The Shipping Great Work Field Guide


No matter what corner of the organization you’re working from, you are responsible for upholding your organization’s values and standards.

The Shipping Great Work Issue contains a collection of tactics for helping everyone at the organization produce high-quality work. This field guide is designed to help you bring that spirit to not only your work, but also those around you, while the work is happening.

For Leaders: Questions to ask in reviews

Most of the work at your company will be done by other people. Leaders are responsible for clarifying and upholding the company’s standards for the work. This applies not only to the work-product, but also the way the work gets done and how you talk about it (internally and externally). Here are ways you can advocate for great work while it’s happening. The more clear and consistent you are about what the company’s standards are, the better your team will get at doing this without you in the room.

If you were to crack open an original Macintosh, you would find a piece of plastic engraved with the signatures of the team that worked on it. Why? Because artists sign their work. As you read these questions, consider what questions you would have to ask to make you and your colleagues want to sign the work you put out into the world.
Think of this section as a script you’re feeding to a little birdie that will live on your shoulder. Better yet, make that birdie a parrot so it’s chirp, chirp, chirping these questions all the time. Translate them into your own style when you take them to the team. When you ask these questions, don’t accept excuses. Even good ones.

Doing the work

  • Ambition
    • How could this work?
    • What does the wildly successful version of this look like?
    • How could this 100x?
  • Front page test
    • Would we be comfortable with this showing up on the front page of a major newspaper tomorrow?
  • Differentiation
    • What have others done? How can we improve upon it?
    • What’s the way to do this that only we could pull off?
  • Edge
    • Who would this offend?
    • What do they believe that we don’t?
  • Quality
    • What would make this 10x better?
    • Who is doing work that we admire here? How would they solve this?
  • Speed
    • How can we ship sooner?
    • How can we improve faster?
  • Vision
    • What does this look like in the end state?
    • Does this serve the purpose of our company?
    • Is this helping us achieve our mission?
  • Users getting what they deserve
    • What’s blocking?
    • How can they get it sooner?
  • Minimum awesome product
    • How can this be launched with less?
    • How can this be validated with less?
    • What small thing can we ship to help us validate the bigger ship?
  • Building from first principles
    • If you were to start from scratch, how would you build it?
    • Why are we doing it this way? Why? Why? Why?
  • Simplicity
    • How would you expect someone to explain this in a tweet?
    • How can we pare it back to its most essential components?
  • Talking up
    • How would you say it if you assumed the user knew a lot about this already?
  • Precision about language
    • What do you mean by that?
    • Can you be more specific?
  • Compelling
    • What would make someone want to tell someone else about this?
    • Why would someone subscribe to hear more from us about this?

How we get there

  • The right people in the room
    • Who should be included in this decision/discussion?
    • Who is closest to this work?
    • What does $person-with-critical-context think?
  • Small groups cranking
    • How can we streamline the working group?
    • Is everyone contributing meaningfully?
  • Levity
    • Have we had any fun with this lately?
    • How can we introduce more joy?
  • Turpentine
    • Have any users seen this yet? What did they say?
    • Whose problems are we solving?
    • How would our users talk about this?
  • Sound decisions
    • How did we make this decision?
    • How confident are we?
    • What would increase our conviction?
  • Peer reviewers
    • Who outside the core working group looked at this? What did they say?
  • User feedback
    • Who from your target audience has tried this or seen this? What did they say?
  • Data-informed
    • What would the data dictate we do?
    • How would the data answer this?
  • Surfacing fears, uncertainties, and doubts
    • What do you have FUD about here?
    • What isn’t working?
  • A few choices
    • What are my discrete options?
    • Why would I choose one over the other?
    • What would you choose?
  • Intuition
    • What does your gut say?
  • Planfulness
    • How does this fit into our broader company plan?
    • Are we doing what we said we’d do?
  • Bringing others along
    • How were those impacted by this decision, but not included in making it, informed?
  • Self-sufficiency
    • How can you get this done?
    • How can you unblock yourself on this?
  • Ownership
    • What can you do, alone, to improve it?
    • How can you specifically contribute?
  • Papertrails
    • Where is this documented?
    • If the working group disappeared tomorrow, how would someone else know how to pick the work up?
  • Building organizational context
    • How can I follow along with how things are going?
    • Where can the rest of the company go to learn about this?

For Operators: Owning your work and making it great

Think of this section as a prescribed set of health checks you apply to your work and how you show up before it goes out into the world. Plus, if you’re sick, you might be contagious; it’s best to get well before you get shipping. Tune the criteria to match your own style when you use them to evaluate or express yourself. 

This work

  • Four “ayes”
    • At least four (ideally discerning) people (ideally with some expertise or take in the outcome) have looked at this and agreed it’s ship-ready.
  • Home page test
    • If my work ended up on our company homepage, it would fit right in. I’d be proud of it and I’m confident others across the company would be too.
  • The person I admire
    • If this work got in front of someone I admire (make that person a specific, not generic, person), I’d be proud they saw it. I’d be enthusiastic if they assumed the quality of this work representative of the quality of all my work.
  • Point-of-view
    • My work has a clear perspective or differentiator.  
  • User perspective
    • I can speak confidently to what the consumer of my work will think of it once it ships.

Getting it there

  • Escalated appropriately
    • I’ve consulted the appropriate decision-maker for any aspects of my work I wasn’t sure about
  • Dirt under fingernails
    • I’ve gotten into the weeds on this work to make it great. Others can tell because the small details are polished.
  • Refusal to be blocked
    • When things that have impeded my progress or speed, I have been relentless about finding ways around them
  • Speaking up with good feedback
    • For the work I contribute to, but don’t own, I’ve spoken up with feedback that contributes to making the work better
  • Bake cupcakes first
    • When faced with a big idea or project, I validate my assumptions and build conviction through smaller initiatives

All work

  • Awareness
    • I am clear on my company’s values and standards. And if I’m not, I’ve asked for clarification.
  • Self-awareness
    • I know what role I play in this work. I know how I can and should participate and contribute (or not!) to the current work and its evolution.
  • Stewardship
    • I know how I am expected to uphold our company’s values and standards in my work, and I do that.
  • Modeling
    • I believe my attitude and work product is an example for others at the company. I am proud of how I show up to my interactions with others.
  • Values <> Behavior alignment
    • The behavior I observe aligns with the company values that have been articulated to me. When they don’t, I ask for clarification.