Making executive onboarding a smooth journey

At the start of this year, my employer’s previous CEO transitioned into the Executive Chair role, and our current CEO joined. Along with this leadership change, several new executives joined, including the one that now oversees my department. I suddenly had to bring these very senior and experienced C-suite members up to speed on my part of the business.

I’d never been in the position of onboarding my own boss, let alone multiple execs at once. There are lots of online resources and books about onboarding yourself, such as what you should do in your first 30-60-90 days, or how to create onboarding plans for others. But most focus on certain roles (like engineers) or direct reports. 

Through my experience, I learned that organization, vulnerability, and open communication were some of the most important skills for successfully helping to onboard others.

Getting organized

As soon as you know what’s happening, try to get organized. This can be difficult, considering most announcements of senior hires are pretty tightly controlled. You may be lucky and get a good amount of notice, but equally, don’t be surprised if your new colleague lands on short notice. 

Before they are officially brought in, pull together materials you already have and identify gaps, and prep your team on your expectations moving forward. For example, new content you’d like them to explicitly create, or at which stage of the process you’ll be involving them.

Your existing onboarding materials should contain a lot of useful material, but a new joiner is a great motivation for a tidy-up and refresh. There’s nothing like the prospect of a new CTO digging through documentation and tickets to push you to finally clear those descriptions you’ve been meaning to add all quarter.

Acknowledge the vulnerability

Regardless of the excitement you may feel about a new person coming in, acknowledge that this is a period of big change. Your team members, or even you, may feel vulnerable about how you may fit into the executive’s future plans. 

A new person can come in forming opinions and making judgments, sometimes very fast: it takes just one-tenth of a second for people to judge someone and form their first impression. The new leader will want to see who they can rely on, where there are gaps, and maybe even identify where there could be friction. 

Your team may find this concerning, and it can cause individuals to feel strong emotions rooted in their core needs. People’s sense of belonging, predictability, being in control of choices, or even their personal status could feel in flux and uncertain. While you can’t promise that the new leader won’t trigger a reorg, you can work with the new individual to communicate your team’s feelings and work on building the relationship both ways. This includes developing trust.

Despite hesitations, this kind of change can also bring a lot of positives. It can be a chance for everyone to reset, including you. Try to use it as an opportunity to be deliberate about the relationship you’d like to have, or if there’s any objectives you’d like the executive’s help to push forward.

Similarly, it can be an opportunity for you to shine the spotlight on others in your team and help them build great relationships with the new joiner from the start. But make sure they’re aware of these introductions – dropping a 9am meeting in calendars with an executive with no warning is not likely to go down well.

Ask what they need, and share what you can give

The easiest way to understand how to be successful in this situation is to ask the person what’s useful, and how you can best support them. What are their expectations? What’s worked well for them in the past? What hasn’t gone so well?

You can also ask them how they best learn – are they the kind of person that’s happy enough spending a couple of days reading documents, or would they prefer live sessions, or direct time with individuals? Find out where your area of the business sits on their priority list. They may be juggling a lot of information all at once, and your proposed topics may not be top of that list.

That said, it’s also important to be honest about where you may have trouble meeting their expectations. As a couple of examples: if your new executive wants to spend their first week holding an extensive set of meetings with engineers, but those people are committed to delivering a project to a set deadline, it’s worth giving your exec the visibility. Or if they’ve asked for a system diagram that doesn’t exist, you could quickly create one, or you could be honest and let them know it doesn’t exist. This can be an opportunity to discuss gaps in your processes.

Most executives will come in being in “sponge mode.” They’ll be keen to dig in and understand as much as possible, but if absolutely everything is made out to be perfect, they’ll likely get a bit suspicious that you’re not presenting the full picture.

Some common areas of interest

Leaders will likely want to be informed about certain areas when they join the team. For some newcomers, a one-slide, high-level view of your org may be enough, but others may require a lot more detail.

Here are common areas you might want to share context on: 

• Your org structure. This includes an overview of the team remit, the roles within them, and skill gaps or challenges you may have with the current structure. They’ll also want to understand how your org fits into the big picture – what are your overall responsibilities, what’s your mission, and how does it tie into others’? 
• Your key stakeholders and customers. The people that your teams work closely with, and who their work serves to benefit.
• Team members. They will likely be interested in an overview of engineering levels and roles, and how this fits to your team. Make sure you have a view of who your most influential people are, who they can trust and lean on whilst they onboard, and who’s looking for stretch opportunities. Prepare to discuss people’s compensation (including your views on whether this is or isn’t aligned with internal salary bands and market rates), performance/potential, the likelihood and risk of the team members leaving. Your executive may also want to dig into manager/managee ratios, to better understand people’s capacity and levels of support.
• Roadmaps and objectives. Execs will also likely want to know about the processes you have to track against your objectives. Review everything yourself with fresh eyes before handing over and make sure you’re not using unnecessary acronyms, codenames without context, or anything else that will make it difficult to understand.
• Metrics. You will need to convey how you measure and judge your success. Share the metrics that matter, how to find them, and how to interpret them.
• Systems overview. If your executive is from the product or technical domains (but not exclusively so), they will likely want an overview of all of the systems you own, including any third parties that you integrate with.
• Budgets. If your company has a dedicated finance team, your new exec or senior leader will likely have separate sessions of all things financial. However, providing them with a view on budgets isn’t out of the question. This will include sharing who’s responsible for different subscriptions or how you typically handle processes that involve money, like travel or promotions.
• Risk, compliance, and policies. These will all be important elements. Again, these elements may be handled by other teams or individuals if you’re in a larger company, but don’t be surprised if you’re asked for some information directly.
• Wider context. The new executive probably won’t want to be added to every Slack channel, but the main ones will be of interest. Share key communication channels where their involvement will have the most impact. They may also be interested in any historical context, for example, decisions that were made recently, or topics that have been put on pause waiting for input.

Not reinventing the wheel

Focus on gathering evergreen documents and references – those key materials that remain relevant over time and can be used repeatedly. Much of the information will be just as relevant to new engineers as a new exec so make sure to provide a practical narrative rather than a “perfect” one.