The conversations leaders should be having now to prepare for tough times

When challenges loom, it can be tempting to wait for the storm to hit before taking action. After all, we’re not exactly sure what will happen or how it will affect our teams. We only know that tough times are coming. Whether it’s budget constraints, environmental shifts, skills shortages, industry transitions, or regulatory hurdles, businesses face multitudes of pressure.



Yet amidst this uncertainty, challenge, and change, there’s a proactive stance we can take. While it’s crucial to remain flexible and adaptable in response to unforeseen circumstances, starting conversations now to achieve clarity and alignment better equips us to tackle upcoming challenges.   



This proactive approach isn’t about fixating on worst-case scenarios or avoiding reality. It’s about readiness and making informed decisions about how we intend to respond to adversity. Confronting harsh realities may be uncomfortable but it’s where resilience begins to grow. It’s about striking a balance between optimism and realism, a principle known as The Stockdale Paradox, particularly when the future is uncertain.



The Stockdale Paradox, named after James Stockdale, the U.S. military officer who endured eight years of captivity during the Vietnam War, highlights the importance of maintaining faith in ultimate success while facing the harsh realities of your situation. It’s about hoping for the best while preparing for the worst. 



Clarity of purpose and alignment of expectations 



So, what discussions should we be initiating to prepare for the challenges ahead, even if we don’t know their exact nature? First and foremost, discussions that promote clarity and alignment are crucial. Establishing a shared vision and strong purpose can serve as a guiding light for teams navigating through turbulence. Without this clarity, it’s easy to lose your way and veer off course, succumbing to reactive impulses rather than strategic foresight. Equally important is clarifying expectations for performance and behavior under pressure. This ensures that everyone understands their role and is committed to maintaining a positive culture while moving in the same direction.  



But these discussions shouldn’t be one-sided directives from leaders. They’re opportunities for open dialogue and shared commitments. When individuals contribute to creating these agreements, they are more inclined to be accountable for upholding them, fostering a culture of shared responsibility and resilience.  



Questions to ask and answer 



Specifically, what conversations should you be having with your team now to prepare for tough times? Here are some questions to guide your discussions:



How do we want to navigate the challenges ahead?




What does success look like for us?



What core purpose or vision will we unite behind when the going gets tough?



What can we control and influence, and what do we need to let go of? 




Once you’ve explored these initial conversations, get clear on your shared expectations for behavior by discussing questions like:




What do we want the experience of being part of this team to be regarding how we communicate and behave towards each other under pressure?



What behaviors or actions must we avoid? What does good behavior and performance in adversity look like?



What are our nonnegotiable team values and core behaviors?



What are our expectations of each other?




Use your answers as the starting point to create three to five specific, plain-speak ground rules you all agree to live by. 



Engage in open dialogue to ensure all voices are heard, invite curiosity, and make team commitments. These conversations clarify expectations and uncover valuable insights, concerns, and feelings from your people that will help you lead them through challenges in a way they want to follow. The more you can understand your team’s fears, concerns, and frustrations about what lies ahead, the better you can address them. 



Adjust your sails 



As American motivational writer William Arthur Ward wrote, “The pessimist complains about the wind; the optimist expects it to change; the realist adjusts the sails.”



Ask yourself and your team: What sails can we adjust to prepare for the tough times ahead so we can weather the storm and emerge in the best shape possible, perhaps even stronger? 



By proactively engaging in these conversations early, we equip ourselves with the clarity and resilience needed to navigate challenges and change.