Leadership Confidential with Lena Reinhard

Lena Reinhard
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Leadership Confidential with Lena Reinhard

What does it take to be a leader in tech? The 'born genius', bold visionary? Can you lead if that's not you? I'm Lena Reinhard, long-term technology leader, and I believe that leadership can be learned. Many of us face similar challenges in this work, but we don't talk about them enough in the open: The difficult choices, hidden doubts, lessons learned the hard way, and growing the skills not all of us were born with. My guests and I are here to change that: You'll get real talk on hard things in technology, finding community, and becoming the engineering leader you can be. Join us!

  1. APR 15

    Real Talk on Allyship in Engineering: Using Your Position to Support Others

    "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. Full episode transcript link. Resources People of Color in Tech: Empowering Diversity 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.

    52 min

  2. APR 1

    Supporting Neurodivergent Employees: A Guide for Engineering Leaders

    “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: How neurodivergency impacts communication, collaboration, and career progressionThe subtle but pervasive ways ableism shows up in techWhy many neurodivergent employees hesitate to ask for accommodations—and how leaders can change thatPractical strategies for making workplaces genuinely supportiveWhat managers and peers need to unlearn about “normal” work behaviors 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 Book recommendation on Amazon Goblin Tools: Productivity tools for neurodivergent people Flown: Focused work environments Neurodiversity Employment Survey: Adjustments Interim Report Law Society: Reasonable Adjustments in Organizations - Best Practice for Disability Inclusion HR Magazine: Neurodiversity and PIPs - Dropping the Mask 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.

    1h 9m

  3. MAR 18

    When Your Boss Won't Let Go: Surviving Micromanagement

    “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: Recognizing the difference between hands-on leadership and controlling behavior Understanding the underlying causes of micromanagement at the executive level Maintaining your team's trust while managing up to a controlling boss Setting boundaries without damaging important relationships Specific tactics that worked (and didn't work) in shifting the dynamic How to avoid becoming a micromanager yourself when under pressureTogether, they examine how to navigate this challenging dynamic while staying true to your leadership values and supporting your team. ___ ⁠⁠⁠Full episode transcript link⁠⁠⁠. ___ Resources ⁠⁠Effective Skip-Level Meetings: A Guide and Templates for Managers of Managers How to Manage Your Boss (With a Free Communication Template!) Managing Up: The Most Important Skill for Anyone Who Has a Manager___ 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.

    1h 15m

  4. 12/10/2024

    Debugging Product vs Engineering: Breaking Down Silos and Building Trust

    “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: What makes some product-engineering partnerships succeed while others falter How to identify and address common friction points between teams Building trust and psychological safety across organizational boundaries Setting clear expectations and aligning incentives Moving from finger-pointing to shared ownership Creating feedback loops that actually work Together, they explore actionable approaches for both product and engineering leaders to foster better collaboration, improve communication, and ultimately deliver more value to users. ___ ⁠⁠Full episode transcript link⁠⁠. ___ Resources ⁠Goblin Tools ___ 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.

    1h 5m

  5. 12/03/2024

    Cutting Through the AI Hype: A Practical Guide to Building Your AI Strategy

    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 Checkly's Proof of Concept: SREBot Research & Studies: The Root Causes of Failure for AI Projects (RAND Study) O'Reilly: Hands-on Large Language Models Frameworks & Tools: SuperAGI Microsoft AutoGen CrewAI Technical Resources: Prompting Guide AutoGen Web Scraping Examples Vector Search with ClickHouse Mistral AI Documentation AutoGen Research Paper GitHub Projects: MetaGPT Aider Code Assistant AgentCoder OpenHands SWE-agent Additional Resources: Awesome AI Agents AIxploria AI Tool Directory mem0 RAG 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 *** Full Transcript *** 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.

    48 min

  6. 11/26/2024

    From Metrics to Impact – Making Engineering Work Count in Business

    “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: Partner effectively with analysts and product managers to understand key business metrics Develop empathy for users to create truly impactful products Handle increased pressure to track and demonstrate progress Communicate engineering value clearly to stakeholders Adapt to management responsibilities when thrust into the role Together, they explore practical strategies for engineering leaders to understand, measure, and articulate their team's business impact in an environment of constant change. ___ ⁠⁠Full episode transcript link⁠⁠. ___ Resources ⁠Thinking, Fast and Slow by Daniel Kahneman (Book)⁠ ⁠Founders First Blog⁠ ⁠Founders Network: Startup Metrics 101: What to Track and Why It Matters Lena published a Series on Productivity, with articles such as: Engineering Metrics Guide for Leaders⁠⁠ ⁠⁠How to Understand, Measure and Improve Team Productivity⁠⁠ ___ 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.

    53 min

  7. 10/29/2024

    Handling Ambiguous Environments

    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. ___ ⁠⁠Full episode transcript link⁠.⁠ ___ 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.

    1h 9m

  8. 08/12/2024

    Surviving the Job Search While Staying True to Your Values

    "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. ___ ⁠Full episode transcript link⁠. ___ 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.

    44 min
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What does it take to be a leader in tech? The 'born genius', bold visionary? Can you lead if that's not you? I'm Lena Reinhard, long-term technology leader, and I believe that leadership can be learned. Many of us face similar challenges in this work, but we don't talk about them enough in the open: The difficult choices, hidden doubts, lessons learned the hard way, and growing the skills not all of us were born with. My guests and I are here to change that: You'll get real talk on hard things in technology, finding community, and becoming the engineering leader you can be. Join us!

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