Understanding the need for a 90-day plan

When you start in a new CIO or CISO role, there is always much anticipation. The prior incumbent would have announced their departure, and the team and your future colleagues would be in a state of anticipation – expecting both good and bad to come from the change. There is always going to be some natural anxiety from the technology team regarding work that is in progress. In addition, they might feel a sense of loss in that all the deliveries that had been completed before might perhaps not be recognized.

It is in this spirit that I wrote the 90-day plan. The plan was to both guide myself and inform my stakeholders in what areas I would spend this time. By default, it would also detail where I wouldn’t be spending my time, which is also instructive to the broader team. As I noted earlier, I had transitioned through five earlier CIO roles that also had their own first 90 days. This new CIO role was not close to being as large or complex as some other CIO roles that I had successfully navigated. However, I really wanted this to be a winner. Therefore, I formalized my 90-day plan as a written document.

But why is this a must-do for you too? To get offered the CIO role might have been a career ambition for you. And while this is likely not to be your last CIO gig, you would really want to make this first role a success. There will be other larger CIO roles or Group CIO positions that you will want to consider in the future. But if you fail at this initial attempt, then that will certainly reduce your probability of success. Using this approach, I would reference the 90-day plan at my lead team meetings, and then email it to my staff for their consumption and so that they could also share it with their teams. In addition, as I met with all my peers and key stakeholders, I would share the 90-day plan, with one slight variation – I would also ask for their input: “Have I missed anything?” This is also an opportunity to elicit any quick wins that they would like me to consider. This is specifically called out in my 90-day plan.

Setting this tone will be critical to your success. If you don’t set a tone yourself, then you will find others doing it for you, which may not be to your liking. For instance, it would be quite commonplace for your first month’s schedule to be full, with internal and external stakeholders all wanting to schedule meetings with you. Generally, I would focus on the internal stakeholders first and only take meetings with external stakeholders regarding issues that were time-critical or regulatory-based.

Having first established your own ground rules with your team, and in particular your executive assistant, decide how you want to work together. There are many things to address, and some can’t be decided immediately. Some of these are as follows:

• One-to-one time with the direct manager
• One-to-one time with direct reports
• The team meeting structure and format
• Managing external meeting requests
• One-to-one time with the head of HR
• One-to-one time with the CFO
• One-to-one time with other key internal stakeholders

Note that HR and finance are important foundational stakeholders that you must build a strong working relationship with from day one. It is important to listen to these stakeholders more than trying to sell to them; it would be too early in the first 90 days to attempt to sell a new vision.

With your executive assistant, you must also agree to protect your schedule and allow yourself some thinking time so that you are not overwhelmed with superfluous meetings. One easy guideline is to limit these meetings to a shorter duration, around 20–30 minutes. Any requests for an hour’s meeting should be scrutinized and take place only if you agree to it.

Your time is precious, and you are on the clock in terms of making your 90 days a huge success. In that regard, being in sync with your new manager is of critical importance. This means not only securing regular face-to-face meetings but also finding out their preference in terms of what medium to use – phone, text, email, and so on.

It is, of course, extremely important that you take the time to run through this 90-day plan with your new manager and ask for feedback and input. It is likely that they will have already suggested some potential quick wins to consider.

Your own personal test would be to figure out how to assign those potential quick wins to your team and, in some cases, combined tech/business teams to address them. It is likely that the incumbents that you ask will have tried or failed in their attempts to address these in the past. This is where your emotional intelligence has to be preeminent, but also be aware that you will probably have to be hands-on to drive the transformational change and ensure that this is indeed a quick win.

Your new manager will have staked their own reputation in bringing you on board, and that is something you have always been aware of. It is not blind loyalty but a realization that this leader has your back and wants you to succeed. Each manager will have a different set of expectations, as they themselves are at different stages of their own career. Some will want to know all the fine details; others will only want to be notified about important strategic aspects. But all managers will want to know about bad news as soon as possible and not have it sprung on them. Yes, you want your boss to look good and, most of all, not make them look bad.

Armed with an understanding of the need for a 90-day plan, let’s now shift our focus to the practical steps involved in crafting an effective 90-day plan. In the following section, we’ll break down the process, providing actionable insights and guiding principles to help you build a roadmap that accelerates your impact as a technology leader. Let’s now take a close look at how you can build your own 90-day plan.