I hope you are enjoying that morning coffee as you read this. Or perhaps you are on your way to your seventh meeting in a row that’s only 30 minutes, with barely enough time to use the restroom? Regardless of where, when, and how you are reading this, one thing is certain for you: Life as a CIO is hectic, the environment around you is increasingly volatile, and you continually have to achieve more with less.

Sound familiar? It’s nothing new. This has been happening to the CIO since the role was introduced. What is impactful, however, are those super-important, gnarly parts of the job that a surface-level “What are the biggest issues facing the CIO today?” thought exercise will not touch. What are those, you ask? Read on!

How Long Can You Afford To Stay On The Tech Debt Treadmill?

The type of company you sit in will dictate how severe a problem this is for you. Perhaps this is not an issue if you are in a newer company, a tech-forward department within a larger company, etc. But if you are at a multinational, part of a large domestic organization, or at a company that has undergone many acquisitions, your tech debt is likely off the charts. There’s a giant hole in the boat, and at best, the bucket you have just keeps enough water out so you can survive.

Do you just want to survive, though? Is the CEO paying you to simply make sure you bail enough water out of the boat? Is that the legacy you want to leave behind when you leave the company? Or do you want to patch that pesky hole and move onward to greater destinations?

Perhaps it is time to declare tech debt bankruptcy. Declaring technical bankruptcy is a bold move, where the approach is to outsource legacy system maintenance and free internal teams to create a modern, cloud-native platform. While risky, this approach may be more strategic than juggling old and new systems simultaneously. Change management will be a huge challenge, but ask yourself honestly: Is it any harder than what you are doing now?

How Strong Is Your Partnership With The Rest Of The C-Suite, Really?

When was the last time you helped someone move or moved yourself? You know that 8 million-pound piece of furniture that you can barely shimmy across the floor? How much easier is that to move when you have a few people helping? Much easier, of course, and the same can be said for achieving technology outcomes. Sure, you can get to a certain point by yourself, especially if the work is largely self-contained, i.e., infrastructure lifecycle patches. But that ERP system? Good luck getting that done on time and budget with little help.

Relationships with the rest of the C-suite and their team are crucial to your success. Ask yourself, how strong are these relationships, really? How do you know? If your company culture is conflict avoidance, how do you truly know whether there is full trust between your teams? A lot of time can pass with quiet disagreement and slow erosion of trust when simple, honest, and direct conversations at regular intervals could have prevented this from happening.

If you are not asking these hard questions, it is time to start — today. Here’s a few starter ones to consider that are simple, direct, and perhaps uncomfortable to ask but necessary. Adapt them to your context: 1) If a critical project was on the line, how confident are you in me to deliver? 2) Do you trust me to act in your best interest? 3) Do you feel comfortable sharing anything about our work together openly with me, such that we can have a high-performing partnership?

How Much Do Employees Truly Believe In Your Strategy, Priorities, And, Most Importantly, You?

You’ve asked the hard questions of your C-suite pals and now are in a place where the relationship is strong. Congrats to you; that is hard work, and you’ve achieved it. But what if your employees think you are full of hot air? How do you know? Do you have their buy-in or do you have their compliance? Are they motivated by financial means to provide for their family only, or do they have this base level of motivation and a deep belief that their work meaningfully contributes to a strategy worthy of their time?

Perhaps you already have a good handle on this through internal surveys and other mechanisms. But just like with your business partners, we implore you to find ways to get honest feedback from your employees. As you already know, you’ll never be able to make an entire workforce happy. What is essential, however, is that they trust you as a leader, that they have a good working relationship with their direct manager, that they believe the direction IT is heading in is solid, and that they understand how their work connects to the broader strategy. If these elements are not true, it’s time to sit with your direct team and figure out why.

Engaged employees lead to better outcomes; better outcomes lead to higher levels of trust from your partners; higher levels of trust from your partners lead to you having what you need to successfully achieve your goals. See how it is all related? Don’t abandon the hard conversations. Lean into them.

I invite you to reach out to me through social media if you want to provide general feedback. If you prefer more formal or private discussions, email inquiry@forrester.com to set up a meeting!