Optimistic Realism Improves Performance and Well-Being

We’re all sailors. Whether solo or with a crew, we’re navigating the seas and winds as we seek to make port or round the last buoy to cross the finish line. While there’s certainly a lot that goes into seafaring skill, outlook determines outcome––the critical question being: What kind of sailor are you? Are you “[t]he pessimist [who] complains about the wind; the optimist [who] expects it to change; [or] the realist [who] adjusts the sails[?]” as William A. Ward describes.

Pessimism hinders performance by affecting a person’s capacity to work and make good decisions, to move forward to the finish line. When Henry Ford said, “Whether you think you can, or you think can’t, you are right,” he eloquently and succinctly encapsulated the very pertinent, yet often overlooked, fact that if a person doesn’t believe a solution is possible, they won’t look for it, which all but guarantees that they won’t find it. Pessimism manifests as paralysis and criticism and can overwhelm. It’s bad for performance and well-being. That is the danger of pessimism.

While deceptively seductive, optimism can be likewise dangerous. And this comes from someone who considers herself to be an optimist. While I believe in the power of people to align to solve problems with greater creativity and skill, I also see how blind optimism results from intentional and unintentional avoidance of discussions concerning priorities, expectations and resources. People shy away from acknowledging what won’t get done or that they may be asking too much of each other. Unrealistic expectations undermine well-being as lawyers strive for the unattainable, like sailing directly into the wind. To Henry Ford’s point about mindset affecting actions, a person with blind optimism doesn’t even look for challenges, and therefore, cannot possibly deal with them before a capsize or sinking. The eventual and inevitable scramble to surmount unanticipated gale force winds certainly tries well-being and impedes results. Add that certain goals may simply be unattainable, and you’ve created the perfect storm of frustration and even burnout. 

In characterizing the actions of a pessimist, optimist and realist, William Ward implicitly makes the point that only the realist has hope of success because only the realist takes the necessary actions to deal with what is so. Add a sprinkle of optimism or optimistic realism and the lawyer has the requisite mindset to both believe that a solution exists and recognize that a realistic appraisal of the circumstances is necessary for success. Success is both winning the substantive matter and safeguarding well-being by ensuring that no one drowns in unrealistic expectations.

The Challenge

The most common capsizes occur when lawyers manage complex matters, especially when relying on less experienced crew with whom they haven’t previously worked or perhaps only barely know. Sailboat racing teams consider “time in the boat” together as essential for smooth execution of tactics. Senior lawyers can be impatient with the inexperience of associates, which is then compounded by feelings of stress and overwhelm over having to deliver, and further compounded by concerns that the team is ill-equipped. When partners anxiously press, thereby overwhelming associates, the latter can succumb to fear of failure. Fear of failure is the fear that even the smallest mistake will result in disaster, triggering analysis paralysis and reducing associates’ capacity to work effectively. Partners, sensing that associates aren’t operating at their best, become more stressed about attaining excellent results. The paradox is that all lawyers (and staff) involved are committed to achieving results, but each person’s stress feeds into and perpetuates a team cycle of stress. This cycle harms outcomes, performance and well-being.

Seven Steps to Ensure Smooth Sailing

It also may not even occur to the senior lawyer that both performance and well-being would improve if the lawyer were to realistically assess what it will take to serve a client, given staffing and time constraints. For some, the discipline of detailed planning seems like an impossible indulgence at best and repugnant at worst. Take a deep breath and remember that planned performance improves outcomes. It’s better to check for seaworthiness now rather than bail water furiously as soon as you leave the dock.

1. Clarify tasks. Even if you are a team of one, the likelihood of success improves when you clarify what exactly needs to be done. Using checklists can shortcut the process and quickly highlight what you might be missing. If you are working with a junior associate or someone new to the type of work, clarify expectations down to the most detailed knot.
2. Create the timeline. More complex matters most definitely benefit from a multipart timeline to ensure the team aligns on deadlines. Don’t forget to create timelines for your more junior associates that include sufficient time for you to review work product before it’s filed or sent to the client so that you aren’t both disappointed. Consider using apps such as Asana or GanttPRO if your case management software isn’t up to the task.
3. Be realistic about capabilities. In concert with clarifying expectations, ensure the uninitiated have realistic expectations about how long a project will likely take and when to start working on it.
4. Prioritize. Especially if your resources are limited and time is short, ruthlessly prioritize. You might have to decide what isn’t getting done.
5. Engage and involve the team. To improve understanding and commitment involve your crew in developing the timeline and discussions about work product expectations. You want associates to consider themselves stakeholders in both the process and the outcome, not just remote worker bees.
6. Be real. Don’t shy away from uncomfortable conversations about the level of commitment necessary for success. You need to anchor your plan in realism, not hope.
7. Listen for hesitation. When having uncomfortable conversations, listen for uncertainty or lack of commitment. Ask about it. It may just be a matter of reprioritizing and juggling other work.

While the planning process can itself feel unnecessarily time-consuming and thus stressful, it never helps to panic or let your impatience overwhelm you. Take a breath. Slow yourself down so that you can think clearly about the best approach. Continue to believe that you can, in fact, navigate treacherous reefs and masterfully outsail your competition. You’ve got this!