Outreachy report: February 2025

Highlights

• We opened and promoted our call for communities and initial application period; collected and reviewed Feedback #2 and #3 submissions; and approved the second stipend payment of 25 Outreachy interns — the one missing intern has a 4-week extension. We are currently collecting and reviewing Feedback #4 submissions. We are on track to celebrate the successful completion of all 26 internships at the end of March.
• I started the coordination of process improvement plans that will (1) streamline feedback collection (2) make it very explicit that stipend payments are dependent on presenting public artifacts of work or providing a detailed report of activities (3) change blog prompts, assignments, and intern chats to better showcase the fantastic work of our interns.
• I worked on the script and the slides for my upcoming talk “Anatomy of an open internship program: How we run Outreachy” to be presented at FOSS Backstage 2025. I will be heading to Europe on Tuesday.
• I pitched the idea of an Open Mentorship Initiative as a project submission for DISC Unconference 2025, and I participated in efforts to submit it as a grant proposal.

Description of activities

I facilitated team meetings, kept track of deadlines, tasks, and monitored the progress of our December 2024 June 2025 cohorts.

In respect to our December 2024 cohort, I coordinated efforts to review Feedback #2 and #3 submissions from mentors and interns. I wrote and published internal documentation instructing organizers on how to develop and execute a holistic approach to reviewing feedback submissions, gathering public artifacts produced by Outreachy interns. I mediated payment authorization requests between the Outreachy team and Software Freedom Conservancy, sending payment authorization data to RT and submitting supplementary reports including public artifacts of work whenever needed.

I managed day-to-day interactions with Outreachy interns, mentors, and coordinators. I took care of operational tasks pertaining to bi-weekly intern chats and assignments. I deliberated on and executed a test merger between two intern chats: our chat about informal chats and our chat about next steps in the free and open source community. I was the main point-of-contact for messages related to payment issues.

Omotola Omotayo and Tilda Udufo — who facilitated that merged intern chat — reported that although both topics are related to career development, they deserved an intern chat of their own to be fully explained and explored. In a meeting in late February, we discussed the possibility of approaching our “everybody struggles” topic in an ongoing basis (with closer interactions with interns every week), and changing the intern chat topic proposed for Week 3.

The intern chat topic merger was the proposed mitigation plan in response to the effects of a facet of our technical debt.

During the execution of operational tasks, I took note of the technical debt related to our website codebase. First, RoundPage objects remain inaccessible via our Django Administration panel due to performance issues (our requests time out). That has forced us to execute RoundPage manipulations and changes via Django Shell to add intern chat dates and URLs to email templates. Second, variable names related to intern chats are either non-descriptive, making them difficult to remember:

• Week 1 (“Working remotely”): week_two_chat_text_url
• Week 3 (“Everybody struggles”): week_four_stuck_chat_url
• Week 5 (“FOSS conferences”): week_six_audience_chat_url
• Week 7 (“Careers in FOSS”): week_eight_timeline_chat_url
• Week 9 (“Informal chats”): week_ten_career_chat_url
• Week 11 (“Next steps in FOSS”): week_twelve_interviewing_chat_url
• Week 13 (“Wrap up”): week_fourteen_wrapup_chat_url

Their variable names follow a pattern of week number + 1 for legacy reasons, making it all very confusing for our current operating context. Lastly, both Week 9 and Week 11 shared the same intern chat variables. That had unintended consequences: our website scheduled our intern chat about informal chats on the same date as the chat about next steps in FOSS. A merged pull request I submitted on the first week of February in 2025 fixed our immediate issue, but we have a long road ahead to address deeper debt.

In respect to our June 2025 cohort, I assisted Sage Sharp in the development of changes to the community sign-up flow, in particular with testing the current iteration — deployed in time for the community call for the June 2025 cohort. We co-led the initiative to structure the initial application review process for the June 2025 cohort, selecting strategies and creating their technical implementations to support the review of almost 3,000 pending applications.

I co-led and assisted Tilda Udufo in the development of a module that will collect information on top 5 professional skills from applicants. The data we collect will be used to connect applicants with the right projects, particularly for skills considered to be niche, rare, or declining in use. Tilda and I co-created a technical specification with functional requirements, use cases, and diagrams representing our ideal implementation. Upon receiving her proposed implementation, I tested her code on a local development environment, and provided timely feedback. Her implementation was then deployed on the Outreachy website and tested by thousands of applicants applying to the June 2025 cohort.

Very few bugs were found by our crowd of applicants. The first one was the rejection of the term “machine learning” — it was being filtered out as it contained the word “learning” (we had made the active decision to split skills into levels of understanding and topics, and one of the levels is “learning”). The second was related to the expression “UX/UI” — that / character was being rejected by the system. Both were reported very quickly by our applicants, and a fix was proposed, submitted, and deployed soon after.

I led and assisted Omotola Omotayo in the coordination of initial application reviewers for the June 2025 cohort. I approved reviewers in our system and provided guidance on new changes to the initial application review flow. Additionally, we worked together on an exploration of the decision tree for Outreachy in search for long-term sustainability. In our 1:1 meetings, we focused on the history and material consequences of the current financial model of the program.

I pitched the idea of an Open Mentorship Fellowship as a project submission for DISC Unconference 2025. In April 2023, I attended Latin American Open Science unconference organized by Chan Zuckerberg Initiative in Buenos Aires. I made a presentation about the common struggles prospect mentoring community face to become “Outreachy ready”. At the time, Yo Yehudi suggested that we could form some sort of “open mentorship alliance” to help communities with the goal of becoming “Outreachy ready”.

That idea became somewhat dormant for the last 2 years; a group did submit a project seemingly inspired by this idea at DISC Unconference 2023, but it’s execution covered a much smaller scope than I envisioned back then. Debates around “younger generations no longer interested in FOSS” reignited this idea, thus, I decided to pitch it as a structured way to study, document, and improve mentorship practices across open communities.

In late February, I submitted the project proposal and presented my pitch during a closed virtual meeting for DISC Unconference 2025 attendees. Karen Sandler then reported that she was offered an opportunity to pitch our Open Mentorship Initiative as a grant proposal. We remixed my DISC Unconference 2025 project proposal and used several of the ideas I’ve written down over the years as the foundation of our proposal.

I worked on my FOSS Backstage 2025 talk, “Anatomy of an open internship program: How we run Outreachy”. I decided to focus less on quantitative things (e.g. stipend amount) and more on qualitative things that are often not obvious to an outsider (e.g. our motivations, our structure, our human-centered approach). My main goal of this talk is to answer the following question: “Why do open communities are keep seeking Outreachy after so many years? Why is Outreachy a hidden dependency of the free software ecosystem?”.

All organizers had an input on key topics I’ll tackle, and they all kindly helped me pick a direction. I’m confident this will be an incredible talk.

I created the slides using Marp, an MIT-licensed Markdown presentation ecosystem, after fellow blind FOSS contributor Matt Campbell mentioned using it on Mastodon. That has significantly sped up my slide creation process. As I write this, I’m finishing my script and testing different ways to generate accessible PDFs of my slides.

Lessons learned

• While we don’t regret accepting a new intern so late in the cohort, it is our understanding that such action should be taken only in extremely exceptional circumstances. Having interns in such radically different schedules results in a disproportional amount of hours invested in a single intern; managing interns with the same start date decreases repetition and is much more favorable at any scale.
• I believe we should rethink our current format for blog prompts and intern chats as a whole; we need to make blog posts more relevant for the collection of public artifacts of work, and we need to include a chat about the inner workings of the free software ecosystem to help them navigate its complexity.
• Our feedback submission form needs to undergo several improvements to coach mentors to share public artifacts of work and a detailed report of activities. Additionally, we need to streamline processing extension and mediation requests.

Upcoming activities

I plan to either work reduced hours or to be completely out of office from March 3 to March 16, but I will be representing Outreachy at a professional capacity at industry conferences.

• March 6 to 8 2025: I’ll meet several Outreachy interns, mentors, and coordinators in Berlin.
• March 10 to 11, 2025: I’ll attend FOSS Backstage 2025. On March 11, I’ll present the talk “Anatomy of an open internship program: How we run Outreachy”.
• March 13 to 16, 2025: I’ll attend DISC Unconference 2025, organized by NumFOCUS, in São Paulo, Brazil. I’ll lead and coordinate our Open Mentorship Initiative discussion group.

My main two internal projects for March and April will be:

1. Revamping our feedback collection and submission process. My plan is remix the technical specification I submitted as my final assignment for my Software Design class at Universidade Federal de Goiás.
2. Reviewing and making changes to intern assignments and chats, and automate or facilitate some of the related operational tasks.