How do you respond when your boss or board asks “What's our AI strategy?” In this episode, Lena Reinhard talks with Daniel Paulus, VP of Engineering at Checkly, about developing a pragmatic approach to AI initiatives that creates real value while avoiding the pitfalls of hype-driven development.

Daniel shares his experience leading AI initiatives and provides actionable insights for engineering leaders, including:

Whether you're facing pressure to "do something with AI" or genuinely exploring how AI could benefit your organization, this episode provides a practical framework for moving forward thoughtfully rather than just chasing the latest trend. Lena and Daniel discuss how to balance innovation with pragmatism, and share specific approaches for validating AI initiatives before making major investments.

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Research & Studies:

Frameworks & Tools:

Technical Resources:

GitHub Projects:

Additional Resources:

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Full Transcript

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We want to hear from you! Email us with feedback, questions, or topic ideas; I can't promise we'll always respond, but I can promise we read every email! At [email protected].

“Can you actually explain in clear terms how your company makes money? If you can't, that's a problem.”

In today's tech landscape where efficiency and productivity metrics are increasingly scrutinized, it isn't enough to just write good code. You need to demonstrate how your engineering investments contribute to the bottom line - especially if you've suddenly found yourself in management feeling overwhelmed by new business expectations.

Communicating the business impact of engineering investments is important for decision-making and stakeholder engagement – and ensuring your company knows you’re indispensable if they decide to have another round of layoffs.

In this episode, Lena and Amani explore how engineering leaders can effectively communicate their teams’ business value.

Our guest Amani brings wisdom gained from nearly 15 years of tech industry experience to share how engineering leaders can:

Together, they explore practical strategies for engineering leaders to understand, measure, and articulate their team's business impact in an environment of constant change.

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⁠⁠Full episode transcript link⁠⁠.

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Resources

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Why this podcast exists 

I make this podcast as a space for honest conversations about the hard parts of leadership that most leaders only dare to talk about behind closed doors—after all, we're supposed to be “in charge”, and “on top of things" at all times. But from my close work with dozens of leaders every week, I know that more leaders than you may think are struggling with topics like self-confidence, imposter syndrome, unclear expectations, or difficult bosses. This podcast is where we talk about it.

About your host

I’m Lena Reinhard (she/they), a fractional VP Engineering, leadership coach, mentor, and facilitator. Having served as an engineering executive with companies like CircleCI and Travis CI, and as a SaaS startup co-founder & CEO, I have dedicated my career to helping fast-paced organizations across the globe succeed in times of high change and challenging markets. You can regularly find me speaking at tech conferences and read my practical guides for leaders in the technology space ⁠⁠on my website⁠⁠.

How do you lead your team through ambiguity?

As an engineering leader, one of your key responsibilities is to navigate and guide your team through the uncertainty that often comes with new projects and goals. You are to ensure your team has the information they need to do the work that needs to be done. What, then, if you’ve gone to great lengths to bring clarity to your team, only to realize you’ve reduced ambiguity so much that there is no engaging challenge, no room for creative problem-solving?

In this episode, we discuss our guest’s recent trouble with helping her team gain clarity.

Originally, Sarah thought she needed to bring clarity to take her forming and storming team to a new level. However, over the course of the conversation, we realize that Sarah has focused too much on clarity, and her team needs her support in a different way. She has to reconsider her own role to her team, how she provides value to them, and challenge some assumptions she's made about them.

By the end of this episode, you'll come away with actionable strategies for shifting your focus from constantly driving for clarity to helping your team embrace and thrive in ambiguous environments.

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⁠⁠Full episode transcript link⁠.⁠

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Why this podcast exists 

I make this podcast as a space for honest conversations about the hard parts of leadership that most leaders only dare to talk about behind closed doors—after all, we're supposed to be “in charge”, and “on top of things" at all times. But from my close work with dozens of leaders every week, I know that more leaders than you may think are struggling with topics like self-confidence, imposter syndrome, unclear expectations, or difficult bosses. This podcast is where we talk about it.

About your host

I’m Lena Reinhard (she/they), a VP Engineering, leadership coach, mentor, and facilitator. Having served as an engineering executive with companies like CircleCI and Travis CI, and as a SaaS startup co-founder & CEO, I have dedicated my career to helping fast-paced organizations across the globe succeed in times of high change and challenging markets. You can regularly find me speaking at tech conferences and read my practical guides for leaders in the technology space ⁠⁠on my website⁠⁠.

"Interviewing knocks down pretty much everyone's confidence."

With all the lost time and huge frustration that comes with interviewing, it's easy to compromise your values in favor of feeling the relief that comes from getting to the end of the interviewing process and finally landing a job. In the long run, though, you don't want to compromise your values and non-negotiables.

In this episode, we discuss a massive problem everyone in the tech industry faces:

The challenge of finding a company whose values align with yours and navigating the infamous, often confusing and frustrating, interview process the tech industry is known for.

My guest, engineering manager Alyssa, and I talk about her own experiences interviewing and finding a job that fits her needs and values. Alyssa shares her challenges in finding a company with aligned values, the painful experiences of interviewing, factors to consider in her job search, how to assess fit and requirements, and how to ultimately find what you're looking for.

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⁠Full episode transcript link⁠.

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Why this podcast exists 

I make this podcast as a space for honest conversations about the hard parts of leadership that most leaders only dare to talk about behind closed doors—after all, we're supposed to be “in charge”, and “on top of things" at all times. But from my close work with dozens of leaders every week, I know that more leaders than you may think are struggling with topics like self-confidence, imposter syndrome, unclear expectations, or difficult bosses. This podcast is where we talk about it.

About your host

I’m Lena Reinhard (she/they), a VP Engineering, leadership coach, mentor, and facilitator. Having served as an engineering executive with companies like CircleCI and Travis CI, and as a SaaS startup co-founder & CEO, I have dedicated my career to helping fast-paced organizations across the globe succeed in times of high change and challenging markets. You can regularly find me speaking at tech conferences and read my practical guides for leaders in the technology space ⁠on my website⁠.

“There's way more variability in people than a Python environment.”—Many leaders (myself included) have felt it: “Everyone has it all figured out, but I don’t”, also known as Imposter Syndrome. And you may have been told (unironically) at some point to “be more confident”, “fake it ‘til you make it”, or “better to ask for forgiveness than for permission.”

Working in tech, we’re in a fast-changing space where confidence is currency. And the gnawing self-doubt that’s often described as Imposter Syndrome doesn’t exactly come out of nowhere.

In this episode, we unpack it—all of it:

What imposter syndrome is, and why it, ironically, is a fraud.

My guest, an experienced engineering director, shares his experience with it, how his imposter syndrome shape-shifted going from engineer to manager, and how he’s dealt with it. We talk about the role of trust and vulnerability, community, and handling the unknowns.

I share my own experience with imposter syndrome, and get into:

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Full episode transcript link.

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Resources

Research

Guides for dealing with Imposter Syndrome

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Why this podcast exists 

I make this podcast as a space for honest conversations about the hard parts of leadership that most leaders only dare to talk about behind closed doors—after all, we're supposed to be “in charge”, and “on top of things" at all times. But from my close work with dozens of leaders every week, I know that more leaders than you may think are struggling with topics like self-confidence, imposter syndrome, unclear expectations, or difficult bosses. This podcast is where we talk about it.

About your host

I’m Lena Reinhard (she/they), a fractional VP Engineering, leadership coach, mentor, and facilitator. Having served as an engineering executive with companies like CircleCI and Travis CI, and as a SaaS startup co-founder & CEO, I have dedicated my career to helping fast-paced organizations across the globe succeed in times of high change and challenging markets. You can regularly find me speaking at tech conferences and read my practical guides for leaders in the technology space on my website.

A special episode of this podcast.

Like many of you, during the tech downturn of the last 2 years, I've been trying to understand the real data beyond anecdotes and bold news headlines, on questions like:

I'm happy to share the data with you today in this episode: In The Engineering Leadership Report 2024, which I'm publishing in collaboration with tech events & publishing company LeadDev.

Join me for this conversation with LeadDev's editor-in-chief Scott Carey, an experienced tech journalist. Together, we ran a survey and heard from over 1,100 engineering leaders on:

Note: This podcast goes live while Scott and I present a talk version of our conversation at LeadDev London - this is for everyone of you who can't be in person with us.

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Download the full report at ⁠bit.ly/engleadershipreport⁠.

Full episode transcript.

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We want to hear from you! Email us with feedback, questions, or topic ideas; I can't promise we can always respond, but I can promise we read and care about every email! At [email protected].

What should engineering leadership roles look like, and how "technical" should managers be? What's been a hotly-debated topic in tech for decades has gotten very real, very often for my guest today—because he’s always been a bit of an outlier:

My guest Jay has been an engineering leader for over a decade, has led teams of many different shapes, sizes, and disciplines all throughout the industry. And, unlike the more common path of transitioning from software engineer to management, he wasn’t an engineer before becoming a manager. In an industry that highly values "technical skills" and where there's low consensus on what skills make a good manager, he grapples with finding his place, having an impact, and how to grow his career onward.

We talk about:

Links:

This is part two of our mini series about different shapes of leadership - in the ⁠⁠last episode⁠⁠, I spoke to an experienced tech lead with a more traditional career from engineer, to tech lead, to technical lead of leads. 

Thank you for joining me on Leadership Confidential.

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About this podcast & your host:

⁠⁠Lena Reinhard⁠⁠ (she/her, they/them) makes this podcast as a space for honest conversations about the hard parts of leadership that most leaders only dare to talk about behind closed doors—after all, we're supposed to be “in charge”, and “on top of things" at all times. But topics like struggling with self-confidence, imposter syndrome, growing your skills with little support, or dealing with a micromanaging boss are more common than you may think—and this is where we talk about them.

Lena is a VP Engineering, leadership coach, mentor, and organizational developer, and writer. Having served as an engineering executive with companies like CircleCI and Travis CI, and as a SaaS startup co-founder & CEO, Lena has dedicated her career to helping organizations from startups to corporations and NGOs succeed in times of high change and challenging markets.

How “technical” should an engineering manager be? And what do different paths into engineering leadership look like?—These questions have been the topic of hot debate in tech for a very long time, even more now as the industry is going through big changes with layoffs and strategy shifts. 

That’s why we’re starting this podcast with a two-episode series about different shapes of leadership roles:

You’ll hear from two leaders who both have over 20 years experience, but had very different paths into the technology space and have very different roles now. 

In this episode, you hear from Max, who shares his path from engineer to technical lead of leads. We talk about: 

Find the full transcript for this episode on the podcast website.

Additional resources:

Hear more about different shapes of leadership roles and paths next week, from an engineering manager who moved into this role without prior engineering experience.

Thank you for joining me on Leadership Confidential.

Are you tired of outdated leadership myths, of "real leaders" who are "born with it", always confident, and have it all figured out? I am, because I know the reality: I've been an engineering leader and CEO, and now coach and mentor dozens of leaders every week who feel the same.

Now I invite you into those conversations:

Subscribe now to hear seasoned and newer leaders get real on hard things in technology, finding community, and becoming the engineering leader you can be.

And, by the way: If you have a leadership challenge, burning, question, or need some real talk: Reach out and be my guest! Contact me at bit.ly/leadershipconfidential, I look forward to hearing from you.

Full transcript: lenareinhard.com/podcast/trailer-season-1