Being CIO: 5 tips for surviving the first 90 days

How chief information officers can set the tone during their early days with a new organization.

I’m fast approaching 90 days as the CIO of O’Reilly Media. On the one hand it sounds and feels like a short amount of time, but as I’ve learned it is also a critical and long enough period where the tone and pace of your leadership can be established. Too many mistakes during these formative days can temporarily, and in some cases, permanently hamper the ability for a leader to succeed.

While much has been written on the importance of the first 90 days, nothing beats the real experience. So many of you have asked me about my experiences, I’ve assembled five top of mind tips that have shaped my tenure to date. For obvious reasons I won’t call out the tips I learned from the mistakes I have made, but simply suggest that every good intention is open to revision.

Tip #1: Do a lot of listening

You’re the new guy and people will want to bend your ear. Sometimes if a person can get to you early they can try to influence your agenda in their favor. You’ll hear both sides to everything, so it’s important not to make up your mind too early. This is not a bad thing since you can quickly get insight into how the organization thinks and behaves. Mostly though, listening is about formulating where some of your priorities are going to be. If you’re hearing consistent messages, that’s probably indicative of something important. After the first 90 days, keep listening. I would argue that great listening skills are an essential business and social quality regardless of your role and level.

Tip #2: Learn about the business you are in

You might know how to manage a datacenter, deploy Apache, or write poetic code, but do you know how the product or service that your organization produces is designed and delivered? More importantly, do you know why it’s done that way? Increasingly, business leaders want an IT leader to be a partner not a supplier. Being a partner means understanding and talking the language of the business. They want someone who understands where they are coming from when they describe an issue or solution that requires a technology input. In addition, knowing the business gives your work (and the environment you have inherited) context early and can aid in the initial learning curve.

Tip #3: Think carefully about what and how you communicate

Today, the role of the CIO as both business enabler and innovator has the ability, more than ever, to influence and be held accountable for organizational success. This means that the audience that is listening to you is broad and influential. When you’re in middle management your input can be considered, but not necessarily acted upon. The same doesn’t hold true for the CIO. During the first 90 days (and beyond), it is crucial to be deliberate and thoughtful in your communications. Flippant comments and mere suggestions should be avoided. Mean what you say and say what you mean. Lastly, use all forms of communication channels: in-person, email, instant messaging, telephone, and video. Being available and responsive demonstrates your level of engagement.

Tip #4: Make progress

While you are listening, learning, and communicating during your first 90 days — three things you’ll do a lot of — there is also a business that needs support and an IT organization that needs leadership. You were hired to get things done. In a highly competitive business environment patience is low and expectations are high. So figure out things you can address quickly. CIOs are problem solvers, so I suggest you find something that you can help solve, something that takes a fresh set of eyes to assess or a risk that a predecessor was unwilling to take. In addition, look for ways to demonstrate your ability to make decisions, such as enabling a useful process or approving a purchase. The amount and methods in which you initially make progress will be indicative of your pace and style. Getting it right can ensure you are in sync with the business. Being too slow or too fast has considerable inherent risk.

Tip #5: Work hard not to break anything

Last and most importantly, make your best effort not to break anything. In the future it will be okay to make some big bets that don’t work out the way they were intended. However, in the first 90 days, there is little appetite for a new leader who appears on the scene with ideas and intentions ablaze, only to disrupt and confuse. Put another way, make sure you’re aware of existing priorities and critical systems and avoid partially-baked decisions that could jeopardize essential business functions. While somewhat tongue-in-cheek, this tip is probably the most serious. While you won’t be measured on this quality alone, combined with the other tips, you’ll get credit for keeping the ship afloat while demonstrating authenticity and making meaningful progress.

There’s some irony that the qualities of the technology leader I’ve described above are completely absent of technology skills. But that is deliberate. The CIO is increasingly a business role. And in business, leaders win or lose by their soft skills. Sure, technical skills are important, but it won’t be those skills that your stakeholders will be initially assessing.

Your first 90 days are important. Perform a few important things right and you’ll move forward. While you’re at it, have fun. It’s exhilarating work.

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  • Joel

    Great post, Jonathan. I would argue that listening is already your greatest quality, but coming in a close second is your analytical ability (thus the detailed article :)

    I’m so happy that you were able to land somewhere you can be influential, strategic and effective. Congrats again.