Be the Hero of Your Own Story: Superpowers, Kryptonite and the Leader's Journey

Donna Lichaw began her career in product management and design before becoming an executive coach. The turning point came at a leadership retreat in Silicon Valley, nearly a decade ago, where she was running storytelling workshops because companies wanted their product leaders to be better storytellers.

Several people on the team pulled her aside, bluntly, and told her storytelling would not solve their problems. Executives were in conflict with each other, blaming engineering heads for being jerks or teams for being demotivated, and no one wanted to hear anyone's stories under those conditions. Lichaw says leaders first have to connect with people and feel good in their role before they can really step up.

She left feeling terrible and told the team they needed a coach, but she could not stop thinking about them. She suspected stories were still part of the answer, just not the stories told to others. She spent the next decade working out what makes an effective leader and eventually rebuilt her whole business around it.

Lichaw says everyone wants to be the hero of their own story, and leaders are no different: they have a mission, obstacles that make it interesting but not impossible, and allies. What she calls story-driven leadership treats the stories leaders tell others as only the tip of the iceberg. Some of her clients' teams explicitly ask them to stop the storytelling.

The more powerful stories are the ones we tell ourselves, such as "I'll never succeed" or "he's such a jerk." They are usually not true, she says, but the brain cannot tell the difference, and seeing stories everywhere is its most powerful ability. Her case is that this is neuroscience and psychology, even if it sounds cheesy.

She admits this runs against the user-centered instincts of people with product or tech backgrounds, and she used to believe leadership was only about who you bring along. Now she flips it, citing Ken Blanchard's concentric circles in which you lead yourself, then one-on-one relationships, then teams, then the business. Starting from inside is not selfish, she argues, because purpose supplies the fuel, and fuel that comes from outside is like an eggshell ready to crack.

Lichaw describes a CEO of a billion-dollar company who had just hired a superstar executive team. Outwardly he was polished, but he kept telling himself he was too nice, that nobody took him seriously, and what she calls horror stories, such as "I'll never learn to be a real CEO." Such stories take over your identity, and if you focus on them enough they can become true.

Her method is data-driven: she interviewed his team to learn how they actually experienced him. They did not find him too nice; they found him heartfelt and caring, and that was why they had joined. They also were listening to him, but senior executives do not want to be told what to do. They wanted a grand vision, some goals and problems to solve, and they were frustrated when he disappeared for two weeks.

Together they wrote a better ending, which Lichaw compares directly to customer discovery: you learn what could be possible from your customers, who here are your colleagues, and then co-create it. She says you can do this yourself or have someone else gather the feedback if you are too busy. Guessing and experimenting without talking to people is the weaker alternative.

Lenny asks what happens when the feedback is accurate. Lichaw says that does happen, and gives the example of an executive who was told she was too quiet. Her team read her silence in meetings as disinterest, which hurt their work together, while she was frustrated that they were not stepping up.

When they dug deeper, the executive turned out to be a listener who needed a few hours to process before forming thoughts. The team did not really need her to talk more. They needed to know she had heard them and would act. The fix was not to yell or talk over people but to tell them about her style and her slower processing.

The irony, Lichaw notes, is that opening that line of communication made her talk more, and the team began sharing their own working styles too. She compares this to a personal operating system; Lenny adds that he has heard the same idea called a personal README. The lesson was that the answer was better listening and a better relationship, not simply more speaking.

Asked how to handle imposter syndrome, Lichaw rejects mechanical affirmations in the style of Stuart Smalley and takes a counterintuitive approach. She asks what the habit is giving you, comparing habits to an itch: scratching feels good, which is why we do it, but too much hurts. If calling yourself an imposter has become a reflex, it is serving you somehow.

A co-founder she coached found that every time she felt like an imposter she worked harder, read 20 books or took a class, and she gradually grew into the role. The danger was overdoing it, taking on emotional labor and doing the work of a COO, CFO and CEO at once. Lichaw's advice is to embrace the feeling enough to benefit and not so much that it holds you back, and Lenny notes that in tech many roles are invented anyway.

She extends this idea with her chapter on kryptonite, borrowing from comics: kryptonite is how people operate on Superman, so it can serve a function in small doses. Some kryptonite should simply be avoided or delegated, such as her own trouble with scheduling, which she automates, or toxic people. Other kinds, such as dyslexia or ADHD, may reflect a brain that thinks spatially and big-picture, and may be how a founder built a company in the first place.

The Hulk is her model for a weakness that is also a strength: his anger is both kryptonite and superpower, and if he lost it he would be a very boring Bruce Banner. Her point is that supposed weaknesses become useful tools once you embrace them.

Lenny shares that a coach helped him accept he would never be an amazing public speaker, and that he preferred writing and thinking, which led to his newsletter. Lichaw agrees, citing studies showing people are more effective when they amplify their strengths and calling it a waste of energy to fix what is broken.

She illustrates with their first exchange. She hates email and writing, yet had a newsletter people loved, and she wanted to ask Lenny about it. He preferred to avoid calls, she preferred not to write her questions, and so they ended up talking in a way that suited both. She notes it would have been faster to write a whole book than that email.

Lichaw sees this often with founder CEOs, who feel they must be loud, opinionated and controlling, when some are excellent quiet listeners. She mentions Bob Iger as someone she has heard described as a great listener. Lenny's own unlock was realizing the same results can be achieved with different strengths, whether a loud charismatic visionary or a quiet, deliberate CEO working in small teams.

Lichaw says strengths tests such as StrengthsFinder and the VIA character strengths survey exist and some people like them, but she does not find them helpful because a list lacks context and is easy to forget. Lenny says he found them useful as a supplement, and that they will be linked in the show notes. Her preferred method is to pull superpowers out of stories from your past and present and then transpose them to the future.

She asks for three stories: a peak experience from childhood that lit you up, a recent project in the last decade that did the same, and the meandering path that led to your current work. Peak does not mean happy; it means you were at your best. Laid on top of one another, the three show your superpowers surfacing at key moments.

One executive kept getting "attention to detail" in her 360 reviews even though she hated details and wanted to do strategy. Lichaw says "strategist" is too vague to be a superpower. Digging into her stories showed she was a connector of themes, trends, ideas and people, which became part of her identity and made her more effective.

Lenny tries the exercise live. He describes starting and selling his startup, wanting to prove to himself he could do it, and a chip on his shoulder from being a shy, nerdy child. Lichaw says a theme like "doing it because I can" is a real superpower, but she cautions that every superpower has a shadow when over-indexed, as with a CEO whose problem-solving drags them into the weeds.

Lenny adds that energy is a signal worth following, and recommends executive coach Matt Mochary's energy audit. When he left his job he paid close attention to what gave and drained energy after each meeting, which led him to the newsletter and then the podcast. Lichaw says using your superpowers gives you energy, and that founders especially are often burnt out because they spend energy in the wrong places.

For things you cannot control, such as unavoidable meetings, Lichaw says she is not a career coach, but the answer is to change your context if nothing else works. She brings a ruthless prioritization mindset from product management. Lenny recalls a Steve Jobs line that dreading the day once in a while is fine, but if it keeps happening, make a change.

For smaller drains she shares hacks for Zoom fatigue: limit meetings per day, do active things in between, and use fidgets during calls. She explains that on video the brain gets visual stimulation without the physical cues of being in a room, and fidgets help ground her. She jokes that starting things she does not finish is her kryptonite, as shown by the superhero supply kit of fidgets she prototyped.

Lichaw trained with Gestalt coaches and therapists, whose idea is that lasting change comes from embracing what is working rather than forcing change. You do not change everything at once. You take one tiny step and run an experiment to get data, and she never lets a client leave a session without trying one. Her comparison is to lean methodology: anything you think is true is a hypothesis until tested.

She returns to the quiet executive. The idea of listening silently for a whole meeting terrified her, so they tested it by role-play, with Lichaw talking for 30 seconds while the client only listened. It felt awful at first and got easier over time. She compares this to superhero stories, where heroes who discover their powers wreak havoc and resist them, and even Superman tries to get rid of his.

Unlike product experiments, she says, you run results through three filters, which she calls head, heart and hands: what you think, what you feel emotionally, and what your body does. One client said an experiment was "fine" while her face turned bright red. Lenny adds that the body drives much of our thinking and points to an earlier episode on the nervous system.

Asked how she surfaces goals clients cannot articulate, Lichaw says to start with the ending, whether a quarter or decades away. Close your eyes and engage every sense: what you hear, see and feel, who is there, what you have accomplished. Then write the journey backward as an experimental roadmap, beginning with the first thing you need to learn.

If no vision appears, she says to sit with it as long as needed, because you cannot write the journey without the ending. She is not claiming you get anything you say aloud, and what you create will probably differ from what you imagined, but a picture fuels you. Lenny jokes that in tech everyone's five-year vision is not working, and Lichaw says what matters is clarity on the impact you want, and acting true to yourself.

In the lightning round, she says the book she now recommends most is her own, since it collects her favorite ideas, and she likes the show For All Mankind and the leadership lessons in Ted Lasso. Her favorite interview question asks clients to imagine the best year of their life and write the ending, a twist from Benjamin Zander's The Art of Possibility. Her motto is a mentor's phrase, "Isn't that interesting?", a non-judgmental curiosity, and her favorite Dolly Parton line is "Find out who you are and do it on purpose."