In this transitional age, workplaces can consist of folks from four generations, with Baby Boomers meeting Gen Z and Millennials working alongside Gen X. As you bring a diverse group together, how can you bridge the gap and promote professional development across generations as a leader? Tune in as Deputy Director at the US Department of Homeland Security, Stephen Kalayil, shares insights on how to lead a diverse workplace and talks about the importance of building relationships to get to know your team on a personal level. He highlights how these factors drive performance and avoid attrition for your organization. Plus, Stephen offers tips on getting creative on seeking avenues to level up your leadership skills to advance in these challenging times. Learn more in his chat with host Dr. Santor Nishizaki in this episode.

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Leading Yourself: Professional Development To Level Up Your Leadership Skills With Stephen Kalayil

Stephen Kalayil is a Deputy Director at the US Department of Homeland Security with many years of experience in IT governance, corporate strategy, biometrics, human resources, finance, procurement, program management, and project management. He loves spearheading a program strategy and objectives to assess how they will impact organizational operations and goals. To accomplish this, he focuses on dependent business operations and projects to help reach the program and the organization’s overall goals.

Kalayil has enjoyed many senior positions in his program and project management career. His professional and personal experiences have taught him the following about himself. He can successfully build a multimillion-dollar program that will impact organizational change by managing internal and external stakeholder expectations, implementing complex and efficient program strategies, and executing and deploying technical procurements.

Stephen can align programs and projects to big-picture goals by advising fellow senior leaders on the direction of the organization, measuring ROI, and assessing the health of an organization. He’s been able to hire top talent, execute hiring strategies for an organization’s needs, and understand what positions are needed to maximize the organization’s potential.

Stephen is a graduate of the University of Louisville College of Business with a double major in Finance and Marketing and a minor in Communication. He’s also a graduate of The George Washington University: Center for Excellence in Public Leadership, which is a senior leadership program. Kalayil has received multiple joint awards committees for innovation and leadership within DHS.

Additionally, Kalayil serves as a Cofounder of the nonprofit equity through sports and is a lead member of the MBA to Louisville grassroots campaign. Before his tenure at DHS, Mr. Kalayil was a Financial Contractor with Science Applications International Corporation, SAIC, supporting the US Army’s BRAC effort in Fort Knox, Kentucky. Mr. Kalayil also holds professional certificates as an agile scrum master and information technology infrastructure library ITIL V3, along with a project management certificate from The George Washington University. Let’s hear what Stephen has to say about professional development and helping us level up.

Welcome to the show, Stephen. I’m so happy to have you here.

Thanks for having me.

I appreciate it. Tell me a little bit about your story and journey of how you got to where you are now.

I was born and raised in Louisville, Kentucky. I went to the University of Louisville for my undergrad and graduated with a double major in Finance and Marketing, and I had a minor in Communication. Essentially, I wasn’t sure what I wanted to do.

It’s like a lot of us, Millennials.

I graduated and took the role that a lot of people do when they don’t know what they want to do. They become a consultant. You become a jack of all trades. There’s the old consultant joke that you’re good at a lot of things, but you’re not an expert in anything. I took that route and took a job as a Federal Consultant for a large government contractor called Science Applications International Corporation, SAIC. I worked for them for about a year and a half. I worked on the Army BRAC project. They were trying to consolidate a lot of their Army bases and surroundings. That was a pretty rewarding job. Frankly, it was something that I had zero experience with whatsoever from college.

Did they teach you about that in school?

There was nothing about that in school. I did that for a while. I then took a role with the Department of Homeland Security. This job was in the Washington DC area. In that area, those federal jobs are plentiful and all over the place. I was able to hook on with them and did not know what I was getting myself into. I didn’t come from a defense background. I had just held one defense job at this time.

At this time, I was in my mid-twenties. I took that job and started as a Finance Program Manager and then became a Project Manager. I started running small IT projects for them and learning a lot about project management and vernacular curricula, such as the PMP stuff, the PMI Institute, scrum, and everything else like that. I got into that.

I was afforded a couple of cool opportunities within Homeland. The first one was that I was able to start my own branch within the US Customs and Border Protection. I was able to start my own branch there about IT requirements. That was a rewarding experience because, in the federal space, you don’t get a lot of opportunities to start your own thing. Usually, there are established things going on, and you work into it. I was able to create a branch from scratch, hire my own people, and work on these IT requirements that were being collected at a lot of the facilities that we were standing up.

Being able to start with a blank slate is always nice. It’s almost an entrepreneurial type of atmosphere in the federal government. That sounds like a fun challenge.

After that, that was when I was able to step into a larger leadership role. I was able to become a Deputy Director that manages all of our IT portfolios. It’s all the Customs and Border Protection’s IT portfolio. We started a brand-new division and I took that leap to be a director for that.

We were talking about this term before, the Geriatric Millennials, even though we are still under 40. Elder Millennial is another term that I heard, which I like as well. You and I have used that term before interchangeably. You’ve accomplished so much in your career. Would you say that you’ve dealt with imposter syndrome? What are your thoughts on imposter syndrome? How are you able to overcome that?

I’ve dealt with imposter syndrome. It’s pervasive in the federal space because the makeup of it is a lot of older generations. When you’re someone who’s relatively young like me and who was beginning to progress in their career at a fairly rapid pace, I had a lot of imposter syndrome. I’m always the youngest person in the room. There’s a lot of the old guard that said, “You didn’t do that,” and made you feel you didn’t accomplish a lot. It was pervasive throughout my career. To be frank, I don’t think that I got out of that personally until then. It still exists.

Even though it still exists, how are you able to channel it or quiet that noise?

My skill set wasn’t as strong as I thought my peers were outside of the government. I would talk to them a lot and try to do a little bit of comparison of what I’m doing versus what they’re doing to give myself a little bit of a heat check a little bit. Even my own peers within the federal government or even with my own agency, if I felt like I was doing some of those things that they were doing, I was like, “This can’t be imposter syndrome. I am succeeding.”

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I was also fortunate to have a couple of good leaders above me who did believe in me and told me, “You’re doing the right things. You’re taking the right training. You’re showing the right leadership characteristics.” It was a little bit of a combination of me checking myself against my peers and also having a couple of good leaders and mentors above me.

Your story is pretty unique. Tell us a little bit about how you dealt with adversity and also being resilient throughout the pandemic.

My story is interesting with the pandemic. I lived in Washington DC for ten years. When the pandemic hit, truthfully, as a department, we weren’t completely set up to deal with it well. No one was using platforms like Microsoft Teams or anything else like that. My individual team is one of the few that was using it. During those couple of days in March 2020 when they told everybody to go home, they charged my team to say, “Can you teach everybody how to use Teams? We are already in a virtual environment.” We did some crash course 101 type of deals before we brought Microsoft experts to help us out.

In my case, we had a lot of challenges because we were a group that was supposed to show up to the work four days a week minimum. Everyone was going to our multiple offices throughout the National Capital Region and showing up and doing that stuff. This was a massive change. No one had managed virtually either, especially a lot of the leadership that was older than us. They were the type of individuals that wanted you to come to their meeting room and had something to say. That’s when they would tell you. They weren’t going to call you and tell you that, let alone speak to you on a Teams call. During my experience, I was able to combat that. I ended up moving during the pandemic.

Did you move from DC to another state?

I spent some time in Louisville, Kentucky, temporarily before I ended up moving to Chicago, Illinois, which is where I live now. I ended up moving to Kentucky. I explained to the team that I had the realization with my bosses. I was like, “I don’t have to be here for my job.”

Were you paying that high rent for DC?

I didn’t have to pay that rent and be there. It took some convincing at first because everybody was so ingrained that you need to be the National Capital Region. Frankly, we were telling ourselves that we were going to come back to the office. At this point, we’re finally reintegrating into the office. We’ve given up almost all of our space in the Ronald Reagan Building, which is one of the nicer federal buildings in the US. We give tons of the space up and return it all into hoteling space. I was a little ahead of the curve than the whole agency because I petitioned and said, “I want to transition out. I wanted to be closer to family and friends. I didn’t need to be in that area.”

My next question is about being a Millennial leader. Would you say that’s what makes us unique as Millennial leaders as being able to be agile? I met a lot of Gen X-ers and Baby Boomers who are agile, too, as you probably can attest. What do you think it’s like to be a Millennial leader nowadays?

Like we were talking about earlier, we’re elder Millennial leaders. We’ve got this geriatric cover. We have a distinct advantage even with our other Millennial leaders because we grew up without a screen, specifically that subsect. We can relate to the older generation and the younger generations. We’ve experienced life without it. Being a millennial leader, especially in our subsect, has been advantageous to us in many ways. We were relatable. We have the ability to stay sharp but know how life was before screens. We’re a strong group.

The generation behind us, Gen Z, was born from approximately 1995 to 2012. What would you say their greatest strength is? What advice would you give to people who are managing them?

Their greatest strength is their ability to learn. A lot of the Gen Z colleagues and Gen Zs that I’ve managed have been the best learners that I’ve ever been with.

They’re so sharp, and they pick things up like that.

They pick things up quickly. They’re sharp. They have a good appetite for learning. I’m impressed by that. I love it. I like having a lot of good Gen Z employees on the team. My advice is to give them their space because a lot of them are self-learners and self-starters. There’s a good balance between giving them their space but also checking in and making sure that they feel appreciated and are feeling good about what they’re doing. Give them good opportunities to learn. I’ve noticed in my experience that you got to give them those opportunities to learn. Give them the right training because they eat it up.

Those are great tips. It’s funny because, now, we’re older people. I’m sure the other generations are going to be laughing when Millennials and Gen Z are clashing. That’s why I have to ask this question. What can we learn from them? When we came into the workplace, as we’ve talked about before, we’ve had a lot of clashing between different generations. What is work defined as? Is it being at work? Is it getting stuff done? That has shifted during the pandemic.

I want to shift back to you a little bit. What have you done to accelerate your career so quickly from a professional development standpoint? You’re running almost all of the IT for the whole country for Homeland Security. What advice would you give to those out there? What do you do from a professional development standpoint?

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There are two things that come to mind for me. One is that I network well. I met the right people and showed a lot of interest in some of the larger initiatives that were going on. I went out of my way to try to meet those people and speak to them, even if it was getting coffee with them and trying to get ten minutes on their calendar to speak to them. Those things made a big difference because those people remember who I was as I was continuing to do strong work in what I was doing.

You’re not just like a social butterfly. You’re getting your stuff done at your desk right or wherever that takes place.

You’ve got to produce. You’ve got to be strong at what you do but also network. Networking gets you ahead. That was a big thing for me. The second was trying to take as many leadership classes and continuing education classes as I could. Try to get different certifications. PMP certification was a big one for me and the scrum master.

I graduated from The George Washington’s Senior Leadership Program. It’s all those things. You can keep doing those things. You meet other people you network and it adds to your resume. You then start to become well-rounded and a strong candidate for bigger jobs that you may be interested in. It opens doors.

A lot of that was through your organization. It seems like the government offers a lot of great professional development. What other opportunities for someone who doesn’t work for the government? Would you recommend they do it outside of their company?

I’ve taken some good government training. Also, I have sought a lot of training outside of the federal space. I went to a lot of university training where I would look up their courses and try to see if I could find something that made sense for me. Those are certificate programs. I sought those out myself on the side. I would beg my work to pay for a part of it or all of it if I could.

You got to be creative about that stuff, too, because companies and organizations only have so much for training every year. I was lucky that I called the training vendors themselves and said, “This is all I can spend on this.” A lot of times, they’ll meet you halfway or fully. It’s a good one. A lot of times, they’ll do it because they want to have well-rounded classes. Maybe they need to fill the class, so they’re willing to compromise on a couple of dollars. That’s a tip that I’ve used.

What was the first leadership challenge that you faced? How did you solve it?

The first leadership challenge I faced that was a difficult one was my first leadership role. I was in charge of this pretty large project. The individual who was leading the project was demoted but still on the team. I came on board. It was an interesting dynamic. I was brought on to fix the project and get it in the right place. The individual who was in that role was now reporting to me. That was a crazy dynamic.

The way that I dealt with it from a leadership standpoint is that the first person I talked to on that project was that first one. I made them feel valued and important. I would be leaning on them for a lot of the work that we’re doing. I made them massive contributors. At the end of the project, I gave them a lot of credit. Could we have done the project without them? In reality, we could have, but it made a lot more sense for them to be a part of it and get it going.

My next question is the Great Resignation. It sounds like you moved around, and that’s cool that your employer was able to support you, being able to move from DC to Kentucky to Chicago. What do you think is causing this Great Resignation? What advice would you give to employers and employees during this time?

Some people are unhappy or want to try something different and feel like they don’t have the latitude to do that in their gigs. They’ve taken a leap of faith and decided that they’re going to leave their situation. There are more avenues now to make income in the sense of passive income and different ways. People are doing that stuff.

It’s like Robinhood Crypto.

They’re doing all that stuff. That causes Great Resignation. People are beginning to realize that they want to start doing something that makes them happy. Their situation may not be, and they’re realizing that they don’t have to be loyal to some big company forever. They can jump around.

Do you feel that the Great Resignation was almost saying that the bar for leadership needs to be higher or maybe a correction?

It needs to be higher. For a lot of leaders, if they want to keep employees, they need to make sure that they’re trained in the right way and give them the latitude to do other things. I’m big on giving employees detailed assignments or special assignments to do that are in their wheelhouse or interest area. At the end of the day, you’re never going to have somebody who is going to stay forever. That’s not realistic. To get the most out of them, make them happy. Give them things to do that will pique their interest. Maybe they move on to somewhere else in the company, do good work, and still be in the same group. Even if they leave, you’re going to leave a good impression on them. It’s only goodwill toward where they came from.

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They may come back too or may have a referral for someone that would be a good fit.

You put your best foot forward as a leader when you’re doing that type of stuff and nurturing your employees.

As far as remote work, I know where you probably stand. When you say remote work, in-person, or hybrid, what do you think of the future of work?

I’m a fan of remote work, but there’s a lot of value in being in-person, too. I subscribe to a little bit more of the hybrid method. It’s good to be in the office, however, your schedules are broken up for everything. It could be good to be there every so often because some face-to-face time is good. Being behind a screen is not good all the time. For me, specifically, I don’t have to go to the office at all in Chicago, but I make myself go because we need to see some people. You need to have those interactions. Sometimes, some people’s interpersonal skills shine better when they’re in person. They don’t show as well over a camera. It’s good to have a little bit of both.

You said earlier how you networked a lot and grabbed coffee. You can still do that via Teams. For some of the younger folks out there that are still developing their skills, would you say that might be better to go into the office to have those coffees?

You should. It’s more difficult now because your boss may not want to be in the office, and maybe you do. You’ve got to be a little bit more diligent about planning those things out, saying, “Let’s go to lunch.” Set up those times so they don’t blow you off, etc. Maybe even cater to them quite a bit where it’s like they’re going to be in the office on Tuesday, so you better change your schedule to be in the office on Tuesday. You got to make those many sacrifices or past those little minor inconveniences to get that networking going.

You’ve shifted to working remotely this time and have been managing your teams remotely. What advice would you give to folks who are managing and leading remotely versus hybrid or in-person that are able to shift? That’s not an easy thing to do.

With my main people, I schedule one-on-ones with them. Try to talk to them about stuff that’s a little bit outside of work as opposed to everything that they’re doing. You want to be able to spend some dedicated time to know what’s going on, how they are as people if there’s anything going on, and try to get to know them on a personal level. It’s more important now than ever since we’re moving to a predominantly remote environment.

Did you say once a week?

I do it once a week.

For what? 30 minutes or so?

About half an hour. I’ll usually ask them how everything’s going. Try and get to know them. I’ll remember their spouses’ names and their kids and ask about things. When you gain that personal trust, an employee is always going to perform a little bit better, too. They will also feel more comfortable with you. You get a happier employee and better results.

It feels better, too, because you’re doing something good. You’re being authentic because you care, not just checking a box where you pop your spreadsheet and say, “How’s Jim doing?”

If they’re not happy, you want to know that too and see what you can do. If something’s going on at home, and if there’s something you can do, be happy to help if you can. For us, we have chaplain services or emotional support types of deals. We always stress that stuff because we never know what’s going on, but if we can offer help, we should.

Especially with the pandemic, you never know if a family member has COVID or passed away. Unless you’re not allowed to ask, but it’s about checking in. Being able to see that makes a big difference and shows that you have their back and you care. Here’s my last question. What advice would you give to someone who’s graduating college now, and maybe in a couple of years, they’re going to start a leadership role?

When they’re starting a leadership role and are pretty fresh out of college, I would say, “Listen to your employees. Listen to them and build trust with them. Once you do that, that opens the door to being accessible. If you don’t have trust with them early and do not listen to them as well as you could, it’s going to be an uphill battle for you.” That would be the easy thing I would tell any early leader. If you can build that rapport and build on it, success will happen.

If you put too much pressure on employees to be perfect all the time, they're never going to deliver. Share on X

What’s the best way to build trust organically on a new team?

The way to build trust is to give them work but let them work on it. Let them know that there is a lot of room to make mistakes. Things can go wrong. Let them know that you’re there to help them because if they’re successful, you’re successful. I’m big about, “This is a fail-safe environment. If you screw up, it’s okay. We will all work it out together.” If you put too much pressure on employees to have perfect stuff all the time, they’re never going to deliver.

That’s what micromanagement is, too, because perfect in one person’s eyes may be different from another’s. What’s perfect in Stephen’s eyes may be different from someone else.

I learned that a long time ago. I used to be a perfectionist. I used to be someone where every deliverable had to be perfect. I started to finally realize that it’s okay to be 70% to 80% right for those first couple of drafts. It doesn’t have to be spot on every time because if you’re trying to perfect it too early, you’re wasting your time.

It’s like at the end, where you get to that 80% or 90%, then you tweak and fine-tune it, and then it gets to that 100%. I love that. Stephen, thank you so much for your time. I appreciate it. I’m looking forward to seeing what you’re going to do next.

Thanks for having me on. I’m grateful to be here.


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About Stephen Kalayil

TZL 13 | Professional Development

As a Deputy Director with over 10 years of experience, I love spearheading a program’s strategy and objectives to assess how it will impact organizational operations/goals. To accomplish this, I focus on dependent business operations and projects to help reach the program and the organization’s overall goals.

I have enjoyed many senior positions in my program and project management career.

Skills: Program Management, Project Management, Portfolio Management, Business Operations, IT Project Management, Requirements, Stakeholder Management, Budget, Finance, Strategic Planning, Human Capital, Analytics, Government Affairs, Communication Initiatives, Public Speaking, Federal Consulting, Marketing, Procurement, Management Consulting, Client Management, Data Governance, Product Management, Technology Implementation, Brand Management, Organizational Change Management, Community Leadership