😷 — The Weekly Retrospective: Culture & Community Review

This is your Community, Daily.

Reading Time: ~ 3 min.

Good morning yenizens!

One of the more important things that I do every single week with my own small startup team and the larger community is have alignment & retrospective rituals — a fundamental part of our weekly cadence and the backbone of our “operating system“.

It’s so effective that I’ve long-considered introducing it to our growing yeniverse via the newsletter — today’s that day!

A “retrospective” — or more simply “an intentional review” — is nothing more than a recurring system and workflow that forces important conversations to surface to the top, especially the ones that we’ve been avoiding.

In other words, there are a (growing) number of important conversations that you need to have with folks on your team and inside your larger community that haven’t happened yet!

Every Wednesday we’re going to give you a “kind reminder” (or swift kick in the ass) to have these chats. Feel free to blame us entirely for “forcing” the issue and “making” you to think through these critical things!

Need a place to start? Here are five extremely clarifying questions that can help kick things off for you…

5 Hard But Necessary Questions to Ask (and Answer) About Your Culture:

Review, write down, chat through these five questions with folks that you trust and then, most importantly, schedule in time to answer them intentionally and with the right folks.

Yes, these are hard but they will help you, your business, and your community not just survive, but thrive:

  1. What is one “tough” conversation that you’ve been avoiding with a colleague, friend, teammate, leader, and/or community member? Why? What’s holding you back from having this necessary chat? Or are you just avoiding conflict while everyone pays for the avoidance? Most leaders know — all too well — the cost of not having tough conversations sooner.

  2. What is one anxiety or insecurity that you need to share that you’ve kept to yourself? Who needs to know what you know? What is holding you back from staying mentally fit and healthy? What data is missing (if any) that will help you get more comfortable with sharing?

  3. What are you not proud of right now inside your team, your project, your community and/or the culture that you’ve intentionally designed and built? What needs to change? The beautiful thing about this question is that everyone immediately has a thought (or two) but very few people ever share these thoughts publicly!

  4. What documentation (e.g. culture docs, community processes, operational workflows, etc.) needs to be updated? Remember, a strong team, organization, and community has a strong culture around documentation and keeping it updated!

  5. What cultural debt have you accrued in the last week that needs to be addressed? Another way of asking this: What cultural belief and/or community behavior needs to be addressed, refined, and/or changed? An even more specific way of asking this question: Is there any belief (or value) that we preach but do not actually practice? Address this immediately.

Yes, yesyes… these are hard questions to ask and even harder to answer for oneself! But, I have also experienced the results of when we can honestly approach the challenges and tensions and issues in our life and, without fear, confront them honestly, candidly, and openly.

No one does this perfectly the first time or the five-thousandth time! But, the practice is worth the difficultly, the results are worth the temporary discomfort. Believe it!

I love you and the yeniverse is here to help! Feel free to ping any of us at any time! We’re in this with you, until the very end.

To infinity & community,

— john


A few great links to share and digest and consider:

  1. Rob Fitz and Arvid Kahl. OMFG. This course via Sahil Lavingia!

  2. Bill Gates and Andy Grove. Read this. Seriously. Wattpad + Naver!

  3. How we buy onlineMatterLandbot looks cool. a16z is media!

  4. Templates for remote workshops? Wow. Responsive one-pagers?

  5. Freeze your webcam! LOL. Maximizing dev effectivenessMonitoring.

  6. Cognitive biases suck. Another privacy-focused analytics?

  7. Free email templates. Tailwind CSS blocksTalium.