Deeper dive: shadowing
Where doubt there truth is—'tis her shadow.
In my discussion on onboarding, I talked a lot about shadowing and reverse shadowing as key components in the onboarding process, but didn’t spend a whole lot of time on the details. Let’s look a little closer at a good shadowing program and why it offers insights and expertise that can’t be gained any other way. (I’ll refer throughout to shadower and shadowee, since it’s cumbersome to use ‘onboarding engineer’ and ‘more experienced engineer’ every time.)
First, a little about the mechanics. In an in-office situation, shadowing is as easy to set up as ‘pull up a chair’, but in remote environments you may need to get a bit more creative with remote chat and screen sharing. Depending on your company’s culture you may have video on or off—I’d recommend using the same standard as you use for live customer calls. If you’re normally camera-on, the shadowing process will get the shadower more comfortable with regularly being on video. If video is usually off on customer calls, then that’s another thing that some folks will need to get used to. Inferring customer tone and building rapport can sometimes be trickier without a video component, so it’s good to practice in advance when speaking only to the shadowee.
Plan on having the shadowing session last as long as the shadowee’s time on duty, whether that’s two hours or eight. Whatever the shadowee is doing during that time, whether it’s ticket handling, working on bug reproductions, or simply doing other support work like submitting feature requests, it’s all valuable experience for the shadower. That being said, especially if these sessions are via screenshares and video chat, it’s important to build in some downtime. Hours on end onscreen, or even in person, can be exhausting! For each two hour block of shadowing, plan on at least half an hour break for the shadower and shadowee to step away from the screen and regroup.
During the shadowing process there are a few specific outcomes for your new engineer to achieve:
Learn the established troubleshooting process
Most importantly, the shadowing process is the most efficient way possible to learn the existing troubleshooting process in use by your support team. As the shadower watches, in person or virtually, the shadowee will demonstrate where to go first, what logs to collect, what language to use with the customer, and so on. Support troubleshooting is an ever-evolving process, and the best way to learn it is to watch it in practice. As long as things aren’t too hectic, there’s room for the shadower to ask follow-up questions in the moment about the tools or the troubleshooting process that might otherwise go unanswered in more traditional documentation-based training.
Learn insider details of the product
Though the shadower has already spent some time gaining a strong layperson’s understanding of the product, and hopefully is now as familiar as an end-user (or administrator) needs to be, that is only the beginning of true product knowledge. Support engineers know all of the ins and outs of the product they’re supporting, from all of the documented edge cases to deep understanding of the product underpinnings that aren’t documented anywhere. The best, and probably only, way to learn all of a product’s quirks and secrets is to spend a lot of time using it and troubleshooting where errors occur, and the shadowing process will give your shadower a concentrated dose of both.
Informal Q&A
When things slow down a bit, there is time for impromptu question and answer sessions to help deepen the shadower’s understanding of the product and troubleshooting process. Depending on the individuals involved, these questions may come up naturally as the two converse, but if shadowing downtime devolves into awkward silences, spend some time with the shadowee to put together lists of topics to cover so there’s always something they can be working on together.
Absorb norms, customer voice, other implicit information
Even if you and your team comprehensively document the entire support process, all troubleshooting tools, and all additional procedures (and that’s a pretty big if), there’s still a tremendous amount of information that is implicit to your team. Many aspects of your team’s operations exist only in live settings: norms around ticket handoffs and internal communication, the specifics of the persona used while interacting with customers, and any number of other nuances in the support process. Some of these are specific to intra-team interactions, others are visible only when working with customers. This is important information for the shadower to absorb, but again there is no way to take it all in except for regular and prolonged shadowing to see it all in action. In your regular checkins with the shadowee, a constant refrain should be ‘Is your shadower getting it?’ What ‘it’ is can be impossible to define, but it will often refer to these implicit team norms. ‘Is your shadower learning all of the product ins and outs’ is a straightforward question to answer, but ‘Are they getting it?’ can be a lot trickier and lead to longer conversations between you and the shadowee. Knowledge gaps are always going to exist, and can be addressed systematically. But a failure to pick up team norms, even after the shadower has more explicit discussions with you or with the shadowee, should result in deeper questions about whether this role is right for the shadower.
Reverse shadowing
As the shadowing process progresses, the shadower will continue to gain expertise and troubleshooting facility. Over time they will gradually take on more and more responsibility in their joint troubleshooting work with the shadowee. Usually by the second or third month, the script has begun to flip and the shadower is doing more of the work under the watchful eye of the shadowee: reverse shadowing has begun. In the earlier stages of the shadowing process the shadowee is conducting on the job training by example. Conversely, reverse shadowing is the shadower demonstrating how much they’ve learned and gaining confidence in their own expertise. The shadower can be secure in the knowledge that the shadowee is standing by to step in if things start going off the rails or if the troubleshooting process leads into uncharted waters.
Improving the process
While learning troubleshooting and the overall support process, the shadower will no doubt have opinions, and those are hugely valuable as well. Folks on the inside tend to get into an established routine, but looking at anything with fresh eyes can bring all sorts of useful insights. Even though the shadower doesn’t have enough experience yet to distinguish ‘great idea, let’s do it’ from ‘good idea but won’t work here’ from ‘awful idea’, as a leader it’s important for you to make sure they have space to share these thoughts. Ensure the shadowee is capturing these insights as they come up, as nonjudgmentally as possible. Alternately you can make it a standing part of your regular checkin with the new engineer (you are having those, right?) to bring up and discuss any thoughts that have come to mind during shadowing. Now is not the time to implement them, but it helps set the tone early that everyone can have valuable insights that deserve to be aired and discussed.
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