Issue #5

Prompt: the power of language, business executive speaking in front of a crowd of people, majestic, inspirational, futuristic

Welcome to Issue #5! We’re back after taking a couple of weeks off to visit family in J’s hometown of Denver, Colorado ⛷🏔. We packed this one full of more good stuff to make up for that two-week hiatus 😄

WHAT'S INSIDE

• 🖖🏽 Are you embodying the language of a leader? How does language affect the way we — and our teams — think and approach work?

• 😵‍💫 Floundering in chaos? Use the Cynefin Framework to set guidelines for approaching ambiguous or complicated situations

• 🔎 If you’re on the hunt for a new role, check out these new senior openings at companies like Techstars Boston, a16z, and Maven Clinic (a Series D Oprah-backed startup)

• 🛫 Southwest made massive profits in the ‘90s by hedging jet fuel while fuel prices skyrocketed — and their strategy is working again in 2022. How can you take an industry risk and use it to your advantage at your own company?

A DEEPER DIVE: THE POWER OF LANGUAGE

Leaders know that messaging is everything; body language, energy, tone, and the words we use to communicate have a huge impact on our teammates and counterparts. Today we’re drilling down into tips on effective communication, and ways you can wield the power of language

Avoid Mono-Processes but Embrace Shared Language

What it's about: John Cutler, a product leader at Amplitude, breaks down why standardizing processes across teams with different workflows can be problematic. Instead, he proposes building a taxonomy of language that’s unique to your organization and the work you do.

TLDR / Key Takeaways

• Many product leaders use the same language to describe all product work stages and phases, without considering nuances or context specific to their product teams

• When you use the same approach to time-box estimates for different types of work (e.g. bug fixing, refactoring code, building for a new persona, and business-as-usual development), you could end up constraining your team by standardizing workflows that don’t make sense for the problem each individual team is trying to solve

• The most effective teams support multiple ways of working, while standardizing only in the places where it really adds value. Importantly, they evolve a shared language to describe the differences

• Shared language does not equal shared process, rather it allows you to define categories of work that may follow a different process. For example, your teams may have criteria to help categorize types of work such as: "knowledge of key persona", "prior work in this area of the code" or "high profile task with many dependencies”, all of which are unique to your organization and have different best practice processes for how to tackle that type of work

• Defining this taxonomy (and the assumptions underlying it) is a useful step in building a high-performing culture. If you’re struggling with an underperforming team, look to see if there are old assumptions that underlie the language your team uses, and whether a change in language can change the culture

Digital Body Language

What it's about: In the digital world, we can sometimes be less in-tune with the indirect messages we’re sending to others. This article by Erica Dhawan shares ways to think about using your “digital body language” in order to build rapport and connection

TLDR / Key Takeaways

• In traditional office settings, we show that we are actively listening by nodding our heads, making eye contact, etc. The digital version of this is seen when praising someone’s input in an email, using the “like” or “thumbs up” reaction on a text message, or making a detailed comment or question rather than sending only a thumbs up response. Even the quickness with which we respond can signal whether we’re paying attention to the conversation and giving it the attention it merits

• On phone and video calls we laugh and wish someone a good weekend, etc. In text messages, we can show friendliness in other ways, such as using more exclamation marks or more emojis, eliciting a more casual tone from someone we want to be friendly with

• To show empathy in-person, we maintain eye contact and move closer to the other person to show we’re engaged. In digital body language, showing empathy could look like quick and thorough responses, and avoiding interrupting the other person. The equivalent of physically moving closer would be moving the conversation to a more personal medium (e.g. from email to a video call, or from text to a phone call)

Action shapes Thought

What it's about: Psychologist and Stanford University professor Barbara Tversky covers her deep expertise in cognitive psychology and lessons in communication (this is a long podcast, so we added clip markers in parentheses)

TLDR / Key Takeaways

• 👁👂Learning is multi-modal: Tversky ran a study where she gave complicated study materials to research how subjects learn, and found that those who gestured and made ‘spatial-motor’ models for what they were learning ended up remembering the materials better. Representing something in space (such as diagrams or hand gestures) is often better at helping people retain abstract ideas compared to describing with just language alone (16:40 - 23:00)

• 🗺🥪Diagrams provide layers of information: Visual representations are more effective than text-based language for conveying conceptual information because they provide an opportunity for inference (i.e. information can be layered inside of a visual in a more efficient manner than language alone). Diagrams also help provide checks for coherence and completion of information (i.e. it’s more clear in a visual vs. in text when key details are missing) (24:00 - 31:00)

• ✍️🎙Spatial visual cues show up in verbal and written language: Our preference for spatial cues to impart information is evident even in print. We indent paragraphs, bold important topics, place headers in larger font, etc. We also raise our voice to add emphasis, pause to add dramatic effect, etc. which are all spatial devices to convey meaning. Here’s a tip: use the human desire for spatial visual cues to your advantage by incorporating a compelling visual into your memos or presentations that signifies your message (like we did with the emojis in this section, as well as in our cover image!) (34:30 - 38:00)

• 💡🏢Collaborative work benefits from shared physical spaces: Zoom meetings provide fewer visual cues than typical working environments (e.g. no whiteboard / table, only face and shoulders). Even working on a virtual whiteboard through screen sharing loses the rich information found in hand gestures and movement around a diagram that people would typically do in real life. Shared physical space has been found by research studies to be the best environment for collaboration (which could be a justification for using VR whenever shared physical spaces is impractical). However, if the goal is only to teach rather than collaborate, Zoom does help facilitate understanding with features like transcription and recording (49:30 - 56:30)

MENTAL MODEL OF THE WEEK: THE CYNEFIN FRAMEWORK

Leaders know there’s no one-size-fits-all approach to decision making. Still, effective leaders are able to use good judgment to consistently triage issues and determine the best course of action. The Cynefin Framework is one way to approach the triage process.

Cynefin, pronounced "ku-nev-in," is a Welsh word that means "place" or "habitat." This framework was developed by David Snowden in the early 2000s during his work with IBM, and is based on concepts from knowledge management and organizational strategy. The framework lets you find a home or domain for each type of problem you encounter, so that you then know how to deal with it.

For: Decision making

What is it: A way to think about categorizing different types of problems to determine the best decision to make

When it’s used: Management, software development, military strategy

When it’s NOT used: If the problem has underlying historical issues or power and politics dynamics that the framework can’t account for

There are five domains in the Cynefin Framework, and each has a different approach to resolving problems:

Obvious “Domain of Best Practice”: This is when there is a clear ‘right’ answer. The approach of “Sense-Categorize-Respond” places the emphasis on categorizing; if you know what type of problem it is, you can then base your response on a best practice.

Complicated “Domain of Experts”: Complicated problems are ones where there are several good answers. This is the domain that consultants often work in, hence the most popular answer to any question you ask a consultant is “it depends” 😆. Unlike complex domains, complicated problems are still resolved with established systems and processes, though you might need more involvement from experts (whether those experts are external consultants or internal functional experts) to help determine the course of action. The approach of “Sense-Analyze-Response” places the emphasis on analysis and the inclusion of expert opinion to solve these types of problems.

Complex “Domain of Emergence”: Complex problems are where you find the ‘unknown unknowns’. It is the domain of experimentation, where there may be some clues and direction derived from past examples, but there is a lot of unpredictable behavior caused by unknown factors. The approach of “Probe-Sense-Respond” places the emphasis on probing to figure out how this problem is similar to past problems (and what their solutions were), before sensing and inspecting this problem’s unique aspects, and responding (adapting) to those unique aspects and deciding whether you need to probe other examples.

Chaotic “Domain of Rapid Response”: Chaotic domains have little relationship between cause and effect, so the goal is to establish order and stability as quickly as possible. Because chaotic situations are typically crises or emergencies, speed is critical. You’re looking for a good enough solution rather than the best solution, so that you can re-establish order and move the problem into the Obvious or Complicated domain. The approach of “Act-Sense-Respond” places the emphasis on action, before sensing and evaluating the result, and responding to that result and determining if you need to act again.

Disorder: Disorder is the state before it reaches any of the above classifications. In this state you might fall back on decision-making techniques that are known and comfortable, but these may not be the most appropriate for the problem at hand. In this situation, the primary goal is to gather enough information so that you can confidently move the problem into the appropriate domain. In some cases, it helps to break down the problem into smaller components that are more easily categorized.

Additional resources: The Cynefin Framework: Complex vs. Complicated, How to Use the Cynefin Framework to Make Better Decisions

YOUR NEXT STRIDE

We’ve streamlined the Jobs section to make it more scannable. Here’s our 5 top jobs of the week!

• General Management Managing Director, Techstars Boston. You’ll be leading the accelerator and investment strategy

• Product Director, Product Management, Harness. Modern software delivery platform. Raised $230M Series D in April ‘22 from investors like Norwest, JP Morgan, Menlo Ventures, etc

• Venture Partner, Consumer Growth Marketing, a16z. You’ll advise portfolio companies on Go To Market efforts

• CoS Chief of Staff, Mutiny. No-code AI platform that helps marketers convert their top of funnel demand into revenue. Raised >$71M from investors like Tiger Global, Sequoia, etc

• HR / Talent Chief People Officer, Maven Clinic. Largest virtual clinic for women’s and family health. Raised >$200M from institutional investors like Lux Capital and Sequoia, and celebrities like Oprah Winfrey, Reese Witherspoon, Mindy Kaling, and more

LIFESTYLE

Wellness 🏅

5 exercises to strengthen your knees Didn’t think we’d be looking at solutions for knee pain in our 30s, but here we are

Watch 🍿

The Janes tells the story of a group of unlikely outlaws who risked their personal and professional lives to help women in need. At a time when access to safe abortions is a polarising topic in America, this documentary set in the 70s makes us wonder how we’re in this situation half a century later 🤷🏽‍♀️

Read 📚

Measure what Matters by John Doerr. You’d have probably heard of OKRs by now. As you do performance evaluations, and set goals for the next year, this is a good read to help teams align and excel

Listen 🎧

Encyclopedia Womanica Quick 5-minute episodes profiling women throughout history

RANDOM BUT INTERESTING

This section is going to feature one item a week that we found interesting - but couldn’t really fit it in anywhere else. You can think of it as coming down the rabbit hole of curiosity with us just because — or fodder / anecdotes for your next speech 🤷🏽‍♀️

How Southwest made Money from its Oil Hedging Strategy - Launched in the 90s, Southwest’s hedging strategy still works in ‘22

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👋🏽

​Jay & Zi