If my three-decade journey in the corporate world has taught me anything, it’s that in business, as in life, the only certainty is uncertainty. In the past 20 years, periods of upheaval, from pandemics to financial crises to AI hysteria, have restitched the fabric of how we work, travel, and communicate. While this uncertainty can generate tension and turmoil, it also forges the best leaders.
I’ve seen bosses and colleagues navigate all types of volatility, where the margin between success and failure can come down to a single action or inaction. So, what distinguishes leaders who can successfully shepherd teams through uncertain times from those who can’t?
I believe those who can share these three distinct characteristics.
DOUBLE DOWN DURING DOWN TIMES
There’s a tendency for companies to become ultra-cautious in times of uncertainty. While this may seem prudent, it’s difficult to get ahead of what’s coming with your head down. The best leaders look ahead and make smart investments even when markets are down and sentiment is grim.
In the wake of 9/11, I was at GE Aviation (now GE Aerospace). Overnight, the airline industry was grounded. While other manufacturers hunkered down and leaned on existing IP and products, we increased our budget on new jet engine development. Counterintuitive? Perhaps. But we were confident in one thing: People would fly again.
Typically, a new engine has a combined new product introduction cycle and payback period of 15 to 20 years. With such an extended runway for ROI, manufacturers that don’t make a bet to capture market share often struggle to get back into the game. Eventually, airline demand resumed, as did the need for next-gen engines, and we were one of the only companies that could deliver.
ABSORB THE FEAR
In Stephen King’s The Green Mile, prisoner John Coffey has a remarkable gift: He absorbs the sickness and pain of others, assuming their burdens at significant personal cost. Sci-fi? Yes, but it symbolizes a skill every leader needs.
During times of change and anxiety, leaders must absorb the emotionalburdens of their employees, their fear and insecurity, and then project a path forward. The best leaders I’ve seen take on their stakeholders’ doubt and replace it with a clear-eyed vision of the opportunity that exists amid the chaos. Listen, digest the concerns, and replace apprehension with hope.
The pandemic was a period of intense uncertainty for companies, and Twilio was no exception. It was also the catalyst for equally intense growth, as circumstances and shifts in consumer behavior accelerated digital transformation.
Nearly every organization needed a way to engage its customers digitally, and we were there to help build it. But by early 2024, when I became CEO, we had a lingering post-pandemic hangover. We simply weren’t winning as fast or frequently, and without credible points on the board, I could sense increased anxiety across our employee base.
Hope is the currency that reenergizes teams and reassures external stakeholders, but empty hope is useless without a concrete path forward. I made it my mission to deliver that. For us, hope meant aligning on a clear, measurable vision for continued growth and a roadmap that everyone could get behind. This served as a compass, allowing our 5,500 employees to rebuild momentum and get us to the other side.
CUT SUGARCOATING FROM YOUR CORPORATE DIET
There’s an inclination for leaders to protect their people during periods of uncertainty. Withholding information, changing the message for each audience, or filtering it through rose-colored glasses insulates your stakeholders from the reality of what needs to occur. Fight those urges. Be transparent, while adjusting the altitude of information nuances required for each audience.
In my first year as Twilio CEO, I was on the road meeting with stakeholders roughly 70% of the time. I sat down with customers, employees, investors, and board members to listen and communicate the company’s path forward. My goal was to candidly talk about where we were as a company and where we were headed, so that everyone with skin in the game had the same playbook.
Without candor and a consistent message, stakeholders can’t grasp the full picture and the steps needed to fix it. You can’t obfuscate the truth or change your tune depending on who you’re talking to. You have a board, shareholders, hundreds or thousands of employees, and customers relying on your transparency.
Whether it’s at a monthly town hall, an industry roundtable, or deskside conversations with investors, open and consistent communication simplifies your job as a leader. That’s the real gift of transparency: There are no skeletons to remember to hide or stories to change. Most critically, it reinforces trust, which puts points on the board.
THE UNCERTAINTY IS TEMPORARY
There’s no telling how any leader will respond to periods of uncertainty or hardship until they’re faced with them. No matter how impassable the road looks, the upside of uncertainty is knowing “this too shall pass.” After 9/11, we flew again. After the pandemic, we gathered again. And even as AI reshapes our work fundamentally, we’ll continue to have meaningful careers.
These periods of uncertainty are temporary, but when you string them together, they make up the long-term success or failure of your company. So, when the future isn’t fully written, our job as leaders is to make smart investments, absorb the fear, turn it into clarity, and build trust. Do that, and in my experience, there are always better days ahead.
Khozema Shipchandler is the CEO of Twilio.
