Carolyn Parent, president and CEO of Conveyer, joins Aileen Black on this week’s Leaders and Legends to discuss leadership in the technology sector.

Conveyor is a provider of an AI-driven document virtualization platform that transforms instructions into friendly, easy-to-follow, mobile-first applications that customers can retrieve with QR codes and view on any device.

Prior to joining Conveyor, Parent led companies at the forefront of SaaS technology innovation in real-time digital communications, mobile, AI, data and security analytics. She founded companies, managed new growth-oriented software technology business units, and helped navigate organizations through six profitable evolutions or exits (IPO, M&A, privatization and large-scale divisional spin-offs).

Throughout  her career, Parent has built high performance teams and led organizations to their highest levels of success. She did that by leading with “optimism and enthusiasm,” and keeping the lines of communication open so that all stakeholders from the individual contributors to the board of directors have the information they need meet their objectives.

According to Parent, she tries to ensure that there are “no surprises” during the decision making process. That way everyone knows where they stand and what to do.

She says “The more informed people are the better they can do their job.”

Parent believes that leaders of any organization must empower and support their teams then stand aside to let them find their own paths to success. She tries to lead by being what she calls a “velvet hammer” — strong but not abrasive. It’s a lesson she learned from a former mentor.

Parent said strong effective leaders must be able to “work with people and get to know them so they can see your point of view. Coming on too strong without understanding where or how that person may perceive it could cause issues. ”

She said leaders must always be able to adapt to change because “nothing lasts forever,” and she recommends networking with other leaders and executives as you make your way up the corporate ladder.

Networking comes naturally to Parent because she loves people and learns from everyone she meets. She added that networking has paid off over the years and has fueled her success. In fact, she said networking is the key to having a successful career.

Parent is passionate about helping the next generation of women leaders and she has some advice for them.

“Don’t let someone else pick your path,” she said. “Every company is a tech company these days. You don’t need to code to be in tech. You don’t need to be an engineer to work at STEM companies. They need sales, marketing and customer service people too. Remember if you can see it, you can be it. With hard work you can make anything possible.”

Robert Gibbs, associate administrator for the Mission Support Directorate at NASA, joins Aileen Black on this week’s Leaders and Legends to discuss his career and his approach to leadership.

Gibbs joined NASA as the assistant administrator for the Office of Human Capital Management and NASA’s chief human capital officer in 2017. In this role, Gibbs had stewardship responsibility for  NASA’s workforce, carrying out responsibilities in accordance with the Chief Human Capital Officers Act of 2002. His responsibilities included setting the agency’s workforce development strategy, assessing workforce characteristics and future needs based on the agency’s mission and strategic plan, and aligning the agency’s human resources policies and programs with organizational mission.

Gibbs describes his leadership style as one that has “to be adaptable to every circumstance and every situation.”

“I focus on what  we are going to do as leaders,” he said. “How are we going to solve problems? How are we going to accomplish the mission and take care of our folks? I think we should focus on leadership principles.”

According to Gibbs, the most effective leaders make decisions after listening to employees throughout their organizations. That’s because, he said, the best ideas don’t always come from your executive teams.

“When you’re looking for opportunities to try and find a way to leverage a certain circumstance or respond to a threat, you have to be willing to say, okay, folks, what is the best idea, and I will tell you my experience at NASA, sometimes that doesn’t come from executive suite,” he said. “It comes from the deck plates on a lot of the things that we’ve done. We have to be willing to put our egos aside and listen for the best idea.”

Gibbs said communication is the key and good leaders need to find ways to motivate and support their employees so they can go out and solve the most pressing problems in their organizations.

“I think some of the most critical parts of leadership, and this may sound kind of silly, but I think it’s listening,” he said. “Really understanding the problems that you’re facing, really understanding what you’re trying to accomplish.”

Gibbs said authenticity is another important leadership quality. It’s important to “be yourself,” because employees will know when you aren’t being straight with them.

“You really have to be who you are. Your folks will know,” Gibbs said. “They’re going to see someone who lacks authenticity from a mile away. You have to be willing to accept and understand you don’t have the answers. But you’re putting service first, and you’re willing to listen, and understand and pursue the bigger goal.”

Gibbs also offered some advice to the next generation of leaders saying they need to work hard and be willing to take on the hardest jobs to help their organizations meet their missions.

He added that he has been inspired by some of the younger workers that he has met in recent years.

“They think differently,” he said. “And I think they look at problems differently, and they assimilate information differently. And honestly, I think all of those are good things. I’m super excited for what the future holds.”

Jennifer Bisceglie, founder and CEO of Interos, joins Aileen Black on Leaders and Legends to explain how she turned a small startup into a dynamic supply chair risk management and operational resilience company.

Interos has disrupted the traditional supply chain risk  management discipline, bringing 24/7 real-time visibility into every supplier at every tier  and at every location around the world.

It gives companies the tools they need to detect and respond to supply chain crises before they happen. Clients include the Defense Department, NASA and a host of Fortune 500 companies.

Bisceglie described Interos as a “see everything, do anything, operational resilience company” that is now valued at more than $1 billion.

According to Bisceglie,  she was able to set a clear vision for what she wanted to accomplish at Interos. She then “hired a great team” to carry that vision out.

Bisceglie said one of the keys to effective leadership is to give  your teams all the resources they need to do their jobs and then get out of their way. She describes her leadership style as “up and out, not down and in,” and now focuses most of her attention on moving the company forward.

Bisceglie also believes that culture is key to a successful strategy execution. She interviewed the first 150 people hired at Interos because she wanted to be sure they shared her vision on the organization’s culture.

“It is important that we have a culture that values mutual respect. It is OK to have healthy friction, but with respect. My door is always open and you need to value everyone’s opinion,” she said.

Bisceglie’s leadership style was also influenced by one of her favorite books: Sharon Hadary’s How Women Lead: The 8 Essential Strategies Successful Women Know. She said the book taught her how to use information to drive results and how to make that information your ally.

That lesson stuck with her when she went to Sand Hill road in the Silicon Valley to meet with potential investors for her company.

She learned that “first you need to be a ‘subject expert.’  Second, you need to be sure you are solving a problem. Third, you need to have ‘grit and be scrappy.’ The fourth is you need to know your numbers and the story and the results that can be driven. Build business acumen.”

Bisceglie also shared her thoughts on what government can do to build a more resilient supply chain.

“Get rid of uncertainty and mandate transparency in the supply chain. This will allow people to visually see the supply chain, the risks and the ethical issues associated with it. This will allow us to de-risk our supply chains and allow people to make choices on where and what they consume,” she said.

Bisceglie also offered some advice to the next generation future women entrepreneurs.

“Just do it. If you have an idea, you can make it happen,” she said. “Ask for help. Have persistence and apply grit. Just do it.”

Dendy Young, managing partner of McLean Capital, joined host Aileen Black on this week’s Leaders and Legends to discuss leadership and the importance of driving toward success with no regrets.

McLean Capital is based in McLean, Virginia, and manages an investments in early-stage companies. In addition to being a managing partner at McLean, Young is also a member of Blu Venture Investors, an angel investment group that supports early stage companies in the Washington, D.C. area.

Previously, Young served as CEO of GTSI Corporation, an enterprise services and solutions provider. Prior to GTSI, Young served as founder and chief executive officer of Falcon Microsystems and, before that, Falcon Systems.

Young  was born and raised in former Rhodesia (now Zimbabwe) which he said was very much like growing up in the American Midwest. He got a full scholarship to the Massachusetts Institute of Technology after participating in a tech event at the American embassy. Young won the event by building a computer from circuit boards — this was in the 1960s, long before anyone knew of Steve Jobs or Bill Gates. He holds a bachelor of science degree in Electrical Engineering and Computer Science from MIT and an MBA from the Harvard Business School.

Young described his leadership philosophy as one that focuses on today’s problems with an eye for the future. It’s something he learned at an early age from his grandfather who owned a successful business. He said his leadership style evolved over the years but it always centered on the customer.

“Focus on listening to where you are and what is going on around you. Focus on the customer and their needs and you will be successful,” he said. “Let the market drive you and be prepared to pivot and adjust to continue on the path of success.”

Young believes leaders should be bold and aim high when setting goals for their companies, and adds they should not be afraid of risk and what the critics will say if they fail. He said a quote from President Theodore Roosevelt became his guiding principle:

“It is is not the critic who counts: not the man who points out how the strong man stumbles or where the doer of deeds could have done better. The credit belongs to the man who is actually in the arena, whose face is marred by dust and sweat and blood, who strives valiantly, who errs and comes up short again and again, because there is no effort without error or shortcoming, but who knows the great enthusiasms, the great devotions, who spends himself in a worthy cause; who at the best, knows in the end, the triumph of high achievement, and who, at the worst, if he fails, at least he fails while daring greatly, so that his place shall never be with those cold and timid souls who know neither victory nor defeat.”

Young said an effective leader must also be a great listener.

“You need to make a decision in the moment with the information you have. Many times you may be wrong but just be ready to pivot,” he said. “What I learned at Harvard was that no one really knows the answer because every situation is different.”

Young also offered some advice to the next generation of leaders, saying they should look for innovative technologies to solve today’s most pressing problems. To do that, he suggested hiring workers with expertise in Quantum Computing, Zero Trust technologies and Cyber.

Karen Dahut, president of  Booz Allen’s Defense Sector, joined Aileen Black on this week’s Leaders and Legends  to share her thoughts on leadership, and the need for strong leaders to be passionate and inspire their teams.

Dahut leads Booz Allen’s $4 billion global defense sector, which represents half of the firm’s annual revenue. Under her leadership, the company has become the premier digital integrator helping the Defense Department prepare for the new digital battlespace by using advanced technologies to enrich data for operational decisions.

Dahut previously served as Booz Allen’s chief innovation officer, where she led the firm’s innovation business. Her team imagined and built a dynamic innovation agenda that transformed the firm with new capabilities in cyber, data science, and digital technologies.

Prior to joining Booz Allen, Dahut was an officer in the U.S. Navy and served as the controller for the Navy’s premier biomedical research institute.

Dahut joined the Navy after graduating from college. She said it was in the military where she first learned how to be a leader.

“The Navy taught me leadership in a way that you would never get at that age anywhere else. I was 21 years old, leading people much older and more mature than me,” she said. “The Navy thrust me into leadership and I had to find my way. That’s something I continue to rely on today.”

She said one of the keys to being an effective leader is building a strong team around you and giving its members the tools they need to solve complex problems in innovative ways.

But to be truly innovative, she said leaders need to encourage risk.

“We have to take risks to accelerate innovation. I gave laminated “Get Out of Jail Free” cards to my leadership team, just like in Monopoly. If they try something and it fails, I tell them they can bring that to me to “get out of jail free,” she said. “It was a way of encouraging them to take risks and try new things.”

She added that, “It is more important to be lucky than good when it comes to success. This may sound like a cliché, but it comes down to hard work.”

Dahut offered some advice for the next generation of leaders saying they need to eagerly take on new challenges and be open to learning. Maintaining one’s intellectual curiosity throughout their career, seeking advice and counsel, are key. Dahut also believes it is important for companies to “accelerate the next generation”.

“Strong mentorship programs matter. Make sure that you’re building those kinds of programs across your institution,” she said.

Nicolas Chaillan, former Air Force and Space Force chief software officer, joined Aileen Black on Leaders and Legends to talk about his experience leading the Defense Department through the software development process. He also shared his frustrations in trying to streamline this process and make it more effective.

Chaillan was appointed as the first Air Force chief software officer (CSO), and was responsible for guiding Air Force programs through the transition to agile software development and DevSecOps. He established force-wide DevSecOps capabilities and best practices, including continuous authority to operate (c-ATO) processes and faster streamlined technology adoption.

In addition to his public service, Chaillan is a technology entrepreneur, software developer, cyber expert and inventor. He has over 19 years of domestic and international experience with strong technical and subject matter expertise in cybersecurity, software development, product innovation, governance, risk management and compliance. Specifically, these fields include cloud computing, cybersecurity, DevSecOps, big data, multi-touch, mobile, IoT, mixed and virtual reality, and wearables.

Chaillan decided to come work for the federal government after the Paris terrorist attacks and started at the Department of Homeland Security. He then went to DoD to bring innovation to the war fighter and ensure that younger citizens have a fighting chance against China in the future.

“It is disgraceful, and it is not too late but we have to have a sense of urgency if our kids and grandkids are going to be able to compete with China,” he said.

According to Chaillan, the United States need to rapidly invest in software innovation and agile software development to stay ahead of China.

“Software can make the difference between getting ahead or staying ahead. Our government leaders urgently need to embrace innovation and we need leaders that understand technology,” he said. “We are running out of time. China is not waiting for us to figure it out.”

Chaillan also believes that the U.S. should invest more money in education to train the next generation of leaders. He said national security will be an issue in the future without that investment.

“We need to invest in curriculum for our schools that are not 10 to 15 years behind as they are today.  We need top talent to go back and teach these future leaders. AI , cybersecurity and data science need to be invested in to help develop our future talent. We don’t have the luxury of time, we need a sense of urgency to do this now,” he said.

Chaillan added that the federal government needs to do a better job of keeping top talent from leaving public service and going to the private sector. In fact, he described the entire system as broken, saying government agencies need step up efforts to partner with other organizations and with businesses in the private sector.

“We see all the bright ones leaving. The entire model is broken, the pay is too low, and there is no progression of titles without going into management,” he said. “This is not a model that will let us succeed.”

He expressed frustration at what he called the “DoD bubble” which lacks competition and uses only large traditional contractors.

“Projects need to be cut up and have more diversity on who does the work. We need to partner to get to joint outcomes. Many times the tech stacks are the same,” he lamented. “If you add to the lack of innovation and no software agile training, all these compounds — it is an incredible waste of tax dollars.”

Chaillan believes that “DoD bubble” also hurts the department because it prevents federal managers from easily bringing in outsiders, resulting in an agency run by employees who spend their entire life within and only know what’s happening in the DoD space.

He also said Congress needs to take on a greater role in getting DoD and other agencies to embrace innovation in the software development process.

“Congress has to wake up, raise the awareness, raise the sense of urgency. It is not too late to fix it.  When you come from a startup and then go to a massive organization like DoD, it is frustrating to see the DoD staff wanting to do the right things but the system is broken,” he said.

He resigned from his post as chief software officer in part because he shared many of those same frustrations. He hoped his departure would raise awareness of what he said was “Too much talk and not enough action, particularly around funding, staffing and prioritizing basic IT issues across DoD.”

He added, “DoD remains stuck in the outdated water-agile-fall acquisition processes that are inhibiting programs to move at the pace of relevance.”

His perspective on leadership and culture in the workplace is that good leaders empower their employees by letting them participate in the decision making process. As for the next generation, he had some advice:

“Believe in what you want to do and go do it. Believe in yourself, don’t listen to others, just do it. Work hard and make things happen. Don’t think about money — money will come if you do the right things.  Believe in yourself.”

Dawn Meyerriecks, former chief technology officer for the Defense Information Systems Agency, joined Aileen Black on Leaders and Legends to talk about leading teams through big technology changes and the importance of caring for your people.  She explored past leadership challenges and the importance of “ruthless execution”.

Meyerriecks is a leading voice at the intersection of science, technology, and government. During her tenure at DISA, she managed a $5 billion budget and a military and civilian staff of 8,200. She established the agency’s technical strategy, revamping and modernizing the Global Command and Control System between Desert Storm phases I and II. Most recently she was the former  deputy director of the CIA for Science and Technology, and lead a multidisciplinary team to deliver intelligence critical to achieving national security objectives.

Throughout her more than 40 year career in government and industry service, Meyerriecks led some of the most notable technology change projects in the intelligence community.  She was able to do that by finding common ground with others and making sure they are all aligned with the agency’s  agenda.

“First you need to have an agreed vision and an agreed imperative. You need to do the review of the options and then most importantly have ruthless execution.”

Meyerriecks said she received some great advice earlier in her career from a mentor who encouraged her to speak up in meetings. That mentor, former Principal Deputy Director of National Intelligence Stephanie O’Sullivan, told her that speaking up is important because its adds another voice to the discussion.

“In meetings, you need to take your seat at the table and come prepared to add value. If you don’t speak up and contribute you shouldn’t go to the meeting. If you go, bring value. Take your place at the table and own it,” she said.

According to Meyerriecks, she was an effective leader because she was willing to have the “tough conversations” with members of her team.  It’s a lesson she learned early in her career with when she had to speak up and do the right thing even though it was counter to her boss’s view.

“It’s important to be transparent and be willing to take the risk of speaking up when integrity is on the line. If you can’t have the hard conversations and be able to disagree and discuss, you should not be in technical leadership,” she said.

Meyerriecks said she tried to be a leader that put her people first, and she sets aside time in her schedule to meet with them even it was just to talk about their lives outside of work or to share a meal.

“I don’t want to only own your head but your heart. If we only have your head we will get the action from your lips not the outcome from your passion,” she said.

Finally, Meyerriecks offered some advice for the next generation, saying future leaders need to “Own it. Know what pushes your buttons and passions.” And if you wind up in the wrong job with the wrong boss, use it as a learning experience.

“You can learn just as much from a bad boss as a good boss,” she said.

But she added that the key to becoming a good leader is to develop “robust relationships” at every stop in your career: “If you have robust relationships with people who know what you can do, you will never need to look for a job.”

Retired Lt. Gen. Charles Luckey, former chief of Army Reserve and commanding general of the U.S. Army Reserve Command, joined Aileen Black on Leaders and Legends to discuss leadership and the importance of empowering your team to do its best.

During his career, Luckey led a community-based force of more than 200,000 soldiers and civilians with a “footprint” that includes 50 states, five territories, and more than 30 countries.

He was commissioned in the Army after graduating as a Distinguished Military Graduate from the University of Virginia in 1977.  He was recalled to active duty in 2008 and selected to serve as the chief of the Office of Security Cooperation in Baghdad, Iraq.  As a civilian, Luckey is a litigation partner in the firm of Blanco Tackabery & Matamoros P.A., located in Winston-Salem, North Carolina.

Luckey described his leadership style as one that “continues to develop, grow and change over time to meet the current needs.

“I like to think of my style as mission command, and I strive to empower others to be better and do their best,” he said, adding that his leadership philosophy is “leading with love.”

Luckey said he learned how to be a more collaborative leader after leaving his battlefield command as chief of Office of Security Cooperation in Bagdad to become the assistant to the Chairman of the Joint Chiefs of Staff at the Pentagon. He said that transition from combat to being a “senior leader” at the Pentagon taught him that to be an effective leader, you have to “be a curious and a continuous learner and must be able to adapt to meet the current challenges.”

Luckey went on to say that a general officer’s authority is much different on the battlefield than it is at the Pentagon.

“You must understand ‘the building’ to be effective and throttle it back. My staff taught me that this is a different form of combat and you don’t want to create enemies with people reading your sense of urgency as not caring about others’ goals,” he said.

The retired lieutenant general said people in power could learn a lot about leadership from Julia Galef’s book, “The Scout’s Mindset,” which read recently, and explained that the scout mindset is about pulling out a field telescope and looking at the times we succeeded and and what we can learn from those successes. Luckey believes that by focusing on the good instead of the bad, “we can learn to be more enlightened, less confrontational, make better decisions and enjoy the process of learning.”

He said that’s especially important while leading during these challenging times of the pandemic, insurrection and social justice. According to Luckey, “Leaders need to find common ground, be steady and calm,” and he quoted author Carl Miller who analyzes power in the digital age. Miller believes epistemological warfare is a good description of what’s happening underneath the surface froth of disinformation, and Luckey agreed.

“This is the age of epistemic warfare. People are fighting about what they believe, not about the values of who they are.  People need to talk to each other, be civilized.  Human interaction builds trust and then common ground can be found”.

He said compulsory service in the military could help in that effort. As  commanding general of the Army Reserve, Luckey had an all volunteer force, but he believes compulsory service could “break down barriers to create common ground and bring the nation together.” Luckey believes there are many ways in which to serve, not just in the military, but bringing young citizens from diverse backgrounds together to serve a common goal under shared conditions for a few short years would weave a stronger national fabric over time.

Luckey also described the proudest achievement of his 43  year career, when he helped the reserve become more agile so it can react quickly to a wide variety of challenges.  He was especially proud of the reserve’s ability to act when the pandemic hit.

“The Army reserve is a major portion of the medical capacity of the military. In 2.5 weeks we were able to reorganize and re-task the medical capability within the reserve into Urban Augmentation task forces and provide forces to support local hospitals as they dealt with the onslaught of the pandemic,” he said,

Luckey also offered some advice for the next generation of leaders:

“I will summarize it in one word with three parts. Fitness: Intellectual, spiritual, physical. Intellectual fitness is remaining curious and learning from each other, being civil. Spiritual Fitness as a leader doesn’t mean telling people what to believe but finding your own spirituality to ground yourself, realizing that there are forces bigger than yourself.  Physical fitness is just that: No matter who you are, stay in shape, get good sleep and take care of yourself. You may not live longer, but you will live better and excel.”

Lynne Chamberlain, president and CEO of SUSE Rancher Government Solutions, joined Aileen Black on Leaders and Legends to discuss leadership and how to find your true identity as a leader.

Chamberlain brings more than 20 years of diverse technical experience as a sales executive. As president and CEO of SUSE Rancher Government Solutions, she leads the oversight for business matters to help public and private clients operate in a regulated sector. Her first assignment is to create a FOCI SUSE/Rancher Federal Organization for the parent company’s growing business in the U.S. market. SUSE and Rancher Federal are driving the SAP Hana and Kubernetes Container strategy throughout the federal government.

Previously, Chamberlain worked for 16 years at IBM/Red Hat as vice president, where she led the Government Capture/Business Development organization. She also served as vice president and general manager within the Federal Systems and Technology Division at Unisys Corporation.

Chamberlain said her goal as a leader is to create a collaborative working environment built around high performance teams. In order to do that, she said leaders must have a clear sense of their own identities. To illustrate her point, she quoted American singer and actress Judy Garland who once said you must “always be a first rate version of yourself and not a second rate version of someone else.”

Chamberlain also said empathy, transparency and clarity are keys to being an effective leader. Communications need to be clear and repeated often so employees understand what is expected from them. But she added it is important to show  your employees that you value them even when they are not on the clock.

“Pick up the phone and ask how they are doing. Show you care and if they are sick, check on them and send food,” she said.

According to Chamberlain, this is a challenging time to be the head of a fast growing organization like  SUSE Rancher Government Solutions. She said the book, “Team of Teams,” by Stan McChrystal helped her develop practical management practices that made her team more adaptable, agile, and unified.  Her team has grown to more than 70 people in a few months and it has the freedom to experiment and share what it learns across the entire organiza­tion. Chamberlain said this collaboration allows her team to respond more quickly, communicate more freely, and make better and faster decisions.

She offered some advise for the next generation of leaders saying the best leaders are continuous learners who are fearless and unafraid to challenge themselves when making make tough decisions.  To quote Eleanor Roosevelt, “You gain strength, courage, and confidence by every experience in which you really stop to look fear in the face.”

Tina Dolph, president and CEO of Siemens Government Technologies (SGT), Inc., joined Aileen Black on Leaders and Legends to discuss leadership and the importance of taking care of your people.

SGT is the separate but affiliated U.S. government arm of technology powerhouse Siemens. With
project teams across and outside the U.S., SGT is a cleared provider of Siemens products, technologies and software to solve some of the most complex government challenges in energy, automation and digitalization.

An accomplished executive leader with more than two decades of government industry experience, Dolph has often led large, diverse teams through complex transitions.

She held wide-ranging operational and functional roles at leading federal contractors including Lockheed Martin, PAE and ASRC Federal. During her time at Lockheed Martin, she was instrumental in the company’s integration of and subsequent divestiture of PAE, where she served as executive vice president of Company Operations for a $2 billion enterprise. Most recently, she served as chief strategy officer at CRDF Global, a non-profit focused on promoting global safety, security and stability through science and innovation.

Dolph described her leadership style as one centered around the people she works with. She said she encourages her employees to share their thoughts even if they disagree with her because it’s important to “create an environment where your team can be their best selves and do their best work. Include them in decisions, motivate them and create a culture that they feel valued.”

It’s a lesson she learned early in her career while working in the finance program at Lockheed Martin. She learned there is only so much a leader can control, and so effective leaders need to build strong teams around them, to help them avoid any “blind spots” when making tough decisions.

Dolph added that she continues to grow as a leader because “The minute you start to be complacent you will struggle to be the great leader you need to be. I use coaches as mirrors to help implement action plans to improve. You need to take chances and get into your discomfort zone if you are going to continue to grow.”

She also offered some advice for the next generation of leaders, saying, “The price of admission is working smart and hard but to grow yourself and your career you have to network. People underestimate the importance of networking. It is important to invest the time and grow those relationships in and out of work.”

Dolph has been recognized throughout her career for her contributions to the government marketplace. She was recently named as a 2020 NVTC Tech 100 executive for leadership and innovation in the Greater Washington region’s technology community, and has been named twice to
Washington Executive’s “Top 25 Execs to Watch” list. She is also a three-time recipient of the Wash100 award from Executive Mosaic.

In addition, Dolph serves on the Northern Virginia Technology Council Board of Directors and the Board Council for the post-9/11 veteran and military family serving national nonprofit Hope for the Warriors.

Karen Evans, former chief information officer at the Department of Homeland Security, joined Aileen Black on this week’s Leaders and Legends to share important leadership lessons and advice on how to build strong teams.

Evans has more than 30 years of executive-level management experience focusing on cybersecurity, national security, technology innovation and supply chain risk management. She served in three Presidential appointed positions in two administrations.

Evans described her leadership style as demanding but added that her employees always knew where they stood with her.

“I think I’m pretty clear about the results that I want the team to achieve. I hope and what I expect is, that the communications are open so that I can get them the resources they need to be able to achieve those results,” she said.

Evans went on to say that she often relied on feedback from her employees when making big decisions. It was a lesson she learned from a branch chief she worked for earlier in her career when her boss pulled her aside to say that they saw something in Evans.

“She saw the potential that I had. And I thought to myself, if she thought that much of me to take me aside and talk to me about what I needed to improve in myself, you know, I should really take the time to go back and honor that, and really look to see what types of things I need to improve on,” Evans said.

After that conversation she enrolled in some management training courses offered within the federal government, some of which she actually ended up teaching later on in her career.

During her tenure as DHS CIO, Evans said she realized how important it is to find talented technology professionals and convince them work in the federal government. Recruiting that talent is one of the biggest challenges facing federal agencies today, she said, adding that “It’s all about the people. I always said a fool with a tool is still a fool, right? So it’s not about the tools. It’s about the people and the education of the people.”

Evans suggested viewing this as a  continuum, such as skill sets between one and 10: “Not everybody needs to be a 10. It’s like medical school, you know, like, we need brain surgeons, but not all doctors become brain surgeons, not all lab technicians [become] brain surgeons, right? They become the best lab technician that they can.”

She said we all have a certain amount of cyber savvy because we use technology every day., but there is a need for cyber acumen and it’s time for Congress to allocate the resources  to get everyone educated up to a certain level.

Finally, she had some advice for the members of the next generation who want to follow in her footsteps, saying it’s important to know your strengths and weaknesses and to base any career  decisions on your core values.

While it’s hard to be reflective and look inward, if you do so, “It’s easier to make the decisions that you need to make going forward for your career. It’s easier to build the teams, because you know, your own weaknesses, so that you can hire people that complement your weakness so that you’re really a strong team going forward,” Evans said. “But if you, hire everybody who looks like you, then you’re going to have blind spots. And when I say look like you I’m not talking about all women, or who are Japanese-American, like myself. I am talking about folks with different strengths and perspectives.”

Renee Wynn, former chief information officer at NASA,  joined host Aileen Black on this week’s Leaders and Legends to share important leadership lessons she learned during her career.

In addition to her time at NASA, Wynn also served as deputy CIO at the Environmental Protection Agency. Although recently retired, she remains active as a board member and advisor. She frequently uses LinkedIn to highlight trends and her thoughts on federal IT, and remains a sought-after voice on government technology. Among her post-federal pursuits, she is a fellow at the National Academy of Public Administration.

According to Wynn, her leadership style evolved over the years, partly out of necessity and partly through natural maturation. She said she was exposed to some amazing leaders at NASA who taught her many important lessons. One former NASA administrator told her to, “’Take care of your people, and they will take care of the work.’ I have really tried to emulate him and his success.”

Wynn said an incident when she worked at the EPA also influenced her leadership style. She said her last year at the agency was a tough one in part because she poorly handled what she called  a significant leadership challenge. According to Wynn, “The EPA had selected an individual to be the CIO and she was so well suited for the position. The nomination process was very long and went on and on. This was difficult to navigate what that meant and I hadn’t really been through something like that before. I was frustrated with the process. I just didn’t handle it very well.”

A few years later Wynn read a book titled “Leadership and Self-Deception: Getting Out of the Box” by The Arbinger Institute. After reading the book she realized that her co-workers probably felt she was angry with them and unsupportive of their success.

But the reality was quite different.

“I was struggling to keep up with the work. I was stressing myself out more than probably necessary. I can reflect on that point in time now and know that I own my behaviors, and they weren’t the best that I could put forward,” she said. “I know that from that ‘a-ha’ moment forward, when I get into a stressful place, or into a chaotic place, I really started to say, Okay, what’s important to them? How do I situate myself and how do I listen? Because they need to know that I care. And they need to be able to trust me to help solve their problem.”

Wynn said that unfortunately the lessons she learned came at a great cost. Some working relationships and friendships at EPA were damaged but she hopes that time will heal them.

“I think maybe all of us have grown from that situation so that would be the near term story. I’m sorry for my approach back then,” she said. “I know I could have done better.  I’ve really strived to do better since that moment.”

Wynn said while the book helped her work through the challenges she was facing, it also  offered guidance on how to build a productive relationship with your team.

“As a leader, it helps you realize, where are you with the issue? Where are you with the individual that you might be working with at the time and if you feel heartfelt, genuine care to help them and support them? Then you can be genuine and it will come across to your team,” she said. “I really pivoted to try to focus on that mindset. Taking this approach your leadership style evolves kind of naturally, to fit the situation and to fit the person.”

Wynn also said that anyone who would like to be the CIO of a large agency should interview some CIOs to get their thoughts on leadership.  She said they will likely tell you that effective leadership boils down to  your ability to listen, collaborate with challenging people, to solve problems and to treat people well.

“Then put yourself on that journey to make sure that you’ve got those skills,” she said. “The CIO job is not about technical. It really is about the people part. So you need to show yourself his ability to lead people and to get those results, no matter how challenging the job is.”

Soraya Correa, former chief procurement officer for the Department of Homeland Security, joined host Aileen Black on Leaders and Legends, to discuss her long career in the federal government.

Correa retired earlier this year after a 40 year career in public service and had been with DHS since its inception, serving in key leadership positions including head of Contracting Activity for Immigration and Customs Enforcement, and associate director of the U.S. Citizenship and Immigration Services Enterprise Services Directorate.

She was appointed as DHS Chief Procurement Officer in January 2015, and before that held leadership positions at the Naval Sea Systems Command, the General Services Administration, NASA, and the Immigration and Naturalization Service — now USCIS.

She began her career as a clerk typist and worked her way up to lead one of the largest procurement organizations supporting a cabinet level agency, by being able to adapt quickly to different situations. She describes her leadership style as being “what it needs to be at the time. In other words, I adapt to the environment, the situation and what’s needed from me by my team.”

According to Correa she learned a hard lesson early in her career when she realized that you can’t always say what you are thinking.

“I am very open, I am very direct, and I am very honest. I had to learn to manage that,” she said. “I remember, one time I worked with an individual who said, ‘Soraya you have to slow down a bit.’ I had a leader that actually said that to me, after a meeting. He said you can’t always say what you’re thinking in the meeting, you got to gauge the room. You got to learn to listen to people, and you need to understand other people’s perspectives.”

Correa said she that when she took her first leadership job, she decided to be the type of leader she wanted to work for: Always present and available, one who communicate both good and bad. Her accomplishments as a leader are well recognized by the government and industry communities, having received the Secretary’s Award for Excellence, Management Support Awards, Federal 100 recognition, Public Sector Partner of the Year, Top Women in Tech, and several other accolades. These reflect her commitment to the acquisition workforce, procurement innovation, and promoting meaningful communications with industry.

“In other words, I wanted to make sure that I was thinking of those things that were important to me as I came up through the ranks because I started as a GS-4 clerk typist,” she said. She changed positions mid-career, and then came back into the procurement profession. “So I’ve done a lot of different things. And I was always known to be creative, very direct. I was the person that took on the challenges, when there was a not so gracious project or the project that nobody else wanted to do, I might raise my hand and take it, because somebody’s got to do it right. And you can find success and a lot of the interesting challenges that are out there.”

Correa, who won a 2018 Presidential Rank Award for Distinguished Service, also shared her advice for the next generation of leaders, saying they should do something that inspires and motivates them.

“I’ve spent 40 years doing what I love to do, and working with people that I just thought were incredible and phenomenal for agencies that I thought had great and exciting missions. Don’t be afraid to try new things. Don’t be afraid of the challenges,” she said. “Finally, this is our country. This is our government. We make it better by being a part of it. I encourage you to come work in our federal government be a part of the solution. I think you’ll enjoy it. I think you’ll find it invigorating and rewarding.”

Amazon Web  Services Vice President Sandra “Sandy” Carter joined host Aileen Black on Leaders and Legends to discuss being an authentic leader in these challenging times. She was a general manager at IBM from 2013 to 2016, and in April 2017 she became a vice president at Amazon Web Services.

Carter’s authenticity is a big part of her leadership style saying, “I don’t try to hide the fact that I am a technologist, I like to say that I’m a geek girl, and I really love it. I don’t hide the fact that I am a woman. I still wear pink. In fact, if you could see me right now I am wearing pink. I truly try to be who I am at all times, and not try to be someone who I’m not.”

She shared an “AHA!” moment that she experienced shortly after joining AWS, when she made what she called a pretty big mistake.

“One of my bosses asked me to come and present in our leadership meeting how I made this mistake.  This meeting was not a small leadership meeting. Hundreds of people were in the room and there’s people listening from all over the world,” she said. “My leadership wanted me to come and share my mistake and how I’d gotten through it. I had seen this happen before with some other folks but no one at my level, and no one who really had shared something like this before.”

It was a real leadership challenge for her, as she feared being branded a failure or making a mistake only six months into her tenure, but Carter listened to her boss, and shared her experience as well as how she changed the situation.

“Then other teams raised their hand and to say, ‘Hey, I had that situation, too. I’m going to use your best practice.’ And the bottom line was, it ended up that all these other teams wanted to know how I could do it, and how I could share that with them,” she said. “It really taught me a lot about failure. You know, people always say that you learn the most from your failures. But typically, you don’t want that to be so visible. And for me, this was a big challenge, something I got through and was very encouraged, because my boss had challenged me to do it in such a way that led to great outcome. “

When asked why she is able to stay so positive and passionate about her job, Carter said it’s easy because she has an amazing team and “the best job in the world.”

Having a good network around energizes her. She pointed out a necklace she always wears, which has a stone in the center of several smaller stones.

“My grandmother gave me this necklace to say that you’re in the center — you can’t sparkle, you can’t shine, you can’t glitter without that support network around you. You need that family, that team, those friends, you need all of that in order to be successful. That’s the way I’ve maintained my energy and my positive thinking,” she said.

Carter described hiring great people as the most important thing an effective leader can do. In fact, she said she tries to over-hire for the role, bringing on people who are smarter than her. Investing in them, developing them out, growing them and giving them great big opportunities is the way to grow a business as well, she theorized — “be curious, create a sense of purpose on the team. And don’t be the smartest person in the room.”

Carter shared that her team is relationship-driven when working with their partners and customers.

“Our job is to go out and meet with them and talk to them and listen to them and help them solve their problems. That was really hard during COVID, because all you had was virtual. So I tried to lead by example, and one of the things that I kicked off was 100 by 100 tour,” she said. “When I worked pre-Covid, I traveled to 87 different countries but this wasn’t physically possible now. The goal of my 100 by 100 tour was I wanted to meet with 100 partners in 100 days.”

She said it became a model for her teams and other teams and organizations, as a ways to connect. Sometimes that meant staying up until two o’clock or four o’clock in the morning because she wanted to make it convenient for the partner.

Carter is also the chairman of Girls in Tech, and very passionate about helping startups and other organizations find their way.

“No matter where you make it to whatever level you are, to be successful, you’ve got to reach back and pull others with you. I believe that’s what it’s all about is being active in your community. If you can’t pull others forward with you, if you can’t bring them along with you, you are not truly successful,” she said. “When you get to the top you’re going to be super lonely and I feel it’s our responsibility to pull others up and to support that next generation of leaders.”

She partners closely with Girls in Tech as well as other organizations to pull others up, which she said makes all the difference in the world.

Carter holds a Bachelor of Science in computer science from Duke and an MBA from Harvard.  She is fluent in eight programming languages and is the author of five books, including “The New Language of Business: SOA & Web 2.0,” which won the Platinum MarCom Award in 2008; and “The New Language of Marketing 2.0: Social Media,” which won the Silver Marketing Sherpa award in 2009.

She is also chairman of the board for the non-governmental organization WITI and an adjunct professor at Carnegie Mellon University. Carter is also a founder and CEO at Silicon-Blitz and has helped many start-ups and companies with technology, cognitive diversity and innovation.

Los Angeles Chief Information Officer Ted Ross joined Aileen Black on Leaders and Legends to discuss his leadership philosophy.

In addition to his role as CIO, Ross is also general manager of the city’s Information Technology Agency (ITA). His department has over 450 employees and delivers enterprise IT services to 48,000 employees across 41 City departments and digital services to over 4 million residents. He also oversees a 105 million dollars budget.

When discussing his leadership style Ross shared that he is a strong believer in situational leadership. He said, “ I firmly believe that you got to match your leadership style to the readiness of the staff,. With that being said, I think quite often I’m democratic, I work with IT professionals, I work with elected leaders, and I work with knowledge workers. I think in my experience, it’s really important to engage them, you have to listen to them, you’ve got to explain fully the decisions you make then you’ll find that when they make decisions on their own, they will be tighter in alignment to the goal of the organization.”

Ross says it’s also important for leaders to encourage their employees to share their thoughts and not to be intimidated by your title. He says, “One of the things I did not enjoy about becoming CIO is I stopped being Ted and I became sir, in the elevator. And while I don’t mind being called sir, and people giving me a certain level of respect, I feel quite what often quite happens is they start distancing themselves from you. I believe to be a great leader, I don’t want to be distant, I want to understand where they’re at, I want to be able to help lead. I don’t want to be segmented off to a corner office or an ivory tower, and just a sir. So I think it is important to have a good dose of humility, this has always helped me out.”

When asked about his thoughts on leadership versus culture and how he kept his team on the path of innovation, Ross said the question really feels like “the Achilles heel of government”. He passionately shared that nowhere is leadership more important than in our government, where they make such important decisions almost every day.

Ross says, “Historically, government culture is known to be some of the worst, you know, when it comes to compare with private sector, nonprofits, etc. So this is an extremely important conversation. Leveraging a quote from Peter Drucker, “ culture eats strategy for breakfast”. So culture has to play a huge role in any organization. Honestly, if culture is the set of values, the beliefs, the behaviors of an organization, then I feel leadership either is reinforcing the existing culture, or is in the process of changing that culture, for better or for worse. So leadership has, I think, a tremendous responsibility of promoting an effective culture. So it’s not just we want to have one in which it’s cool to relaxing, people want to go to work, people want to engage. That’s extremely important. But also effective when people want a piece feel like they’re contributing, that they’re doing good job. And it’s got to be a culture that to other management, or to our elected officials is a culture of success, one in which you are delivering on what you promise, you’re able to deliver it on time or under budget, or you’re able to make the right adjustments. “

Ross also said great leaders must have humility and a continuous learner if they want to be effective during good times and when facing big challenges. He says “ I think there’s a lot to always be learned, even if you consider yourself a great leader, there’s still a lot that you can learn from the folks all around you. So I think a good dose of humility is important.”

During his time as CIO of the City of Los Angeles, Ross has had to deal with huge challenges ranging from Fires to Earthquakes to the Pandemic. He says he has been proud of how his staff addressed all of those challenges and actually keeps a log so he can remember all “the great things” his staff has been able to accomplish. He says his department’s finest hour was its COVID response. He added, “I’ll never forget, basically, you know, getting an announcement on March 19 of 2020, that we are going to move to full time telework, an organization that has 35 teleworkers before that announcement, and we had to get us up to 18,173. I couldn’t be more proud that we had 10,000 teleworkers within 72 hours. We knew that this could be a possibility so we had already built out the platform, and we were already practicing on it with some of my own staff. Another accomplishment was the COVID testing app. Can you imagine getting a phone call on a Friday night from a deputy mayor saying on Sunday, we need to announce a COVID testing app. This was very early on in the COVID pandemic, before people were really testing, within 72 hours, we had that app up and running. The mayor announced it on a Sunday. Within four weeks of that we had helped schedule 60,000 COVID tests. These tests were for critical people that would keep our city running. They were medical workers, Uber drivers, and restaurant workers. Key people that early on in that pandemic kept our city running needed access to testing and vaccinations. Other early efforts of the CIO team that helped keep people from being homeless was developing a way to apply and receive rent relief. In a city as large as the City of Los Angeles, you can imagine so many people were devastated by COVID economically, and our ability to deliver over $105 million in rent relief early in the pandemic, to which we had over 221,000 applicants for that money was critical. The team had the app up and running in record time. I couldn’t be any more proud of the work that my staff as well as other city leaders performed during that time.”

Finally Ross shared the best piece of advice he ever received, “I learned this piece of advice from a council member named Michael Woo. His advice was to watch out what you say in the elevators. You’d be surprised the terrible things people have said in crowded elevators, not realizing all the people who are listening in on it. So I know during COVID that might seem a little strange because most of our elevators are pretty empty. But watch out what you say in elevators.”