Stop the bleeding and prioritize

Building company cultures that prioritize

4 strategies to help your organization create space and work on what matters
Building company cultures that prioritize

Image for article titled Building company cultures that prioritize
Illustration: Grace Danico ( (In-House Art)

🖋️ Editor’s Note: Your people are desperate for capacity

I see it in the dozens of people waiting in line for advice after I deliver a keynote speech on company culture. I hear it in the tear-filled phone calls during executive coaching sessions. I feel it in the one-on-one meetings with leaders full of frustration.

These are my signs that your people are desperate for capacity. Desperate for the breathing room to do their best work, make an impact, and feel accomplished.

Our lack of priorities is a problem, but there is hope. There is much that an individual employee could be doing to reclaim their time. Progress from leaders who slow down enough to listen, then take action to support their employees. But, for the kind of progress that impacts a company’s bottom line, we need change at the organizational level.

Our companies are systems that require auditing, adjustments, and action to do things better or differently. Our fourth installment in our series on prioritization gives companies four strategies to implement, with numerous routes to make an impact.

Share the idea with your leader. And your leaders’ leader. And your people operations (human resources) team. Kick up some dust and ask for change. If you don’t, who will?


Let’s get to work,

Anna Oakes

p.s. Special thanks to September’s contributor-in-residence, Banks Benitez, and our artist-in-residence, Grace Danico.

Building company cultures that prioritize


Banks is the founder of Smart Workweek, helping businesses transition to the 4-day workweek and was the co-founder and CEO of Uncharted, an entrepreneurial accelerator.

When setting priorities, there’s more within our control as individual leaders and employees than we often admit. Yet, employees are limited if companies don’t adopt organizational systems, practices, and cultures that value the importance of prioritizing.

Teams and employees that can combine individual habits with organization-wide processes and behaviors will be able to spend more time on the most important work, which can translate into a competitive advantage.

Here are four routes companies can pursue to help them prioritize better, leaving old habits behind.

⬅️ The power of pushback

It can be counterintuitive to consider that for a company to grow and achieve more than it has in the past, it might need to focus on fewer things. Yet, many companies and teams continue to take on more until they burnout, fail, or get into a rut. It’s often easier for employees to say yes to something exciting than to say no in an effort to prioritize important work.

I fell into this trap as the founder and CEO of Uncharted several times when doing our annual strategic planning. My eyes were bigger than my stomach, and I overestimated the number of activities that were truly important. To keep up, our team would have to sprint to do it all, often leading to burnout and confusion about how all these different priorities connected. Over the years, we involved more people from across the company in the strategic planning process, allowing diverse voices to weigh in, challenge leadership’s thinking, and raise the bar for our top commitments.

Teams and individuals can interrupt these tendencies by embracing the power of pushback, or the behavior of teams when they challenge each other, debate approaches, and believe that it is safe and productive to disagree on the best way forward. I like the framing of pushback (as opposed to just feedback) because it sets the expectation and the permission for people to disagree and debate.

Define reality and understand trade-offs: Raise your team’s awareness of their own time and resources. Set aside time in big decision-making meetings to consider trade-offs.

🧭 How to: 

  • List all current projects
  • Assign time commitments
  • Ask: Which projects or activities bring the company the biggest ROI? For those that are not, can we scale back efforts or stop altogether?

Create the space for pushback: Your team’s intelligence and wisdom are only as good as the space that’s created to invite them. Yet, most teams don’t schedule time for debate, pushback, and discussion around big, strategic decisions.

🧭 How to:

  • Carve out ample space in your meetings for discussion and debate. For meetings focused on making a decision, I recommend at least 15 minutes of space for discussion and debate.
  • Give participants pre-work or advanced notice of the topic so they come ready to discuss. This levels the playing field for those with more introverted tendencies who aren’t as comfortable participating in impromptu group discussions.

Create psychological safety: When pushback is normalized, disagreement and debate become valuable ingredients in decision-making, as a team and individually.

🧭 How to:

  • Agree on ground rules in the first scheduled discussion, as this will help minimize unproductive conflict during or after the sessions. In turn, this provides safety for true behavior change outside the meeting.
  • One ground rule should focus on how we collectively agree to receive pushback. We may agree that we won’t jump to defensiveness when pushback is given.

Explain how decisions were made: Companies should focus on transparent, frequent communication to develop a culture where debate and pushback are normalized. When teams view pushback as a tool to move important things forward, they’ll feel more comfortable contributing in the future.

🧭 How to:

  • Tell stories about how hard decisions were made, and the role pushback played in those decisions.
  • Avoid being seen as Pollyanna and share the tough stuff too. Hubspot, a customer relationship management system company, holds failure forums asking volunteers to share their failures. Sharing the decision-making process and what didn’t work can help refocus pushback as a tool.

📊 The importance of performance metrics

Many employees struggle with being held accountable for multiple metrics while simultaneously being told to get better at prioritizing. Will they be penalized for deprioritizing some of their work? Can they leave work undone without being fired?

Before shifting to a 4-day workweek at Uncharted, I often heard similar concerns from our team. So, we started by getting better at deprioritizing. The pushback techniques above helped move our ideas forward while creating the capacity for new, valuable work. But, we know what gets measured gets managed.

To support a culture of prioritization, a company needs to define, track, and report on performance metrics that matter. While increased accountability may be on our minds when we talk about metrics, let’s not miss the motivating factors. Instead, reward the behavior of prioritizing.

Consider shifting performance indicators to measure the number of projects or activities someone deprioritized, and publicly recognize those employees who demonstrate these skills. In addition, you might consider expanding promotion criteria to reward an individual’s proven ability to focus on the most important work.

🔤 The value in vocabulary

The vocabulary in an organization is full of clues about what the organization values. While companies tout a feedback culture, it’s often filled with phrases like “you’re crushing it,” or “they always go the extra mile,” or “they worked nonstop through the weekend to get it done.” These compliments praise long hours, over-committing, and hustle culture as behaviors to be celebrated and rewarded.

Every organization already has a shared vocabulary of common words, phrases, and themes. In that case, we might as well own the vocabulary and intentionally expand it to reinforce the new behaviors we want.

When I moved my company to a 4-day workweek, we all read Essentialism by Greg McKeown, a book that focuses on the disciplined pursuit of less. McKeown challenges his readers to distinguish essential work. As we piloted the 4-day workweek, the words “essential” and “non-essential” became part of our everyday vocabulary, and they often sparked rich conversations around our priorities.

Company values are most powerful when they’re part of everyday conversation. Can you tie principles of prioritizing to one of your company values? For example, one of our values at Uncharted is “take the long view,” which is referenced when we struggle to balance urgent and short-term work. When we leverage this value, it recenters us and puts things in perspective, allowing a more sober-minded consideration of what’s truly important.

Leaders need to model vocabulary, both in using it and celebrating its use across the team. Publicly highlighting those who embody the values through everyday actions is a great option. For example, some companies use large group meetings and town halls, while others leverage technology by using employee recognition software.

🧠The need for reflection

The art of prioritizing is an ongoing practice that requires nurturing. The workplace offers many opportunities to practice the art of prioritizing. Still, to see your company’s practice forward, the organization must build in time to reflect on past decisions, identify the lessons, and determine how they’ll do it differently next time.

For reflection to happen at the company level, it must occur at the team level. As the founder and CEO of Uncharted, I often moved too quickly. Before I had a chance to reflect on how that strategic planning process led to 12 different priorities, I lept to the next thing. Or, positively, how a recent decision was informed by honest dialogue and helpful pushback.

Here are three steps to increase company and team reflection:

  1. As individuals, then as a team, carve out time to briefly reflect on major decisions. It can feel uncomfortable to revisit mistakes or past decisions you regret (this has happened to me a few times). Still, I’ve found it therapeutic to revisit the factors and the mindsets involved in big decisions. What worked? What didn’t? What will we do differently next time?
  2. Find the individuals and teams who lead the way on healthy prioritization. Why are they successful? What behaviors do they exhibit? What support or resources do they leverage? How can we replicate this elsewhere in the company?
  3. As an executive team, discuss how and when you have struggled to prioritize in the last quarter. Client demands, a fast pace, unclear metrics? How might we restructure our work, reset our relationships, and redefine our metrics to get around those barriers? Sometimes the best way to get better at something is to identify the barriers that stand in our way.


From the rise of remote work to demands for innovative, user-friendly systems, the tech needs of the workforce are quickly evolving. The tools to move businesses forward are advancing to meet these challenges—but many companies aren’t keeping up. Join us for an expert panel to discuss the needs of today’s workplaces, and strategies to align the operating systems of your company with the tools that can make a difference. Register here.

Friday, Sept 30, 2022, from 5-6pm BST / 12-1pm EDT




Perhaps like many of us, you’ve started to question aspects of work that we once took for granted. Like: Why do I work five days a week when I could get just as much done in four? Could offices be designed better? Why is good feedback so hard to get, and to give?

These questions didn’t appear out of nowhere. Companies and employees have been slowly changing things for years. But the pandemic pushed many to pick up the pace. And now, for the first time in a long time, widespread transformation feels possible.

This moment of change is exactly what we’re documenting in Work reconsidered, a new podcast from Quartz.

Image for article titled Building company cultures that prioritize
Graphic: Quartz ( (In-House Art)


💪 October brings a new 4-part series for The Memo with a focus on women in the workplace. It’s an exciting line-up of topics and experts and I can’t wait to see it

🤼 This week’s edition of The Memo was brought to you by Banks Benitez, Anna Oakes, and artwork by Grace Danico.

🌄 Get the most out of Quartz by becoming a member