Many people view the end of the year as a time for reflection: a time to think about accomplishments and setbacks. With 2019 headed towards us at a lightning pace, it’s easy for us to become excited about all the work we have done, but we need to remember that it’s also a time for us to prepare – for the big year ahead, and for some of things that will lead us to greener pastures and impactful change in 2019.

On this episode of IT Visionaries, we got a chance to chat with not one – but two CIOs in our first ever “CIO Roundtable”. Mark Settle from Okta and Paul Chapman from Box share their insights on how not to get fired in 2019, and what security and compliance will look like in the coming year.

Don’t Get Fired in 2019

When we asked Mark Settle about how not to get fired in 2019, he mentioned that endless meetings prevent your people from doing the work you hope to empower them to do. This, of course, will put you on the fast track to getting fired.

“I think part of the way to not get fired is to not spend endless hours in conference rooms with members of your own staff showing you the one hundredth PowerPoint slide of the day, and really doing the jobs that the people that report to you should be doing.  You should exercise the prerogative that you uniquely have as the CIO to spend time with the other business members of the executive team, and look for opportunities to insert technology, and the capabilities of the IT organization, into the day-to-day operations.”

Losing your job, or being fired from a company, is always on top of mind – especially in the competitive landscape of tech. Paul Chapman explains that developing relationships with people is a great way to keep the job you love.

“One thing I always think about is getting people to like you. It’s important, when you develop relationships with other executives in a company, to have a two-dimensional relationship, which is something I don’t think a lot of IT executives do. They tend to have more one-dimensional, transactional relationships – where they show up on the doorstep of a colleague and they either want forgiveness or money. There’s a social dimension that needs to be added. We have casual, everyday conversations and interactions that we have about hobbies, our families, schools we went to, and everything in between… and we have built up social capital because of it. With that capital, you have to invest some real time in understanding how the business operates through the eyes of your colleagues. Learn the world through their eyes, and they will respect you.”

“I have this term that I’ve used in the past: “Invisibility is a fate worse than death.” Generally, people that come through a technical background have a bit more of an introvert personality or style. Perhaps that is the thing that drew them into engineering or software development in the first place. You’ve got to get comfortable with being uncomfortable as a CIO – regarding getting out there and being more socially participative. I saw this chart many years ago, and it was showing this change in style from individual contributor to a manager to leader and executive, and you saw trends of task orientation going down and social participation going up.  As a CIO, you have to figure out how you will add the most value to your business and typically, it’s not inward facing like keeping the lights on and running operations. It’s taking an outside-in view rather than an inside-out view.”

Machine Learning and Change for 2019

One of the bigger trends we have started to see and hear from our guests on IT Visionaries is regarding “machine learning”. Many companies are starting to incorporate machine learning into their businesses – including products and practices. Paul mentions that while he is evaluating himself and organization’s 2018 performances, he sees machine learning capabilities giving tons of opportunity to add more value to his business practice.

“I’ll look at how I was directionally aligned coming into 2018, and then I’ll look to 2019. I believe that we see what the future state looks like – regarding our architecture needs – and we have guiding principles that are taking us in that direction. I think about how I can continue to leverage the best ecosystem that’s available to bring in what I think is going be more of a focus. With machine learning capabilities starting to emerge, we can start to bring in more digital labor into our environment, into our business processes.”

On the other hand, Mark Settle sees that while these new trends can be helpful and impactful for business in 2019, as a CIO, you still need to look at your organization and see how you are doing business regardless of the benefits machine learning and big data can bring to the table.

Mark Settle: “I think a lot of the newer offerings we see in the startup community are leveraging machine learning – or some form of artificial intelligence – in many of the classic application areas. I don’t think they’re inventing new business problems to solve, necessarily, and some people will challenge you, saying that “This is such revolutionary new technology.” But, you need to step back and think about the ways you are doing business.”

Security and Compliance in 2019

Another big topic both CIOs touch on was the importance of security and compliance. Paul said  that it is often overlooked in organizations, and – at times – it feels as though security needs to be recognized as a top priority for major organizations.

“I think that one of the biggest challenges of being a CIO is the inward facing part of the role, especially with security. Anytime security is underrepresented in an organization, there is a lack of awareness about what’s going on. It often feels like it’s secret stuff. People only appreciate what they can see, touch, feel – and when they can’t, they do not give it the attention it deserves. With security, there’s a natural lack of appreciation and even compliance, to some degree. I think one of the things that are missing with the role is the outward facing communication and awareness of what’s going on in the world.  There’s a lot of data-driven stuff that you can share to create awareness around security. If you’re not doing that – and something terrible happens – then you can get fired. I think that that’s incumbent upon the individual to be out in front of creating awareness, communicating, and making sure there are the right trade-offs, and that risky investments are being made in those spaces.”

To hear the full episode and check out the show notes from this discussion, visit here.