Leadership Confidential with Lena Reinhard

"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. [https://www.lenareinhard.com/articles/real-talk-allyship-engineering-lpcs01e10] Resources * People of Color in Tech: Empowering Diversity [https://perscholas.org/news/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 [https://www.lenareinhard.com/].

“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 progression * The subtle but pervasive ways ableism shows up in tech * Why many neurodivergent employees hesitate to ask for accommodations—and how leaders can change that * Practical strategies for making workplaces genuinely supportive * What 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. [https://www.lenareinhard.com/articles/supporting-neurodivergent-employees-guide-lpcs01e11] Resources: * LinkedIn post about communication feedback for autistic people [https://www.linkedin.com/posts/lizzie-somerfield-37b231a4_neurodiversityatwork-dei-actuallyautistic-activity-7223583103078805505-GoIA] * Manual of Me: Personal user guides for better working relationships [https://www.manualof.me/] * Book recommendation on Amazon [https://amzn.eu/d/0tsoHLy] * Goblin Tools: Productivity tools for neurodivergent people [https://goblin.tools/] * Flown: Focused work environments [https://flown.com/] * Neurodiversity Employment Survey: Adjustments Interim Report [https://axia-asd.co.uk/wp-content/uploads/2020/10/Neurodiversity-Employment-Survey-Adjustments-Interim-Report_v1.0.7.pdf] * Law Society: Reasonable Adjustments in Organizations - Best Practice for Disability Inclusion [https://www.lawsociety.org.uk/topics/disabled-solicitors/reasonable-adjustments-in-organisations-best-practice-for-disability-inclusion] * HR Magazine: Neurodiversity and PIPs - Dropping the Mask [https://www.hrmagazine.co.uk/content/features/neurodiversity-and-pips-dropping-the-mask] * Harvard Business Review: Stop Asking Neurodivergent People to Change the Way They Communicate [https://hbr.org/2022/10/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: * 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 pressure Together, they examine how to navigate this challenging dynamic while staying true to your leadership values and supporting your team. ___ ⁠⁠⁠Full episode transcript link⁠⁠⁠. [https://www.lenareinhard.com/articles/handling-a-micromanager-a-real-experience-and-practical-solutions-lcps01e10] ___ Resources * ⁠⁠ [https://goblin.tools/]Effective Skip-Level Meetings: A Guide and Templates for Managers of Managers [https://www.lenareinhard.com/articles/effective-skip-level-meetings-guide-templates-managers-of-managers] * * How to Manage Your Boss (With a Free Communication Template!) [https://www.lenareinhard.com/articles/a-template-for-weekly-updates-to-your-boss] * * Managing Up: The Most Important Skill for Anyone Who Has a Manager [https://www.lenareinhard.com/articles/managing-up] ___ 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 [https://www.lenareinhard.com/articles/].

“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 [www.lenareinhard.com/articles/debugging-product-vs-engineering-breaking-down-silos-building-trust-lcps01e09]. ___ Resources * ⁠Goblin Tools [https://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 [https://www.lenareinhard.com/articles/].

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 [https://github.com/checkly/srebot] Research & Studies: * The Root Causes of Failure for AI Projects (RAND Study) [https://www.rand.org/pubs/research_reports/RRA2680-1.html] * O'Reilly: Hands-on Large Language Models [https://www.oreilly.com/library/view/hands-on-large-language/9781098150952/] Frameworks & Tools: * SuperAGI [https://superagi.com/] * Microsoft AutoGen [https://microsoft.github.io/autogen/] * CrewAI [https://www.crewai.com/] Technical Resources: * Prompting Guide [https://www.promptingguide.ai/guides/optimizing-prompts] * AutoGen Web Scraping Examples [https://microsoft.github.io/autogen/0.2/docs/notebooks/agentchat_webscraping_with_apify] * Vector Search with ClickHouse [https://clickhouse.com/blog/vector-search-clickhouse-p1] * Mistral AI Documentation [https://docs.mistral.ai/guides/prompting_capabilities/] * AutoGen Research Paper [https://arxiv.org/pdf/2308.08155] GitHub Projects: * MetaGPT [https://github.com/geekan/MetaGPT] * Aider Code Assistant [https://github.com/Aider-AI/aider] * AgentCoder [https://github.com/huangd1999/AgentCoder] * OpenHands [https://github.com/All-Hands-AI/OpenHands] * SWE-agent [https://github.com/princeton-nlp/SWE-agent] Additional Resources: * Awesome AI Agents [https://github.com/e2b-dev/awesome-ai-agents] * AIxploria [https://www.aixploria.com/en/category/ai-autonomous/] * AI Tool Directory [https://aitoolfor.org/categories/agents/] * mem0 RAG [https://github.com/mem0ai/mem0] 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 [https://www.lenareinhard.com/articles/cutting-through-the-ai-hype-lcps01e08] *** 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.