Establishing a productive working relationship between yourself as an IT leader and your CEO is foundational to your ability to succeed. No matter what company you’re at, there will inevitably be a dichotomy between the two roles at one point or another, and it’s crucial to establish a good rapport to collaborate effectively.
How to collaborate with the CEO
Based on years of working with various CEOs and C-suite executives, here are a few pieces of advice I offer to create a successful CEO-IT collaboration:
1. Communicate effectively
Everyone has their own individual style and needs when it comes to communication. When establishing your working relationship with a CEO, take the time to understand how they like to be communicated with.
This can vary greatly depending on their personality. Do they prefer Slack, email, collaborative documents, or frequent touch-base meetings? Ahead of meetings, do they want details surfaced or is a high-level agenda documenting what you’re going to talk about ahead of time sufficient – and do they like to do a pre-read and comment period prior to meeting with a larger group?
[ Want more leadership advice for the challenges ahead? Read 4 soft skills leaders will need in 2022. ]
Whatever their preferences are, it’s important to match your communication style to the form in which your CEO prefers to receive it in order to be most effective.
2. Be prepared to share
Beyond the method of communication, get a good sense of the style and level of detail you must surface. Most CEOs do not want to hear technical speak, and your communication style needs to remain focused on the business outcomes you are helping enable or create.
Being prepared to answer a few key questions will set you up for success. How will this project affect the company as a whole? What’s the impact if we don’t move it forward? How will your customers be impacted? How will we know we are successful? How much, all in, will this cost initially – and in the long term?
And while the outcomes need to remain in focus, don’t forget that IT leaders will also be expected to provide the technical details and project plans to support these initiatives on demand when asked, so always be prepared to share specifics.
3. Align on expectations
As companies scale, it becomes important to look further out in the future. When I first joined my company in 2018, I led only engineering – it was a small, largely unknown company at the time. As we rapidly scaled to more than 1,000 employees and 150,000 customers in a condensed timeframe, things changed very fast.
In a small company, it can feel like things are harmoniously operating – after all, there are fewer people available to take on projects and keep aligned. However, this is exactly when you need to be opening the dialogue with your CEO and the executive team around where to take the company over the next two to three years.
Deeply challenge whether your expectations of yourself and of your team are going to get you to that point. Timing and alignment always matter, and it’s particularly important for a fast-growing company.
So, aligning expectations with your CEO is important across a few areas – and one of the most important artifacts for an IT leader to maintain, report progress against, and consistently re-evaluate and realign to the businesses’ needs, is your roadmap. There’s a common misunderstanding that CEOs and executives only operate at a 10,000-foot view and don’t get close to the product. In my experience, that’s simply not true. Every executive I work with frequently reviews the details of our business and questions if what we are doing continues to be the most effective approach. You must show up with perspective, and you can only offer meaningful perspective if you understand the vision for where the company needs to go in both the near and mid-term.
There will inevitably be conflict – whether it’s on the roadmap or elsewhere in the business – and you’ll need to get comfortable with conflict and how to approach it with your CEO. If you’re being asked to do something on the technology side of things that could waterfall into a serious consequence, stand your ground to ensure that a negative outcome doesn’t happen. Show up and speak your mind to establish your value, and don’t allow yourself to take it personally in the process. Just make sure that when the conflict is resolved, all parties are aligned on expectations and have clear next steps.
4. Understand the goals and get hands-on
Your CEO will send signals to tip off their priorities, and if you don’t pick up on those signals, there won’t be a meaningful dialogue between the roles.
Understanding the goals your CEO has for the company and then mirroring expectations around these goals will go a long way to creating a successful working relationship. In my case, I surface technical details from customer reviews to ensure we’re implementing this feedback into future roadmaps.
Additionally, learn who your CEO is held accountable to, which could include a board, employees, customers, etc. While the CEO is in charge, there are a lot of built-in accountabilities to others hidden within the role. As an IT leader, make it a point to understand this accountability and give your CEO the information they need to be able to effectively communicate.
Establish a plan and get in the habit of transparently reporting any risks and your risk mitigation strategy, and personally take the time to review progress routinely. CEOs are often looking at the level of R&D needed for the business to be successful, and CTOs are responsible for making this happen – while also making sure the CEO is capable of speaking to their audiences about the outcome.
This all ties back to aligning on expectations, as well as communicating effectively to ensure you are translating technical details into business outcomes. Doing the legwork to establish these pieces of the relationship with your CEO will ultimately help you better understand not only the company’s goals but your goals within the IT leader function.
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