Digital transformation: 5 leadership oversights and how to correct course

Successful digital transformation takes both broad vision and attention to detail. If you're stalled or disappointed, consider these often-overlooked pitfalls
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digital transformation reality check

Have you hit roadblocks in your digital transformation journey?

You’re not alone. According to a recent study by IDG, 51 percent of IT leaders have stalled or abandoned some transformation initiatives, and 44 percent have made no process, operational, or technology changes whatsoever. But don’t let these sobering statistics discourage you.

With three successful transformations under my belt, I advise you to take stock, evaluate the five considerations below, and assess how you can adjust course and move toward your ultimate goals.

[ Get answers to key digital transformation questions and lessons from top CIOs: What is digital transformation? A cheat sheet. ]

1. You're thinking too small about digital transformation

If you, your leadership, and your teams thought only about digitizing a single analog process during initial discussions and planning, you didn’t think big enough – and you probably didn’t budget correctly.

If you thought only about digitizing a single analog process during planning, you didn’t think big enough.

Start by considering your objective and end goal: Is it reducing costs, increasing or driving new revenue, growing customer satisfaction, or a combination of these? Your objective should be transformational; reaching this goal likely means transforming the entire operating model for the business, not just one aspect of it. This takes imagination, thinking at scale, and investment.

It can be easy to overlook what you’re going to spend money on (tools, vendors, partners, etc.), and issues with underbudgeting or double-spending could put your progress at risk. Revisit and realign your strategy, and moving forward, make your finance team and CFO your best friends.

[ Is your digital strategy up to date? Read also: 8 digital transformation trends for 2020. ]

2. You didn't take all your stakeholders into account

Digital transformation needs to be top-down and outside-in. Any digitalization needs to align with a bold company vision for the future while helping to meet customer, client, and partner needs and the company’s own challenges. When everyone is aligned, you can create a justification “umbrella” where everything being done is in service to and is consistent with company vision and stakeholder goals. Questions and feedback such as “Why are we/you doing this?” and “I don’t understand the importance of this” will be less frequent, and clients will be less likely to try to block your changes.

It’s also important to recognize and avoid “weakest link syndrome,” where a single output of your digital transformation (a new product or process, for instance) may not work for one of your stakeholders. Account for this pushback in your planning and design. Consider what will work for 80 percent of your stakeholders, and what you might be able to keep or adjust for the remaining 20 percent who might not share your digital timeline.

3. You didn't account for learning time

Digital transformation is an iterative process in which the work continues to grow.

I like to say that digital transformation is never “done done.” Instead, it is an iterative process in which the work continues to grow as new use cases, clients, partners, etc. join the business. You must improve constantly. And in a digital transformation, don’t assume early success – rather, assume early learning and then pivot from those learnings. You likely faced difficulties if you did not create space for your team to learn, if you didn’t scale from those learnings, or if you neglected to celebrate both wins and failures. The bottom line: Plan to learn and plan to fail.

4. You might have staffed incorrectly

Remember that during a transformation, your business is doing two things at once: running and changing. If, during planning, leaders allocate for transforming the business but not for continuing to run it, staffing can become a twofold problem. There needs to be a synergy. If staffing has you stalled, rethink how you’ve budgeted and organized your resources.

[ How does your talent approach measure up? Download the Harvard Business Review Analytic Services report: IT Talent Strategy: New Tactics for a New Era. ]

5. You aren't communicating enough

Digital transformation touches everyone and everything in your organization. Open, transparent, and consistent communication is key. Team relations are also important and ignoring or neglecting them can hinder your progress.

Understand and communicate how jobs will be redefined, how teams will be impacted, how success will be defined, and how failures can be used as lessons learned. Also, keep morale high by finding ways to unlock value, especially for teams whose platforms, projects, and/or budgets are being scaled down or phased out.

Whether your transformation is stalled or not yet started, keeping these five considerations in mind can help you achieve your goals.

[ Culture change is the hardest part of digital transformation. Get the digital transformation eBook: Teaching an elephant to dance. ]

As Chief Digital Officer of Agero, Bernie Gracy brings over 30 years of technology experience helping drive new product/platform introduction, client delivery, and the establishment of new software-enabled business models.