Editor’s note: The following is excerpted with permission from “Founders, Keepers,” copyright 2025, by Richard Hagberg, Tien Tzuo and Gabe Weisert. Reprinted with permission from Matt Holt Books, an imprint of BenBella Books Inc. All rights reserved.
By Richard Hagberg and Tien Tzuo
Founders tend to be a pretty adaptable bunch (and that’s not just survivorship bias talking — we have the data). They have to navigate treacherous waters, switch strategies, and continuously innovate.
So why, even within this inherently flexible group of humans, do so many of them struggle with adaptability? This is where personality data really gives us insights. When we combine founders’ personality assessments (their own opinions of their needs, behavioral tendencies, emotional reactions, cognitive approach, social style, and general identity) with their behavioral 360 ratings, some clear patterns begin to emerge.
It’s an ironic truth — founders, who are notoriously averse to bureaucracy and organizational inertia, tend to generate lots of it. They either pontificate and prevaricate, or they jump wildly at every opportunity, immolating their team members in the process. They don’t allow themselves to be open to different experiences and perspectives, so they become the obstacle instead of the accelerant. They slow everything down.
These founders might appear adaptable (chasing after the latest trends, obsessing over the competition, etc.), but their personality scores reveal that they’re actually incredibly rigid. They talk the talk, but they don’t walk the walk. They struggle to let go. They prefer to stick to familiar methods that have worked in the past. They tend to anchor around past successes.
In short, their general cognitive posture is closed, not open: “Does not appear that he has developed as a leader. Instead, he tends to avoid leading by locking himself in the back room.” They consider themselves completed projects, so they can’t be bothered to ask for advice: “He seems completely unable to change his behavior. He keeps approaching problems the same way, hoping for a different result.”
They admit they hate ambiguity, so they perceive change as a threat. They much prefer clearly defined situations. They desperately seek black-and-white answers in a world of shades of gray: “Has very little tolerance for ambiguity — most discussions and worldviews are presented as black and white without nuance.” As a result, they struggle to make decisions based on incomplete information (i.e., practically every single one): “He has a real problem with analysis paralysis.”
They’re exceptionally mistrustful. They’re much more likely to believe overly optimistic people have a naive view of the world. They also describe themselves as being incredibly selective about who they choose to open up to. Here’s another jaw-dropper: “He defers communication, and you often learn about things through an accidental path. You might be uninvited to a meeting or become aware of a new reporting structure by reading it in a new presentation. At the end of the day, we are all people and want to be treated like we matter. The least you could do is look us in the eye when you deliver your decisions.”
These founders are seen as profoundly dictatorial — when you don’t listen, it’s difficult to recognize the need to change. They self-report that people find it very hard to convince them that they are wrong on a point(!).
To the surprise of no one but themselves, there’s a marked difference between their own perceived capabilities in their self-reported personality tests and the frank assessments of their coworkers: “He needs to feel like you know exactly what you are doing, and he does not adjust his behavior. He is who he is, and gets passionate and loud, thinking that it is going to yield the result he wants.”
So they come across as headstrong assholes, pushing for their own views, resisting disagreement, and generally ruining everyone’s lives: “He assumes the original model will work, or that the new model recommended to him was what he was thinking all along. He does not seem to be able to keep all interdependencies in mind when recommending solutions.” They are momentum killers: “He creates the ambiguity and then becomes the obstacle. He gets very upset and negative when he doesn’t get his way or gets pushback on a project.”
Their self-reported personality scores also reveal that they are profoundly anxious, insecure, and secretive. They tend to see other people as antagonists, so they hold their decisions tight to their chests. Instead of seeking change and opportunity, they build walls and silos: “I often worry that he has Machiavellian tendencies when it comes to getting things done. He has explicitly told me not to tell people what I’m really doing or tell them something else instead of what is actually happening.”
The result is a vicious circle. They are aware their job performance is negatively impacted by their behavior and admit to getting upset when criticized, but that only reinforces their rigid approach. They suffer from high anxiety, pessimism about the future, and low energy levels, but they have zero ability to recognize that they are the cause of all this consternation. Unsurprisingly, their 360 comments show that they plainly suck at team building and inspiring people. They often share this awareness, but the tragedy is that their response is to circle the wagons.
They also struggle to empower and delegate, so they can’t enable change: “He doesn’t have to get better at working on the product himself. He just has to learn to empower the great team he put together.” As a result, their stakeholders feel unheard and undervalued, resulting in a quiet reluctance to support decisions made in such a blatantly dictatorial manner: “He defaults to telling you your commitments, as opposed to leading you there.”
Their impatience and instability prevent them from thoughtfully considering feedback or adapting their strategies, contributing to their lack of adaptability. They score low on patience and high on time urgency. They strongly agree with a statement that says they get frustrated by people who can’t make quick decisions.
As a result, they are perpetually stressed. They’re completely strung out. They confess that they find it difficult to concentrate, and sometimes they don’t even have the energy to think. They also self-report that their job performance is affected because they are frequently upset. So they make more impulsive decisions, they make more dictatorial statements, and the doom loop rolls on.
So, what concrete steps can you take to increase your adaptability?
Moving forward
If you’re struggling with adaptability, your ego is probably clouding your ability to listen, respond, and bring people along.
Stop playing the tyrant. Be aware of your own warping effect when it comes to group dynamics. Here’s a suggestion from Tien: Head into your next meeting telling yourself that you’re only allowed to ask questions, not make declarative statements of any kind. This will feel like pulling teeth at first, but it will open up new insights.
Develop a relationship with ambiguity. Many things are beyond your control. Focus on what is tangible and achievable — and don’t worry about the rest. Look at unseen challenges and curveballs as opportunities to learn something new. Want a Benioff-approved reading suggestion? Try Zen Mind, Beginner’s Mind by Shunryu Suzuki.
Stop spreading yourself thin. Address your inability to let go of things. Your job is simply to find the biggest problem (there’s always one), fix it, then move on to the next one — that’s it. Prioritize. Pick your battles, and delegate everything else. Protect your focus and avoid the death of a thousand cuts.
Interrogate your decision-making. Encourage other people to question your assumptions and push you to consider what might go wrong: “What am I missing? Why might my approach fail?”
Consider yourself a perpetual learning project. Make a habit of reading, taking courses or attending workshops that push you out of your comfort zone and help you develop new perspectives.
Trust your people. Give them challenges. Start with small tasks and gradually increase the level of delegation. Provide support and guidance when needed, but allow them to come up with their own solutions.
Be proactive about addressing your stress. Find out what works for you: meditation, exercise, a hobby that preferably has nothing to do with technology. Learn how to take a break. Tien likes to take a couple of weeks off every year in order to “let the company run itself.”
Ask yourself: Is there anything else going on internally that’s affecting your ability to iterate? Is your relationship suffering because of work? Any unresolved grief or trauma issues? It might be time to think about consulting a shrink. Walking through that door for the first time will be painful, but it’s invariably worth the effort.
Ultimately, the data doesn’t lie: Adaptability isn’t just a competency that’s “nice to have.” It’s an imperative. It’s not only a pathway to personal growth but a key driver of business success.
Richard Hagberg and Tien Tzuo are the authors of “Founders, Keepers: Why Founders Are Built to Fail, and What it Takes to Succeed.”
Often referred to as “Silicon Valley’s CEO Whisperer,” Hagberg is a trained psychologist who has spent the past 40 years of his career as an executive management coach for more than 6,000 executives. Since 2009, he has worked with companies like Tinder, Twitter, Dropbox, Mixpanel, Zendesk, Quora, Asana, Pinterest, Salesforce 1, Munchery, Reddit, Gusto, Cruise, Optimizely, Instacart, Patreon, Nerdwallet and Super Evil Megacorp (it’s a gaming company).
Tzuo, founder and CEO of Zuora, evangelized the shift to subscription and service-based business models, coining the phrase “subscription economy.” In an effort to empower this new economy, he created what became an award-winning monetization suite capable of powering any recurring revenue model. Before Zuora, Tzuo was one of the “original forces” at Salesforce, joining as employee No. 11. In his nine years at Salesforce, he built its original billing system, later serving as chief marketing officer and chief strategy officer.
Illustration: Dom Guzman
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