Episode 498: Testing in big corporations and how to get my first management job

8 snips

Feb 2, 2026

They tackle how to get busy coworkers to test rough prototypes early and avoid last-minute panic. They diagnose why late feedback shows up and debate incentives, feature flags, and quick user sessions to encourage participation. They also explore practical steps to break into engineering management without prior title experience and how to start practicing leadership now.

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ADVICE

Ship Early And Book User Sessions

Put working prototypes in front of users early by shipping incrementally behind feature flags.
Force synchronous feedback by scheduling half-hour user sessions on their calendars and watch them use it.

INSIGHT

Internal Apps Let You Pivot Fast

Internal apps allow faster pivots because you control the users and rollout.
That makes frequent incremental releases and gated feature flags a practical strategy.

ADVICE

Make Feedback Pay Off Quickly

Incentives matter: testing asks compete with long to-do lists so make the benefit clear.
Show quick value by acting on feedback promptly so people learn that participating pays off.

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In this episode, Dave and Jamison answer these questions:

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Hi Dave and Jamison,

Internal dev asker from the second half of Episode 441 checking back in. Your “ask what scared the previous dev” advice in particular has paid off handsomely; I now carry around a little book of eldritch warnings and, somehow, people keep bringing me their unknowable monsters to interpret. It’s almost as though the previous dev knew these sorts of things would happen! I didn’t set out to acquire Lovecraftian knowledge, but here we are, still in one piece.

Today’s puzzle: getting busy humans to test our stuff early, while feedback can still make it into production. We’re trying to build a culture where people will poke at a rough prototype now, instead of filing a Very Concerned Ticket three hours before release. How do we get people to test and provide feedback earlier? Do we stay disarmingly warm, promise tiny time boxes, and make a public show of “you said / we changed” until participation feels like the default? Or do we wave our terminal windows around threateningly on a screen share and promise doom (and minor annoyances) until they comply?

Thanks for lending sanity to the abyss, —An increasingly arcane internal apps dev
I have been listening to your podcast regularly and am inspired by how the podcast and the community have grown.

I am a developer with over 10 years of experience and have moved to Sweden from a country outside Europe, with the ambition to build my long-term life and career here.

For several years, I have tried to take that step myself, but often encounter the same obstacle: I am told I need experience as an engineering manager — but without the role, I can’t get the experience, and without the experience, I can’t get the role.

I have invested a lot of time and energy in developing myself: learning about leadership, coaching, communication, and team dynamics.

Despite this, I find it difficult to see a clear path forward. With everything happening in tech right now, I sometimes feel stuck and uncertain how to break this cycle.

My question is: how did you take your first step? How can one realistically enter an engineering manager role when the door seems closed without prior experience?

Thank you for creating such an honest and inspiring podcast. It already means a lot to me — and to many others, I am sure.