Leadership Confidential with Lena Reinhard

In our work as engineering leaders, there aren't a lot of places where the way that we lead becomes super widely visible to a lot of people. Maybe you give a presentation at some point to your entire company or at a conference. A while ago, though, I was able to watch someone lead who made me really curious about how he does it. He leads in a very public way. I watched a conductor leading an o...

We've all been there - That moment when you know it's time to have that conversation you've been dreading. The one that makes your stomach clench. The one you would rather run away from. So, how do you handle these conversations? How do you keep it from becoming such a big thing in the first place? This episode is a deep dive into what makes some conversations feel difficult: being tor...

Small gaps in alignment at the leadership level become canyons by the time they reach your teams. Alignment, as in people really agreeing on what to do, why, and how to get it done. It's also one of those leadership things that sounds so simple and straightforward in theory. But we all know that it's not always that easy in practice. My guest for this episode, Neil, brings his experiences...

When you're ill or disabled and working in the tech field, the long hours can be not just counterproductive, but discriminatory. And it is also because of these stated ideas of productivity and leadership that disabled leaders often remain invisible, but they do exist, and we are here to talk to one today. Our guest is Sally Lait, an experienced senior leader with two decades experience in rol...

“What does a leader look like?”, is a question we come back to here often, and this time, we take it literally: I meet with five exceptional senior leaders to talk about what it’s like being interested in style and fashion in tech, of all places, where it’s long been seen as most fashionable not to care about these topics, where an implicit but strongly-enforced dress code of dark hoodies, t-shirt...

The Leadership Confidential podcast is back from a short hiatus. New episodes coming soon!

"I don't think about being an ally as a badge or a thing... I start from the point of view of wanting to be a better person and be good to the people around me." While many discussions about allyship in tech focus on company-wide initiatives, what concrete steps can individual contributors and technical leaders take to create more equitable environments? How can you use your influence, expertise,...

“People don’t always take it well, unfortunately. But managers, a lot of the time, don’t do it out of malice.” Neurodivergent employees face unique challenges in tech—struggling with information overload, unspoken workplace norms, and the pressure to mask their differences. Yet, many organizations fail to provide the support they need to thrive. In this episode, Lena sits down with Adya, an experi...

“The micromanager is rather someone who uses the details for control. You want to assert your own perspective on most things. You take the lead in driving projects, making decisions, taking direction, and not allowing your team any room or space to do that.” While most advice about micromanagement focuses on quick fixes or confrontation, the reality of handling a controlling boss – especially at t...

“This collaboration and making it work really well is such a critical factor to delivering great software for your clients.” In theory, product and engineering teams share the same goal - building great software that solves real problems. Yet in practice, these teams often find themselves working in silos, dealing with misalignment, and sometimes even engaging in blame games. What separates organi...

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 le...

“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 o...

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’...

"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...

“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-chan...

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: What does the tech industry look like now? How exactly have organizations and their priorities changed? What impact and influence do AI actually have, beyond the hype? And what is it like to...

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 t...

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:...

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 ge...