New York

October 15–17, 2025

Berlin

November 3–4, 2025

London

June 16–17, 2025

Debugging the most critical relationship in your work life: How to work better with an imperfect boss

Many bosses, despite their best efforts, struggle with communication, delegation, and career support for their teams. This talk explores how to navigate the complexities of working with your boss, balancing honesty with career impact, and building a more effective partnership.

Speakers: Lena Reinhard

June 25, 2025

As much as many bosses try their best, they may not always be the stellar leaders and managers that we all wish we had: Hyper-busy, not great at communicating changes, having trouble sharing their expectations or articulating strategy, oscillating between micromanaging and being very hands-off or even absent, or overloading their reports, many of them struggle to grow their own role as the organization changes. You may even work for someone who has less management experience than you do! And while many bosses care about their direct reports’ career growth, many don’t have the space to do it as effectively as you may want or need.

While many engineering leaders invest heavily in managing their teams and stakeholders, many struggle to effectively manage their relationship with their own boss, leading to misalignment, friction, and frustration for all parties involved. And how effectively you manage up becomes increasingly critical as you advance in your career, as bosses typically become less and less involved.

At the same time, bosses are in positions of power, which makes this whole topic often even trickier to navigate: What they think of your and your team’s work can have a drastic impact. But how honest can you really be with the person who also decides about your career progression and future employment?

As a former VP of Engineering and startup CEO who now works as a leadership and executive coach, I’ve seen all sides of this complex dynamic: I’ve had a wide range of bosses myself, have been a (not perfect) boss myself in fast-growing organizations, and I’ve worked with hundreds of leaders to improve how they partner with theirs.

You’ll learn how to reverse engineer the way your boss works and walk away with a practical framework and tools that you can start using immediately and that will improve how you manage up, including:

  • Signs that you need to invest more in how you manage up, common pitfalls, and how to address them
  • “Is it me?”: How to assess what you can change and what to ask your boss for
  • How to get your boss out of your business: Tools to drive alignment and clarity between you and your boss, and manage their perception of your and your team’s work

As a bonus, you’ll get tips that you can share with your own direct reports or teammates to help them develop this critical skill, too.
This talk is for anyone who has a manager, No matter if you’re a senior engineer transitioning to leadership, a technical lead or engineering manager looking to scale your impact, or a senior leader aiming to improve how you lead, this talk will provide you with practical approaches to transform your relationship with your manager and accelerate your career growth.