“One thing I’ve learned from Miles: It’s all possible!”
-Gwen Stacy (Spider-Woman) in “Across the Spiderverse”
This line from the Spiderverse1 sequel struck me with the force of a thunderous Shohei Ohtani homerun. Despite her skepticism, Gwen (Spider-Woman), chooses to adopt Miles Morales’s (Spider-Man) trademark optimism in the face of what seems to be insurmountable odds.2
Leadership principle: Skeptical optimism allows us to navigate complexity and take risks with new technology.
Last month, I was similarly inspired by the line of a senior leader I deeply admire: “There is always a way to figure it out!” Sounds reminiscent of Miles Morales. One reason this leader embraced this mindset was due to having observed resolute conviction in his mother, who confronted hardships and heart-wrenching tragedy as a refugee and immigrant, and yet always found a way.
Both Miles and this leader are not naïve. They confront and seek to understand the challenges and uncertainties and yet, still choose optimism. This mindset is called skeptical optimism.3 It is an underrated superpower that can actually be developed over time unlike superhuman strength or “web-slinging.”
Having observed leaders of all walks of life (from CEOs to school principals to pastors) that embrace skeptical optimism, the benefits are numerous: better decision-making, a willingness and sense of conviction to tackle seemingly undefeatable enemies (e.g., cancer, climate change) and the ability to rally and inspire those around you.
Interestingly, there is a fair bit of psychological research that reinforces these observations.4 Two psychologists, Charles Carver and Michael Scheier highlighted the importance of maintaining a positive outlook while also acknowledging potential obstacles. Their work connects “realistic” optimism with motivation, resilience, and goal attainment and even better health.
From a real-time, practical application standpoint, my observation is that skeptical optimism is a mindset that will separate winners from losers as executives confront the opportunity and uncertainty of generative AI. I see three reasons why this is the case:5
Fostering Innovation and Adaptability: Executives that embrace skeptical optimism are more likely to invest in innovation powered generative AI. This mindset inspires creative thinking, pushing boundaries, and generating as many innovative ideas as possible for leveraging AI's potential (as opposed to beginning with pointing out all of its shortcomings). Additionally, it equips executives with the agility to learn from setbacks and failures (versus just giving up), design follow-up experiments, and navigate the changing landscape of AI technology as it evolves.6
Informed Decision-making: Skeptical optimism helps executives make well-rounded decisions about generative AI. They consider the potential benefits, while also being aware of the limitations and possible risks.
Ethical Implementation: Skeptical optimists ensure that ethical considerations are at the forefront (vs. being an afterthought). In particular, they work with their teams to test for bias and privacy issues, two of the areas that concern me the most about AI applications, particularly in the human capital space.
Whether it’s applied to generative AI or other complex decisions, the reason skeptical optimism is so powerful is that it helps us strike the delicate balance between audacious goals and realism.7
Given this, I invite you to tap into your inner Miles Morales and start (or continue) strengthening your skeptical optimism muscles.8
Take Action: Practical and Proven Steps
Reframe a hairy challenge as an opportunity. Pick a specific challenge that may even seem insurmountable. Dedicate 30 minutes to written reflection or dialogue where you commit to looking at the challenge through a new lens - the opportunity lens. Ask yourself: How can I reframe this challenge into an opportunity?9 When framed as an opportunity, what are 2-3 potential solutions that could help me / my team capitalize on this opportunity? What is at least one no-regret experiment we can run to test each of these potential solutions? Even if these experiments fail, what can we learn from them that will be beneficial? What new skill or mindset can I personally develop in tackling this opportunity? Have a “parking lot” where you can write down other risks or obstacles that come up, so that you don’t get stuck on these. The goal of these questions is to encourage a positive perspective by looking at challenges as opportunities for learning, innovation, and personal development. Start to build this behavior into a habit. You can even invite others to answer these questions with you.
Embrace and encourage positive self-talk. Pay attention to internal dialogue and replace negative self-talk and doubt with positive and empowering thoughts. I love Alisa Cohn’s concept of: "“the first person you lead every day is yourself.” The only way to foster a culture of skeptical optimism is to take the time yourself as a leader to foster this mindset. Then (and only then) can you encourage team members to engage in this way, fostering a culture of self-belief and optimism.
Spend more time with skeptical optimists. Interacting with skeptical optimists can be profoundly beneficial, both personally and professionally. They’ll provide you with a balanced perspective, enhance your strategic thinking, and fortify your resilience.
Amplify the ‘impossible’ successes. Repeatedly recognize accomplishments that people doubted were possible. One of my recent favorites is Pfizer’s ‘impossible achievement’ of developing a COVID vaccine in less than one year.10 Start to develop a mythos of ‘impossible achievements’ that can serve as the history for your organization. These stories boost morale and reinforce the belief in future success.
Reflect: Some Questions to Consider
What is a lingering challenge you are facing that you can reframe into an opportunity?
Who are one or two skeptical optimists in your network? How can you systematically spend more time with them?
What are your favorite stories of ‘impossible successes’ both for your organization and in general? How can you get better at telling these stories to rally your team?
If this week’s Friday Reflection was practical or enjoyable (or maybe even both!), please share it with your colleagues and friends.
I have no idea how the writers pulled this off, but in my humble opinion “Across the Spiderverse” is even better than “Into the Spiderverse.” This is coming from someone who was inspired to make a career pivot based on a quote from the predecessor movie. I loved the first one, but this one takes it to a whole other level. All I can say is…go see it! I will now commit to seeing any movie or work of art that is written by Phil Lord, Christopher Miller and David Callaham.
On a related note, this post from a friend demonstrates the power of representation in these films:
If y’all could have seen the look on his [son’s] face when I told him that he kind of looks like Miles Morales….
He kept saying “ Really? Are you serious? Are you just saying that?!?”
He then does this pose [Spider-Man] and someone else said “Yo, you look like Miles Morales!”
His smile beamed so large after that! #representation matters
No spoilers here…but damn what a cliff hanger!
I first came across this term in a conversation with a CEO I advise. Later I found that at least one prominent thinker, Shane Snow, has written a fair bit about skeptical optimism. Though I know less about him and his work, I found this post from 2015 to be an excellent deep dive on the topic. I plan to dig into his work some more as he has three books and some compelling thought pieces including this one on “How to Lead During a Crazy Hype Cycle.” Maybe they’ll be more Shane Snow citations in the future or maybe I’ll find that I needed to have more skepticism as I came across his work. Ha!
In fact the research takes it a step further, it claims that dispositional optimism can improve health outcomes in the face of health challenges.
There are probably even more.
As a side note, this feels like such a Herculean task as there seem to be game-changing developments daily. One tool that has helped me is short newsletters that focus on AI. Two that I’d recommend are: Superhuman (general) and Healthcare AI News (healthcare-specific).
As an executive coach, I see this as one of my most important roles: helping leaders balance what seems like untenable contradictions (e.g., realism and audacious goals) in order to realize their business goals and personal ambitions.
The recommendations below are universal vs. how to specifically apply skeptical optimism to generative AI, but I do think many of these universal ideas are relevant for this more specific application.
An example: From “New technology will make some of our analytical services obsolete” to “New technology will enable us to have more time to deliver our higher value solutions to a wider range of customers than we currently serve today.”
Sally Susman’s recounting of this story in her book, Breaking Through, is riveting. It has really compelling macro stories as well as practical insights. One highlight is the chapter entitled “Can You Hear Me Now?: Perfect Your Pitch.”