I was fortunate enough last year to nominate Fito von Zastrow to participate in a Cisco program called Next Generation Leaders. The program intends to increase the ranks of African American and Latín leaders within Cisco. Individuals attend the program with their managers.

Wow! What an amazing experience! I learned so much about unconscious bias and the lived experiences of people from different backgrounds than mine. And, we were challenged to expand our vision of ourselves as leaders. I feel like I entered the program an accomplished manager and exited an aspiring leader.

During the program we created several artifacts, from a personal vision statement to a value proposition. The program culminated with an exercise to define the why behind what we do. It was inspiring to hear what everyone else wrote. But, it was also a mind expanding exercise for me.

The final artifact we produced was a "leadership deck" — a kind of resume presentation that goes into more detail than a typical CV. I'd like to share mine here. It is deeply personal. On purpose. I want people to leave the presentation knowing me well enough to trust me to lead their teams. That takes vulnerability. And, this deck is packed with it.

So, without further ado, here is my leadership deck with speaker notes...


Alan Ridlehoover's Leadership Deck - Title Slide with my headshot

Hi! I’m Alan.

I’m a passionate and accomplished software engineer. I’m an empathetic and effective engineering leader. And, I’m a fallible human being.

If that’s all the time you have, thanks for reading this far. 😀

Alan Ridlehoover's Leadership Deck - About Me slide, including photos of things that are important to me

Here’s a bit about me…

I am an environmentalist, a feminist, and an ally because I care about the world I’m going to leave behind for my children.

I am an artist, a musician, and a goofball because that’s how I express myself.

I see software development as a craft to be practiced. I write software in my free time. A friend and I release open source software under the name First Try! Software. I also write and speak about writing software because teaching recharges me and because the more I build my personal brand within the Ruby and Rails communities, the more effective I can be at attracting talent.

Alan Ridlehoover's Leadership Deck - My Journey and Endorsements slide with company logos, titles and 10 endorsements from current and former colleagues

Here's a bit about my journey as an engineer and a leader...

On the left is a mostly complete history of the roles I’ve played over the years showing the progression of my responsibilities, from intern, to Enterprise Architect, to Senior Engineering Manager, on my way toward my next gig as Director of Engineering at some point in the future.

On the right are a few of the endorsements and encouraging notes I’ve received over the years. If you’d like to speak to any of those folks, just let me know.

Alan Ridlehoover's Leadership Deck - Strengths and Vision slide with photos of my teams

I am a teacher. I connect dots—both people and ideas. I take care of my team. And, I influence the direction we’re headed. These are my strengths because they energize me.

I am a passionate, empathetic engineering leader, recognized for building trusting teams, empowering them to thrive, aligning them with the vision, and inspiring them to deliver.

Alan Ridlehoover's Leadership Deck - My Value Proposition slide with photo of me with my maximum COVID beard

This is the value I bring to the organization...

I am a fallible human being, supporting other fallible human beings through empathy, mentorship, and growth (both mine and theirs). I foster the trust and psychological safety required for my team to thrive by leaning into my mistakes as learning opportunities, allowing those around me to do the same.

As a highly accomplished platform engineering leader, I have a track record of growing my team 800% in four years (from 4 to 36) in order to ship several major, compliance-related upgrades, supporting over $2.5 billion of existing and potential revenue, while simultaneously renewing our application from the inside out to further increase the efficiency, features, and quality of our platform so that other engineering teams can meet the needs of their customers securely and efficiently.

Alan Ridlehoover's Leadership Deck - My Leadership Principles slide with Venn diagram of how my principles interact

Talk to my teams, talk to my peers, the number one word they’ll use to describe me is empathetic. I lead with empathy because I’ve been there. I know what it feels like to work for someone who doesn’t understand me. It feels like they don’t care whether you succeed or fail. I never want my teams to feel that way. I want them to know that I’m pulling for them.

My passion comes from the pure joy I feel when writing code. I’ve loved software development from the moment I first typed “Hello World!” I don’t get much time for it at work these days. But, I encourage my team members to bring me technical problems from time to time during our 1:1s. It gives me a chance to demonstrate my passion for development, which shows them how much I care about what they do.

It also gives me a chance to admit that I don’t know. That kind of fearlessness shows the team that I feel safe enough around them to admit my shortcomings. I want to inspire them to be that way with their teammates. It’s how teams grow together and form the trusting bonds that allow them to perform at their best.

Finally, the combination of being empathetic and being fearless gives me the awareness and courage to stand in allyship with those in need. I see the problem. And, I take action.

Alan Ridlehoover's Leadership Deck - The other side of fear quote slide

Finally, I want leave you with three thoughts…

The first is about fear. It’s not something we talk about much in the software industry. But, it’s here with us, whether we acknowledge it or not. It’s in our projects. It’s in our code. It’s in our relationships. It’s here because we’re here. And, we bring fear with us everywhere we go.

We hesitate to estimate work. (They might hold us to the numbers we give them!) We avoid working in certain areas of our code. (We might break it!) And, most damagingly, we each construct impenetrable fortresses around ourselves to cower behind alongside our imposter syndrome. (They might find out we’re a fraud!)

That’s what things look like on this side. What do things look like on the other side of fear?

Alan Ridlehoover's Leadership Deck - Why do you want to be? slide with text on a whiteboard that reads "What do you want to be when you grow up?" and a todler with a puzzled look on his face superimposed - the word What is scratched out and replaced with the word Why

The second thought is about finding your why.

Adults often ask children, “What do you want to be when you grow up?” A better question would be: “Why do you want to be when you grow up?”

Asking why changes things. It forces you to introspect. And, when you can finally answer your why, your what will become both obvious and varied.

Alan Ridlehoover's Leadership Deck - My why slide with photos of thing that are important to me including my family

So what is my why?

Well, take a look at this picture. Sunset on Baker Beach in San Francisco, California. My children dancing with the waves. Not a care in the world. Just peace and joy and the laughter of children.

I want my grandchildren’s grandchildren to be able to experience that with their children and grandchildren. But, global climate change might prevent that. The global rise in fascism might prevent that. And, the global rise in hate speech, anti-semitism, and violence against people of color, indigenous peoples, and the LGBTQ+ community might prevent that.

If we’re going to save the planet, stem the tide of fascism, and live in free societies where who you are is celebrated and the color of your skin is irrelevant, we’re going to need empathetic, passionate, fearless leaders.

That’s why I lead the way I do: to inspire others to become leaders in their own lives. My legacy will be their amazing accomplishments and those of the people they inspire.


I'm grateful to Dr. Summer Allen and Greg Magennis for facilitating the classes. I'd also like to thank the hard working Cisconians who run the NGL program, especially Heather Ramsay. Most imporantly, I would like to express my deep gratitude to all the participants in Cohort 18. I learned so much from each of you. I am inspired by all of you. I wish you nothing but success and joy in life.

Stay empathetic! Stay passionate! Stay fearless!