The increased complexity and endless disruptions of the modern world brought on by the transition to the digital age means uncertainty is everywhere. All across our businesses, we face new challenges, as what used to work no longer achieves desired outcomes. The self-awareness of admitting what we don’t know is the first step toward figuring out new best practices.

Fundamentally, people must act differently in the face of uncertainty. Businesses need to adopt learning strategies in order to improve, adapt, or even reinvent their execution strategies. 


The biggest obstacle leaders face in adopting learning practices is fear that the work takes away from normal execution. 


Leaders often say, “we don’t have time” or “we must hit our numbers,” etc. When uncertainty exists, jumping straight to execution without pausing to learn, rarely ends well. Conversely, rapidly iterating and learning leads to getting it right the first time. Balance search and execution across the organization improves the efficiency of work. 


The biggest obstacle employees face is not having the time, space, or safety to learn. 


Learning mode requires “failing” small while on the way to figuring out how to execute within new conditions. It’s not failure at all, of course. Scientists don’t view disproving assumptions as failure. On the contrary, they view it as a step towards finding answers. It’s important that leaders not only reassure employees of this point, but that they also exhibit learning behavior themselves.

The challenges of the 21st century require purposeful learning — exploration work — be democratized throughout the company. It’s a long and difficult journey to implement this mindset change. Here are 5 jobs to get you on the path. 


Job 1: Find Your Champions

Your organization already has people who demonstrate learning behavior.  They may be design thinkers, agile developers, or people who have worked in startups before. They may even be tinkering with their own ideas on the side.  They’re likely in all levels of the company from solo practitioners to leaders. 

Find them by forming a new channel in your company messaging app, e.g. Slack or MS Teams. Start a weekly “entrepreneurial spirit” happy hour or zoom call. See who shows up! Some of these people will be your proselytizers, coaches, and mentors.


Job 2: Define Your Entrepreneurial Spirit

Some people call it agile. Some, design thinking, human centered design, or lean startup. But what is this new mindset?

In the end, you must see specific behavior that represents learning mode. Combine the practices already exhibited in some areas of your business into your version of “entrepreneurial spirit” or “innovation mindset.” Make it your own so it fits your business mission and your culture. There are myriad frameworks and models from which you can derive your own flavor. Have your champions hash this out.


Job 3: Define Your Challenges

Learning mode should be applied whenever uncertainty rears its befuddling head. You should also, however, seek out uncertainty. Uncertainty keeps executives up at night — some issue or challenge they’re having trouble resolving. Product teams have ideas for improvements, but they’re not sure if they’ll work. Marketing and sales folk perhaps struggle to achieve their growth targets.

In other words, business challenges that require learning before executing live in the hearts and minds of all your employees. Go get ‘em!


Job 4: Upgrade Leaders’ Game

Leaders must walk the talk. Not only should they demonstrate learning, they must learn new skills to manage learning. Middle management and senior leaders reinforce learning behavior by admitting when they don’t know, when they’ve been wrong, or even when they failed.

To provide time and space, they must consciously allocate “tasks” that practice learning behavior. Agile sprint planning or kanban can be helpful in organizing and scheduling learning activities that tie directly to team missions. 

Learning mode requires leaders to act as mentors asking the right questions, questioning assumptions, and holding teams accountable to learning metrics, rather than only outcomes. Leaders must have the team’s back and help remove organizational obstacles that slow down learning. 


Job 5: Invite Support Functions to the Party

Believe it or not, internal company support departments like human resources, finance, operations, legal and so on face uncertainty. They have issues best practices don’t always resolve. They also have a unique perspective of the company and see challenges others don’t. They must also learn before executing. 

These functions will not only improve their service to internal customers, they are also a key part of enabling employees to work in this new way. New guidelines, rules of engagement, funding, hiring and so on, help create the culture of learning mode.

Everybody inside the organization has a customer. Everybody can go and develop empathy for them.

Establishing a new mindset will take a bit of planning, experimenting, and iterating to find what works. In other words, even establishing the new mindset is an exercise fraught with uncertainty. So you must apply the “entrepreneurial mindset” to establish it! See my article on the 5Es for more tips on establishing a new mindset.



Brant Cooper is the author of the NYT bestseller, The Lean Entrepreneur. His next book, Disruption Proof is available for preorder now. Order from your favorite retailer or for bonus bundles, go to