In business, every great outcome starts with a great decision. But how do tough calls get made under pressure? And how do you make confident choices when so much of our world is in flux?
We just completed the first season of Right Decisions, Right Now, a new podcast that seeks the answers to those daunting questions. Now I’m eager to share some of the wisdom I gained interviewing executive peers across a variety of leading organizations in a series of insightful discussions.
When we set out to create a podcast, we wanted to focus on fostering concise but candid conversations with a diverse set of leaders who have powerful stories to tell. These are stories of relatable, high-pressure scenarios with actionable guidance for current and aspiring business leaders of all stripes.
Time is a precious resource, and we’re all busy, which is why each episode is around 15 minutes, so you can fit them in without disrupting your schedule. We get right into it, unpacking pivotal moments in the careers of our guests to better understand what separates the good from the great: the quality of the decisions we make and the success of their impact.
I encourage you to listen and find your own aha moments, but here are five of my takeaways on how to achieve next-level decision excellence for your business.
1. Admit you don’t have all the answers
Zevia CEO Amy Taylor led the organization through a transformation that turned its brand into a household name. Amy has found the sweet spot between executing with confidence and humility. She’s learned the necessity of developing a “minimum viable level of expertise” across all business domains to effectively lead a turnaround. She knows it’s not her job to have every answer, but to have the prowess to convene the right experts and guide them to a solution.
By serving as great convener and ultimate decider, Amy was able to align her entire organization around a shared vision. Her priority was not brand-building alone, but rather resetting and reconnecting the entire foundation. This involved portfolio optimization, supply chain redesign, cost reduction, and more — all of which required her to have the right people and the right intelligence in order to make one right decision after another.
2. Cure “shiny-object syndrome” with a focused bet
When Bob Segert stepped in as chairman and CEO at athenahealth, the organization lacked strategic clarity and was wasting R&D on half-finished projects, including a difficult venture into the hospital market. He made the pivotal decision to make a clear, “all-in” bet on the core, higher-growth ambulatory care market and divest from the hospital segment.
But he didn’t make this bet on a gut feeling. This decision was backed by extensive data: market studies, consultant reports, and customer conversations. These sources confirmed that the real growth was in ambulatory care, not the crowded and slow-growing hospital market. Bob narrowed his organization’s focus to where he believed the future was heading, and they never looked back.
3. Be patient — persistence is its own strategy
Tony Stubblebine, CEO of Medium, brought the company back from the brink of financial collapse and reignited its mission to empower writers and readers. In our conversation, he stressed the importance of giving yourself the grace to learn and the patience to grow as a leader over time.
His ability to lead successfully was not an overnight achievement but the result of 15+ years spent improving his leadership chops across multiple companies. Small, consistent course corrections can be just as powerful as a single bold move — and can help restore trust and momentum when morale is low. He believes a leader’s most important job is to instill confidence. This involves creating a clear plan, finding early allies, and securing small wins to show the team “This is going to be different. We’re actually going to succeed this time.”
4. Know when to cut the bait
I asked Kim Castro, a former financial transformation leader from the likes of Gap and CVS, what was the most powerful lesson she’s learned about high-stakes decision-making. She believes one of the biggest inhibitors to success is the inability to walk away from a sunk cost. Leaders must be willing to admit when an initiative isn’t working and pivot, rather than throwing good money after bad in the hope of saving a doomed project.
“You made a decision, you went down this path, and you may have spent millions of dollars trying to implement a new technology, a new process, a new initiative,” Kim said. “‘Learn fast, fail quickly’ doesn’t always play out that way. Once you’re emotionally attached to that decision and the investment you made and wanting it to pay out — I’ve seen a lot of money get thrown after something that it shouldn’t have.”
5. Prioritize personal interest over short-term gains
Vineeth Subramanyam, managing director, global head of Spring by Citi, shared a life-changing moment from early in his career when he was a software engineer on a management track. He faced a tough choice: either stay on his clear, upward path or take a role in business analytics that was a step back in seniority and compensation but would teach him something new.
He advises focusing on what energizes you and on acquiring new skills. He explains that by pursuing what interested him — understanding the “why” behind the software he was building — he developed a unique combination of skills in software, analysis, and strategy. Ultimately, this made him more valuable in the long run, as “the whole is much, much more than the sum of the parts.”
It’s not about what you decide — but how you decide
In an era where it seems a new podcast is born every minute, I know the last thing you want to hear is “check out our podcast.” But if you’re interested in delving deeper into the stories behind the critical decisions that defined these successful careers and companies, I promise this show will be right up your alley.
The people shaping the future of business are building organizations that are strategically and technologically enabled to consistently make the best possible decisions in real time, every time. It’s been a privilege speaking to these inspiring leaders on the first season of Right Decisions, Right Now, and I can’t wait to have more of these conversations soon. Until then…
