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Six Culture Red Flags that can tank your Future of Work Strategy

As the pandemic upended the world of work almost overnight, we saw organizations scramble to maintain the organizational cultures they worked so hard to cultivate. For many, their culture was centered around in-person interactions and relationships. So, when everything turned virtual, leaders had to figure out how to hold onto that culture, while rapidly changing how they worked.

A year later, leaders are now facing another, possibly thornier challenge when it comes to cultivating culture: the introduction of new, more flexible work models. According to a Gallup study, flexibility at work is what most American adults are looking for above all else. And it’s clear flexibility has many benefits for both employees and business. (In fact, Forbes conducted a study that showed worker productivity was up 47% last year!).

So as companies determine whether to implement a hybrid model, go back to the office full-time or continue to work remotely on a permanent basis, they will need to figure out how to adapt for their future while keeping their culture in place.

And it’s critical that leaders get this right. When a company builds a culture that supports its strategy, productivity and revenues rise, customers buy more, good employees stay, and great employees join.

As you start to define how you’ll work in the future, here are the six red flags to watch for so you can keep your culture strong:


As awful as 2020 was for so many people, one silver lining was the benefits people discovered from having more flexibility with when and where they work. To sustain this need for more flexibility, leaders are figuring out what work model to choose and what expectations to set when it comes to where and how work happens.

While there is great debate about which model is the right one in the new world, the truth is none are actually inherently better than any other. What is “right” is assessing which model supports your values, culture, industry, and strategy, and then thinking holistically about how the model you choose impacts your culture. This means thinking beyond just the day-to-day – how does the chosen model impact development, collaboration, recruitment, work/life balance, and wellness … just to name a few. Thinking through these implications takes time and attention but is crucial for continuing to cultivate the right culture for your organization.


Developing and empowering talent can no longer be based on “face-time” in the office. Usually rooted in a lack of trust and fear of losing control, many leaders – even some who would consider themselves progressive – are falling victim to the assumption that “If I can’t physically see my employees working, they must be slacking off.” This won’t work as the world of work becomes more flexible, hybrid, asynchronous, and dispersed.

To continue to cultivate and develop talent, leaders must challenge their assumptions about how work gets done, focusing more on the outcomes of that work rather than the process it took to get there. As they make this transition, leaders may need to consider new ways of connecting and coaching team members, assessing talent, recognizing success, and delivering feedback.


As organizations craft their post-pandemic futures, culture and values need to be front and center in the conversation. As companies take on more flexible models, your culture can guide how you adapt processes, structures, policies, and ways of working. As an example, one of our clients traditionally held in-person all-employee meetings for 90 minutes every quarter to share the latest information and align people to changes. They realized quickly in 2020 that this wasn’t going to work in the new world. With their value of speed at the center, they reimagined their employee communications to short, monthly video segments from the CEO and other leaders to share what employees most needed to know.


Over the last year, leaders have had to make some tough decisions. They were tested in new ways and had to quickly adapt to changing circumstances – in many cases, overnight. But this doesn’t mean they have all the answers, all the time. In an environment where everything is changing rapidly, leaders need to act with both agility and transparency.

The problem is, these rapidly changing environments are when employees need to hear from leaders the most. When there’s silence, unproductive rumors and anxiety kick in. So instead of shutting down because they don’t have all the answers, leaders need to open up, communicate what is known, promise to communicate what is not, and give employees a platform to ask tough questions.


Almost every client we work with has told us that they want to hang on to the agility 2020 demanded of them and for good reason – they accelerated change faster than could have ever been imagined, innovated how they worked, delivered for customers, and found new ways of collaborating that was better for people and the business.

Now the challenge becomes, how do you avoid lapsing back into old ways of working and hang onto that agility? To do this, leaders can take a step back to reflect on what made these new ways of working a success. What barriers were cleared? What did we stop doing? How did our mindsets change? It’s one thing to carry 2020-influenced processes into 2021 and beyond, but it’s another to look deeply at those processes to figure out what cultural barriers were let go so you can be sure not to pick them back up.


No matter how an organization decides to work in the future, one thing that will stay constant is the continued blending of our work and personal lives. More flexibility generally means more flexibility to incorporate your personal needs into your day, whether that’s taking time for personal wellness, spending time with family, or focusing on work when you know you’re at your best.

As leaders and managers work with their teams to chart a path forward, conversations may need to be a bit more personal. If an employee works best in the morning, they may ask to work from 7 am – 3 pm. If someone else cares for an aging parent on Tuesday afternoons, they may need to adjust their week to accommodate. Having these conversations requires psychological safety and empathy from leaders. We all have cognitive biases that can impact who and how we empathize, and the challenge leaders face is seeing and overcoming those biases so they can stay open to what their people need to be at their best.

As you determine what working model is best suited for your company, bearing in mind these six red flags will help keep your positive culture in place. 

Loren Heller is a Principal at Daggerwing Group where she helps clients create and execute employee engagement and communication strategies that help businesses achieve success by engaging their greatest asset – their people. Loren has a passion for customer service and is dedicated to making her clients’ needs her primary focus. Her background in communications and employee engagement helps bridge gaps between leaders and employees and helps her clients solve their most complex change and communication challenges. When she’s not at work, Loren can be found baking her famous chocolate chunk cookies and spending time with friends and family.