation, and manage the entire technology evaluation process collaboratively, so you find the right partners.

91% of businesses engage in some form of digital transformation, a practice that has been a priority now for a decade. Yet, despite the unanimous priority and years of failures to learn from, 70% still won’t achieve their desired digital transformations results.

Entire industries are forced to participate along a knife-edge of risks with obsolescence on one side and costly failure on the other. Feeling the pressure to keep up, US companies will funnel another $6.5 trillion into digital transformation by 2024, but why? The failure rate suggests $4.5 trillion of that will be pointless.

The system and process for choosing the right software to transform the business is a complete mess. As a result, digital transformation leaders, CIOs, and digital consultants are cobbling together old-school tools to solve entirely new problems. This week, for example, we asked a prospective client how they currently run technology evaluations in partnership with one of the big five consulting agencies. He said they still run the entire process using spreadsheets.

As Gordon Ramsey says, “Never trust a skinny chef.” Love him or hate him, he makes a good point. So why are companies entrusting digital transformation to folks who have not yet embraced it in their field? Why invest in a tired old process built to serve an entirely different problem in a different tech era? Is it not ironic that the leading brands that sell digital transformation services or consulting use old technology and processes to find new technology?

The failure rate is so high because we haven’t changed the process. We just changed the expected outcome. We use the same waterfall system, except now we’re in too much of a hurry to innovate to notice the costly pitfalls.

So before you unintentionally accept the many risks and obstacles of digital transformation, here’s what you can do to acknowledge and mitigate them.

1. Avoid the most significant risks to digital transformation

Change comes with risk. It is inevitable and concerning but understanding your exposure is a necessity.

Transformation Speed Risk

As a CIO, consultant, or digital transformation leader, you’re in a catch 22. To get the most significant competitive advantage, you need to adopt new technology early but not doing due diligence is a recipe for disaster.

Rapid digital transformation is riddled with problems: poor integrations, lack of team involvement, and naive strategies, to name but a few.

If you rush, you jeopardize implementation. The ‘Find me the Best’ approach is seldom practical because you overlook the actual needs of your team and business. Urgency leads to poor decision-making, disenfranchisement of your stakeholders, and inevitable failure.

The process takes time. You can speed it up, but it must be honored.

Knowing Who to Trust

There is a naivety to CIOs and digital transformation leaders. Just because you’re ready to take the plunge and make the investment doesn’t mean the market won’t take advantage. The reality is this: technology vendors and salespeople have had the power in the market for a very long time. They sell their solution, not your solution. This is a massive part of the problem.

What’s worse is that this power inequality is supported by market evaluator sites like G2, Capterra and Gartner. They give vendors an upper hand by taking money to feature them on their sites. What does that mean for you? It means that when you search for particular software, the answers you get are not ranked based on the best fit for you. They are based on a pay-to-play system. It undermines transparency and credibility.

The buyer-seller relationship is a risk without an expert sifting through for best match solutions.

Security Breaches

As soon as stay-at-home orders were given, all companies shifted to remote work as best they could. For the agile and adept, it went reasonably smoothly. For others, it has been severely challenging and damaging.

The risks associated were given little time, which is the perfect explainer for the security concerns we now have. In addition, a new work lifestyle and digital transformation introduce a host of new devices and cloud-connected software to your tech stack that all bring added risks.

Employers no longer control where the team logs in from, if the connections are secured and what you are exposed to. It has led to 41% of remote workers experiencing cybersecurity incidents through 2020.

The entire national health service of Ireland suffered a large-scale data breach because of these exact risks. Before that it was the UK’s NHS, Canva, LinkedIn, Adobe, My Fitness Pal, Zynga, and more. People logging into the internal network from unsecured connections can easily lead to breaches, and rushing into upgrades contributes handsomely.

Cyber attacks cost the world economy $1 trillion last year. However, more tech can bring more risk if you’re not careful.

Regulatory and Compliance Failure

The Facebook and Cambridge Analytica scandal explained just how powerful data capturing and digital manipulation are in layman’s terms. The blatant disrespect for personal digital autonomy through cookie manipulating tech giants and ever-evolving cyberthreats has forced change.

The EU went first in 2018 with enhanced GDPR requirements, and all other first-world countries followed suit. This throws the digital gauntlet down to businesses of all sizes because regulation and compliance is constantly changing. As just one example, HIPAA court payouts against healthcare offices have broken the $15 million mark so responsibility is needed.

CIOs are more responsible than ever for ensuring that any innovation they are considering is compliant with local law. Take the example of article 33 of the French Justice Reform Act. The article states that predictive AI used on judges is now illegal. That same law doesn’t exist in Canada or the US. Therefore, you need to ensure that your software purchases are appropriate and legal in all countries where you operate. Otherwise, you run the risk of violating compliance law.

2. Avoid These Digital Transformation Obstacles

Along with the plethora of implementation and compliance risks, there are several obstacles to contend with.

Lacking expertise in Software Procurement

High psychological safety is the biggest factor affecting team functionality, according to Google’s Project Aristotle. What is it? The ability to admit mistakes, concerns, and limitations without fearing embarrassment or the label of incompetence. It also happens to be a problem for digital leaders and CIOs who feel the entire weight of the transformation falls on their shoulders.

Not every CIO will know every emerging piece of technology out there, let alone how to use them. How could they? The role of the CIO should be to guide the process with the use of expert help, not to be a demi-god of digital transformation. Not having appropriate insight and unbiased expertise on hand can make scouring the market for perfect solutions a challenge rife with thorns.

2. Lack of Employee Involvement

There are several stress factors involved in a digital transformation. Time is likely the biggest. You want to transform urgently. You want to become more efficient. You want to save processing time. You want to speed up your CX or EX. That’s fine, but that time has to come from somewhere. For most, it ends up coming from stakeholders. Cut corners now, and you will need to invest in fixing the results of a shortcut later.

Hurried CIOs or businesses think time spent going through the process and hearing from employees can be cut out. It can’t. Digital transformation is a team sport.

If you don’t involve the team in each part of the transformation, expect low user adoption. Consistent communication is a requirement. Think about it. If you advance your tech stack without informing or advancing your team in line with it, what will happen? Nobody will know what’s going on, concerns will heighten, employees will resist change, and the fear of being replaced by robots will grow. Overall, excluding critical voices will result in a lack of trust in the digital transformation strategy. 

Granted, the time it takes to keep people involved can be significant, but it is not worse than a failed implementation. It’s an obstacle, not a dealbreaker. With the right process and tools in place, collaboration can be improved.

3. Unclear Organizational Strategy

23% of companies have a digital transformation strategy, but 90% are digitally transforming. So, 67% of you are driving blind?

Digital transformation isn’t just about seeing slow, repetitive processes and replacing them with tech. That’s how you end up with 100s of independent software tools that don’t work together. Eventually, you will end up replacing some or all of them with holistic models.

Like any other part of your business, you need the vision to guide team decisions. What are you aiming for with your digital transformation strategy? What does success look like? What is guiding decision-making?

In addition to the strategy needs, it must be understood that digital transformation is not the responsibility of a singular department or leader. Each department should be involved and organizational structures shouldn’t get in the way. Everyone at the company is likely to be responsible for executing on the strategy, so allow them a voice.

Streamline your software selection process

Digital transformation is a journey. Risks and obstacles are frustrating and the process is a nightmare, but you can achieve success if you block out all the noise and distraction. Early and successful digital leaders see revenue grow 1.8 times faster than the competitors they leave behind, and the enterprise value increases 2.4 times as much. In competitive global economies, that type of growth is powerful.

If we’re going to mitigate these risks and achieve the growth preferred, we need to go back to basics.

In truth, there is nothing wrong with much of the process. It’s just painfully drawn out and it doesn’t have to be.

Olive honors the thoroughness of the digital transformation process but drastically reduces the time it takes. We don’t skip steps. We streamline them with automation and agility in a way that keeps your stakeholders involved throughout the software selection process. Our approach?

How to manage the entire technology evaluation process collaboratively, in one tool, designed for digital transformation


1. Discovering Your Digital Transformation Strategy with Olive

We centralize your digital transformation process giving every stakeholder and contributor a voice. We begin by building from your business needs. What are your pain points? What is the strategy and end-game vision? We use the initial discovery to set the stage for your digital transformation and give your team a clear framework for decision-making.

2. Gathering Stakeholder Feedback

Once we have ironed out your overarching vision and the issues we’re collectively trying to solve, stakeholders are invited to contribute. Olive issues a discovery and feedback survey to elicit their opinions. What do your stakeholders want in the perfect solution? 

3. Gathering Requirements

Our surveys auto-populate into a usable file and folder so you don’t have to endure the overheads of meetings, job shadowing and the many other requirement gathering techniques. This is shaving weeks and months off the process without foregoing the input of key voices.

Olive surveys streamline your requirement gathering process. Just in case you don’t feel everything has been captured, we even offer you an extensive library of requirements to include or just jog your memory.

4. Ranking Requirements and Contacting Vendors

As soon as you have gathered all requirements, we make it easy for your stakeholders to prioritize and rank them.

While they do that, we invite a host of vendors to respond. To be very clear, one key difference with Olive is that we don’t take any commission or collect any fees from vendors. We are very protective about our credibility. We are serving your needs only. Period!

5. Shortlisting, Evaluating and Choosing Between Vendors

The vendors who respond to your needs are given a rating as to how well they match your needs. You know immediately who is and is not a match. There is no messing around trying to figure out bias and risks. We give you the information you need to make a decision. Clean and clear.

Choosing Olive – One tool for successful digital transformation

Look, in all honesty, we worked in the software sales space long enough to understand two things.

1. Digital transformation brings huge cost and time savings and allows companies to achieve far more than they ever thought possible. You can reach customers in new ways and markets, optimize employee performance and become a seamless, modern organization.


2. Buyers are at the wrong end of a power dynamic. Salespeople have had all the power, and it became about their needs rather than yours. Why else do you think 70% of digital transformations fail? The process is flawed and doesn’t prioritize the client and their stakeholder needs.

Olive was founded to disrupt the digital transformation industry. We protect our clients from bias. Vendors know that if a prospect is contacting them through Olive, they show up in full honesty to serve you or they don’t get a seat at the table. No BS – everything is timestamped in Olive. Furthermore, we give everyone at your organization a voice because digital transformation is a mindset shift and brings with it massive change. Everyone needs to paddle in the same direction.

Olive is here to provide you with a singular, trusted tool for your digital transformation. We’re here to give you honest, expert guidance, rid you of legacy software holding you back, streamline your process of evolution and get you the tools you need. We’re here to help you transform.

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