Digital transformation: 3 priorities for CIOs facing a tough climb

Leading a successful digital transformation is like leading a mountain climbing expedition: It takes courage, leadership, and perseverance. Consider these tips from a leader who's done both
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CIO as Digital Leader

Mount Hood in the U.S. Pacific Northwest is not just another tall mountain. The 11,000-foot stratovolcano is visible from Portland, Ore., and though dormant, could potentially erupt without warning. So you can imagine why my family wasn’t enthusiastic when I first suggested that we climb Mt. Hood. I knew, however, our endeavor would teach lasting life lessons.

For CIOs, leading digital transformation is not unlike my family’s expedition up Mount Hood.

In most digital transformation initiatives, 20 percent of the job is technology and 80 percent is the change management necessary to get there.

In most digital transformation initiatives, 20 percent of the job is technology and 80 percent is the change management necessary to get there. You may find that ratio surprising, but after navigating both Fortune 500 and high-growth startups through the journey, I can tell you first-hand that setting goals on the “people” side is the pathway to success.

Elevating your organization and preparing for the future requires a new way of thinking. And at its core, digital transformation might also be defined in exactly that way: a new way of thinking.

[ What success milestones should you look for in your digital transformation journey? Read also: Digital transformation: 7 signs you're making progress. ]

3 digital transformation goals to emphasize

Here are three goals CIOs should move to the top of their priority list when it comes to digital transformation.

1. Look far beyond today

When we began our climb, we could not see the top of the mountain. Clouds had descended, and our vision was blocked.

We all know that there is no straight line when it comes to digital transformation – but you must inspire others to believe with you. To do that, share the big vision. Align strategy and execution. Show others what the peak looks like, and don’t be afraid to admit defeat the first time around.

Looking far beyond today means preparing your mindset and that of your team. Take a pulse check early on. Create a benchmark or assessment of the current state: Where is your organization now, and where do you want them to be?

2. Prepare and stay the course

Imagine boiling the ocean in one day. That’s how digital transformation feels sometimes. The psychological impact becomes unbearable and overwhelming. By preparing and staying the course, however, digital transformation becomes an achievable feat with lasting outcomes.

In the case of our climb, preparing meant wearing the right clothes, packing the right things, communicating with each other, trusting one another, fuelling ourselves with energy bars, breaking down the path into smaller chunks, and learning about the road ahead. As a leader, I ventured to turn our performance up that mountain from mediocre to exceptional.

In digital transformation, this may mean upskilling the workforce and adopting new platforms. It may mean hosting team meetings with various groups within the company to understand their daily challenges and how they might benefit, not just from a change in technology, but from a new way of thinking.

Many companies change the strategy based on that first rainy day.

The first day of our climb started with a three-hour drive from Portland. It was raining. We didn’t see very much. Did we waste our time? No. We learned from that experience. On the second day, it was sunny.

Many companies change the strategy based on that first rainy day. If they fail certain initiatives the first time, they don’t try doing them again. As a leader, you need to have the guts to admit when you don’t achieve the goal but press on.

[ Get answers to key digital transformation questions and lessons from top CIOs: Download our digital transformation cheat sheet. ]

3. Inspire believers

Climbing Mount Hood was precarious and mentally and physically difficult. I never wavered. I stuck to our goal because I knew the outcome would benefit everyone in my family. To soldier on, you must be that persistent.

It is easy to get frustrated when you don’t see a result, so you need to encourage your team and celebrate small achievements. When we were climbing that mountain, my entire family said, “We are wasting our time, we’re not going to see anything.”

I countered, “No, our view here is different than our view up there.” Sometimes in digital transformation, you don’t see any progress; it’s a new disruptive world, but you must continue to lead your people and say, “We’re going to do this.”

All along the trail, no one believed me.

As you adopt digital transformation, you too will be held accountable to the end goal. Embrace this.

I was so excited to prove them wrong. From the first minute until the end, I believed the cloud would not be there when we got to the top. In contrast, it was as though they came along to prove me wrong. 

As you adopt digital transformation, you too will be held accountable to the end goal. Embrace this. Take it on. Lead with confidence. Prove the naysayers wrong. Show them the way to a better organization and a more customer-centric organization.

Reinforce why you are making the journey

Setting a priority list for digital transformation will lead you to the global stage. You must take your team with you – every person from every part of your organization. You must have tremendous clarity and efficiency of core practices and you must show why you are making that journey so that it matters to everyone on your team in the same way it matters to you.

You must create believers, as I did with my family. Things will not always go as planned, but believers will stay with you even when they can’t see what is in front of them and even when things go terribly wrong.

All of this leads to one thing: owning the future as CIOs successfully leading the way up the digital mountain.

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

Helen Yu
Helen Yu is the founder and CEO of TigonAdvisory. She drives growth for tech companies from start-ups to global titans like Oracle and Adobe, and helps CEOs achieve multibillion-dollar revenue growth and record profitability. She’s a board advisor to fast-growth SaaS companies and is on the board of the Global Cybersecurity Association.