What is the toughest lesson you’ve had to learn so far about being a leader in the software industry?

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VP of Engineering4 months ago
A critical lesson I've learned is the importance of communicating risks on projects and initiatives. As engineers, we often take pride in overcoming challenges, but as leaders, we must also consider the risks involved. It's vital to communicate these risks early and keep the executive team informed, even about minor setbacks. This transparency allows for informed decision-making.
VP of Engineering4 months ago
One of the toughest lessons I've had to learn is the importance of providing direct feedback. Early in my career, I failed to communicate concerns about a team member's performance and attitude to his manager. This omission came to light during a performance review period, causing confusion for both the team member and myself. This experience taught me that withholding feedback does no favors. People want and need critical feedback for their growth.
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CTO in Media4 months ago

I echo Rich's sentiments on giving bad news early. The conversations we shy away from the most are the ones we need to focus on as leaders. It's about helping people grow, and that involves addressing the hard stuff. It's crucial to differentiate between being nice and being kind. Being nice often involves sugar-coating issues, which only delays and potentially exacerbates problems.

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CTO in Software4 months ago
One of the toughest lessons for me was knowing when to stay close to a project due to its critical nature versus when to pull back and trust the team and middle managers to make decisions and achieve success on their own. It's important to cultivate an atmosphere of trust and ensure that team members are growing in their positions.

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Associate Director of Software Engineering in Finance (non-banking)4 months ago

Building on what Jonathan mentioned, I learned to choose my battles. Early in my career, I was passionate and eager to improve things, often getting involved in every detail. However, it's important to give people space to learn and grow on their own. It's about deciding which battles to fight, which to delegate, and which aren't battles at all.

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VP of Engineering20 days ago
Because it's hard! ;) Understanding actual product usage often involves a variety of feedback loops including production telemetry, business metric tracking, qualitative and quantitative customer feedback, etc. When engineering ...read more
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