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 roles, including engineering director and VP of Engineering. Sally's insights about energy management, boundary setting, and intentional leadership are wonderful for all of us.
This conversation was recorded in August 2024.
Resources
Find the full episode transcript here.
“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-shirts, and jeans reigned, and where the resulting “uniform” culture has been hard on everyone who doesn’t fit traditional ideas of what an engineer, a “technical person”, a “geek”, a leader looks like. So, how do you convey that you are all of those things, when you don’t look like the stereotype of someone who is?
We talk about our journeys in attempts to fit in, exploring ways of expressing and being ourselves, and the stressful mental gymnastics involved in calculating how our appearance may support or undermine how we’re viewed and treated. We dive into being “firsts” in visible positions, and how we found style as a tool for empowerment, connection, and representation, and close with some favorite styles and recommendations to find your own. I loved having this conversation, and I hope you enjoy it too.
“I think style and fashion is such an important part of self-actualization, and becoming that greater version of yourself, and it is a big part of how people perceive you, so it gives me great joy to feel self-actualised on a particular day and feel like I am representing the true version of myself.” — Christina
This conversation was recorded in October 2024.
Find the full episode transcript here.
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, and social capital to support colleagues from underrepresented groups?
In this episode, Lena speaks with Leo, an experienced staff engineer who shares practical, behind-the-scenes ally actions that senior technical contributors can implement, regardless of their management status.
This conversation explores:
Understanding the socio-technical systems that shape workplace dynamics
Simple meeting tactics that create space for more voices to be heard
How documentation can serve as a powerful tool for influence and recognition
Building relationships and trust that enable you to advocate effectively
Learning from missed opportunities and growing as an ally
Using established credibility to challenge unfair practices
Whether you're a senior engineer, tech lead, or individual contributor with influence through tenure, expertise, or connections, this episode offers actionable approaches to supporting colleagues and creating more inclusive environments.
Resources
Why this podcast exists
Leadership Confidential provides a space for honest conversations about the hard parts of leadership that most people only discuss behind closed doors. From my close work with dozens of leaders every week, I know that many struggle with topics like creating inclusive environments, navigating power dynamics, and supporting team members effectively. 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.
“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 experienced professional in tech, to explore the lived realities of being neurodivergent at work. From navigating ableism in performance reviews to advocating for accommodations, Adya shares deeply personal stories and actionable insights for leaders who want to build truly inclusive teams.
They discuss:
This conversation is a must-listen for anyone who wants to better understand neurodivergency, create more inclusive teams, and move beyond performative allyship to real change.
Full episode transcript link.
Resources:
LinkedIn post about communication feedback for autistic people
Manual of Me: Personal user guides for better working relationships
Neurodiversity Employment Survey: Adjustments Interim Report
Law Society: Reasonable Adjustments in Organizations - Best Practice for Disability Inclusion
Harvard Business Review: Stop Asking Neurodivergent People to Change the Way They Communicate
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.
“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 the executive level – requires a more nuanced approach. How do you maintain your autonomy and leadership presence while working with someone who wants to control every detail?
In this episode, Lena and Claire explore practical strategies for handling micromanagement through the lens of Claire's multi-year experience with a C-level micromanager.
Claire shares honest insights about:
Together, they examine how to navigate this challenging dynamic while staying true to your leadership values and supporting your team.
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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.
“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 organizations where this partnership thrives from those where it struggles?
In this episode, Lena and product leader Reina unpack the complexities of the product-engineering relationship and share practical strategies to strengthen it.
Drawing from her extensive product management experience across multiple organizations, Reina shares candid insights about:
Together, they explore actionable approaches for both product and engineering leaders to foster better collaboration, improve communication, and ultimately deliver more value to users.
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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 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:
How to identify genuine problems AI can solve vs. solutions looking for problems
Ways to validate and experiment with AI solutions while containing risks and costs
Practical considerations around compliance, privacy, and security
Strategies for managing team excitement and maintaining focus on core deliverables
Tips for evaluating AI technologies and building initial proofs of concept
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.
Resources
Research & Studies:
Frameworks & Tools:
Technical Resources:
GitHub Projects:
Additional Resources:
Chapters
00:00 Navigating the AI Landscape
02:48 Understanding AI Strategy
06:07 Identifying Real Use Cases for AI
08:49 Building an AI Strategy
12:05 Feasibility and Risk Assessment
14:56 Finding AI Expertise
18:08 Developing Proof of Concepts
21:04 Budgeting for AI Initiatives
23:55 Compliance and Ethical Considerations
27:11 Managing AI Risks
29:59 The Future of AI in Business
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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 pod@lenareinhard.com.
“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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Resources
Research
Prevalence, Predictors, and Treatment of Impostor Syndrome: a Systematic Review - PMC
A Surprising Number of Americans Think They Could Beat Wild Animals in a Fight
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:
Leading in organisations: How companies changed, what they prioritise
Being and becoming a leader in 2024: The impact of those changes on leaders, interviewing, and roles & time spend
Industry trends and outlooks: What engineering leaders are excited & concerned about, and the influence of AI
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.
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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 pod@lenareinhard.com.
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:
The relevance of fruit baskets: Max’ career from a computer science graduate in the early 2000’s, to getting into his first informal, then first formal lead role
New skills to learn, new fears to face: How he adapted to his new roles, changed his approach from direct involvement to empowering his teams, and how he dealt with the emotional and practical aspects of ~leadership~.
Knowing if you’re doing your job well, a.k.a. “When You Do Things Right, People Won’t Be Sure You’ve Done Anything at All.” (Futurama)
Guidance for Aspiring & New Leaders: Practical advice for everyone in technical roles considering or new to a leadership path.
Find the full transcript for this episode on the podcast website.
Additional resources:
LeadDev Engineering Leadership Survey: How exactly have tech leadership roles changed? Spend 5-10 minutes sharing your experiences anonymously, and help create more clarity for the engineering leadership community. The survey is still open until Apr 12, 2024.
How to work with your peer leaders as a “first team” and why it matters
StaffEng - reports from staff+ engineers in different companies about the different shapes of the role
Book: Tanya Reilly, The Staff Engineer’s Path
Book: Will Larson, Staff Engineer: Leadership Beyond The Management Track
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