Onboard Like A Boss
Successfully integrating your new hires, one Apprentice at a time
So you found someone really promising to bring aboard your team to take on the cut-throat competition, and made them an offer they could not refuse. You can’t wait to see what they can bring to your mission. Let’s call you “Boss”.
Perhaps you are on the other side of this Corleone equation as the new hire nervously looking forward to your new challenge, a new team, a new opportunity. What should you expect or choose to ask for, to help you settle in quickly? Let’s call you “The Apprentice”.
Let’s remind ourselves that the Apprentice is already likely to be psychologically inhibited in this new context and that getting them to have a swagger soon is in everyone’s interests.
While a plan is no guarantee for success, not having a plan is the same as planning to fail. Let’s craft a plan that spreads across 4 stages of your Apprentice’s succesful onboarding.
Prepare
Warm Up
Talented people have access to multiple opportunities. While not every boss excels at making irrefutable offers, perhaps we can start by having the Apprentice look forward to something. A conversation to talk about plans, schemes and projects, and to field any questions or concerns really helps. Set this up well before they start, thank them for accepting the offer, and aim to convert any nervous anxiety into optimistic anticipation.
If the start date is too far, do this more than once. Share public documents for them to read up on so they get a taste for what to expect. Follow up over email to see if they have any new questions based on their reading.
Buddy Up
Appoint a Buddy from your team who will be your Apprentice’s BFF during their first 30 days. The Buddy can help with anything from filling holes in your documentation, to setting up the workstation, to beating the crowd at chow time. It helps to introduce the Apprentice to their Buddy even before they start.
A Buddy is ideally from the same function and, to the best of your knowledge about them both, shares multiple traits with the Apprentice. Make sure the Buddy understands their responsibility well so they can play a major role in the Apprentice’s early success.
Roadmap
Prepare a 30 or 60 day plan to act as a set of milestones that describes an ideal early journey. This period typically matches any probation period you retain in the offer. If this seems daunting to create, it helps to remember that it is reusable with a few tweaks, including across functions. You can choose to describe the plan in excruciating detail or keep it a little informal so you can discuss the details during regular catch-ups.
The roadmap is a means to setting reasonable expectations of how the early weeks should pan out and what you believe is attainable in terms of progress. As a Boss, you come across early like someone with a plan and with predictable expectations.
Induct
Red Carpet
While welcoming the Apprentice is a basic need, can you add a simple, personal touch to make this a tad special? Perhaps you can personalize the onboarding of the new kid by creating a page just for them on your wiki that would say “Welcome to the team <Apprentice’s name>”. It is fully expected that you are efficiently lazy so that most of this information can be reused for the next Apprentice who joins.
Meet and Greet
It goes without saying that meeting a familiar face - the Boss who recruited the Apprentice - helps settle the nerves on Day Zero. Make sure their BFF-for-the-next-30-days also meets them. This is also when you share the personalized onboarding material, including the roadmap you crafted just for them.
Group Inception
Drop a welcome message on your internal messaging platform highlighting not just what the Apprentice is assigned to, but also a few of their exploits from a past life. Add a human touch by throwing some light on their personal selves, and a tinge of inspiration by reminiscing what stood out during the interviews.
Within the first week, find an opportune moment, like a team meeting, to invite the Apprentice to share a few words about themselves and break the ice with the broader team. If you work in person, breaking bread together early is also a very good idea.
Kit
Whether you induct in person or remote, having all logistics sorted out as well as having the necessary tools and infra setup for the Apprentice is mandatory. Don’t have them fumbling around for logging in to something they need on Day Zero or worse, not have a laptop ready to go.
If this is a remote induction, ensure you ship sufficient swag to help them deck their workstation with your branding and your messaging. After all, they were serving on another team until last Friday from this very workstation, and on a Monday, need help to remind them often that they are now on a different but exciting, new journey with a new team.
Settle
Check-ins
When someone just begins to learn to drive or to steer a boat, adjustments and course corrections are more frequently required. Plan to meet your Apprentice at least once a week while they are still new. Check-in on how they are doing, fill holes the buddy could not, and use the roadmap as a tool to talk about their experience.
Quick wins
Nothing boosts confidence like confidence. Help your Apprentice rack up a few early wins to build a head of steam. Talk about these wins in team meetings, and encourage them to show and tell with a demo. Enable them to win the trust and approval of their new team members.
Brownies
There is no better way to test your onboarding process than to have someone new go through it. There is also no one better than the Apprentice to fix or improve what didn’t work for them. Train them early to be good scouts/guides and make the campground a little better for the next Apprentice.
Ramp up
By gradually making the tasks more challenging, help your Apprentice go through the gears. First bug fix, first deployment, first enhancement, first demo, first tech talk, first incident response, first design proposal. Ideally the roadmap is already setup this way, but a good Boss never lets an everyday crisis go to waste, leveraging the opportunity to give the Apprentice a chance to help the team and bed in faster.
Integrate
Calibrate
At the end of the probation period, review the progress against the roadmap and discuss what Boss and Apprentice have learned from the experience. Ideally, Boss now has a good idea of what the SWOT analysis for the Apprentice looks like. This can be used to align work to their strengths, as well as who they would work best with. Take the opportunity to also identify what skills they need to work on to fit in better.
Iterate
Gather feedback about the buddy process, the roadmap and the onboarding experience in general to understand how it could be improved. Make quick tweaks that make sense so they can benefit the next Apprentice who onboards and tries to settle in. Review the brownie points the Apprentice has already collected by making their own little tweaks to pay it forward.
Launch
With a better understanding of the Apprentice’s capabilities, it is now time to call an end to the probation and promote them to Capo-in-training. Review responsibilities, assign them a new project or new goals, and setup a new but less frequent 1:1 cadence to continue the conversation.
It’s time to congratulate them for this first major milestone, give them your blessings and let them loose. Let’s move on to watching with pride what they can achieve with you and your team by their side.
Many thanks again to Saif for recommending I write about this topic.
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