#WorstWorkWednesday

This post is in reply to a Tweet from Sara Soueidan about only sharing our best work. It is a conversation how people don’t share negative things on social media, especially in the context of a professional account.

#WorstWorkWednesday, the title of this post, is a hashtag coined by Matthew Howell. I quite enjoy it!

My reply to Sara on Twitter was telling her about a “show me your worst stuff” meeting we used to have on a semi-regular basis. The meeting’s format was the designers would gather to share and talk about their work in, specifically things that we were unhappy with.

Unhappy is the operative word here, in that the shared work could be:

• Ugly designs that didn’t work,
• Ugly designs that did work,
• Pretty designs that didn’t work, and
• Pretty designs that did work.

The meeting is about vulnerability. It was a great experience, and helped me relate to, and bond with my coworkers.

The meeting’s goal is to normalize the design team being human, and humans are fallible. The scope of shared work was also intentionally loose, because it was about how you feel about what you’ve done, and not if it was perceived as successful or not.

Sharing

I’ve shared work in these meetings that was seen as successful, yet I wasn’t happy with. When you’ve been in the industry as long as I have this kind of output is an inevitability. I’ve also unfortunately had my share of ugly designs that didn’t work. I’ve shared those too.

My partner is a good listener and incredibly supportive, but doesn’t work in the same industry I do. It wasn’t until I had a meeting like this that I could use jargon and really discuss things with people who would instinctively understand the particulars.

Public-facing

Our professional lives don’t give us many chances to acknowledge and unpack what we consider to be failure. It’s an incredible shame.

The working world also largely disincentivizes broadcasting weakness, which is a huge loss given failure represents an opportunity to teach others about what you’ve learned about the experience.

Making mistakes—and learning from them—is one of the best ways to grow as a person. Failure is also a good way to probe the explicit and implicit limits of the systems you operate in. Being able to explore these spaces in a safe and controlled way is a wonderful gift.

The flip side of this—only showing success—is a subtle trap. Modeling your notion of what success is from what others publicly share doesn’t grant you the vital context of why they made the decisions they did, and what constrains they had to work with. This can create a number of ugly things, including:

• A toxic culture of hero worship,
• Survivor bias-derived decision making,
• Parroting dangerous, flash-in-the-pan usability trends, and
• Reinforcement of white supremacy culture of perfectionism.

Does this all sound compelling to you? Interested in running your own #WorstWorkWednesday meeting?

Before you try to run a meeting like this

Be aware of the power dynamics at play with setting up this type of meeting, as well as the potential consequences of conducting it in an irresponsible manner.

Maturity

There’s a certain level of maturity your organization needs to have in order to accommodate expressions of vulnerability and failure without fear of punitive action or retribution.

Nearly all of this maps back to trust. Be aware of predatory personalities in the workplace may use the information generated in this type of meeting for their own agendas. Be sure to plan for what you can do to guard against that.

Status

A senior designer can say they don’t know what something means and be applauded for it, while a junior designer can say the same and be fired. This phenomenon extends to how someone vocalizes failure, and how their status affects their perception.

Bias

Also be aware of the many conscious and unconscious biases that affect how we view and treat our minoritized peers, and how this type of meeting might feed into these prejudices.

Tokenization

Don’t allow the people affected by your work to be tokenized by your experience of it. User test participants, peers, managers, subordinates, and end users are all people, and not narrative vehicles for you to exploit.

Sensitive content

Failure often deals with negative experiences, and sometimes the circumstances of these events have been shared by other people.

Opt-in content warnings about sensitive topics can be a helpful tool for meeting participants to know what will be discussed before becoming involved. This allows them to consent to participating in the meeting and also choosing their level of exposure.

Legal liability

Also be cognizant of the industry you work in. The main factor to consider here is legal liability with regards to what you share with who, and why. Be aware of what is shared verbally and how, versus what is documented and where.

Also know that if you genericise your experience to be able to discuss it that a sufficiently motivated individual may be able to tease apart the particulars to de-anonymize it.

You can remove someone’s name from a document, but still be able to identify them from their writing style. Think critically about the particulars of what you’re talking about, as well as the larger context it exists in.

Growth

With all of that said, also know that a meeting like this can help to grow your organization’s maturity, strengthen existing relationships, and forge new ones. It can also model positive behaviors for new and existing employees.

Running a #WorstWorkWednesday meeting

The first bit is this doesn’t have to be on a Wednesday, silly.

I’d advise ensuring there’s time afterwards for processing and decompression when planning when to schedule the meeting.

Talking about dissatisfaction, failure, and shame can bring a lot of heavy feelings to the forefront. You’ll want a buffer before hopping on a call to talk about OKRs or whatever.

Make information available beforehand

This builds off the sensitive content concerns mentioned earlier. You’ll want to provide attendees with the following:

• The date, time, and location of the meeting.
• A code of conduct that outlines acceptable and unacceptable behavior.
• A loose agenda, as this kind of topic is difficult to timebox.
• A way to denote participants who:
  • Want to have a discussion afterwards about what they discuss,
  • Are okay with questions being asked while they speak, and
  • Do not want either of the previous two items.
• Camera, mic, and chat etiquette if it’s a virtual meeting (and in this day and age I really hope it is).
• An understanding that while the meeting is recurring, participation is optional.
• An understanding that it’s okay to leave the meeting before it has concluded.
• Links to supporting content.

Acknowledge the fourth wall

This is a meeting about failure conducted in a work context, with your peers, and potentially superiors and subordinates.

Verbally acknowledge this fact, and touch on the issues outlined previously. This helps to ensure all participants have full working knowledge of the framework the meeting facilitates, as well as signal you’ve thought about the various implications of irresponsible stewardship.

Following that, it can be helpful to restate the overall goals of the meeting.

Prime the pump

It can be very difficult for someone to be the first participant in this sort of thing.

After running intros and covering the schedule, you’ll most likely have to lead by example. Come prepared with something to discuss. Also be okay with having a discussion and answering questions—be sure to explicitly mention that before you begin. This will all help to communicate the norms you expect for the meeting.

Encourage active listening

Even if you’re okay with questions, you’ll want to teach your participants about how to practice active listening. It’s a valuable skill to cultivate, even outside the scope of this meeting.

Some good advice about active listening I’ve learned is to be a walkie-talkie: you can either speak or listen, but you can’t do both at once.

If participants ask questions when the speaker has expressed a preference for no questions, gently remind the question-asker. This will take the pressure off the speaker to enforce their own request.

Don’t be afraid to ask a speaker open-ended questions if they indicated the preference for questions, clearly wants to talk with someone about their work more in-depth, and other participants are hesitant to initially speak up.

It can also be helpful to repeat notable concepts and phrases mentioned by the speaker back to them, to both demonstrate you are listening, and to give them the opportunity to clarify things.

Be comfortable with uncomfortable silences

Silence can be a space where someone is collecting their thoughts, or is working through their feelings.

It can feel tempting to fill an awkward silence with a comment, or a joke to break some perceived tension. Don’t. These moments of silence can be pivotal experiences, and you don’t want to center yourself in them when they occur.

Navigate sensitive topics

Speakers and participants may share things you don’t agree with. These things are sometimes highly private, concepts like political worldview, religious beliefs, ethical frameworks, and aesthetic sensibilities. These concepts help inform how many of our choices are made (or not made), and consequently may create dissatisfaction and friction.

It’s not your job in these situations to debate them. Remember, the conversation is not for your benefit. Listen to what they’re trying to communicate—and importantly, why—and use that to engage with them on their terms.

Thank people for sharing

Showing vulnerability and talking about things you’re not proud of, or happy with takes a lot of courage. A simple acknowledgment of that may mean a lot to the person, especially if they’ve never done it before.

Control the information

If artifacts are generated during these meetings, make sure you control who has access to what, and share that information with the group’s members. Allow everyone the opportunity to remove anything they want from the archive, and don’t ask them why.

Also consider things like text-based communication and calendar invitations as part of the scope of artifact generation.

Failure is relative

Remember how I mentioned someone can be dissatisfied with a pretty design that did work? You can’t really know all the circumstances of how someone came to not like something they produced. All you can do is listen to them when they provide the greater context.

A beautiful, successful design brought to the table might make you question your own abilities. Know that someone else’s strengths and successes aren’t reflective of your own capabilities and experiences, and you should be hesitant to judge yourself by their standards (see hero worship and perfectionism).

Don't fetishize it

#WorstWorkWednesday does not give its participants carte blanche to be irresponsible. It is about unpacking decisions you’ve made that you’re not satisfied with, as well as asking for advice from peers with a range of backgrounds and experiences.

At the end of the day, we all still have to produce value for the place that employs us, with value being highly dependent on the organization’s priorities. #WorstWorkWednesday provides (dare I say it) safe space for industry practitioners to talk shop about a facet of their job that typically isn't supported.

You also want to avoid a codependent negativity spiral. This is something I’ve run into with a few other coworkers over the years, where you start to look for excuses to complain because it gives you attention. Brains are weird, patchwork, pattern-matching machines: they can make you feel good by making you feel bad. It’s best to not become addicted to that.

Sharing on the web

#WorstWorkWednesday can also not be a meeting! Be it a blog or social media post, know that most of what I’ve outlined still applies.

I would personally love to see this kind of thing normalized more, as I think it’d help incentivize healthier conversations around intent and constructive criticism. Just know that if you do this on the web that the biggest things to watch out will most likely be:

• Predatory personalities,
• The fact that you can’t control information as well, and
• People attempting to de-anonymize any and all information you disclose.

That said, I am constantly pleasantly surprised by stuff I put out there, and how it comes back to me in positive and surprising ways.

Failure can be fun

All the criteria listed previously can seem intimidating, but it is listed out so you can provide a safe and constructive environment for talking about a concept that is highly stigmatized in the contemporary working world.

All that said, there’s a reason we laugh at pratfalls.

Our “show me your worst stuff” meetings started off awkward, but quickly evolved into a fun and engaging activity. Once trust and behavioral norms were established, bridges were built—people felt comfortable enough to open up more, and the tone shifted away from serious.

In addition to helping people work through challenges they were grappling with, the meeting helped foster a sense of camaraderie for designers who didn’t always get to work closely with each other. In fact, some of these designers I still chat with on a near-daily basis despite no longer working with them.

So, where’s your worst work, smart guy?

Stay tuned!