Onboarding Executives: A Field Guide for Chiefs of StaffFeatured

An employee/employer relationship is a value transaction - what the former offers to the organization and what the organization offers them. It’s risky, as both sides need to offer equal value. There’s a bigger risk when an employer hires an executive because they tend to be people that are seasoned, strongly invested in their ability, and have a critical role to play in an organization's success. The value transaction depends on the executive’s ability to jump right in and start bringing value. It’s the company’s responsibility to make sure that happens.The word “onboarding” is misleading, as we tend to think that their first day is when their onboarding starts. For most yes, but it’s not so for executives. Once they sign, the onboarding begins. As a Chief of Staff (former c-level executive assistant) my approach is simple. An executive doesn’t need training, they need to be integrated into the organization - the culture, its people, and its vision. FAST. So what does integration mean?It means they start before they start. - Ensure they have their team’s contact info and bios. - Ensure they understand the company’s vision, mission, and values (including the company’s OKRs).- Send them a brief “history of the company”. Believe it or not, company lore goes a long way. It means they will understand that joke that one time in that one meeting and won’t feel excluded. - Set them up on their work email then the technology your company uses day to day e.g.slack, notion, etc.- Offer to “show them around the office” with floor plans outlining the office facilities - kitchen, supply room, and washrooms. This doesn’t matter now as they know where their bathroom is in their own house.It means you start integrating them into the day-to-day. - Book 1:1s with their direct reports (offsite) and book a team meeting as soon as possible. Offsite 1:1s allow for a more honest and open conversation when it comes to department successes, failures, and insight into their team’s experiences and career growth. Since most of us have moved to remote working and online anyway, the “offsite” is irrelevant.- Make sure that they are invited to every leadership meeting and stand-up. - Make sure they have the last Townhall deck and pitch deck. This provides context and reveals the comms within the organization. Now, the executive understands what we share across the organization and what we celebrate.Invite them to the platforms they need to get historical context (e.g., Notion).It means they understand the important policies and the culture.- Make sure you run through the important policies first, ones they will need to know to support their teams. - Have them meet with the company’s culture carriers about what they love and what the company can do better. Culture carriers are those that connect people, make your company what it is. They are the ones who are always at socials, are well-liked, are the go-to person, and are someone who loves the company and lets it show.- Introduce them to the finance and HR departments. Again, they need to know how to approve expenses for their team and who they can talk to if one of the team members has an issue. Do all the above so when day one comes, onboarding is complete and they can hit the ground running. Their first day becomes purposeful, value-driven, and seamless. One caution, do not overschedule the first day. Leave it for the most important meetings; exec team stand-up, 1:1 with the CEO, and the first team meeting. Now what? The last integration point is supporting them through their 30, 60, and 90-day plans with their team, making sure that they are aligned with the company’s OKRs and the expectations set out by the CEO.You should:- Check-in a lot. Sometimes, it’s as easy as confirming or providing context. It fast tracks their understanding of team dynamics and culture. This is one of the most valuable services to offer. - Be their workplace buddy. You have more context than most. You know how the other executives work and how they function as a team. Your knowledge is vast and deep, help them out when you see they are not sure or about to step on a landmine.- Book regular meetings with their manager (CEO) to ensure alignment.Of course, COVID-19 has changed the work landscape significantly. Online tooling and connection are more important than ever. Make sure they are comfortable with online video conferencing and the tools the company uses to connect. Keep the communication light and open for the first week.That’s it! Taking these actionable steps will ensure a smoother integration into the company. I would love to hear what YOU do and continue to refine executive onboarding.
Great actionable steps to take! Appreciate the way you’ve laid this out as a master checklist to follow.
So much value all wrapped up in one clean post, and such a generous offering of your expertise. Thank you!
Thank you Jamie! I appreciate the kind words!
Appreciate this post! In fact the company I work for just had a new CEO join last week. In my first meeting with him, he asked me to come with a list of recommendations, which I was happy to do :) In the week that he's been here so far, besides providing him with a basic roadmap of how our operations work, I've found that he prefers to set his own rhythm and plan for how he wants to be on boarded. The only advice I would add to yours, is that different execs (and people in general) have different styles, and so I always like to start by asking them how I can be helpful, how they prefer to communicate, etc.Agree that it's good to do everything possible to help them to hit the ground running!
Thank you! Agreed!