4 Challenges Facing CXOs in A World of Digital Everything

by Dormain Drewitz October 19, 2022 | 7 min read

As a busy executive, taking time to attend an event and listen to sessions is a luxury. And yet, I know that many of my best breakthrough ideas on how to lead my teams have come from taking those moments to tune into new ideas. The challenge is figuring out where the hidden nuggets of wisdom are buried in a mountain of content.

PagerDuty Summit 2022 generated about 15 hours of content, much of it for site reliability engineers, platform teams, and engineering managers. But there were also some great takeaways for more senior executives. As executives, we’re driving growth through innovation, operational efficiency, and risk mitigation. And many of our biggest challenges lie in how we lead the people on our teams through the changes to drive those outcomes.

I’ve parsed through much of the content from the PagerDuty Summit to find the most useful insights for executives. Many of them feature hearing from other senior leaders, who face similar challenges. Dig in to the full replays linked from each section.

Shaping a culture of accountability

Accountability always seems to roll uphill. While executives are and should be accountable, a lack of localized accountability leads to “not my problem” syndrome. But distributing accountability is hard as organizations grow and systems become complex.

The “you build it, you run it” mantra of DevOps is about embracing a culture of accountability. As I’ve written before, the litmus test of any culture is what happens when things go wrong. What are the artifacts? Are folks happy to be accountable when the dashboards are green, but reluctant when systems are down?  

When team members don’t feel like they are equipped to deal with issues, the accountability flows uphill. For some great insights on how tech leaders across industries are empowering their teams when things go wrong, catch the “Delivering Value: A two-way Street” keynote panel from the Sydney Summit. You’ll hear from Andre Lachmann, Director of Technology at Nine; Sourav Lala, Head of Cloud & Platform Services at Carsales; and Gurnam Madan, Head of Engineering at Wesdigital.

  • Madan talks about getting trust right with the right foundations. What does that mean? Hear him describe adhering to SLAs and SLOs with PagerDuty. He also recommends embracing chaos engineering to break things in a controlled environment. “Don’t wait for things to break.”
  • Lachmann highlights the importance of being able to get the right person involved when pressure is high. After all, “Every day is like the Super Bowl in media.”
  • Lala sets the bar high, aiming to resolve incidents before teams notice, let alone customers. He brings cloud, automation, and PagerDuty to make this possible.

Doing more with the same: Operational Efficiency

Even without the backdrop of economic uncertainty, find me an organization that isn’t trying to do more with the same? According to the Gartner® report “The Chief Technology Officer’s First 100 Days,” operational efficiency is one of the common metrics used to measure CTO success.¹ But getting more out of the resources you already have does have a cost: change.

Leading your organization to change their behaviors will make or break an efficiency initiative. Jamie Vernon, SVP of IT at ResultsCX shared some great insights on leading change in his session, “Cultural Adoption of Automation.” After all, automation holds great promise for driving operational efficiency, if you can manage the change to adopt it.

Vernon stresses understanding your authentic reasons to automate. “Your motivations, your passion, your enthusiasm, your being genuine and authentic… is going to be part of how you sell it to your stakeholders.” Humans are wired to find patterns and set into routines. People need a compelling reason to manage the discomfort of change.

For teams that are asking for more staff to help, Vernon shares a great idea. He describes how they anthropomorphized their automation efforts into RITA. The team trained RITA like they would onboard a junior member of the team.

Another session that offered a great blueprint for enabling teams to change was from Schneider. Jared Vils and Dana Dickrell covered a lot in “The AIOps Outcome That Smashed It,” including how they onboarded 480 responders across 74 teams. About halfway through, they share the internal video that they produced to get the organization engaged. If you have initiatives that should be driving operational efficiency that are stalling, you’ll find some great ideas here.

Connecting the dots on Customer Experience

According to Forrester Research, 82% of customers say they are likely to spend more with a brand that makes them feel appreciated and respected.² Anyone in leadership positions knows that cultivating positive feelings takes deliberate effort. One negative experience can wipe out five positive ones.

Delivering a positive experience is an “all hands on deck” situation, but not every team experiences that the same way. In the fireside chat with Fiona Gill, Vice President of Customer Success for Americas at Anaplan, she highlights the need for internal collaboration. After all, customer-facing teams get frequent and direct feedback from customers. Developers and engineers, however, get less exposure to customers.

It’s easy to work in silos, but that puts the customer experience at risk. Gill highlights how folks in the field are experiencing first hand if customers are not having a good experience. This is a critical signal for engineering teams. How are your engineering teams getting that input?

The hard stuff: Change, legacy, and trust

Like accountability, “hard problems” also tend to roll uphill to the executive suite. But successfully tackling hard problems requires bringing the organization along. On hard problems, I recommend the “Real Talk: PagerDuty’s Product Impact” keynote panel from the Sydney Summit. It features Fiona Muller, Group Principal Products and Services at Telstra, and Iain Phillips, General Manager of Site Reliability Engineering at Xero.

Changing behaviors is hard. We covered this earlier with respect to accountability and operational efficiency. But the same goes for anything, including resiliency engineering. “We treat SREs as an enablement team,” says Iain Phillips. Making it someone’s job to enable change goes a long way. But forcing change doesn’t work. As an example, hear how Fiona Muller explains how tools at Telstra get promoted organically, rather than mandate.

Dealing with legacy (or “heritage”) is also hard. And it’s everywhere —yes, even startups and so-called cloud-natives. A strictly “bi-modal” approach can leave teams working on heritage apps demoralized. How are you bringing your heritage apps and infrastructure along as your teams adopt DevOps and SRE practices? Fiona Muller shares insights from Telstra’s journey.

Finally, trust is hard earned. As Jenn Tejada, PagerDuty’s CEO, likes to say, “Trust is earned in drops and lost in buckets.” Fiona Muller echoed this in her discussion of why her team spends so much time on security and reliability: “People have a really long memory for the bad things and a short memory for the good things.”

Hopefully, as a leader, you’re taking time every day to invest in yourself and learn. Let me know if these insights from your peers have been useful!


¹Gartner, The Chief Technology Officer’s First 100 Days,  Samantha Searle, Nick Jones, Arun Chandrasekaran, September 7, 2022. GARTNER is a registered trademark and service mark of Gartner, Inc. and/or its affiliates in the U.S. and internationally and is used herein with permission. All rights reserved.

²Forrester Research, Customer Service Unplugged: How To Scale Empathetic Customer Service, Max Ball, July 26, 2022