Simon Willison’s Weblog


14 items tagged “will-larson”


Engineering leaders, especially at large companies, are managing a team of a couple hundred people. That team might cost $50 to 100 million in salary a year. So as a CEO, when you hear from your eng leaders that ‘Engineering is an art, and you can’t predict how it’s going to work,’ it’s frustrating. They’re sitting there thinking, ‘They’re telling me this is art, but I’m spending $100 million on this art each year.’ That’s not reassuring.

Will Larson

# 31st May 2024, 7:53 pm / will-larson, management

The most effective mechanism I’ve found for rolling out No Wrong Door is initiating three-way conversations when asked questions. If someone direct messages me a question, then I will start a thread with the question asker, myself, and the person I believe is the correct recipient for the question. This is particularly effective because it’s a viral approach: rolling out No Wrong Door just requires any one of the three participants to adopt the approach.

Will Larson

# 23rd May 2024, 2:48 pm / will-larson

Notes on how to use LLMs in your product. A whole bunch of useful observations from Will Larson here. I love his focus on the key characteristic of LLMs that “you cannot know whether a given response is accurate”, nor can you calculate a dependable confidence score for a response—and as a result you need to either “accept potential inaccuracies (which makes sense in many cases, humans are wrong sometimes too) or keep a Human-in-the-Loop (HITL) to validate the response.”

# 10th April 2024, 11:14 pm / will-larson, ai, generative-ai, llms

The challenge [with RAG] is that most corner-cutting solutions look like they’re working on small datasets while letting you pretend that things like search relevance don’t matter, while in reality relevance significantly impacts quality of responses when you move beyond prototyping (whether they’re literally search relevance or are better tuned SQL queries to retrieve more appropriate rows). This creates a false expectation of how the prototype will translate into a production capability, with all the predictable consequences: underestimating timelines, poor production behavior/performance, etc.

Will Larson

# 10th April 2024, 11:09 pm / search, will-larson, ai, generative-ai, llms, rag


Solving the Engineering Strategy Crisis (via) Will Larson’s 49m video discussing engineering strategy: what one is and how to build one. He defines an engineering strategy as having two key components: an honest diagnosis of the way things currently work, and a practical approach to making things better.

Towards the end of the talk he suggests that there are two paths to developing a new strategy. The first is to borrow top-down authority from a sponsor such as a CTO, and the second is to work without any borrowed authority, instead researching how things work at the moment and, through documenting that, write a strategy document into existence!

# 22nd October 2023, 9:18 pm / will-larson, management


People are complex, and they get energy in complex ways. Some managers get energy from writing some software. That’s great, particularly if you avoid writing software with strict dependencies. Some managers get energy from coaching others. That’s great. Some get energy from doing exploratory work. Others get energy from optimizing existing systems. That’s great, too. Some get energy from speaking at conferences. Great. Some get energy from cleaning up internal wiki’s. You get the idea: that’s great. All these things are great, not because managers should or shouldn’t program/speak at conferences/clean up wiki’s/etc, but because folks will accomplish more if you let them do some energizing work, even if that work itself isn’t very important.

Will Larson

# 1st December 2022, 6:35 pm / will-larson, management


Stories of reaching Staff-plus engineering roles (via) Extremely useful collection of career stories from staff-level engineers at a variety of different companies, collected by Will Larson.

# 11th September 2020, 3:30 am / will-larson, careers, management

How the Digg team was acquihired. (via) Useful insight into how a talent acquisition can play out from Will Larson, who was an engineering leader at Digg when they negotiated their acquihire exit.

# 3rd January 2020, 2:27 am / digg, startups, will-larson


Our provisioning tools for developer environments broke and no one knew how to fix them, so we reassigned new hires the zombie VMs of recently departed coworkers.

Will Larson

# 2nd July 2018, 5:27 pm / digg, will-larson

Digg’s v4 launch: an optimism born of necessity. Riveting behind-the-scenes story of the disastrous Digg V4 launch by former Digg engineer Will Larson.

# 2nd July 2018, 5:25 pm / digg, will-larson

Migrations are both essential and frustratingly frequent as your codebase ages and your business grows: most tools and processes only support about one order of magnitude of growth before becoming ineffective, so rapid growth makes them a way of life. [...] As a result you switch tools a lot, and your ability to migrate to new software can easily become the defining constraint for your overall velocity. [...] Migrations matter because they are usually the only available avenue to make meaningful progress on technical debt.

Will Larson

# 23rd April 2018, 3:03 pm / migrations, software-engineering, will-larson, technical-debt


django-springsteen and Distributed Search. Will Larson’s Django search library currently just talks to Yahoo! BOSS, but is designed to be extensible for other external search services. Interestingly, it uses threads to fire off several HTTP requests in parallel from within the Django view.

# 25th February 2009, 10:28 pm / concurrency, django, djangospringsteen, http, python, search, threads, will-larson, yahooboss

The Django and Ubuntu Intrepid Almanac. Will Larson’s impressively comprehensive guide to configuring and securing an Ubuntu VPS from scratch to run Django, using PostgreSQL and Apache/mod_wsgi behind nginx.

# 14th February 2009, 3:42 pm / apache, django, modwsgi, nginx, postgresql, sysadmin, ubuntu, vps, will-larson


Replacing Django’s Template Language With Jinja2. Part of Will Larson’s series on taking advantage of Django’s loose coupling.

# 22nd July 2008, 5:18 pm / django, jinja, jinja2, loosecoupling, python, will-larson