Enterprisers Project

The Enterprisers Project by Red Hat and Harvard Business Review

Digital transformation: How emotionally intelligent leaders aid success

No digital transformation project is guaranteed to succeed. The reason that many fail is not because of technology, but rather a lack of motivation and understanding on the part of leaders and employees. At Clearbridge Mobile, for example, the most challenging parts of our transformation were centered on training, skill sets, and eliciting buy-in from our employees.
Digital transformation and the human factor
The key to digital transformation success in 2020 and beyond lies with an organization’s ability to change not only its technology stack but also the attitude and mindset of its employees and leaders. For most organizations, the human aspects of change will be a greater challenge than the technology.
Let’s look at three of the most common human barriers to successful digital transformation and explore how emotionally intelligent leaders can overcome them.
1. Inertia
Inertia is defined as “a tendency to do nothing or to remain unchanged.” Many business leaders don’t recognize that their environment and industry are changing until it’s too late. This is particularly common when things are going well: If everything is working and the company is making profits, employees might even question your decision to transform based on industry trends.
[ How strong is your EQ? See our related article: Emotional intelligence test: 5 self-evaluation tools for leaders. ]
However, inaction is the arguably biggest barrier to a successful transformation. If you wait until there is a crisis, it might be too late to transform effectively. If you don’t see the need for change and aren’t being proactive, your competitors will fill the void by providing the services your customers expect and demand.
If you wait until there is a crisis, it might be too late for digital transformation.
How to apply emotional intelligence:
Address inertia directly by communicating to employees that current success does not necessarily guarantee future success. Leaders with emotional intelligence can share their passion for the work being done and motivate others to shift from resistance to acceptance. Paint an aspirational view of the future to deter resistance and move beyond the “things have always been done this way” mentality.
2. Self-doubt
Every organization that has successfully implemented a digital transformation project can attribute that success, at least in part, to leaders who fully believe in and support the transformation. But when those who are responsible for driving change have doubts, transformation almost always fails.
Even if leaders understand that change needs to happen, they may lack confidence in their ability to successfully drive it. Such self-doubt may result from previous negative experiences or even failure with transformation projects. Doubt can be one of the hardest barriers to overcome.
How to apply emotional intelligence:
Emotionally intelligent leaders usually also have a high level of self-awareness, or the ability to recognize and understand personal moods and emotions and how they affect others. Self-awareness plays a large role in combating self-doubt.
Emotionally intelligent leaders understand that in times of uncertainty, team members look to leaders for reassurance.
Emotionally intelligent leaders understand that in times of uncertainty, team members look to leaders for reassurance. Rather than doubting your ability to guide a transformation, apply your insights from previous experiences (even failures) to your current transformation project.
Remember, successful digital transformation depends on your organization’s ability to fail fast, learn, and improve. If a previous effort failed due to lack of employee buy-in, for example, invest in more coaching and training to ensure that everyone clearly understands the vision for the organization.
3. Cynicism
Perhaps the trickiest challenge to successful transformation involves cynics – team members or even other leaders who refuse to get on board. Every project will inevitably run into issues that will impact the direction of the transformation, and cynics will point to these problems to call out flaws in planning, execution, and leadership. Using challenges and small failures to reinforce their distrust, cynics will try to influence their colleagues – and without buy-in from everyone on your team, your transformation cannot succeed.
How to apply emotional intelligence:
Empathy is another critical quality that emotionally intelligent leaders possess, and it can help overcome the cynicism barrier. Empathetic leaders are conscious of all team members and make sure that everyone feels heard. This helps all team members – including the cynics – find common ground and work toward a shared goal.

Just as cynics can influence other members of an organization, early adopters and champions of change can do the same. Identify the supportive members of your team and encourage them to educate and influence colleagues in implementing your transformation strategy.
Leaders who exhibit high emotional intelligence through self-awareness, self-motivation, empathy, and other such qualities will be best positioned to foster digital transformation and build a more innovative organization.
[Learn more: 8 powerful phrases of emotionally intelligent leaders. ]
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Digital transformation success depends largely on a leader’s ability to motivate their team members. Here’s how to overcome three often overlooked challenges using emotional intelligence

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Digital transformation: 3 ways to ease the fear factor

As we enter the new decade, more companies are sharpening their focus on digital transformation. These changes are about much more than just keeping up with rapidly improving technology and trends; digital transformation is really about enabling customer intimacy.  Every successful business is customer-centric, and digital transformation initiatives are aimed at utilizing digital technologies to create new or improved business processes and customer experiences.
Undergoing a digital transformation is a logical strategy for any company focused on improving its customer experience, but some remain hesitant to commit. Most business leaders have encountered employees who are resistant to the changes new technology will introduce. After all, change means moving away from the safety of what is known and embracing the unknown, and that can be scary. IT teams, in particular, can be risk-averse as they are tasked to deliver stable operations.
Here are three actionable steps that can help you get all your employees excited for change – even the digital transformation naysayers.
[ Is your digital strategy prepared to handle the challenges of 2020? Read also: 8 digital transformation trends for 2020. ]
1. Commit to strong communication
Effective communication is the first and most important requirement for successful digital transformation. It’s even more essential when dealing with folks who adamantly oppose change because they are the ones who will speak the loudest, ask the most questions, and call out any holes or weaknesses.
Steady, comprehensive communication can help ease their anxiety. Create an open forum where employees can submit questions directly. This gives everyone, including the skeptics, a platform to contribute and ensures that everyone feels heard.
For communication to be impactful and help turn naysayers into advocates, go beyond explaining what changes are happening and instead address why they need to happen. Explain how these changes will benefit your employees and the customers they serve.
[ Read also: Change management: A better way to explain the “why” ]
Convey what the state of the business could be like without digital transformation. Understanding that the company’s future could be at risk and that their skills will become obsolete with antiquated legacy systems will likely have a significant impact on everyone.
Remind employees that digital change is about designing and delivering better products and services and that this is why many people get involved with IT if the first place – to make a positive change. Positioning change in this way can help everyone see it through a different lens.
Be direct and honest, especially with employees who actively oppose change.
Be direct and honest in all your communications, especially with employees who actively oppose change. State what the goals are, what the rollout will look like, and what the benefits will be for customers and partners as well as employees. Create a conversation and openly acknowledge concerns. Don’t shy away from difficult conversations – these are the ones employees will focus on, and failing to engage in them will drive the message that change is unpalatable.
Partner with resistant individuals and invite them to join more strategic conversations. Giving them a seat at the table will help to shift their mindset and create new ambassadors who can help rally others.
Finally, make sure communication around the digital transformation process is ongoing. A handful of emails or a company meeting won’t cut it. A steady stream of updates will help ease the minds of all your employees.
2. Understand that digital transformation is a journey
Digital transformation is a process, not a one-time project or a single event. It requires a long-term plan with many milestones and sub-steps. Part of the journey is getting everyone on board by helping them realize that embracing change is a win for everyone. Another part is testing tools and solutions to determine which ones to implement.
This is a perfect opportunity to connect with employees who might have a more cynical outlook. Ask them to join a pilot group to test new solutions. As part of this process, seek out technologies that will benefit employees by enhancing their skill set.
Customers and partners will also have questions along the way, so be sure to point out how the change will help your organization deliver better solutions and services that align with customer needs. Every step of the journey brings its own challenges, and it’s important to stay grounded, communicate often, and pivot when necessary.
3. Celebrate small successes quickly
Make it point to celebrate small successes early in the transformation process. Starting with an initiative that is helpful but not overwhelmingly difficult and time-consuming will help to ease concerns and generate broader buy-in. Be honest about the process – openly discuss what’s working and what’s not. Naysayers will be quick to point out when communication fails or the timeline falls behind. Get ahead of this by celebrating wins and being transparent about setbacks.
It’s important to show the initial benefits of digital transformation, so share testimonials from employees who have already benefited from small changes. In some situations, hearing positive updates from peers can be more impactful than hearing them from leaders.

With the speed of innovation and the pace of competition in today’s world, companies cannot afford to stand still – and that means embracing digital transformation. To overcome resistance to change, partner with the cynics. Talk through their concerns, involve them in the process, and reward even small successes. In that way, you will turn skeptics into supporters.
Remember: Change begins at the top. Leaders who are able to inspire and drive change within their organization will find success in digital transformation.
[ Culture change is the hardest part of digital transformation. Get the digital transformation eBook: Teaching an elephant to dance. ]
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Change means embracing the unknown and that can be scary. Here are three actionable ways to ease the pain – even for the digital transformation skeptics

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Digital transformation: 3 reality checks if you’re stalled

We’re used to hearing about failed digital transformations, but stuck or struggling transformations are just as common. This IDG research finds that 51 percent of organizations have stalled or even abandoned parts of their transformation initiatives because of challenges they faced.
Encountering obstacles doesn’t have to mean the end. Here are three key areas leaders should focus on in order to get their digital transformation back on track.
[ Culture change is the hardest part of digital transformation. Get the digital transformation eBook: Teaching an elephant to dance. ]
1. Don’t get hung up on the word digital
People often see digital transformation as different from business transformation. It’s “digital” so it’s an IT thing, right?
We have this discussion with our clients time and time again. When we frame it as “business transformation” we naturally focus on the transformation aspect. Digital transformation should be no different.
You can deploy a bunch of tools to allow you to do what you do cheaper or faster, but this isn’t digital transformation.
You can easily ask your CTO to deploy a bunch of tools to allow you to do what you do today cheaper or faster, but this isn’t digital transformation. When leaders get stuck, it is often because the transformation is being driven purely by technology and the organization has lost sight of what it wanted to achieve in the first place. Constantly reminding yourself, and your organization, of your original business objectives is vital.
[ Some people despise the term “digital transformation.” Here’s how to speak to it without getting burned. ]
Another issue is that there are lots of great tools on the market today – perhaps too many. These technologies open up almost infinite possibilities, which can be game changing but also counter-productive. If you lose focus and purpose around your transformation vision, and more importantly your roadmap, you can tie yourself in knots trying to do too much without making any tangible difference to your business.
That is another reason why revisiting your business objectives is so important. And regardless of what you’re trying to achieve, recognize that this remains, at its core, a business change program.
2. Communicate, engage, and listen – more
A transformation program I recently worked on demonstrated what can go wrong if a business operates in a vacuum. The company had introduced a new self-service model but couldn’t understand why its employees were doing everything they could to avoid using it. Turns out the business hadn’t involved its people in any aspect of the transformation, simply presenting it as a “fait accompli.”
Your entire organization needs to understand the journey you are taking, what it means for them, and for the customers they interact with. Failure to do so not only puts your vision at risk, it could also jeopardize how customers receive your transformation. Unhappy employees usually lead to unhappy customers.
[ Read also: Change management: A better way to explain the “why” ]
People are naturally suspicious, and when you start introducing digital enablers, particularly automation, the natural assumption is that their jobs are at risk. You may not need your people to do exactly what they do now in the future. However, understanding the value of their knowledge and how this supports your digital future and their future opportunities is central to your transformation journey.
If you haven’t engaged your people, it’s not too late. Develop your change program, undertake impact assessments to understand how the transformation will affect your employees, and establish an engagement model to support its roll-out.
Of course, external users (i.e., your customers) are equally important. Whatever your objectives, transformation will in some way impact the delivery of services to your customers. So, have you communicated with them?
Customer-first must be a mantra within your digital transformation.
I’ve seen digital transformation projects fall flat because the business has made assumptions about what the customer wants. They’ve designed new services around back-end processes – not around how the customer actually wants to use their services. Customer-first must be a mantra within your digital transformation. If it’s something you’ve neglected up until now, pause, reflect, and consider how you can design your new service with your customers. Engaging specialist skills in user experience and interaction design is recommended.
3. Answer big data questions early and often
Holding data, collecting data, and being able to manipulate data in new and interesting ways can fuel your digital transformation. However, starting out without a clear understanding of the data you have, the data you need, and how it will be used, both now and in the future, could stall your progress and leave you with a problem that is both costly and time-consuming to fix.
If you run into difficulty exploiting your data assets to support your transformation objectives, you will almost certainly require some form of intervention. Exactly what form that intervention will take depends on the business you are in and the type of transformation you are trying to achieve, but some common steps apply: 
Clearly distinguish between your data model and your data content,
Stay focused, and balance short-term improvements with longer-term data modeling (don’t get bogged down!), 
Combine the expertise of people in your business who know your data inside-out with experts in data architecture and design.

Don’t let these common problems trip you up. Keep in mind that digital transformation isn’t simply about the smart selection and configuration of new technologies.
First and foremost, you should approach this journey as a business transformation and recognize the importance of investing the time, capital, and emotional energy you would in any other business change program. Get this right and you will avoid pain along the way.
[ Struggling to attract and retain digital transformation talent? Get the Harvard Business Review Analytic Services report: IT talent strategy: New tactics for a new era. ]
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Many organizations have stalled or abandoned their digital transformation initiatives. Ask yourself: Are any of these 3 sticking points to blame?

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9 must-read technology books for 2020

How do you keep up with technology change, given the exponential rate of tech advances today? It’s not easy and it’s not optional. Since technology underpins the competitive stance of most organizations, maintaining a working knowledge of current and emerging technologies is as important for IT leaders as building their soft skills or leadership abilities.
To that end, we’ve pulled together a reading list for CIOs and IT leaders seeking to increase their tech skills in 2020. This covers everything from digital systems and architecture to AI and deep learning, plus the ins and outs of tech experimentation and innovation.
Enjoy these nine books for a thorough dive into key technologies and the related business and leadership challenges:
Designed for Digital: How to Architect Your Business for Sustained Success
By Jeanne W. Ross, Cynthia M. Beath, and Martin Mocker


Book description (via MIT Center for Information Systems Research): “In the digital economy, technologies and customer demands are changing rapidly. As a result, business strategies are constantly evolving. Only agile companies will survive! Most business leaders rely on organizational structure to implement strategy, unaware that structure inhibits, rather than enables, agility. To execute digital strategies, companies must abandon structure and instead rely on business design.
“Designed for Digital: How to Architect Your Business for Sustained Success discusses five capabilities—we refer to them as building blocks — that together enable established companies to execute, and constantly refine, their business strategies. Published by MIT Press, the book explains how companies can evolve into digital powerhouses without compromising current sources of revenues and profits.”
Why you should read it: Ross (principal research scientist at the MIT Sloan Center for Information Systems Research) and Beath (Professor Emerita at the University of Texas McCombs School of Business) have decades of experience examining corporate IT organizations to uncover best practices for technology-enabled competitive advantage. In this book, along with fellow author Mocker, they dig into five years of research and in-depth case studies at digital leaders (Amazon, BNY Mellon, LEGO, Philips, Schneider Electric, USAA, and more). What emerges is a practical guide to what they have found to be the foundational components of digital business: shared customer insights, an operational backbone, a digital platform, an accountability framework, and an external developer platform.
Artificial Intelligence: The Insights You Need from Harvard Business Review
By Thomas H. Davenport, Erik Brynjolfsson, Andrew McAfee, and H. James Wilson


Book description (via HBR): “Companies that don’t use AI will soon be obsolete. From making faster, better decisions to automating rote work to enabling robots to respond to emotions, AI and machine learning are already reshaping business and society. What should you and your company be doing today to ensure that you’re poised for success and keeping up with your competitors in the age of AI?
“Artificial Intelligence: The Insights You Need from Harvard Business Review brings you today’s most essential thinking on AI and explains how to launch the right initiatives at your company to capitalize on the opportunity of the machine intelligence revolution.”
Why you should read it: This collection of previously published articles by a veritable Who’s Who of Tech Thought Leaders provides a high-level overview of AI as seen through a practical business lens: what AI is and isn’t, how it’s impacting organizations and markets, the implications for business leaders, and more. Each article ends with practical takeaways. HBR’s Artificial Intelligence: Tools for Preparing Your Team for the Future is an optional companion, including a slide deck highlighting the most critical information presented in the book; discussion questions corresponding with each article; and two Harvard Business School (HBS) case studies.
The Future Is Faster Than You Think: How Converging Technologies Are Transforming Business, Industries, and Our Lives
By Peter Diamandis and Steven Kotler


Book description (via Amazon): “In their book Abundance, bestselling authors and futurists Peter Diamandis and Steven Kotler tackled grand global challenges, such as poverty, hunger, and energy. Then, in Bold, they chronicled the use of exponential technologies that allowed the emergence of powerful new entrepreneurs. Now the bestselling authors are back with The Future Is Faster Than You Think, a blueprint for how our world will change in response to the next ten years of rapid technological disruption…
“Diamandis, a space-entrepreneur-turned-innovation-pioneer, and Kotler, bestselling author and peak performance expert, probe the science of technological convergence and how it will reinvent every part of our lives — transportation, retail, advertising, education, health, entertainment, food, and finance — taking humanity into uncharted territories and reimagining the world as we know it.”
Why you should read it: There are recommendations from the likes of Ray Kurzweil, Pharell Williams, and Tony Robbins for this guide to the next decade. Diamandis and Kotler explore how the convergence of exponentially advancing technologies – AI, robotics, virtual reality, digital biology, IoT, 3D printing, blockchain, global gigabit networks – will transform industries and impact society overall.
Soonish: Ten Emerging Technologies That’ll Improve and/or Ruin Everything
By Kelly Weinersmith and Zach Weinersmith


Book description (via Amazon): “In this smart and funny book, celebrated cartoonist Zach Weinersmith and noted researcher Dr. Kelly Weinersmith give us a snapshot of what’s coming next – from robot swarms to nuclear fusion-powered toasters. By weaving their own research, interviews with the scientists who are making these advances happen, and Zach’s trademark comics, the Weinersmiths investigate why these technologies are needed, how they would work, and what is standing in their way.
“Soonish investigates ten different emerging fields, from programmable matter to augmented reality, from space elevators to robotic construction, to show us the amazing world we will have, you know, soonish.”
Why you should read it: This digestible and funny book from Dr. Kelly Weinersmith and her cartoonist husband looks at ten technology breakthroughs that may have an enormous impact on the future. Combing through existing research and conducting interviews with those at the forefront of these emerging technologies, from augmented reality to space travel, the duo offers a peek at some possible tomorrow worlds and what will need to happen to get us there.
The Power of Experiments: Decision Making in a Data-Driven World
By Michael Luca and Max H. Bazerman


Book description (via MIT Press): “Have you logged into Facebook recently? Searched for something on Google? Chosen a movie on Netflix? If so, you’ve probably been an unwitting participant in a variety of experiments — also known as randomized controlled trials — designed to test the impact of different online experiences. Once an esoteric tool for academic research, the randomized controlled trial has gone mainstream. No tech company worth its salt (or its share price) would dare make major changes to its platform without first running experiments to understand how they would influence user behavior.
“In this book, Michael Luca and Max Bazerman explain the importance of experiments for decision making in a data-driven world.”
Why you should read it: This forthcoming tome (March 2020) examines the role experimentation has played in the success of some of today’s tech giants (StubHub, Alibaba, Uber, eBay). HBS business professors Luca and Bazerman outline the rise of tech-enabled experimentation in organizations, the powerful role that data-driven tests can play in decision-making, and how business leaders can most effectively harness this powerful tool (made infinitely more doable in the digital age).
Let’s look at the next four books:

Digital transformation: How to strengthen results by nurturing Millennial talent

As we settle into 2020, here’s a staggering workforce stat for you: It’s estimated that this year, Millennials will represent more than one-third of the global workforce. With Millennials (born 1982-1996) overshadowing GenXers as the largest generation in the labor force, you might think that every organization would have a strategy in place to harness the capabilities of this growing workforce. 
But that doesn’t appear to be the case. Instead, we’re still regularly reading about how Millennials are being pitted against Baby Boomers and GenXers. We Millennials still hear the stereotypes about how we’re entitled and must receive a pat on the back for every minor task we complete. 
Today’s Millennials range in age from 23 to 38 years old: That’s right, some of us are almost “over the hill.”
Yes, in many ways, Millennials are profoundly different, as detailed by Gallup in its recent research, How Millennials Want to Live and Work. But we’re not children anymore. Today’s Millennials range in age from 23 to 38 years old: That’s right, some of us are almost “over the hill.” 
In the years ahead, we will continue to disrupt everything about the world we live in: This represents a great opportunity for organizations willing to cast aside the stereotypes of our generation, and instead  harness the drive, loyalty, and innovation that Millennials bring to the table.
CIOs and IT leaders in particular need to recognize the role technology now plays in partnering with the business to enable the success of the organization. One of the key ways to meet those demands is by tapping into your Millennial talent, and giving us an opportunity to be a part of the decision process.  
Understand where Millennials are coming from
As (what feels like) one of the few IT executives who is also a Millennial, I can tell you that contrary to the stereotypes about our generation, we do not ruin everything, nor do we think we are always right. We have a knack for coming up with creative ways to approach problems and thinking outside of the box. We question the status quo with why and why not. We challenge the folks around us to be more accountable, to mean and do what they say in a timely manner. Sometimes we’re thought of as impatient, but we value time lost. 
We want to be part of a revolution that helps organizations change their mindset from “We’ve always done it this way.” 
More than anything else, we want to have that feeling that we belong and are valued – that we are not just there to fill a checkbox or to say we are in the room. We want to be active, listened to, and heard. We want to be part of a revolution that helps organizations change their mindset from “We’ve always done it this way.”
3 questions to help guide your efforts
How can your IT organization do a better job welcoming this generation and setting them – and by extension, your transformation efforts – up for future success? 
Here are three questions that can help you be more deliberate in your efforts to tap the power of your Millennial talent. 
1. What programs are in place to develop Millennial leaders to take on greater roles within the organization?
Most organizations already have Millennials working within the company. This is an opportunity to give them bigger roles, with mentorship and a safety net to learn. While Millennials have great ideas and a vision of what the future should look like, their methods may need tweaking and guidance will help.
Hopefully you’ve already begun to do this, if not, it’s time to shift your thinking on this. Many Millennials are ready to take on bigger roles, if given the opportunity. Consider roles where they can be a part of strategic decision making and help the business to cater to their Millennial colleagues. It’s  a positive side effect: They will help you redefine how to optimize your workplace to better accommodate and help make this generation more productive in the workplace. 
2. How far along are you on your journey  to redefine your culture, and what’s most important to the organization?
This is more than just about the technology. Let’s be honest, there are a lot of talks about what used to be the norm, or the famous “we’ve always done it this way,” on issues that need to change. The issues range from silly policies around work hours and location, to dress codes, processes, and yes, even, applications. Millennials grew up learning how to be concise and getting whatever is needed that allows them to be most successful. Organizations need to learn how to harness that instinct and provide the right tools.
3. What does success look like?
The first two questions can obviously be broken down to address basic shortcomings. Regardless of how you are examining the current state, as you think about your strategy around Millennials, it’s most important to understand what success will look like. It needs to be something you aspire to and something that can be measured. This would be a good time to gather thoughts from the Millennials you already have within your organization.
Some quick metrics can easily help you gauge how you are doing. One is the number of Millennials you have within your organization and the percentage of them in a leadership position (and who feel their voice is being heard.) Second, what percentage of your workforce would say your organization is Millennial-friendly and would recommend their Millennial colleagues come work for your organization? Make a deliberate effort to move the needle on elevating the role of Millennials in your IT organization. The key here is to not lose sight of what’s most important.   
Recognize Millennial value
One company that has recognized the value Millennials have on their business as customers is Nationwide. So much so that they planned a roll out for a completely separate branded company on a digital platform, catering strictly to Millennials. It goes to show the power this generation is having on the future of business.  By no means am I saying every company needs to go and create a new brand for Millennials, but what I am saying is that the old ways of doing things and the old tactics often will not work for Millennials.

Millennials believe all actions matter, big and small, and are eager to work if given the chance. They are looking for opportunities to make an impact and disrupt the status quo. If you’re ignoring this group, you could be thwarting the future of your organization.
[ Want advice from top CIOs on solving talent challenges? Get the Harvard Business Review Analytic Services report: IT talent strategy: New tactics for a new era. ]
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By putting Millennials in more strategic and leadership roles, you could advance IT innovation and digital transformation. Here are 3 questions to ask about how well you’re utilizing Millennials

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20 digital transformation leaders to follow on Twitter in 2020

One of our New Year’s resolutions was to refresh and expand our Twitter feed for digital transformation leaders, reviewing them not just for the use of the right hashtags but for the content they share.
There are a few repeats from a similar list we shared last year, but for the most part we tried to give you new Twitter handles to follow. This year’s list includes CIOs, authors, consultants, and cloud computing leaders. Some only post on technology topics, while others share thoughts on family, culture, politics, and favorite movies.
The common denominator we looked for was a thoughtfully curated feed that’s not entirely self promotional but adds to the conversation we’re all having about how to understand the potential of digital transformation and put it to work for our organizations.

Martin Mocker aka @martinmocker
Follow @martinmocker
Bio: Co-author of Designed for Digital. Professor at ESB Business School, Research Affiliate at MIT. My views are my own.
Why to follow: “Designed for Digital” from MIT Press provided powerful insights on how to achieve transformation success and how to organize for transformation. The book left us wanting more, and Mocker tweets more frequently than his research partners Jeanne W. Ross and Cynthia M. Beath. For example, he recently shared an interview he conducted with Mattias Ulbrich, Porsche CIO and CEO of Porsche Digital.


Melissa Swift aka @meswift 
Follow @meswift
Bio: The human side of the digital journey. Senior Client Partner at Korn Ferry, Leader, Digital Advisory for North America/Global Accounts. All opinions are my own.
Why to follow: Swift has been one of our most popular writers here at Enterprisers Project, because she calls it like she sees it when it comes to digital transformation. In her work with Korn Ferry clients, she gets a clear understanding of the realities of transformation. Follow her for a breath of fresh air on getting things done and leading people through change.

Sarbjeet Johal aka @sarbjeetjohal
Follow @sarbjeetjohal
Bio: Storyteller, Architecting #Cloud & #DigitalTransformation programs/teams. ex: @ORACLE @Rackspace @VMWare @EMC Investor/Advisor @TheBatchery Incubator
Why to follow: We featured Johal in our recent article on Digital transformation: How to personally brand yourself as a leader. One reason he has built a large following for cloud and digital transformation topics is the effort he puts into his feed. “If I cannot read that thing, I will not post it, I will not comment on it,” Johal says. In other words, he makes sure everything he shares is something he either recommends or has some additional insight to offer on.

Rahul Welde aka @RahulWelde
Follow @RahulWelde
Bio: EVP Digital Transformation at Unilever. Love for travel,food & sports. Passion for people & brands. Zest for life & doing good. Always excited. Liverpool Red.
Why to follow: Welde is one of the executives who has “digital transformation” explicitly in his title, meaning he takes the lead on adding a digital component to Unilever’s consumer products. Want to know what’s on his radar screen? Most of what he shares is content from others that he finds interesting.


Joanna Young aka @jcycio 
Follow @jcycio
Bio: #CIO Unplugged, #Digital Advisor, #603 by way of UK #WomenInTech #leadership #STEM #Broadband #UNHWildcat
Why to follow: This former higher ed and insurance CIO now serves as a digital advisor to the C-suite on how best to take advantage of accelerating technology change for competitive differentiation. As a result, her tweets offer a great overview of components of digital change and leadership as well as tutorials for educating C-suite peers and board members.

Didier Bonnet aka @didiebon
Follow @didiebon
Bio: @IMD Affiliate Professor of Strategy & Digital Transformation, EVP @CapgeminiInvent – Digital Practice, Chelsea FC, good food + wines, drummer in Mockchop
Why to follow: Bonnet shares insight from the perspective of leader at a global consulting firm. He speaks on how to speed up digital transformation work, for example. Based on his feed, he has an interest in quantitative analysis of many kinds (and shares a variety of enlightening stats) – plus a fondness for robots.


M. Nadia Vincent aka @ITTransLeaders
Follow @ITTransLeaders
Bio: Author, Keynote Speaker, Digital Strategist, MIT Certified CXO Advisor, MBA, PMP #DigitalTransformation #Leadership #AI #Strategy #Innovation #Digital #CXO #CIO
Why to follow: Vincent, who offers training and advisory services for IT and business leaders through TransformationalLeaders.com, frequently writes and posts on AI topics and digital strategy. 

Kevin Coluci aka @kcoluci 
Follow @kcoluci
Bio: Chief Information Officer, Technology Leader, Digital Transformation, #CIO #CyberSecurity #Boston #GovTech #LegalTech #FutureOfWork
Why to follow: This CIO of the Massachusetts Attorney General’s Office since 2011 (and Deputy CIO before that) shares insight on digital transformation, particularly as it relates to government entities.

Marc Touitou aka @TouitouMarc 
Follow @TouitouMarc
Bio: Digital Transformer, former CIO of the World Health Organization, frmr CIO of San Francisco, Master Change Jedi. Loving father, husband, friend. Chess geek.
Why to follow: After serving as CIO at the Nature Conservancy and the World Health Organization, Touitou is currently on the market as an interim CIO / CXO and advisor to digital leaders under the umbrella of 2e2 Digital Transformation Consulting. Posts about AI, cloud, and other transformational technologies.

Leon Wilson aka @leon_clevefdn 
Follow @leon_clevefdn
Bio: Technomist, Chief of Digital Innovation and CIO – Cleveland Foundation; tweets are mine.
Why to follow: It’s wise to follow some CIOs outside your industry, perhaps in academia or non-profits, like Wilson. He is particularly active with posts on leveraging technology for social good, like this one. He also posts with an eye to interesting finds on innovation, education, open government, broadband access, and  5G.

Adriana (Andi) Karaboutis aka @AndiKaraboutis
Follow @AndiKaraboutis
Bio: B4:[email protected] & GM; [email protected]; [email protected]; Now: Chief Info & Digital [email protected]; BoD AAP & Perrigo; ALWAYS: DIGITAL= INNOVATION*IMAGINATION+TECHNOLOGY
Why to follow: Currently the CIO/CDO of National Grid, the multinational electric and gas utility, Karaboutis has worked across a variety of industries. She brings an infectious enthusiasm to her feed, always looking to celebrate the transformational power of technology and innovation.

Jesus San Segundo aka @JesusSanSegundo 
Follow @JesusSanSegundo
Bio: CDO CIO Technology expert. Digital transformation leader through Innovation. Opinions here are my own.
Why to follow: Segundo is Group Digital Transformation Director for Spain’s Banco Santander, which last year put out an investor day press release pointing to digital transformation as the key to the company’s future growth. One progress report he shared to Twitter was the announcement of a blockchain-based bond.

Giuliano Liguori aka @ingliguori
Follow @ingliguori
Bio: Digital Transformation Advisor | CEO @glwebeu | CDO @BE_Informatica | #CIO | #InnovationManager | #AI #Cybersecurity #IoT #DigitalTransformation #Blockchain
Why to follow: Liguori is the CIO of CTP Napoli (operator of public transport services for the City of Naples, Italy) and an advisor to other CIOs. He also serves as Data Protection Officer to a number of other firms, meaning he supervises their compliance with Europe’s General Data Protection privacy rules. A prolific tweeter, he often posts about AI, cybersecurity, and the evolution of cloud technologies.

Tim Crawford aka @tcrawford 
Follow @tcrawfordi
Bio: CIO Strategic Advisor | Board Member | Host of The CIO In The Know podcast | #CIO #DigitalTransformation #Cloud #AI #Edge #CIOitk
Why to follow: Crawford, a prognosticator of all things tech, generously shares other people’s content rather than only promoting his own. This former CIO shares insights from many industry conferences. He also hosts the CIO In The Know podcast, featuring lessons from IT leaders in a variety of industries.

Jacob Abboud @jacob_abboud 
Follow @jacob_abboud
Bio: Leader and CIO in Financial Services & Insurance – named on Global BT150. Digital/AgileTransformation champion with Interest in Data, IOT, AI and Fintech
Why to follow: Abboud maintains an active feed on digital transformation, particularly as it applies to financial services. You’ll also find many posts highlighting privacy and security articles.

Les Ottolenghi aka @LesOttolenghi 
Follow @LesOttolenghi
Bio: Founder of entrepreneurial ventures. Contributor to @CIOonline All opinions & expressions are solely mine #ces2020 #entrepreneur #investor
Why to follow: This 30-year IT veteran has an eye for emerging trends. He posts frequently (often several times per day) about topics in technology and leadership. He has a particular interest in data analysis and AI issues. See his inspirational note for 2020.

Jay Ferro aka @jayferro 
Follow @jayferro
Bio: #CIO for the @Quikrete Companies | Dad | #Speaker | #Angel Investor | #Board Director | Love #Leadership & #Technology; Hate #Cancer | #ENTJ | #GoDawgs
Why to follow: “I like ‘concrete’ steps,” said the CIO of Quikete, when sharing an article he wrote on how to tame big data and analytics — one published here at The Enterprisers Project. Ferro has long taken an active role in promoting the community of CIO leaders. He’s a former CIO of the American Cancer Society.

Marcus East aka @marcuseast
Follow @marcuseast
Bio: CTO with a passion for tech for social good. Technical Director in Office of the CTO at Google HQ specializing in Cloud, eCommerce and Digital Transformation.
Why to follow: Besides providing a Google perspective on the future of digital, East has a work history that includes a stint as CIO/CTO for the charity Comic Relief. Thus his emphasis on apply “tech for social good.” Among his first posts of 2020 was one celebrating the potential of AI to spot breast cancer better than any expert.

Peter Weis aka @PeterFWeis
Follow @PeterFWeis
Bio: Digital transformation leader, advisor, #CIO, speaker, teacher, dad, husband, citizen. Trying to do it right.
Why to follow: Weis formerly served as CIO of trucking and transportation company Matson Navigation, where (as he puts it on his LinkedIn profile) he led a “9-year transformation from a 100 percent legacy environment and culture into a company that now operates 100 percent in the cloud.” He now works as an advisor to other business and technology leaders and teaches a graduate course on “Where Business Meets Technology” at University of California, Berkley. He also wrote one of our site’s most popular articles on digital transformation: See Matson CIO: The most painful, gut-wrenching part of leading transformation.

Marcus Borba aka @marcusborba 
Follow @marcusborba
Bio: Top Global Influencer: #AI #MachineLearning #DataScience #BI #DigitalTransformation #BigData #Analytics #IoT #ArtificialIntelligence | #BBBT Member | Consultant
Why to follow: This consultant and entrepreneur offers a strong variety of news and analysis related to AI and big data. He’s also a former CTO.
[ Culture change is the hardest part of digital transformation. Get the digital transformation eBook: Teaching an elephant to dance. ]
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Committed to digital transformation this year? Follow these people for perspective and emerging lessons

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Digital transformation: 5 uncomfortable truths in 2020

It’s a new year, and a new decade – and for many of us, that brings excitement and optimism. But digital transformation in 2020 is not all sunshine and roses.
Success this year will require looking at some uncomfortable truths about what’s really slowing – or even stopping – digital progress. Five issues are putting the brakes on digital transformation, and here’s another truth: Most organizations suffer from some version of all five.
Let’s dig in:
1. You don’t have the people you need for digital transformation – and you can’t go buy them.
Organizations have been looking at the digital talent question like an exciting new recipe: They know they can’t cook it with what they have in the kitchen, but they can go buy the ingredients. The problem is, today’s digital talent market is more Soviet supermarket than Whole Foods:
Today’s digital transformation talent market is more Soviet supermarket than Whole Foods.
There’s not much on the shelves. Even with an unlimited budget, certain talent populations are highly elusive, especially in smaller cities.
What can we do?
Ruthlessly streamline and prioritize your digital talent needs. What do you really need, and who is the least skilled person who can do it?
Map the gaps using data – and consider both skills and behaviors. It’s easy to underestimate the populations you already employ – and to discount the role of learning agility. You may do better reskilling a highly fluid learner with 20 percent of the current skills needed than a passive, process-driven individual with 80 percent of the skills you need. It’s critical to know on a fact-driven basis who is who.
[ Culture change is the hardest part of digital transformation. Get the digital transformation eBook: Teaching an elephant to dance. ]
2. Jobs are going to be fluid for the next few years … at least.
New jobs and new job titles abound and keep morphing, with organizations frantically writing and rewriting job descriptions even as employees craft their roles into something else entirely. As a result, a hugely valuable exercise – capturing how work is transforming – veers into open silliness more often than we’d like to admit.
What can we do?
Shift the focus from titles and taxonomy to teams and trust. Endless work on defining “this combination of words means this person does XYZ” is the digital equivalent of … well, I won’t say it, but it involves striking a deceased equine. Instead, think about what teams of individuals need to accomplish – in aggregate – and give them just enough guidance on how to parcel out work to get them going.
Stop “writing your jobs down in permanent marker.” The rate of change in digital work is poised to accelerate, not slow down.
Stop “writing your jobs down in permanent marker.” The rate of change in digital work is poised to accelerate, not slow down. So make sure your systems and processes around jobs and roles can accommodate constant shifts – and a “minimum viable product” approach to capturing what’s in a job at any given time.
3. The understanding gap between business and IT leaders has never been greater.
Now more than ever, IT and the business need a shared language – the work being done is ever more integrated. Too often, each side sounds to the other like the adults sounded to the kids in Charlie Brown cartoons: “Mwanh mwanh mwanh, mwanh mwanh mwanh…”
IT leaders have embraced a whole new lexicon to keep up with rapid and non-linear technological progress, and business leaders often lack the vocabulary to shape business challenges into well-framed technological questions. On both sides, constant pressure to act like a “next-generation leader” (without the right enablement to do so) often leads to leaders clamming up and not asking the right questions.
What can we do?
Make simple, informal communication the rule, not the exception. The hoary chestnut “explain it to me like I’m a third-grader” actually holds up in practice – most popular books, fiction and non-fiction, are written at a ninth-grade level or below. So there’s no shame in saying that your organization’s internal communications – written or spoken – should be written such that a middle-schooler could understand them, dramatically reducing the risk of misunderstanding. Also, have conversations informally and in real time as often as possible. People who speak regularly – and feel safe asking questions, especially in small groups or one-on-one – understand each other better.
Structure matters, too: Is yours strangling your progress? Let’s examine:

Digital transformation: 9 ROI factors when upgrading legacy systems

For enterprise technology organizations, tackling legacy systems and infrastructure is expensive, extraordinarily complex, and often impossible to justify with a traditional ROI model that weighs cost against demonstrable return on capital.
On the other hand, the accumulation of applications, different tech stacks, and hard-coded solutions have created Frankenstein IT environments that are costly to operate, vulnerable to failure, unlikely to be understood from end-to-end, and detrimental to speed, flexibility, and agility. For technology professionals, these systems distract from the day-to-day work required to support critical business strategies and opportunities.
[ Culture change is the hardest part of digital transformation. Get the digital transformation eBook: Teaching an elephant to dance. ]
Of course, many creative, forward-thinking CIOs have made progress “ring-fencing” legacy systems, building connectors to new digital interfaces, and extracting and replicating critical data. This admirable effort keeps the business moving, but it may no longer be enough.
When legacy tech is a barrier to digital transformation
Today, companies must deliver a strong digital experience to engage customers, and complex legacy technology is a significant barrier to digital transformation. There are signs that companies recognize this as a significant threat and are starting to change course.
You need an ROI model that reflects the many hard and soft implications of falling behind in your digital transformation.
According to Gartner, operating costs increased from 67 percent of IT budgets in 2013 to 71 percent in 2017, while budgets for digital transformation decreased. But now IT departments are spending more on software applications that drive revenue from digital business channels and shifting to off-premise platforms including cloud services, software-as-a-service, integration platform as a service (iPaaS), and application platform as a service (aPaaS), according to Gartner research.
Today, we may be approaching a tipping point where the burden of legacy IT systems is untenable and modernization is essential. If so, the people I think of as tech whisperers – those who recognize oncoming disruption, provide strategic guidance, and marshal support and resources – need a more expansive ROI model that reflects the many hard and soft implications of falling behind in your digital transformation.
9 ROI factors to consider about legacy tech
To that end, here are a few things to think about as you develop a business case that will compete with, say, investment in a new business or product offering:
Old systems are budget killers — If you’re spending 70 to 80 percent of the IT budget operating and maintaining legacy systems, there’s not much left to seize new opportunities and drive the business forward. And this expenditure will grow as technology ages and becomes more susceptible.
Everything new is built in the cloud — All new technologies are built using cloud architectures and approaches, while options available to monolithic legacy shops continue to narrow. What is the long-term value of leveraging the best new technology for your business and customers?
Missing out on technology’s full potential — A critical factor driving legacy upgrades, according to a recent Deloitte survey, is technological relevance. “Legacy solutions lack flexibility and carry a significant technology debt due to dated languages, databases (and) architectures,” Deloitte reported. “This liability prevents many organizations from advancing and supporting analytics, real-time transactions, and a digital experience.”
Talent issues pose a risk — It’s increasingly difficult to find people to operate and support legacy technologies. After all, no one is studying mainframe systems, COBOL, and Fortran. As your team ages and retires, then what? And how do you attract today’s best young talent – the people your company needs to thrive in the digital-first era – with a tech environment that can’t keep pace with competitors?
Customers expect a satisfying digital experience — And they’re getting it from digital-native firms that can iterate continuously as they monitor customer interactions and react to the feedback. Legacy environments rarely can adopt this type of iterative customer engagement. Your new ROI model should address the impact a legacy system upgrade will have on customer experience.
The need for speed to market — In the Deloitte survey, companies said the primary reason they initiated IT upgrades was to better support product strategy and objectives— that is, to go-to-market faster. The days of quarterly releases and 18- to 24-month projects are gone. Speed is a true competitive differentiator.
Security risk — While the security of cloud solutions still requires care, it is clear that older technologies are more difficult to control, monitor, and secure as security paradigms and solutions evolve. How much risk does your dated technology pose?
Data management & privacy – There are a growing number of data-related regulations and policies being enacted. It’s difficult to comply with these practices and controls after the fact, especially when information is squirreled away in multiple legacy systems and data has been replicated in myriad warehouses and data stores. Your ability to comply with current and future policies is severely hampered in this type of environment. At what point do you lose the trust of your customers, regulators, and control functions?
New markets and ecosystems – Increasingly, enterprises are embracing opportunities to enter new markets, engage and delight customers, and rethink business models through digital platforms and tech-enabled ecosystems. This is difficult to do – perhaps impossible when your IP is trapped in bespoke legacy systems.
It’s time to engage your business partners – including finance, HR, product development and strategy – to develop a new ROI model to assess potential legacy migration and retirement efforts.

Quantify the risk factors and opportunity costs of failing to deliver a competitive customer experience, attract talent, speed products to market, protect and leverage data, and be equipped to respond to fast-changing market conditions and operational demands.
[ Read also: Why you’re managing digital transformation wrong: Think portfolios. ]
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If you are putting off IT modernization efforts due to complexity and cost, consider these ROI factors associated with legacy systems.

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