Summary
This livestream, hosted by Andrew Murphy of Tech Leaders Launchpad, focused on leadership, communication, and managing up effectively. Key topics included the distinction between leadership and management, fostering trust, handling political or risk-averse organisational cultures, and navigating confidence issues as a junior staff member. Shirley Ha, guest speaker for the session, shared insights on adapting to diverse leadership styles, gaining stakeholder buy-in, and cultivating professional resilience. Emphasis was placed on teamwork, self-ownership, and incremental cultural change within organisations.
1. Introduction to Leadership and Communication
Andrew welcomed attendees to the livestream. He outlined that the workshop would cover leadership mindsets, essential skills, and communication techniques, particularly the distinction between features and benefits.
Insights:
Workshop aims to explore leadership, mindsets, communication, and the emotional journey of leadership.
The session is split into two segments: leadership fundamentals and advanced communication skills.
Focus on leadership as a multiplier effect.
2. Introduction to Andrew and Interactive Workshop
Andrew shared his extensive experience in the tech industry, including leadership and coaching. He reiterated that this workshop would be a dynamic, interactive discussion rather than a lecture.
Insights:
Andrew has 20 years of experience in engineering.
Leadership for 15 years, with a focus on—and growth from—past mistakes.
Current focus on coaching, teaching, and Tech Leaders Launchpad's leadership development programs.
Encouraged interruptions and discussions to guide the session content.
3. Introduction to Leadership and Management
Overview of the differences between leadership and management. Leaders inspire, help others grow, and create multiplier effects for organisations. Managers focus on processes and transactional tasks.
Insights:
Leadership is people-focused and about driving mutual goals and growth.
Management is transactional, focusing on systems like timesheets and leave arrangements.
Being a leader doesn’t require being a manager; leadership impacts outcomes through others.
4. Managing Up: Common Misconceptions and Strategies
Shirley discussed the concept of "managing up," including common misconceptions and effective ways of communicating with managers. The need for ownership in one's role and fostering open dialogue was emphasised.
Insights:
Managing up involves proactive accountability for workload/performance, avoiding passive interactions.
Misconceptions: assuming managing up is questioning authority or overstepping hierarchy.
Importance of transparent career conversations with managers.
Adapting to managers’ various working styles and proactively communicating workload capacity.
5. Building Trust with Managers and Stakeholders
Insights:
Trust takes time and varies depending on personalities and organisational environments.
Managers who demonstrate early openness ease conversation.
Shirley stressed clarity in motives to avoid misinterpretation, e.g., “I want to learn, not overstep.”
Trust enables transparency in conversations and career support.
In cases of bad organisational culture, pockets of good individuals can still be found for collaboration.
6. Influencing Risk-Averse and Political Cultures
Shirley and Andrew delved into strategies for overcoming cultural resistance to risk and change, including navigating objections and gaining broad stakeholder buy-in.
Insights:
Risk-averse organisations often incentivise avoiding failure over pursuing better outcomes.
Incremental change is less likely to encounter resistance than abrupt reforms.
Stakeholder buy-in is critical for advancing ideas—one-on-one pre-meeting influence is effective.
Transparency can be affected by company, country, and team culture, warranting adaptive approaches.
7. Overcoming Confidence and Imposter Syndrome
Advice for junior professionals struggling with confidence and self-doubt when managing up. Suggestions included seeking advice, building connections, and practising communication skills.
Insights:
Networking meetups and professional groups are invaluable for perspective and feedback.
Practice conversations with trusted peers before addressing managers.
Ownership over one’s career decisions requires speaking up often, ensuring managers recognize personal needs.
8. Final Thoughts and Next Steps in Content Series
Insights:
Session concluded with reminders that self-reflection, incremental decision-making, and resilience are crucial factors in long-term leadership success.
Topics for future sessions include engineering-oriented product metrics to align outcomes with organisational objectives. Andrew recommended a newsletter subscription for updates on Tech Leaders Launchpad events/workshops.
Transcript
[03:33] Welcome and what this livestream is about
Andrew Murphy: Hello, everybody, and welcome to another Tech Leaders Launchpad Livestream. This is a series where I share the people I know—the folks who’ve helped me and who I know can help you get better. When I started as a tech leader 15 years ago, there wasn’t a lot of help and support out there in the community. We didn’t have the books, resources, blogs, and live streams that exist nowadays. I had to learn everything the hard way by trying things and making mistakes. There are more resources now, but there’s still a heap of stuff we need to talk about more—that’s what we do here. I pick topics and speakers who’ll give you the guidance you need to be better technology leaders, and we learn together. Today we have Shirley Ha. Welcome, Shirley. Tell the audience a bit about you and why we chose this topic: how to get your boss to listen to your ideas.
[04:42] Guest intro and why this topic matters
Shirley Ha: Thanks, Andrew. Good morning! I’m Shirley, currently a founder of a cybersecurity startup that’s undergoing restructuring and development. My background is in project management, mostly in not-for-profits and government. This topic matters because it’s the webinar I wish I could have attended at the start of my career. Managing up wasn’t something I was naturally good at, and they don’t teach it at uni. In the working world, there’s the people element and the task element—most of us are stronger in one than the other, but you need both to do well in your job.
Andrew Murphy: Exactly. Universities are great at theory and academic practice, but the real world is different. You get in and wonder, “Why can’t I just do the thing they taught me? Why do I have to deal with humans, projects, biases, and politics?” It can be a big culture shock.
[06:11] Managing up: definition and common misconceptions
Andrew Murphy: Let’s reset the topic: managing up—how to get your boss to listen to you. What are common misconceptions people have, especially when their ideas are ignored or someone else’s get chosen?
Shirley Ha: First, define managing up: it’s moving from a passive team member to being proactive and accountable for your workload and performance. You’re building self-sufficiency and assisting your manager with their workload. Misconceptions include: telling your boss what to do, questioning their leadership, trying to overstep or take their role, angling for a promotion faster than them, or believing it’s better to do as you’re told and never question anything. In reality, it’s about open dialogue: you were hired to solve problems—how can you help the team? With that mindset, you avoid tricky conversations and blind corners.
[08:00] Ownership mindset and live Q&A housekeeping
Andrew Murphy: There’s a lot to unpack there, especially ownership of outcomes. It’s your job to own the outcomes of your role—that’s the leadership mindset we encourage here. Part of owning outcomes is managing up: convincing your boss to give you what you need to deliver what they’ve asked for. Quick housekeeping—this is a live stream! If you’re watching live on LinkedIn, YouTube, or Twitch, post your questions and we’ll cover them. If you’re on replay, sorry you missed the live Q&A.
[09:06] Adapting to different leadership styles and aligning working styles
Andrew Murphy: Every boss is different. Some want the minutiae; others say “Here’s the problem—go solve it,” and some want you to define the problem. How do leadership styles affect how you manage up?
Shirley Ha: It depends on your career stage. Early on, you adapt to your manager’s style. Later, you can sense working styles during interviews by asking questions—and decide if that style brings out your best. If you’re already in the role and the style isn’t what you expected, give it time to build rapport. Read the situation—your last manager’s style won’t be your next manager’s style. If, after a while, the style prevents you from performing, have a conversation framed around what you need to thrive, not blaming your manager. Managers (humans!) are more open to ideas when they feel like it’s their idea.
Andrew Murphy: That’s the IKEA effect—our cognitive bias to overvalue things we think we came up with. There’s great research on that.
[12:01] The role of trust and making motives explicit
Andrew Murphy: You’ve implied something important: trust. How important is trust when managing up?
Shirley Ha: Trust takes time. If you’re lucky, your manager is transparent from day one—but often you’re both getting to know each other. I’ve had managers who proactively asked about my goals and how they could help, and others who misread my intent—thinking I was overstepping when I was just keen to learn. In hindsight, I should’ve been explicit: “I want to learn more; I’m not trying to jump the ladder.” If a manager withholds work rather than having a tough conversation, that’s a culture issue. You want an environment where both easy and difficult things are discussed, or issues fester and people leave.
Andrew Murphy: Transparency of motives is critical. Your boss needs to know your goals; you need to know theirs. If you’re doubting each other’s motives, everything becomes ten times harder.
[15:44] Starting the conversation: speak up early and often; own your career
Shirley Ha: Early in my career, I was terrible at this. I’d hint: “I’ve completed this deliverable; I have capacity to help,” hoping it would lead to “I’m not getting enough work.” Now I speak up early and often—otherwise patterns set and people assume all is well. Some managers are task-oriented and think “work is getting done, so the team is happy.” Others balance task and people and can sense undercurrents. But ultimately, you must own your career. No one else is responsible for your trajectory or happiness. You’re hired to solve problems; if you don’t speak up, they’ll assume it’s fine.
Andrew Murphy: Exactly. Your career is the most important thing to you—but to your boss, you’re one of 5, 10, 15 people. Even caring bosses juggle many concerns. Quieter folks who don’t ask questions can be overlooked. You have to advocate for yourself.
Andrew Murphy: We just lost Shirley—hopefully she’ll reconnect. Great time to solicit questions… Oh, Shirley’s back!
Shirley Ha: Sorry—tech gremlins! And yes, to your point: you’re one of several reports, so you must take ownership.
[20:06] Audience Q: Transparency, politics, and reading between the lines across cultures
Alex (audience): Transparency in goals and objectives is often asymmetric. Managers may shield or be political. You have to build trust but also read between the lines. This varies by company, culture, and size.
Andrew Murphy: Great point. It’s not just company culture—it can be country culture and personal background. Shirley?
Shirley Ha: Agreed. I’ve worked across not-for-profits, government, universities, and startups. Cultures vary widely—even within the same org there are pockets of good. If transparency isn’t there, lead by example. In very political environments, consider an action plan with a timebox—try what you can before you tap out. I’ve left orgs for politics only to find the same issues elsewhere; problems can follow if we don’t change how we cope. Also, build a life outside work—hobbies and activities help balance things, especially in tough cultures.
[23:09] When problems follow you: patterns across roles, companies, and self-reflection
Andrew Murphy: If you’re frustrated, look for patterns. Maybe you’re doing the same role across different companies, and the frustration is inherent to the role. Or you’re in the same industry type—large financial services, for example—where certain frustrations are endemic. And, yes, sometimes the problem is you.
Shirley Ha: The universe is funny—if there’s a lesson you need, changing companies won’t avoid it. Since becoming a founder, I can pull valuable lessons from every job—good or bad—even if I couldn’t see it at the time.
Andrew Murphy: Same here. I’ve had shocking jobs with complete mismatches. In hindsight, there’s always a lesson—even about myself. You can’t go back, but you can mitigate weaknesses. I know I’m not naturally organized, so I work with an assistant to help me be better.
[27:04] Influencing in multi-stakeholder environments and pre-alignment
Andrew Murphy: How do you put your ideas forward when there are many stakeholders—your boss, their boss, peers, others—with different priorities?
Shirley Ha: It can feel like too many cooks. Go back to: who are the decision-makers and project owners? Keep within scope. People mainly want to be heard—even if their idea isn’t implemented. Create space for that, and you remove a big barrier.
Andrew Murphy: It’s hard to influence many people in one meeting. I like to do the legwork beforehand—have one-on-ones to understand concerns and build support, so the larger meeting is a formality. Getting stakeholder buy-in ahead of time makes a huge difference.
[31:48] Encouraging change in risk-averse organizations
Andrew Murphy: Many of us work in risk-averse environments—enterprise, government, healthcare—where people are incentivized not to do worse rather than to do better. How do you get ideas heard when the culture resists change?
Shirley Ha: People are creatures of habit. Incremental change is the path of least resistance—small steps that accumulate. A 180-degree pivot invites resistance. Use change management basics: stakeholder buy-in, a coalition of support, and, ideally, executive sponsorship. Without executive buy-in, it’s tough. For example, in a state government agency, the annual People Matter survey flagged burnout as a key concern. When I asked what we’d do about it, the response was, “That’s just how it is—take annual leave.” That’s a band-aid. I asked a CISO in a leadership webinar about burnout; he said leave alone won’t fix it—you return to the same conditions. You need daily routines and preventative measures to decant stress and avoid burnout. I didn’t stay to see the outcome in that org, but the point is: seek allies, escalate thoughtfully, and push for sustainable practices.
[37:39] Planting seeds and finding advocates
Andrew Murphy: One frustration of moving between orgs is never seeing how the story ends. You hope the butterfly effects of your conversations matter. But planting seeds and finding advocates helps—don’t carry the banner alone.
Shirley Ha: Exactly—start the conversation, spark the fire, and bring others along.
[39:10] Confidence for early-career professionals: resources, practice, and asking for help
Andrew Murphy: Early in your career, confidence and imposter syndrome can make managing up hard. Advice?
Shirley Ha: A few things helped me: career podcasts and books (Ask a Manager is excellent—there’s a section on managing up), and tapping professional communities. I’ve attended a Lean Coffee agile group since 2020; they’re great for real-world advice. If tricky conversations feel daunting, practice with someone you trust and get feedback. Think of it like student-teacher dynamics: if you’re struggling and don’t tell your teacher, they won’t know—same with your manager. You want help to do better, which leads to better outcomes for the team and reflects well on your manager.
Andrew Murphy: Communities help you distinguish “me problem” vs “org problem,” especially when you lack experience to judge. Build a bench of advisors—coaches, mentors, sponsors, allies. Your boss can advise on many things, but they’re just one person. A diverse bench gives multiple perspectives. I like to call it the Voltron of leadership—many smaller robots forming a bigger one. No single mentor can cover everything; together they can.
[45:25] One-on-ones: listen first, then pivot; surface objections privately
Alex (audience): In one-on-ones, it’s not always best to sell your idea; listen and pivot.
Andrew Murphy: Absolutely. Those one-on-ones aren’t just for a hard pitch. The goal is to solve the problem. Surface objections privately—it’s easier to hear and handle them one-on-one than in a big room.
[46:27] Wrap-up, what’s next, and where to find us
Shirley Ha: Thanks for everyone’s patience with my technical issues—and thanks, Andrew!
Andrew Murphy: Sometimes it’s funnier to leave it in! Coming up in about a month: I’ll be live with Erwin to talk about product metrics for engineering managers—one of my favorite topics. If you enjoyed this, subscribe to my newsletter for resources, articles, travel and event updates, and the next livestream. I’m also running in-person workshops around Australia and New Zealand on tech leadership, difficult conversations, influence, and more—check the first QR code.
Andrew Murphy: Shirley, where should people follow you?
Shirley Ha: Follow me on LinkedIn. I’ll also send Andrew a list of the resources I mentioned so he can add them to the description.
Andrew Murphy: Perfect—I’ll start backfilling those links on past streams too. Thanks again, Shirley, and thanks everyone for joining and asking questions. See you next time on the Tech Leaders Launchpad Livestream. Goodbye!
Shirley Ha: Bye, everyone!
