How To Build A Successful CIO Career

HOW TO BUILD A
SUCCESSFUL CIO CAREER
COPYRIGHT ©2018 CBS INTERACTIVE INC. ALL RIGHTS RESERVED.

HOW TO BUILD A SUCCESSFUL CIO CAREER
TABLE OF CONTENTS
03 The 10 skills you’ll need to land a CIO job
06 How to land the CIO job: 10 tips
10 How to find your next leadership job: Five tips
14 CXO candidates: Here’s how to answer six common interview questions
17 How to get promoted to a leadership role: Four key skill sets to master
21 Looking to build a career as a tech leader? Here’s why empathy might help
24 How to develop your public speaking skills and advance your career
2
THE 10 SKILLS YOU’LL NEED TO LAND A

CIO JOB
BY ALISON DENISCO RAYOME
The role of the CIO is shifting, with many professionals being called to develop a blend of leadership,
business, and technology skills to spearhead digital transformation efforts.
“There is no one CIO profile,” Ansgar Schulte, a Gartner analyst on the CIO team, recently told TechRepublic.
While CIOs traditionally have a background in either IT or business, Schulte said he’s recently seen an increase
in those taking the job from marketing, product development, and even HR.
“It’s usually easier for a strong business leader to get a necessary understanding of the tech challenges and
have some people on the leadership team helping to address those, than for a tech executive to acquire the
nontechnical competencies like strategy and governance,” Schulte said.
In a shifting landscape, it’s helpful to know what expertise companies are looking for when it comes to hiring
a CIO. Indeed analyzed job postings for the CIO job title in the US and determined which skills were most in
demand for the role by the total percentage of postings that listed those skills in the past year.
“More businesses are embracing digital. As a result, CIOs have been tasked with developing the strategies and
initiatives needed to successfully implement the digital transformation within their organizations,” said Paul
Wolfe, Indeed’s senior vice president and head of global human resources. “Given that responsibility, it comes
as no surprise that we are seeing a mixture of leadership, business, and technology skills being reflected in the
job postings for the role on Indeed.”
Here are the top 10 most in-demand skills for CIOs, according to Indeed.
1. Project management
Project management professionals play a vital role in helping organizations meet strategic goals. A CIO with
project management skills can help their IT team plan, execute, and monitor projects.
2. Agile
Businesses are increasingly turning to Agile project management for continuous improvement in development
cycles. A CIO who is familiar with Agile can help their organization work more closely with customers and
create the right project to satisfy their needs, as well as accelerate product performance and delivery.
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3. Enterprise software development

Enterprise software is used by organizations for a variety of purposes, including managing assets, handling
orders and customer relations, storing data in databases, and working with finances. CIOs with experience using
and developing this type of software can help their company gain an advantage.
4. Budgeting
IT budgeting is a critical aspect of any IT leader’s job. Some 83% of TechRepublic’s CIO Jury members
said that their IT budgets would stay the same or increase this year, potentially giving more room to leverage
technology to meet business goals.
5. Recruiting
CIOs may be responsible for building out a tech team, which is an increasingly difficult task amid a
talent shortage.
6. Business intelligence
As more companies are collecting and analyzing data, skills in business intelligence allow CIOs to help their
company gain the most useful and actionable insights.
7. SAP
SAP’s suite of enterprise software is popular among many companies, and CIOs that are familiar with its
offerings, like SAP HANA, can help their companies best manage them.
8. VMware
VMware offers cloud computing and platform virtualization software and services used by many enterprises.
Again, CIOs familiar with these services are in high demand from companies.
9. Data warehouse
As companies collect more and more data, it helps to have a CIO who understands data warehouse
architectures to adequately store and access this information.
10. SharePoint
Microsoft SharePoint is one of the most common tools used for enterprise-wide communication and collabo-
ration. A CIO experienced with the platform can hit the ground running at many organizations.
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SKILLS PORTFOLIO
A strong CIO candidate must have a large portfolio of skills to confront the challenges of enterprise digital
transformation, said Gianni Giacomelli, business leader, digital solutions at global professional services firm
Genpact.
“Project management, agility, and enterprise software development are more the engineering skills; today’s
CIOs must be more well-rounded in their abilities,” Giacomelli said, with skills in design thinking, customer
centricity, and data science. “They need to know about enterprise processes as a whole and what their
company’s customers want.”
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HOW TO LAND THE CIO JOB: 10 TIPS

With digital transformation efforts underway at many companies, the CIO has an opportunity to become an
important member of the C-suite who can find technical ways to advance the company’s goals. But how do you
actually become a CIO?
While a tech background gives you an advantage in areas such as security and working with vendors, those from
other business realms often have the communication, management, and strategy skills the CIO job demands.
The CIO role is more fluid than it used to be, said Ansgar Schulte, a Gartner analyst on the CIO team. “You
need to be open to different responsibilities coming your way. In the future, the focus of the CIO will be less
on information management and more on reaping business opportunities through digital technologies.”
Here are some of the skills and attributes you need to pick up in your quest to climb the corporate ladder and
land a CIO job.
1. Willingness to take on the hardest projects

David Giambruno, former CIO of Shutterstock, started his career in sales at a networking company, where he
learned how customers were using technology.
How did he move up the ranks? “I took the absolute worst jobs,” Giambruno said. “If someone said, ‘This
project is going to be a total failure,’ I would raise my hand, because there was no downside. It taught me
how to wield technology for an outcome and how to use every single asset at my disposal, including people,
processes, and technology, to get a good outcome.”
This is especially important for CIOs without experience on the enterprise side, according to Matt Guarini, vice
president and research director serving CIOs at Forrester. “If you start with your roots within IT, get outside
and look for opportunities where you can work in the business. It will help you build knowledge of an organi-
zation and business tech and will help you think about innovation and problem solving.”
2. Communication
Hone your communication skills. “Part of the CIO job is to explain technology in a way that people can
consume and to make it approachable,” Giambruno said. “I spend a lot of time thinking of metaphors to
explain things.” Drawings can also help, he said, because a picture gives people something easier to relate to
than a document.
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CIOs must be good at both communicating ideas and gathering feedback, said Dustin Bolander, CIO of
Technology Pointe. “Too many people in the IT industry say, ‘No, it has to be done this way,’ especially the
higher end technical ones,” Bolander said. “The best CIOs I have worked with have the ability to clearly
consider something from the other side’s point of view.”
3. Business acumen over technology skills

“Being a CIO is much more about having a good strategic vision than about being a master of technology,”
said Douglas Shook, CIO of the University of Southern California. Many people focus only on the technology
angle, when in reality, it’s about understanding the company’s core operations and goals and addressing them
with technology solutions.
“As we settle into this world being driven by digital transformation, CIOs are being thrust into strategic
positions rather than purely tactical ones,” said Don Brown, founder of Rocana. “This means they must under-
stand what the business actually needs and how technology can best deliver that vision, as opposed to building
fiefdoms around particular vendors or tools and forcing square pegs into round holes. To do this requires near
constant learning and relearning, and frequently challenging assumptions.”
The role of the CIO has evolved to become more of a business partnership role, said Alan Stukalsky CIO of
Randstad Technologies. “I predict that in the next five years, the strategy of most organizations will transition
from IT being an afterthought to IT being an integral part of leadership meetings, and the role and importance
of CIOs will change accordingly.”
4. Cybersecurity
There are still several core technology skills that are key for the CIO to master, Schulte said. Deep knowledge
of risk and cybersecurity is one. “You need some understanding of how to protect critical information assets
of your organization.”
CIOs must fully understand the importance of security and how to put different security frameworks in place
and work with vendors, Guarini said.
5. Data
A strong foundation in data analytics is also necessary for today’s CIO, according to Shook. It’s key for CIOs
to be able to collect and analyze large sets of data and draw insights that can help the company’s strategy. “The
whole notion of doing data in a warehouse is dead—we’re going to be moving more into live data analytics.”
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6. Configuring over creating

Shook predicts that companies are moving to an environment where all servers are in the cloud and most appli-
cations will come from SaaS providers. “We’re going to lease our software in the cloud and will not so much
be creators of tech as configurers of tech,” he said. “We’re going to acquire software functionality out of the
cloud and will need to configure it to suit our enterprise.”
As products give way to services, a new crop of CIOs is emerging to support their business transformations
in the age of the “subscription economy,” said Alvina Antar, CIO of Zuora. “This innovative group of tech
leaders must be equipped differently to handle a new business model that requires new executive buy-in and the
skills and infrastructure to differentiate their business.”
CIOs must be able to acquire technology and take advantage of changing landscapes in increasingly shorter
time periods, Giambruno said. “The days of taking three to five years to do an implementation are over. You
are now measured in months. The ability to acquire and divest technologies quickly and make quick use of
them is a skill set that will pay people dividends.”
7. Performance management
Aspiring CIOs need to learn to manage an organization of people, Schulte said. “IT is still a people discipline.
You need to be able to guide and motivate talented people who aren’t necessarily always highly communicative.”
This also involves monitoring the performance of people and the service levels you deliver to the organization,
Schulte said.
8. Change leadership
CIOs need to be able to lead broad changes, Schulte said. “Whenever you introduce a tech system in the enter-
prise that influences the way people work, you need to get people to help you shape and define that new tool
or system. Then you need to train them. You need to be comfortable with leading people through change and
transformational projects.”
CIOs live in a constantly moving ecosystem of business units and technology, Giambruno said. “You’re going
to make decisions, and those decisions will change over time. If you don’t like change, it’s not a good fit—the
rate of change keeps increasing.”
9. Orchestration
Technology is now integrated from the start of a business process through the end, Guarini said. Therefore,
“the CIO has to be somebody who can work with folks from operations, marketing, legal, and tech—all of
these different elements that need to be connected” and orchestrate the entire organization’s efforts.
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10. Innovation
CIOs need to lead innovation at their companies, Guarini said. This involves thinking through how to create
and deliver everything from new business models to new solutions and processes, in terms of developing the
idea, incubating it to promote it more broadly, and commercializing it.
“There are so many great opportunities to deliver business innovation for your company that can move the
needle, and the CIO can be an integral role,” Guarini said. “For those folks who come in and do it right, they
can start to be considered for the CEO job.”
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HOW TO FIND YOUR NEXT LEADERSHIP

JOB: FIVE TIPS
Considering a move to a leadership position at a new company can be daunting, but it’s possible to position
yourself for success early on in the process. Here are tips from executive coaches and C-suite members on how
to find the best C-level position for the next phase of your career.
1. Assess yourself and what you want from your next job
Before launching any search, step back and take account of where you are in your career, what’s been missing,
and what you would like to find in your next position, said Colin Moore, partner at Essex Partners, a career
advisory firm specializing in senior executive career management and transition counseling.
“Don’t shortchange yourself when setting goals—if you are really clear on what you want, that’s something we
observe really empowers an individual in the marketplace,” Moore said. “A key ingredient of why some people
get hired versus others is the people who are networking with them or interviewing them sense the passion
and vision.”
Bridget Duffy, chief medical officer of Vocera Communications and Vocera’s Experience Innovation Network,
said her guiding career principle is “Know your gifts.” Then, define the requirements of the work environment
that will enable you to use those gifts, taking into account location, travel, remote versus in office, and other
factors.
Avoid: Launching your search too quickly
“Launching too quickly is sometimes the biggest mistake, not having thought through how to approach the
marketplace,” Moore said. “People are always going to ask, ‘What are you looking for and how can I help?’ Be
ready with clear, profound, articulate answers to those questions.”
This is especially true for a C-level employee who has been terminated from their position, said Caroline
Stokes, executive coach and headhunter, and founder of executive search firm Forward Human Capital
Solutions. “Take time to recover,” Stokes said.
2. Network
About 60% to 70% of most executive jobs are won with some element of networking, Moore said. The
remainder are often found through recruiting firms, with a smaller piece found through online searches.
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“The most productive channel in our C-level executives looking

experience is networking. It plays an ever-in-
creasing level of importance in how C-level for a new job should have an
executives explore their options and transition updated resume with all their
most successfully.” major accomplishments listed.
It’s common for senior executives with a long But sometimes, updating
tenure at one company to have well-developed
networks within their organization but not
your resume means deleting
much in the way of external networks, Moore irrelevant roles.
said. There are a variety of approaches for
C-level executives to strengthen their network. First, you should assess those already in your network who you
can reconnect with, such as old employers, former classmates and board members, and people in
your community.
“You need to look at it as a very thoughtful assessment of the resources that will help introduce you to the
types of organizations where you’re most likely to find the C-level opportunities you’re looking for,” Moore
said. This could also include connecting with principles at top professional services firms such as McKinsey
and Forrester, who have market intelligence and contacts at companies you may be interested in.
Networking can also turn an executive on to companies that have not yet declared their need for a certain
position but that may have internal movement or restructuring. This would put you ahead of the hiring model,
Moore said.
Avoid: Contacting too many people
Be selective about who you contact in your network for information, Stokes said. Don’t send your resume to
everyone. It may also be important to be discreet about your search, if you don’t want your current company to
know that you are looking elsewhere.
3. Develop your resume and LinkedIn presence

C-level executives looking for a new job should have an updated resume with all their major accomplishments
listed. But sometimes, updating your resume means deleting irrelevant roles, said Ted Chan, founder and CEO
of CareDash. “Executives have all done a lot and want to list everything they’ve ever done,” Chan said. “I
secured my latest CEO job when I hired an executive coach who had me delete roles from my resume to make
it more focused.”
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Moore also encourages company leaders to have a substantial LinkedIn presence. This should include a
fully developed profile that mirrors your resume, so all your marketing materials are cohesive. It also means
actively participating in LinkedIn discussions or blogs. “You will be presenting yourself as a prepared,
thoughtful, targeted executive, as opposed to somebody who’s just starting to pick up the phone and call
people,” Moore said.
C-level executives can also use LinkedIn to determine the career paths of others in positions they’re interested
in and the culture of organizations they may want to target, Stokes said. Looking at open positions there and
on other job boards can also help them brush up on the most recent skills demanded in their industry to help
them prepare for an interview, she added.
Avoid: Posting about your search on social media
Do not post on social media that you are seeking work, Stokes said—especially if you’ve been terminated.
Allowing people to see how long your job search takes is also not a good idea. “It devalues your professional
brand,” she said.
4. Get in touch with a recruiter or headhunter

Most companies put a high priority on finding the right C-level executive and will entrust the task to seasoned
recruiting firms that know the marketplace and to a targeted networking campaign, Moore said. In the event
that you do not want your current company to know that you are searching for a new job, a recruiter can help
you reach a new network, he said.
And if you are terminated at the C-level, you should negotiate to have the services of a career management
firm included in your severance package.
Avoid: Accepting a position too quickly
“Avoid moving too fast or taking a position because you’re fearful you won’t find anything else,” Duffy said.
Women also need to be sure to negotiate an offered position. “As a woman, if you don’t have the right title or
report to the right place, it’s hard to lead effectively,” she said. “You have to negotiate that up front and make
sure the role enables you to be effective.”
5. Offer a vision and a strategy

Tech leaders need to ensure that they are current on all the developing technology trends and how the
technology infrastructures at companies they are targeting are working and evolving. “Tech is a key component
of a strategy of any successful organization,” Moore said. “At the C-level, the knowledge and nuts and bolts of
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credentials are kind of assumed. What people are looking for in tech leaders and other C-level executives is a
person who can be a strategist and a fundamental change agent to benefit the company and the markets
it serves.”
Proving you have that capability will help you market yourself to companies, he added.
Avoid: Marketing yourself as only a technologist
Even in the tech industry, being a leader requires dealing with people more than technology, said Lance Hayden,
chief privacy officer of ePatientFinder. “Leadership is the realm of politics, emotions, and inspiration,” he said.
“The great technology leaders I’ve met all eventually made that leap.”
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CXO CANDIDATES: HERE’S HOW TO

ANSWER SIX COMMON INTERVIEW
QUESTIONS
BY MARY SHACKLETT
When hiring for an executive position, interviewers look for qualities like personality, passion, integrity, and
capability. These qualities aren’t typically discoverable from a CXO candidate’s resume, but they constitute key
“need to know” questions for CEOs who interview. So it’s important for CXO job candidates to develop their
understanding about a company as much they can before they walk through the doors for an interview.
It’s equally important to keep this caveat in mind: When companies look for CXOs, they are usually doing it
because 1) they’ve created a new position that no one internally can or wants to take or 2) they want to replace
someone they’ve either lost or fired.
GETTING READY FOR THE INTERVIEW

The key to preparing for a CXO interview conducted by a CEO or other senior person is to anticipate the
questions and issues that are likely to arise. Here are some common questions and issues.
1. Tell me about yourself

As a CXO candidate, I always disliked this question because of its vagueness and its open-endedness, and I
promised myself that when I was a senior manager interviewing my own CXOs I would never ask it. However,
many CEOs and senior officials do ask it. One reason for asking such an open-ended question is to see what
comes to mind first for you when you think of yourself. Here are some recommendations if you get asked
this question.
Try to answer the question with a combination of personal and professional information about yourself. I
accidentally found myself in an advantageous position when I first started interviewing for CIO positions. My
background had been in liberal arts and writing, so I never even thought about becoming an IT professional,
let alone a CIO. However, when I graduated from college, an IT opportunity presented itself and I liked it. In
my interview for CXO, I told my CEO interviewer that—and then went on to say why I liked IT and some of
the things I had accomplished as a manager that I was proud of. This proved to be successful for me, but at the
time I didn’t know why. When I thought about it later, I realized what had happened: I had managed to answer
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the CEO’s open-ended question with a nicely blended answer that combined both personal and professional
information about me—and that suggested to him why I might be a strong candidate for the position.
2. Tell me about yourself: Part two

A professional associate of mine once was interviewed for a CXO position by a newly minted CEO of an
aerospace supplies company. The CEO started with the question, “Tell me about yourself.” My colleague told
me she thought that by asking an open-ended question, her interviewer had found a way to break the ice and
have her take the lead. This is an important element for job interviewees to remember: Your interviewer might
be more nervous and ill at ease during the interview than you are. The more you can help relax the room, the
better your chances of getting that CXO job.
3. Tell me about the greatest career or project challenge you’ve

faced—and how you solved it
If you’re interviewing for a CXO manager position, your interviewer wants to know not only how you solved
a technology or industry impasse, but how you worked with others and provided leadership to overcome a
difficult situation. When you talk about a project, be as specific in describing it and its results as you can. For
instance, “We went live with the project in six months instead of in the one year we had planned. We were able
to do this because....” Don’t forget, though, that your interviewer is also looking at how well you engaged and
motivated your team. In other words, did everyone feel they had a role in making the project successful? How
did you as a manager facilitate that?
4. How do you manage change?

The need for change is a major reason why companies hire CXOs. They want individuals who have experienced
and effected successful organizational change. Knowing this, be prepared to talk about your experiences as a
change agent.
Be ready to talk about the impact changes have had on the company and on your employees. I once had a CXO
candidate who talked about change in his organization and what he told his employees. “I showed them what
an outside consultant had come up with and how and why their jobs were going to change,” he said. “I let
them know that these changes weren’t anything personal. They were needed for the company—because they
just made sense.” Before long, the employees had embraced this change, the candidate said. “All around the
organization, employees were saying, ‘It just makes sense.’” I thought to myself, “Maybe that was the case. But
it could also mean that while the employees were saying this because it was expected, they were also updating
their resumes.” The next question I asked the CXO candidate was what his staff attrition rate looked like.
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5. Where do you want to

be in five years?
It is important to answer this question
firmly and positively because your inter-
viewer wants to hire a CXO who 1)
knows where they are going; 2) would be
similarly focused on helping the company
get where it needs to go; and 3) believes
in the company and its mission. No one
wants to go back to their board and
employees in six months because a newly image: istock/fizkes
hired CXO decides to leave.
Most CEOs or senior interviewers at some point during the interview are going to ask you if you have some
of your own questions about the company. From your previous research, you should already have several
questions in mind. You might also have new questions that have come about as a result of the interview. In any
case, it is important to have questions and to get them answered.
I once interviewed for a director role and was told that a VP’s wife, who was a manager in the department I’d
be leading, would likely have to be let go. I knew I was getting ready to step into a hot situation so I asked the
company president who was interviewing me if he was prepared to stand behind me if I had to fire this person.
The president told me that he would stand with me, and he did. This was an important point for me. If he had
waffled, I wouldn’t have accepted the job.
FINAL WORDS
CEOs and other senior leaders look for CXOs they can depend on, who will contribute value to the company,
and who will stay around. This is what they interview for. At the same time, however, CXO job candidates
need to recognize that they are interviewing the company, too. When both sides come together in a win-win
arrangement, everyone gains and the company employees and stakeholders benefit, as well.
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HOW TO GET PROMOTED TO A

LEADERSHIP ROLE: FOUR KEY SKILL
SETS TO MASTER
Most professionals are familiar with the Peter Principle—the idea that companies promote employees based
on their performance in their current role, rather than on their ability to succeed in the new role. Employees
then stop being promoted once they can no longer perform effectively, and “managers rise to the level of their
incompetence,” as the principle states.
“We promote people who are great at their current level instead of those who will be great at the next level—
people who are good contributors and not necessarily good leaders,” said Scott Drake, vice president of
technology at ScholarRx and the curator of LearnLeadership.org, in a session at the 2018 Code PaLOUsa
conference in Louisville, KY. “And once a person is in a position they are not competent in, they aren’t good
enough to go up, so they get stuck.”
Leaders who micromanage, or those who would rather do the job themselves, are sometimes great contributors
who never learned how to lead, Drake said. And the way organizations choose and develop leaders has been
broken for a long time. When someone is promoted, they often try to study how to manage, but they study the
wrong things.
Drake identified 28 skill sets necessary to rise through the ranks at any organization and broke them into four
levels of leadership to help you map out what you need to master to become a strong leader.
1. LEAD YOURSELF
Leading yourself means leading by example and becoming a role model for others, Drake said. Here are the
skills you need to master at this level:
• Learn how to learn. An ability to acquire skills and knowledge is key to surviving in a modern workplace.
There are many shortcuts to learning, including learning how to study and how to select the right topics.
• Solve problems. When you ask a technologist what they want in a teammate, the top answer is a good
problem solver. “As you move up the leadership ranks, the problems change and intensify, but you still need
to be a problem solver,” Drake said.
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• Make decisions. Learn about the decisions that technologists need to make, including what tech to use and
how often to check on systems.
• Play well with others. “As technologists, our people skills often trail our technical skills,” Drake said. “But
we build tools for people, work with people, and lead people. We need to be team players, good communi-
cators, and good negotiators.”
• Manage information. People in tech are constantly bombarded with information from different sources, be
it emails, feature requests, bugs, or meeting requests. Leaders learn how to keep the important things from
falling through the cracks.
• Manage your time. Jobs in tech often encourage you to do more work than is possible. It’s key to manage
time wisely so you don’t get burnt out or lose your work/life balance.
• Market yourself. If you want to rise through the ranks, you need to learn to market yourself, in terms of
recognizing who you are and what you do and building a story around that. Drake marketed himself as
“a proven team builder interested in solving big problems in education,” which is a story that made him
attractive to the specific jobs he was looking for.
2. LEAD A TEAM
This is the most difficult transition for most professionals, Drake said, as many people leading teams are not
formal leaders but are both leaders and contributors who must shift between those ways of thinking. Team
leaders also have to learn how to delegate work to others without micromanaging and how to set boundaries
with a team.
The skills needed at this level are:
• Communicating vision and establishing boundaries. “The first job of leader is to make sure everyone
on the team knows where you’re going,” Drake said. Everyone needs to have a clear definition of success to
make the best decisions.
• Motivation, purpose, and culture. “Your organization has a vision for how it wants to change the world. A
motivated and engaged team is key to seeing that vision come to life.”
• Delegation. This is where many new leaders falter. You need to learn how to delegate problems to your
team, rather than solutions, and break down large chunks of work into small tasks for the team to complete
over time.
• Coaching. This involves learning how to help teammates solve their own problems without doing it for
them, and providing corrective feedback without killing motivation.
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• Leading meetings. Team leaders need to come to meetings with an agenda that clarifies the team’s vision
and next steps.
• Managing projects. Projects are the organizing structure for most work in the tech function. A good
manager will understand the different types of project management and determine which fits their team best.
• Hiring well. Hiring is a root problem in many organizations, Drake said, and poor decisions can lead to high
turnover and low morale.
3. LEAD A DEPARTMENT
When it comes to leading a department, technical know-how is still helpful, but strategy begins to become more
important, Drake said. A department leader must think bigger than tech and put their problem-solving skills to
work on higher-level issues in the organization. Here are the skills needed to master this type of leadership:
• Execution strategy. Your organization has a vision for how it wants to change the world. You need to
figure out what role your department plays in that vision and how you can break apart that long-term goal
into executable projects and milestones for your team.
• Negotiation. Helping employees settle disputes and arrive at agreements is the job of department leaders.
• Manage products. Product management is a broad discipline that includes customer discovery, product
visioning, and creation, marketing, and support. It generally spans multiple versions over several years.
• Resource planning. This involves determining what people, equipment, facilities, and outside help are
needed to help your organization achieve its vision.
• Personnel development. Your organization will change over time, and your team will need to change with
it. Growth and development are major motivators for employees and need to be leveraged for retention.
• Budgeting. Managers need to make tradeoffs in the initiatives they pursue, the features they include in a
product, and the quality they strive for. Budgeting allows you to allocate capital on paper to make better
decisions.
• Change management. Change is hard, and many people and organizations fight it even when it could
benefit them, so a leader must help in times of transition.
4. LEAD AN ORGANIZATION
At the VP- or C-level, technical know-how is much less important than strategic skills, Drake said. However, “if
you think building tech solutions is fun, you might enjoy building organizations. The work is highly strategic,
which can be a great fit for technologists. The challenge is that it requires exceptional people skills.”
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Here are the skills that organization leaders need to succeed:
• Vision strategy. Organization leaders are the champions of a cause. They must develop a clear vision for
how to improve the lives of their customers and communicate it in ways that excite those who can bring it to
life.
• Cross-discipline leadership. As you rise through the ranks, you’ll likely gain some domain expertise and
understand how certain teams and employees work. The challenge is leading people in departments where
you don’t have firsthand experience with their unique challenges.
• Business development, marketing, and sales. This involves far more facets than an organizational
manager has time for and requires you to determine where you can create a competitive advantage for your
company.
• Operations and execution. This involves determining how the organization creates its products or services
and how it can differentiate itself on the market.
• Relationships and partnerships. “No person or organization can do everything well,” Drake said.
“Good relationships and social capital help find and retain employees, customers, vendors, partners, and
co-champions for the cause.”
• Finances. Managers must learn what capital resources are required to start or grow the organization, how
money flows through the organization, and the critical financial health measures that must be tracked.
• Legal and governance. All organizations exist in a world of rules and laws, which can alternatively be
hampering and create opportunities. A manager needs to have a strong understanding of the laws in their
location and industry.
20
LOOKING TO BUILD A CAREER AS A

TECH LEADER? HERE’S WHY EMPATHY
MIGHT HELP
BY PATRICK GRAY
From an IT leader’s perspective, at first blush, empathy When you plan
might sound like a virtue deserving of one of my
five-year-old daughter’s favorite quips, borrowed from
interactions based
a recent movie: “A bunch of hippie-dippy baloney.” on meeting the other
However, empathy can make you a more effective leader person where they
and broadly accelerate your career growth. Like many soft
skills, part of the reason empathy gets a bad rap is overly
currently are, rather
complicated interpretations of how one practices it. For than attempting to talk
our purposes, it’s the simple ability to see the world from them into accepting
someone else’s perspective.
your point of view, you’ll
SITTING ON BOTH SIDES OF likely take a different
THE TABLE and more effective
Consider the last time you were having a challenging approach.
discussion or presentation. You likely had an objective,
whether it was delivering bad news, convincing a hostile audience to adopt a different point of view, or being
tasked with being on the receiving end of similar content. Perhaps you marshalled your best talking points,
developed slides to make your case, and went into the discussion prepared for battle. How did it go? If you
were the highest-ranking person in the room, perhaps it seemed to go swimmingly, with staff diligently nodding
affirmation to your every assertion, but did you truly convince them of the merits of your case? Among peers,
were there passionate arguments but ultimately several “immovable objects” pushing each other with no
measurable progress?
Now, consider approaching the situation slightly differently. Rather than thinking about what content to
present, try to put yourself in the other person’s shoes. What might they be concerned about? What are they
expecting to hear? What might persuade them to adopt a new position on their terms, rather than being
metaphorically beaten into submission?
21
When you plan interactions based on meeting the other person where they currently are, rather than attempting
to talk them into accepting your point of view, you’ll likely take a different and more effective approach.
EMPATHETIC TECHNOLOGY
For a more concrete example, consider the current state of technology design and implementation. Terms
like user experience and design thinking are now common vernacular, and while there are differences and nuances
among the various techniques for systems design, they all start with empathy and understanding of the end user
as their core.
In the old days of system design, we’d consider the data we needed to present or acquire from the user, with
technical requirements first and foremost. If the end user were lucky, some analyst or developer might spend
a few minutes trying to organize screens and interfaces to at least make them logical. This left us with overly
complex technology that frustrated users. While frustration is generally not a core business metric, these
systems resulted in lower productivity, longer adoption times, and in the worst case, successful technologies that
no one adopted since they were too difficult to use.
Empathy even extends to a basic understanding of how a technology will be used. I’ve worked with several
oil and gas companies and been in the room when technology for field workers was being discussed. Eyes
often roll when a vendor begins regaling the room with tales of the wonders of iPads for every field worker,
a solution that sounds great until you consider many of these workers are wearing oily and greasy gloves and
working in a dangerous environment. The most basic level of empathy for these workers would quickly reveal
that tablet-style computers are not the right tool for their environment. In this situation, emerging technologies
like augmented reality or voice recognition could be beneficial, or at a more basic level, asking whether its
necessary to have men and women working in these conditions interacting with technology at all and whether
the benefits outweigh the inherent risks of their work environment.
Similarly, the new school of systems design isn’t about making people feel good and love their accounting
software; rather, a system that’s designed with the end user at its core often requires less training, quickly gains
adoption, and makes users more productive, all metrics with real and obvious financial benefits.
LEADING WITH EMPATHY

As leaders, it can be difficult to find a unifying theme for how we help guide and develop our people. One
could likely fill a warehouse with books dedicated to the topic, and it can be difficult to determine if you
should “lean in,” “be a servant leader,” be a “360-degree leader,” “start with why,” or “go from good to great.”
When I think of my own career, the leaders with the most impact seemed to understand the challenges I was
22
facing at the time and provided just the right level of guidance. Sometimes, that might have been no-nonsense,
highly prescriptive tactics; other times, it might have been a gentle nudge in the right direction. In all cases,
the best leaders I worked with seemed to understand my situation and showed me the path to a better place,
exemplifying the very nature of empathy.
As you guide and develop your own teams, try experimenting with a bit of empathy. That first-year analyst
likely has different concerns and perspectives from the manager nearing retirement. Rather than filing them
into a contrived model like a Millennial or a Boomer, take a moment to put yourself in that individual’s shoes.
What concerns would you have? What career challenges are you facing? How do you feel going into this
conversation with the boss? As you complete this mental exercise, you’ll quickly identify how to approach the
conversation. Someone who is new to your company and team might be wondering how to fit in and whether
leadership actually cares about their success. A high performer might want to know that their efforts are
recognized and that someone is looking for opportunities to help them excel. Someone who is just punching
the clock might need a gentle reminder of what’s expected and acknowledgment that they won’t be pushed out
of a role where they’re comfortable.
While empathy might not have a cute, book title-worthy tagline, you don’t need a 300-page tome to readily
understand, apply, and see the benefits of applying it to your work and leadership practices.
23
HOW TO DEVELOP YOUR PUBLIC

SPEAKING SKILLS AND ADVANCE YOUR
CAREER
BY PATRICK GRAY
image: istock/DGLimages
Most of us have seen the statistic that many people’s greatest fear is public speaking. Standing in front of
hundreds of expectant eyes can certainly be nerve-wracking, but it’s also a highly effective way to build your
personal brand. When commanding the stage, you have an opportunity not only to present your thoughts, but
also to show your ability to exert executive presence—a key trait for your current or future leadership roles.
Counterintuitively, public speaking is the ultimate tool for introverts. An effective presentation favors the
well-prepared, objections from the audience are usually minimal, and after a compelling talk you’ll have the
crowd coming to you rather than having to work the room yourself.
24
Speaking also allows you to quickly test new ideas or concepts you’re considering in a relatively low-risk
environment. While it might be momentarily painful, I’d prefer to get an hour or two of negative feedback
about a new approach to my work than to test that new approach in the field and put my company at risk.
FINDING A VENUE
We live in a world where it’s easier than ever to find opportunities to hone your public speaking skills. Perhaps
the easiest place to start is within your own company. If you’re not already doing so, perhaps spend the
introductory moments of your next town hall-style meeting delivering a prepared talk about the company, your
group, or an emerging technology or industry trend. Practice your delivery, how you move around the room,
and leverage body language and facial expressions in the low-risk environment.
If you’re already fully exploiting your home court advantage, most midsize and large cities have various
IT-related groups, ranging from those focused on technology employees to associations that target IT leaders.
Your local IT employee association would likely love to have a leader provide perspective to its members in
front of a small and friendly crowd and also to provide conference opportunities that get you to a larger stage
and in front of a bigger audience.
Another underutilized route is your current army of vendors. Most consulting, software, and implementation
providers attend or sponsor massive conferences. Larger ones like software maker SAP’s SAPPHIRE might
host tens of thousands of attendees. These companies love putting satisfied customers front and center
and will not only provide a venue but will often help with crafting the presentation materials and share the
stage with you, providing you with some company under the spotlight. Even if you don’t feel ready for the
main stage, most of these conferences have opportunities for everything from panel discussions to joint
presentations during more intimate breakout sessions.
CREATING YOUR CONTENT

Once you’ve found a venue, the next challenge is creating your content. This is where most new speakers make
a critical error, jumping immediately into slides that share information rather than spending time considering
what message they want the audience to walk away with. Before creating a single slide, ask yourself what two or
three points you want the audience to remember after you talk. Think about what stories you might tell a friend
that would convey those points, using a conversational tone and storytelling techniques. Most audiences would
rather hear a good story that presents one or two points than a highly technical lecture that packs volumes of
information into a dry and forgettable format. Like a good story, your speech should have a beginning, some
conflict or challenge, a resolution, and perhaps a call to action.
25
DELIVERING YOUR TALK

The best advice I ever received about public speaking was to always remember that the audience wants you to
succeed. No one takes the time out of their lives to sit through a speech with the hope that the speaker will fail
miserably. The moment you walk on stage you have a room full of adoring fans, even if they’ve never set eyes
upon you before.
There are hundreds of tips on how to use the stage and the various mechanics of delivering a speech. Rather
than attempting to remember every single nuance, find a couple that you feel can work for you and use them
the next time you give a talk. You might focus on smiling and looking like you’re enjoying yourself, making eye
contact with the crowd, or moving around rather than hiding behind the podium. Aim to succeed at using a
couple of techniques rather than increasing your nervousness by attempting to follow every supposed rule of
public speaking.
If you’re struggling for inspiration, watch a popular TED Talk or well-regarded speaker on YouTube. Notice
how they use pauses, movement, and changes in tone to keep the delivery interesting and relate the content to
the audience at a personal level rather than some cerebral, academic style. I tend to shoot for brevity rather than
trying to pack in every point I’d ever wanted to make. Again, your audience will probably walk away happier
with a short, well-delivered single point than a rambling dissertation.
SPEAKING AND BRAND BUILDING

If you can speak effectively, you’ll quickly find you’re being asked to deliver more talks to larger audiences,
gaining exposure to an increasingly diverse network. Like any personal brand-building exercise, this growing
professional network will provide you with career opportunities that might range from more speaking requests
to publishing opportunities to career opportunities. As with all brand building, done well you’ll soon create a
virtual cycle where interesting people and opportunities actively seek you out rather than your hunting
for them.
26
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Global Editor in Chief ABOUT TECHREPUBLIC
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provides analysis, tips, best practices, and case studies
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The information contained herein has been obtained
Senior Features Editors from sources believed to be reliable. CBS Interactive Inc.
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disclaims all warranties as to the accuracy, completeness,
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or adequacy of such information. CBS Interactive Inc. shall
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Associate Editor Copyright ©2018 by CBS Interactive Inc. All rights reserved. TechRepublic
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How To Build A Successful CIO Career

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HOW TO BUILD A

SUCCESSFUL CIO CAREER

COPYRIGHT ©2018 CBS INTERACTIVE INC. ALL RIGHTS RESERVED.

THE 10 SKILLS YOU’LL NEED TO LAND A

3. Enterprise software development

HOW TO LAND THE CIO JOB: 10 TIPS

1. Willingness to take on the hardest projects

3. Business acumen over technology skills

6. Configuring over creating

HOW TO FIND YOUR NEXT LEADERSHIP

Avoid: Launching your search too quickly

“The most productive channel in our C-level executives looking

Avoid: Contacting too many people

3. Develop your resume and LinkedIn presence

Avoid: Posting about your search on social media

4. Get in touch with a recruiter or headhunter

Avoid: Accepting a position too quickly

5. Offer a vision and a strategy

Avoid: Marketing yourself as only a technologist

CXO CANDIDATES: HERE’S HOW TO

GETTING READY FOR THE INTERVIEW

1. Tell me about yourself

2. Tell me about yourself: Part two

3. Tell me about the greatest career or project challenge you’ve

4. How do you manage change?

5. Where do you want to

HOW TO GET PROMOTED TO A

The skills needed at this level are:

Here are the skills that organization leaders need to succeed:

LOOKING TO BUILD A CAREER AS A

LEADING WITH EMPATHY

HOW TO DEVELOP YOUR PUBLIC

CREATING YOUR CONTENT

DELIVERING YOUR TALK

SPEAKING AND BRAND BUILDING

Editor, Australia DISCLAIMER

Associate Social Media Editor

Cover image: iStock/istocksdaily

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