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3 posts tagged with "leadership"

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Building culture is hard, sustaining it is harder

· 17 min read
TL;DR

I experienced first-hand what it was like to work in a company with a really strong culture of knowledge management, and watched what it took to build and sustain it. I also witnessed the factors that caused it to eventually crumble.

A Roman aqueduct

My current company is struggling with some challenges that are pretty typical for a wildly successful startup that's rapidly grown into a medium-sized company. We've got the expected technical debt, organizational design challenges, and a seemingly infinite number of small systems that work great... until they catch fire as we hit new scaling thresholds.

That one time I did something important

· 16 min read
TL;DR

This is the story of the most impactful accomplishment of my career (building Vistaprint's Studio), which happened to be as an individual contributor.

For those of us who've actively chosen to remain active technologists, and have resisted the pressure to join management, it's important to remember that innovation is ultimately driven by individuals.

Light bulb with a fire in it

A commonly accepted notion in software engineering leadership is that managers have a much bigger potential for impact on a business than an individual contributor. This is certainly a credible argument, given that a great manager can have a huge impact through building a great team. They're responsible for recruiting the right people, steering the culture, and making the biggest decisions about what risks to take, what opportunities to pursue, etc. Ultimately, they're accountable for what the team delivers.

Let a thousand flowers bloom

· 11 min read
Less than a thousand flowers

I've been reflecting recently on a really formative period in my career, when I had a chance to be part of a massive experiment in progressive engineering management.

About 3 and a half years before I left Vistaprint, I was asked to join the Engineering leadership team by our (relatively) new VP of Engineering, Erin DeCesare (who is now the CTO of EZCater). She was a particularly bold leader in terms of her progressive management ideas, and was rapidly reshaping the organization with a strong set of values around empowerment and servant leadership.