Key Takeaways from CIO Classified: Season 2, Episode 1

Meet John Stecher, the CTO of Blackstone, one of the world's leading investment firms. He's joined by Anisha Vaswani, the CIO of Toast and previous CIO of Box, who is passionate about scaling companies and bettering the end-user experience. In this episode of "CIO Classified," Stecher and Vaswani discuss the roles of modern CIOs and CTOs, the importance of encouraging innovation from the ground up, and their leadership methodologies to enable agile teamwork from everywhere and anywhere.

A modern CIO/CTO: what the role means today

"I've always kind of looked at CTO and CIO as slightly interchangeable," Stecher says, before going on to explain that the role varies depending on the organization itself. He believes that the CTO or CIO is responsible for "setting the technology direction for the organization," which "boils down into...[a] software, hardware, and data-centered strategy" that a company has alongside its typical "methodology and standards." 

What Stecher particularly appreciates about being a CTO in today's world is that his role has evolved into a hybrid of technology management and also product management, as he focuses on "influencing and actually driving the product forward."

Vaswani agrees with this and comments that she loves enabling an overall business as its CIO. She leads growth and business operations through technology itself. To her, "modern CIO business enablement is always important," and she enjoys how this pushes her to spend a lot of time with customers to iterate on solutions and products. 

How to encourage innovation: all hands on deck 

At Blackstone, Stecher says that "innovation comes out of the necessity of trying to solve a problem." He encourages his engineers to "listen to what people want and need and synthesize" and to later "iterate on the design [of their products and use that to push] on." 

Most importantly, Stecher highlights that innovation can and does come from "anybody in the firm." Vaswani adds that she saw how the diversity of the employee base at Box provides different perspectives and experiences, which yields key innovation at her former company. At Box, she says, "everyone's a technologist," and it's that lack of ownership around innovation that drives everyone forward. 

When technology enables teamwork: working from everywhere

The world has shifted remarkably in the past year, as companies everywhere have had to adapt to working from home. Vaswani acknowledges that Box has been "fortunate to be in a position that [their] technology helps enable...employees to work remotely and securely." It's the changes brought about by the pandemic that have shown the importance of "device [and location] independent" work, and Vaswani appreciates how committed the company has been to using best-of-breed technologies to continue communicating and collaborating from afar.

Stecher agrees wholeheartedly. He touches on how these adjustments have revealed the impact of technological variances between employees and their organizations, from wifi connectivity to tech stacks. Teams everywhere have had to reevaluate personal versus professional bandwidth. Although he misses "seeing people face-to-face," Stecher is grateful for the manufactured replacements like "virtual lunches" through the "technology tools [that will continue to] evolve."

Vaswani mentions that she was happily surprised to see how the weekly all-hands Friday Lunches at Box transformed since becoming virtual. "Everyone feels like they're more plugged in because everyone's on a level playing field," she reflects, "using technology to [ask better] questions in a webinar or using Slack plus Zoom to make that happen. Actually, we've seen much deeper and [higher] quality engagement." 

Agility over all: the key to high-quality project management

When prompted to speak on the topic of project prioritization during the ongoing pandemic, both Vaswani and Stecher agree that their companies have had to learn to build processes that are segmented and highly-adaptable.

The beauty of an agile approach is that it "break things up into sprints," Vaswani explains. She exposes the value of "building a flexible, iterative, agile delivery model." After all, there is only one way to eat an elephant: one bite at a time (Desmond Tutu). Vaswani believes that having the ability to flex skills and capacity based on business demands has helped Box succeed in an ever-changing world. 

Stecher prefers to focus on the concept behind agile models rather than the prescriptive nature of the methodology itself. Start by defining your target end-goals, ideally ones that have "a quantifiable ROI...something that's defensible." He suggests running from there and being sure to re-prioritize based on what the business needs. "The fun thing to me with the whole agile approach," Stecher remarks, "is that what you're doing is always relevant."

The CIO/CTO's secret?

For Vaswani, one of the most important things a great CIO can do is "to have genuine passion and interest in understanding the business and what it's trying to accomplish." She adds that frankly, "the technology comes later." Stecher expresses his agreement, and boosts this statement by saying that "the more senior you get in your technology career," the more "it becomes about how you can take the world of technology and apply it to solving the business problem." 

All in all, Stecher and Vaswani stress the importance of leading with passion for their work, flexibility for their projects, and empathy toward their people. It's through this balanced approach that CIOs and CTOs everywhere can guide their teams to success, despite the omnipresent challenges of working in tech today. 

Check out the CIO Classified podcast here or on Spotify, and Apple Podcast. 

CIO Classified