CHAPTER SEVEN

The Remote Blueprint

CONSIDER THIS. You’re managing a team of marketers at a fashion brand that has a knack for creating witty, on-point Instagram campaigns, website content, and community events that people actually want to attend. Your company moved to remote-first about six months ago, and the VP of Marketing now wants your team to promote the new line of super-soft, luxury V-neck T-shirts virtually. Usually, your team hosts catered “drink and design” happy hours and a T-shirt designer speaker series at the showroom locally, but you need to rethink how to do an online-only event with national reach this year.

As you begin, you have an end picture of what success looks like. You want your team to create an engaging virtual party for the boutiques that could buy your T-shirt inventory and expand your market outside of the East Coast of the United States. You hope to create an interactive art gallery for the T-shirt designs and include some special surprises, such as a Zoom magic show, and ship all attendees a cocktail-making kit to enjoy during the event.

In all the excitement and rush leading up to the event (only eight weeks away!), you jump in by delegating tasks. Chloe will build out the website promoting the event. Jamal will invite the community and manage attendees. A couple of weeks later, you realize that key activities are falling through the cracks—the invites still haven’t been sent out, the website needs more photos, and the addresses of where to ship the cocktail kits are stored in a few different databases. When confronting your team, you learn that not only have Chloe and Jamal been overextended, but Michelle was out sick for a few days and hasn’t been able to support the team.

You realize that you have no idea how much is on your team’s plate or where the bottlenecks lie in the process. No wonder your team hasn’t reached the vision of success you had in mind.

The challenge for the team was clear, but there wasn’t enough “scaffolding” or administrative structure to support you, Jamal, Chloe, and Michelle in the execution and ownership of the event.

Yes, this is a fictional story. But swap that event for launching a new software feature or determining quarterly goals for your team. Is it starting to sound familiar?

We’ve heard similar stories. This is a challenge that many remote managers face when ensuring alignment to a specific goal, planning the work to be done, and establishing clear ownership and accountability.

SPOTLIGHT STORY: Falling through the Cracks

Carlos Silva, a remote marketing and content manager, could relate to this fictional story. He explained that at one point in his career, he jumped from working independently at a small start-up to being part of a team collaborating together, after a hiring spree. Knowing that having visibility of the work to be done was necessary for the team’s success, Carlos pushed the team to adopt a project management system.

According to Carlos, they used Trello in name only. “No one really checked it, and no one tracked that it was being properly used (or not). There was also no documentation on using the tool or how to track projects.” As you can imagine, this led to team chaos. People were working on the same projects; others fell through the cracks.

They had focused so much on which tool to use that they’d forgotten the most important part: how they would use it together to accomplish their goals.

Carlos learned the hard way that you need a culture of transparency, a well-structured project management system (or Digital House), and proper documentation of the House Rules to run projects successfully. According to Carlos, House Rules need to be “written clearly, publicly accessible, and within a tool that serves. It’s the single source of truth.”

THE RW BLUEPRINT EXERCISE: A FOUR-STEP FRAMEWORK

Imagine how easy planning and project management would have been for Jamal, Chloe, and Michelle if they had taken the lessons learned from Carlos Silva.

We, too, have learned these lessons over time. Early in Ali’s career, Ali was part of the team that decided whether specific sales deals were worth the time and effort at LivingSocial. (Yes, this was 2010—remember the group coupon craze?) The Research team spent a lot of time coordinating between Sales and Operations, making one-off decisions, and forgetting agreements after meetings ended.

Ali saw the need to develop a transparent process; hence Project “CRUSH” (because it helped “crush” sales goals) was born. While Ali had the vision for a tool that would suggest sales and operational guidelines based on city metrics (e.g., population, internet-friendliness), it was her first in-depth attempt at creating a company-wide process involving moving pieces. Rather than planning the project up front, Ali just got to work—stopping and asking questions whenever she got stuck—and later needed to get buy-in from the teams while teaching them how to use the tool.

After too many late nights, she decided there had to be a better way to stay organized and proactively get buy-in from stakeholders. Going forward, Ali learned how to identify key people whose knowledge would help the project’s success and how to communicate a project plan. Years later, at a different start-up, a coworker nicknamed her “Ms. Process,” so we think she succeeded.

While there are lots of project management philosophies and frameworks out there, in this chapter we will walk you through our signature RW Blueprint for you to facilitate with your team. Plus, we’ll continue to imagine how things might have unfolded for Jamal, Chloe, and Michelle had they been using this process.

It’s a simple, four-step process that can work across situations—from a small project to an intricate multiteam product launch. It can take a few minutes, a few hours, or a few days to complete, based on the level of complexity of the task. It all comes down to goal setting, creating a Task List, determining the top priorities, assigning ownership, and setting accountability norms.

By doing this administrative work at the start, your team will save a lot of time and stress in the future. A good process isn’t meant to add more work to your plate. Rather, it’s a set of rules that make real work more manageable in the future.

This “cheat sheet” is a reference, both for learning the process in this chapter and for managing your next project (figure 7.1). It might even make some nice furniture in your Digital House as your team builds their project management muscles.

Now that we have a common framework, here is a sneak preview of where Jamal, Chloe, and Michelle are going in their quest to design the coolest online T-shirt launch in history. The result? Their hard work paid off, and they secured inventory in 20 new boutiques in stores in Austin, Texas; Savannah, Georgia; Detroit, Michigan; and even Los Angeles, California!

So while we settle in and bask in their fake success, let’s break down each step of the RW Blueprint for you to do with your team (for “guaranteed” real results).

FIGURE 7.1 RW Blueprint Framework

HOW-TO: Set Clear Goals

The first step in completing anything is knowing where you want to go. This exercise is aimed to help you set a clear goal, or end state, for your project.

But it’s important not to conflate objectives with completion. Mike McNair aptly compared it to shooting an arrow at a target. “The objective is to hit the target. Completion means I actually hit the target. Between objective and completion, there’s a lot of iteration and clarification going on.”

As with the RW Team Mission Statement and RW Team Charter exercises, we recommend having your team first reflect independently on a set of questions about goals and aspirations and then come together to flesh out the official goals leading up to the project kickoff.

Here are a few questions that can help crystallize your project-specific goals and objectives:

• How does this project help us accomplish our team’s overall mission?

• What do we plan to do?

• What will change if this project or team succeeds?

• What does “done” look like?

• How will we measure success?

After everyone has had a chance to share their perspective first asynchronously, validate and document the final agreed-upon goal. Be as specific as possible. For example, “Selling more shirts” would be too vague for our fictional T-shirt friends. Instead, after they finished the exercise, they decided on the following goal: “To execute a virtual event to launch the new V-neck line on October 19. The launch should be focused on customers outside the Metropolitan DC area, resulting in at least 50 returning plus 50 existing customers in attendance. Success will be measured by secured inventory in new boutiques (at least five new markets) and ROI (at least two times the cost of the event in purchase inventory).”

Pro Tips

• Keep it simple. Focus on one goal at a time. If there are multiple goals that your team wants to cover, we recommend breaking it up into a multipart exercise.

• Goals should be specific, measurable, and actionable. Try to incorporate your existing measurement tools rather than inventing from scratch.

HOW-TO: Create a Task List

Once you have a goal in mind, it’s time to take inventory of what everyone is already working on before you can add new tasks related to the goal. It’s human nature to get excited about a new project and want to start working full-steam ahead. But unless you carve out the time to analyze what everyone is already doing, it will be challenging to understand your team’s previous commitments, which might hinder or distract them from reaching the RW Blueprint Goal.

In order to get a complete picture of what everyone is currently working on (e.g., Business as Usual “tasks”) and what new activities must be accomplished to reach your RW Blueprint Goal set in step one (e.g., Blueprint “tasks”), we recommend building a Task List. A Task List is the “single source of truth” for what’s on the team’s plate with all the tasks that need to be completed. It may be in sequential order or based on themes. This process allows you to dig into the nitty-gritty details of the project and uncover unforeseen tasks and interdependencies required to reach the goal.

The team members should create their Task Lists individually, so they can analyze how they are spending their time and how they plan on contributing to the RW Blueprint Goal. We believe there’s nothing like getting that anxious “I-have-so-much-to-do” swirl out of your head and onto (digital) paper. Later on, you’ll review each other’s Task Lists together to see what should be reshuffled among team members.

You’ll want every team member (including yourself!) to jot down tasks in two buckets:

1. Business as Usual Tasks: All of the routine tasks and existing activities that your team is currently or will be doing that overlap with the RW Blueprint Goal timeline. This may include nonroutine tasks if you are involved in more than one special project. You may look back at your calendar and job description if you have trouble populating this list. Don’t try to eliminate yet—that’s for a later step!

2. Blueprint Tasks: This is a forward-thinking list, where you brainstorm all the necessary steps to accomplish your RW Blueprint Goal. In order to accurately speculate what needs to be done to accomplish the RW Blueprint Goal, you may look at past project plans to forecast what steps should be taken or work backward from your final goal and ask yourself, “What needs to be completed to reach the goal?”

Pro Tips

• Don’t constrain yourself. Right now, you should be focused on adding, not deleting. You want to gather a clear picture of the entire universe of things your team is working on.

• Encourage the team to be honest. This is a no-judgment zone.

• For smaller projects, you may choose to skip one of the lists or do this in your head.

Once everyone has finished their Task Lists, synthesize them into a Main Team Task List under these two categories: Business as Usual tasks and Blueprint tasks. You’ll bring this with you to step three to set Top Priorities.

This is a great time to see if multiple people are working on the same thing (red flag!) or if no one is accountable for something important (double red flag!). During this step, our fictional T-shirt friend Jamal discovered that the invites still hadn’t been sent out. It wasn’t on his Task List, but it also wasn’t on Chloe’s.

HOW-TO: Determine Top Priorities

Remember how we told you to not delete anything from your Main Team Task List yet? Well, now is the time! Let’s start prioritizing.

It is easy to want to prioritize in theory, but in practice, it is just as easy to get derailed. Maybe you feel emotionally compelled to help a team member, even though you don’t have the time right now. Or, like Chloe, Jamal, and Michelle, you prioritized the urgent pings from your manager—even though they weren’t necessarily essential or important.

In chapter 6, we discussed day-to-day strategies to get your work done, like MIT (Most Important Task) and defining a North Star. You can apply these concepts at a macro level during this step. Rather than deciding on a single MIT for your day, you can set a weekly North Star to guide your team in the right direction across the project. If all else fails or goes off the rails on a given day or week, what’s the one thing that must happen to keep the project on course? For the project to succeed, what are the three to five MITs that will help you reach your RW Blueprint Goal?

For example, it is critical for Jamal and his team to send the invites. Otherwise, no one will know about the event, but the event could likely still succeed without the presence of the virtual magic tricks.

After determining your RW Blueprint Goals MITs and North Star, we recommend that you revisit your Main Team Task List with a scrutinizing eye. When prioritizing, you need to make tough choices; otherwise, it’s merely a laundry list.

We like to use the exercise “Stay, Start, Stop, Shift” to help you prioritize.

• Stay: Business as Usual tasks that need to continue during the RW Blueprint project.

• Start: Tasks you need to start pronto to accomplish your RW Blueprint goal.

• Stop: These are the tasks that take a lot of time and are out-of-scope. This might be a bit hard at first, but recognize that stopping activities will give you the time, energy, and focus to prioritize the tasks that really need to be done.

• Shift: These are tasks that need some tinkering. You may want to automate them, delegate them to another team member, or outsource them to a contractor.

If struggling to prioritize, you can ask the following questions:

• For Business as Usual Tasks: If I stopped doing this task during the course of the Blueprint project, what would happen?

• For Blueprint Tasks: Is this required to reach our goal?

Now it’s time to cross items off your list, as promised! We recommend removing any Stops from the Main Task List and rethinking any Shifts.

Once you have a prioritized Main Task List, you’ll need to differentiate tasks. Which ones need to be started first? Which ones are more time-consuming than others? Do tasks need to be completed in a specific order?

You can use a simple three-point scale, such as low-medium-high, to indicate urgency or a chronological prioritization, like now, near, and far. Whatever scale you use, make sure to define what each label means. For example, is “near” in two weeks or two months?

Our fictional friend Jamal made a few tough decisions about tasks originally on his list during this step. He has stopped his biweekly calls with community partners. This should have been transitioned to the Partnerships team six months ago, and the project is a great forcing function to make the introduction. He also stopped brain-storming for an internal design contest for December. The contest is internal-facing and not a top priority; therefore, it can be postponed. Jamal also decided to shift all of his content marketing tasks, like social media posts and blogs, to promote the October 19 event rather than build out two content streams.

SPOTLIGHT STORY: How to TIER Priorities

Remember how Ali used to teach those productivity workshops back in the early days of her career? She’d often receive questions from frustrated junior-level employees along the lines of “What if everything is both urgent and important? How should you prioritize?”

Calmly, she always responded, “Well, if everything is urgent and important, then nothing is urgent and important.” For times when that flippant statement did not put the question to rest, Ali introduced a TIER (time, impact, effort, and revenue) acronym to help teams judge and prioritize tasks based on objective measures for (yep, you guessed it) TIER-ing your priorities.

1. Time: Is there a looming, external-facing deadline? Is the timeline for completing this task a contingency for other parts of the project?

2. Impact: What is the impact of a particular task on the success of the project, team, or company?

3. Effort: What will be the level of effort required to complete the task? Is it something that can be grouped with other low-effort tasks, or can it be further broken into smaller tasks that can be analyzed with the Stay, Start, Stop, Shift method?

4. Revenue: When all else fails, is it a revenue-generating activity (or, for nonprofits, a fundraising activity)? What is the ROI on completing the activity?

By reflecting on those questions, Ali found that teams and managers were able to make clearer and more confident prioritization decisions.

HOW-TO: Assign Ownership, Set Expectations, and Agree on Accountability

Take a deep breath! You’re almost done. Now it’s time to turn all of this plotting and planning into action, which requires ownership and accountability. It’s time to delegate.

First things first: let’s make sure we’re using common language.

• Ownership: An owner, also known as the DRI (directly responsible individual), is the leader and final decision maker for the task or project. The owner is not necessarily the person completing the task single-handedly but rather the person who is accountable for the quality and success of the work.

• Accountability: The act of holding a person responsible for meeting expectations and commitments. This can happen through workforce processes, person-to-person check-ins, and progress tracking. (Ideally, without the manager breathing down your employee’s virtual back.)

Some tasks will have natural owners, but others might be fuzzier (hence the need for clear ownership). You may also discover through the RW Blueprint process that one person has too much on their plate, while another may have too little. You’ll want to reshuffle tasks across owners to ensure an equitable workload split across the team.

As a manager, consider the following when determining DRIs for tasks:

• Expertise: Who has the capability or unique ability to get this job done?

• Excitement: Who is most excited about the job?

• Energy: Who has the bandwidth or energy to complete the task?

Once you’ve assigned DRIs, we recommend enlisting them to set tangible expectations related to the assigned task. As Siobhan McKeown of Human Made said, “In our culture, freedom relies on accountability. Remote work relies on accountability. If people aren’t trying to get the job done and take responsibility for themselves, it just doesn’t work.”

Setting tangible expectations and accountability norms will ensure that your DRIs can work independently toward a goal. It also gives them more skin in the game to problem-solve through obstacles.

Expectations and accountability should include the following:

• A deadline or cadence (if it’s a recurring task)

• Accountability agreements (e.g., do you expect weekly updates?)

• OKRs (objectives and key results) and performance metrics (e.g., what does success look like?)

SPOTLIGHT STORY: Directly Responsible Doisters

At Doist they keep track of work, set goals, and hold people accountable using a few principles. According to Andrew Gobran, “Across the whole company, we implemented something that we call DRD, which is Directly Responsible Doister. It is how we create transparency around who owns what within each team. . . . Each team [identifies] what the core responsibilities are and who is going to be responsible for them. For example, I am the DRD for all our hiring and recruitment. I’m the point of contact for that.”

This concept, while relatively simple in theory, is essential in practice, as it unlocks the ability for companies to operate with a sense of ownership. From there, owners set clear goals of what they are trying to accomplish and report asynchronously on the performance metrics. Chase confirms, “Everybody’s empowered to do their work, without question. Everything is kept in transparent places. Everybody is held accountable. Things are reported daily and weekly, all asynchronously. We’re able to keep work moving seamlessly without a lot of interference from management.”

RW BLUEPRINT IN ACTION

We recommend having a template, like the one shared at the beginning of the chapter, that you can reuse with your team and save in your Digital House. If you’re using a specific tool for project management, like Asana or Notion, consider keeping the template accessible in the tool for quick and easy use. Ultimately, your RW Blueprint should be easy to understand and find so that it is usable by your team.

SPOTLIGHT STORY: RW Blueprint in Action for M&A

Tam couldn’t believe her luck. Her company had acquired Tumblr from Verizon, just as her manager left on a planned three-month sabbatical. She was tasked to lead the M&A integration of 200 employees with their own IT systems, HR processes, and policies under a tight timeline. Nervous to execute such a high-profile project alone but excited about the development opportunity, Tam asked a former teammate to delay his transfer to another team. Together, they worked through a plan for Day One readiness. (Thanks again, Patrick.)

They created a Task List by functional area with all the tasks required for the M&A integration and then prioritized them. Some tasks needed to be completed on Day One (when Tumblr legally became a part of Automattic), like payroll and specific IT systems. Others could be delayed as long as they were completed in the first 90 days after integration, like moving the Tumblr team to a temporary coworking location while deciding if they’d maintain an office. They then assigned DRIs (directly responsible individuals) for each functional category of the integration, like legal, HR, IT, and PR, which included representatives from Tumblr’s leadership team.

Every Monday, Tam and Patrick collected asynchronous task updates from each DRI and then helped unblock any contingencies or hold-ups. The integration went smoothly, which Tam attributes to the clear goals, detailed Task Lists, and awesomely accountable DRIs for each part of the integration. The team accomplished a ton of work quickly, and Tam smiles whenever she reads about Tumblr having a resurgence with Automattic as its parent company—with a new Gen Z cult following. (She’s since revived her Tumblr account.)

Now that you’ve seen the RW Blueprint in action, we recommend trying it with your team. The RW Blueprint is an exercise, process, and tool to make the unknown known and structure chaos. We hope that by having frank and transparent conversations with your team, you can truly understand the task at hand and create a plan to get there. And we hope that by taking the time to structure your work, you can save unnecessary frustration and miscommunication down the road. As Ben Franklin once said, “If you fail to plan, you are planning to fail”!

ALI’S ADVICE

Don’t get bogged down in the details or the how-to. Eventually, the RW Blueprint can become a simple mental exercise that you run through before kicking off a project instead of going methodically step-by-step, as outlined in this chapter.

For me, this activity has become second nature. Whether I’m working on an independent project or leading teams, I naturally run through the four high-level areas quickly (Goal Setting, Task Lists, Top Priorities, Ownership, and Accountability) in my head to structure work. I have used a remote blueprint to create a project plan for hosting a webinar and facilitated the entire series of exercises as part of an in-depth retreat.

Ultimately, it’s all about the larger themes of goal setting, ownership, and accountability. Depending on the goal, the RW Blueprint can be as simple or as complex as needed to bring clarity and organization to your team. Find fun ways to make it your own!

TAM’S TIPS

Do not be afraid to ask questions and challenge the status quo. It is just as important to stop and shift work activities as it is to start them.

Once again, call upon your inner Marie Kondo and find ways to tidy up your work life. Thank projects and tasks that once had meaning, and then politely remove them from your Task List.

Sometimes you need to let go of old work, mental models, and projects to make room for new work and challenges.