6 IT leadership lessons for the future, from New York CIO of the Year winners

Churchill said, "Never let a good crisis go to waste." These CIOs will carry forward 2020's lessons - on empathy, communication, and related leadership skills – as they shape the future
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In the past year, I've heard a fair share of CIOs discuss their response to the pandemic by citing a classic quote attributed to Winston Churchill: "Never let a good crisis go to waste."

This quote (or some flavor of it), has inspired many CIOs to rise above the technical challenges presented by the pandemic, and demonstrate the full capabilities of their IT organizations. 

We caught up with CIOs who recently won the 2020 New York CIO of the Year ORBIE Awards to find out a key lesson they learned while leading during the pandemic. The awards were presented by the New York CIO Leadership Association, a professional community that annually recognizes CIOs for their excellence in technology leadership.

We asked them how that lesson will shape the way they lead in the future. Each of the award-winning leaders had a different take, but together their responses show they aren't letting this moment go to waste. 

6 CIO leadership lessons born from crisis 

Read on to learn the lessons these CIOs will be carrying forward.

1. Manage work, not people

Leadership New York CIO of the Year

Harry Moseley, Global CIO, Zoom: “In the pre-pandemic era, many leaders managed their people in accordance with a defined schedule that specified who was responsible for getting what done. That approach has flipped in the past year. Leadership now, and in the post-pandemic era, is about managing the work to get done and not managing the people. Because of the massive shift to remote work, many people now have the flexibility to define their own schedule, and therefore improve their work/life balance. 

Consider this, 12 months ago, many people needed approval to 'work from home.' Now we need approval to 'work from the office.' This is so profound and evidence of how everything has changed. Leaders who embrace this change and focus on enabling people to get work done will be rewarded with improved employee experience, making it easier for employees to get their jobs done. Not only will this benefit employees, but it will also help organizations be more successful.  

2. Lead with empathy

Super Global New York CIO of the Year

Sal Cucchiara, CIO and Head of Wealth Management Technology, Morgan Stanley: “Over the last year, we have seen the power of leading through change with empathy, and we want to ensure we are preserving this quality in a post-pandemic world. A cornerstone of our organization’s resilience in these trying times has been a workforce that possesses the mental strength and commitment to face difficult times head on – whether that’s a global pandemic, parenting challenges, or work pressures. We can build this organizational strength by putting a strong focus on employee health and wellbeing.

As leaders, this means we must set the tone and empower managers to treat their teams compassionately. When the crisis hit in 2020, our firm reinforced an environment of empathy by supporting our global staff in their diverse work environments and styles, offering greater flexibility to employees. We pivoted from colocation to collaboration, meeting employees where they are with new creative ways to stay in touch and build teams: drop-in Symphony chats, roundtables with no formal agenda, and “networking roulette” sessions on Zoom.

We have continually adapted our strategy to the ever changing technology landscape, but this time, the change is deeper and impacts our culture. Leadership counts now more than ever, and it’s empathy that will empower our employees to thrive in this new normal.”

3. Tap adaptability to move faster

Global New York CIO of the Year

Beth Boucher, SVP and CIO, Sirius Group: "In the past year, I learned our workforce is much more digitally-savvy and adaptable to change than we assumed. Before the pandemic, our organizational norms favored face-to-face interactions and paper-based meeting materials. That all changed over the course of a single weekend in March 2020, when we moved everyone remote, converted to video collaboration, went paperless, and resumed implementation of key initiatives – all without business disruption.

These changes were made without additional training or even a comprehensive communication plan. Everyone quickly adapted, and we saw a dramatic increase in productivity. While I recognize we were operating under highly unusual circumstances, going forward I intend to build on the spirit of being able to pivot quickly when deploying new services and technologies.  

Now that we know our community can adapt so quickly, we will accelerate our approach to introducing new technologies and services.

Without this experience, one of our key deployments would have taken a lot longer. We would have put excessive time into communications, scheduling face-to-face time, training, change management, etc. – and it wasn’t necessary. Now that we know our community can adapt so quickly, we will accelerate our approach to introducing new technologies and services. This insight is a gift and will allow us to move faster."

4. Turning in-person activities virtual has benefits

Large Enterprise New York CIO of the Year

Steve Mills, Global CIO, iHeartMedia: “The pandemic forced us to rethink how we work. It started with a forced move in early March 2020 to working remotely and has evolved to change the way we do most of our work activities. A number of our industry's key business activities that were traditionally viewed as requiring participants to gather in a specificed location are now routinely done in a virtual and distributed way. 

Most notably: On-air broadcast radio shows that were traditionally produced from a dedicated on-premises studio are now often done with a distributed team of talent; and our major national tentpole events, traditionally always held in-person at large stadium venues, have become virtual events in COVID-19 times.

In both cases we have found 'COVID lemonade' opportunities to be more creative, interactive, inclusive, and personal in the way our talent interacts with our listeners through collaboration technologies. We are using similar approaches across our business functions – and we have benefited far more than we would have anticipated, despite not being able to physically get together in an office environment. The big lesson: We do not have to be together to work together.”

5. Understanding of where virtual will work, and where it won't

Enterprise New York CIO of the Year

Michael Salas, SVP, Chief Information & Digital Officer, SUEZ North America: "I’ve always appreciated this quote from computer mouse inventor Doug Engelbart: “Technology should not aim to replace humans, rather amplify human capabilities.” It’s especially fitting for the way our IT organization worked during the challenges we all faced this past year. During the pandemic, our staff has leaned on the technology implemented during our digital transformation to do their best work. 

The IT team did an incredible job pivoting the business to work from home where needed and supporting staff that needed to be at our water plant or on the road maintaining our water assets and services for our customers. As a result, our call center staff was able to work from home without missing a beat (actually, service levels went up); our field crew reprioritized work to avoid unnecessary risks; and our plant operators kept the water flowing safely and remotely. 

A year later, we now have a much better grasp on where we can operate our business remotely and where we need “boots on the ground.”

Prior to the pandemic, we were a business that traditionally had people working in 100 locations around the country. A year later, we now have a much better grasp on where we can operate our business remotely and where we need “boots on the ground.” Going forward, we will use these insights to ensure our IT organization continues to be an extension and amplifier of our business, working together to deliver safe and reliable water services to our customers. 

6. Constant communication is a must

Corporate New York CIO of the Year

Karen Beebe, CIO & SVP, Operations and Ecommerce, Vineyard Vines: “In the world of virtual work, communication is critical – and you cannot communicate enough. Those of us who worked in offices prior to the pandemic know the power of casual conversations. We remember how helpful it could be to run into a colleague in the hallway or stop by their desk for a quick catch up. These days, conversations must be more deliberate. You can’t casually have a conversation when you have 30 people on a Zoom call. You’ve got to make up for that through other means of communications.

I’ve always been a believer in the '7x7 rule' for communication – you have to say the message seven times in seven different ways before it really sinks in. In this new way of working, sharing a message on a Zoom call one time is not enough. It’s important that leaders use every tool they have – from chat to email to whatever else is in their toolkit – to ensure they’re connecting with people in the way that works for them. Using a single tool one way isn’t a sufficient way of communicating in typical times, nonetheless in these times, when work is anything but normal. Leaders need to over communicate. 

In this new way of working, it’s easy to feel more isolated because you’re not hearing the side conversations about what’s happening in your organization. You’re not seeing who’s meeting in conference rooms to clue you in on collaborations that are happening. You’re not bumping into colleagues in the hallway for those quick catch-ups. When feelings of isolation start to set in, people start to make up stories about what’s going on. They may believe something is happening that isn’t. It’s on us, as leaders, to make sure we’re communicating with our teams repeatedly and through different avenues.

[ How do your team meetings stack up? Read also: Zoom tips: 6 ways to make meetings better. ]

As community manager for The Enterprisers Project, Ginny Hamilton helps build the site's community of CIOs, IT leaders, and readers. She is responsible for helping tell the stories of leading IT executives – showcasing the projects, experiences, and challenges they're facing in their roles as IT leaders.

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