In a recent Breaking Changes episode, host Jean Yang had the opportunity to glean some insights from seasoned leader Will Larson, whose experiences as CTO at both Calm and Carta, as well as management positions across many other tech companies, have shaped his approach to leadership in high-pressure environments. Let’s look at some of the key takeaways from their conversation.
Strategic focus: less is more
When facing resource constraints, successful leaders know that making fewer, more deliberate bets is the key to survival. Casting a wide net and hoping for the best can present too much risk. Instead, it’s about whittling efforts down to what really matters—focusing on a few initiatives that align with your company’s core strategy and have the highest chance of success.
For instance, when Larson joined Carta, one of his first actions was to reduce the scope of work across the engineering team. By concentrating the team’s efforts on high-value areas and cutting out projects that didn’t align with the company’s immediate goals, Larson was able to streamline operations and make sure that the team’s energy was directed where it could have the most impact. The data supports this approach as well—a study from Harvard Business School found that companies achieve greater success and create more value by focusing on fewer, higher-impact initiatives (Oberholzer-Gee, 2021).
Advice for leadership: Innovation is the lifeblood of any organization, but in times of scarcity, it has to be tempered with practicality. Focus on what’s essential and most likely to succeed, rather than spreading resources too thin across multiple speculative initiatives.
Consistency: the underestimated leadership virtue
Consistency in decision-making and management practices is crucial. Whether in team structures, communication, or strategy, being predictable helps teams adapt and function more effectively. Inconsistent leadership, on the other hand, leads to confusion, inefficiency, and a lack of trust.
“Almost anything you do is fine, as long as you’re consistent about doing it. Even if it’s bad—people that you work with are smart, and they’ll figure out a way to work around it.”
Larson emphasized that consistency doesn’t mean always being right; it means being predictably wrong in the same way. This might sound counterintuitive, but teams can adapt to a leader’s quirks and shortcomings if they’re consistent. What they can’t adapt to is unpredictability and a lack of alignment.
Advice for leadership: Establish and maintain consistency in decision-making, communication, and management practices. Prioritize clear, predictable behaviors to build trust and reduce confusion within the team. When teams can trust their leaders, they’re more engaged—and nearly half as likely to look for a new job (Gallup).
Adaptability: when to micromanage
While micromanagement is often criticized, there are times when it’s necessary—especially during a crisis or when urgent issues arise. Knowing when to dive into the details and when to step back is a key skill for any senior leader.
Larson discussed the importance of recognizing these critical moments. When things go wrong, there are some cases that require leaders to get deeply involved, understand the root cause, and guide teams through a solution. This isn’t about controlling every detail; it’s about being present when your expertise and oversight are most needed. Showing teams you care about the details (and your employees’ overall wellbeing) is a way to build trust and credibility, according to early pandemic-era research by McKinsey & Company. On the other hand, if you avoid getting into the weeds every time things go wrong, your advice can be too generic because you lack the context to understand where the problem really lies.
Advice for leadership: Begin building the skill to recognize when it’s necessary to step in and provide hands-on guidance, especially during crises or critical situations. Balance involvement by diving into details only when needed. This shows attentiveness and builds trust, ensuring that your team feels supported while maintaining their autonomy in less urgent moments.
Contextual decision-making: tailoring your approach
In leadership, context is key. The best decisions are tailored to the unique challenges and opportunities of the moment, not based on past successes or one-size-fits-all approaches. Larson learned this lesson the hard way when he tried to implement a Kubernetes migration at Stripe. He had just led a team at Uber through a migration from manual multi-step Puppet runs to self-service resource provisioning and was eager to bring these learnings to his new team.
“It’s definitely where I see leaders get into the most trouble—the magic thinking about this big migration they’ll lead six months after they start.”
While his idea was innovative, it wasn’t what the company needed at the time, and he had to step back and reassess. He listened to the engineers’ concerns and strategically deferred the Kubernetes conversation until it became a safer, more advantageous migration path a few years later.
Advice for leadership: Assess the unique context of each situation before making decisions or implementing changes. Avoid relying solely on past successes or applying one-size-fits-all solutions. Regularly engage with your team, listen to their concerns, and adjust strategies based on the current needs and challenges, ensuring that decisions are timely and relevant to the current context.
Effective communication: the power of clarity
Great leaders are also great communicators. The ability to distill complex issues into clear, actionable insights—and do so in real time—is what separates good leaders from great ones. This skill is especially important in high-stakes environments, where confusion can lead to costly mistakes. In fact, the Project Management Institute cites in their Pulse of the Profession report that when organizations prioritize “power skills”—which include communication, problem-solving, collaborative leadership, and strategic thinking—they perform better across several metrics. Not only do 72% of projects successfully meet business goals, but they also suffer less budget loss when projects fail (PMI, 2023).
Larson highlighted the importance of clear communication, particularly in dynamic environments where leaders have to field unexpected questions and challenges. Having the ability to think on your feet and convey your thoughts clearly can make all the difference.
Advice for leadership: Prioritize clear, concise communication, especially in high-stakes situations when things go wrong. Focus on distilling complex information into actionable insights that are easy for your team to understand and act upon.
Learning and self-awareness: knowing when to step back
The best leaders are those who never stop learning. Recognizing when you’re struggling and being willing to step back or adjust your approach is not a sign of weakness, but of strength. Larson noted that this self-awareness is crucial in fast-growing companies, where the demands on leadership can change rapidly.
“In really fast-growing environments, the most valuable thing you can learn to do is give up responsibilities when you’re struggling—which is really hard to do.”
Advice for leadership: Cultivate self-awareness by regularly evaluating your performance and recognizing when it’s time to zoom out. Be willing to delegate responsibilities when necessary. Continuously invest in learning and adapting to the evolving demands of your leadership role to ensure long-term effectiveness and team success.
The challenge and reward of leadership
As you navigate the challenges of leadership, remember that focus, consistency, and adaptability are your greatest tools. Leading through uncertain times requires not just experience, but the willingness to continuously evolve and adapt to new challenges. By applying these insights from Larson’s experience, you can guide your team with confidence, even when the path ahead is unclear.
For more of Will Larson’s insights, check out the full episode, “The Engineering Executive’s Playbook.“ Learn more wisdom from industry experts by subscribing to Breaking Changes on Apple, Spotify, and YouTube.