Support onboarding for everyone
YOU get a shadowing session! And YOU get a shadowing session!

Way back in the dawn of time I talked about support onboarding and today I’d like to return to that topic. But this week let’s look at it from a different angle: what if you leveraged this process to give everyone else a basic grounding in your support processes, values, and outcomes?
What it looks like
If I were king of the world, everyone would go through a full support onboarding when they join a new startup. But here in the real world, there are two things standing in the way of this: time and technical aptitude. Nobody’s got time to do a full support onboarding if that’s not going to be their actual job, after all. And not everyone is suited to being a support engineer! That’s why it can be so hard to find good candidates. So with those limitations in mind, here’s how you can incorporate some support team onboarding and shadowing into the onboarding process for other roles in the company.
Keep it short: at one company where we started implementing a program like this, the support part of the overall onboarding had two parts: first, a short presentation by support leadership (i.e. me) about the support team and how we operate, and a few days of shadowing one support engineer during their on-duty shifts. Time permitting, this shadowing could be extended, but it rarely was except for roles that we’d be interacting closely with like SEs (sales engineers) and CSMs (customer success managers).
Keep it focused: make that presentation and shadowing count. The training should focus on the salient aspects of the support team that are visible from the outside: how you interact with customers, your team statistics, how your team improves customer satisfaction, and how the support team can assist other teams in the company. On the shadowing side, if a session just involves two people sitting quietly together because there’s no active support work going on at that moment, it’s a waste of everyone’s time. Shadowing sessions should function as informal Q&A as much as sitting in on support operations—ensure your support engineers are ready to answer questions about the team, support operations, support trends, and the support mindset.
Remember the audience: getting ahead of myself a little bit, you may want to extend this support training process to more teams than just the obvious candidates of SEs, CSMs, and the like. Less technical new hires can also benefit from learning more about the ins and outs of the support process, after all. (And even if you do restrict it to those teams, CSMs are going to be by and large less technical than your support engineers.) With that in mind, make sure that your presentations and shadowing sessions for these new hires are accessible to folks who haven’t made support their bread and butter and who may not know how to navigate a command line. There’s still plenty they can learn, but make sure that you—and the support engineers you pick to lead shadowing sessions—are prepared to explain your activities and customer troubleshooting in ways that are friendly to less technically-experienced ears.
Why it’s important
For other technical roles
One of the fastest ways to learn the ins and outs of a new piece of software is to support it. The new employee will quickly understand how customers use it, what they love and hate about it, and where all the rough edges are. New software / infrastructure engineers will be able to use this information to speed up their onboarding to their respective roles, SEs and architects will gain a deeper understanding of our customers and their needs, and deployment engineers will learn all of the gotchas and pitfalls to avoid while setting up the product in customer environments. All of these roles, too, will benefit from witnessing firsthand how the support team interacts with customers, and getting some practice with that bedside manner themselves. This is a skill they’ll be able to put to use when they need to interact with customers themselves—much more common for SEs and deployment engineers, but even software engineers may occasionally have to hop on a customer call for deep troubleshooting work. One added bonus: this helps prepare other technical staff to fill in as needed for support engineers, which can be critical to maintaining support coverage when you’re having staffing issues due to vacation, illness, or simple attrition.
For nontechnical customer-facing roles
Many new hires will be joining teams that require them to regularly interact with customers, particularly CSMs and Sales. What they can learn from shadowing your team for a few days is going to focus on two things: the customer and how your team interacts with the customer. On the customer side, they can learn a lot about the nature of your customers—how technical are they, what kind of roles do they have, what are their communication preferences, what problems are they solving with your company’s product? This information is invaluable to CSMs and to Sales, who need to build relationships with these customers and prospects that are much like them. The more information they can gather about the nature of your company’s customers during their time with the support team, the better equipped they will be to successfully build and maintain relationships as part of their core roles.
For leadership
How a company interacts with its customers is a core part of its identity and one that it’s important for new additions to the leadership team to internalize quickly. What better way than to put them on the frontlines with your support team for a few days? Obviously new executives are going to have their hands full with myriad other onboarding tasks, getting up to speed with their own team, and so on, but it’s worth carving out a few hours for some support shift experience too. Depending on their technical skill level, they can also benefit from the experience to start learning the internals of the product.
Everyone else
At this point, we’ve probably accounted for most of the folks in the company, especially in smaller startups. (Internal-only roles that aren’t involved with engineering are thin on the ground in startups until you’re big enough to need, for example, full-time accountants and HR specialists.) So since we’ve already made a rotation on the support team de rigeur for most new hires, why not go whole hog and have everyone give it a try? Allowances need to be made, of course, for the level of technical aptitude of the new hires you’re press-ganging into support service, but everyone can learn something from the experience:
Customer interactions: I’ve belabored this point enough, so suffice it to say everyone in the company can benefit from seeing firsthand how your organization interacts with customers and learning how to do so themselves.
Breadth of customer base: Companies often have a wide variety of customer archetypes, and there’s nothing that will drive this point home faster than directly working with a cross section of them during support shadowing sessions. A deeper understanding of the customers your company serves will be useful at some point to almost every role.
Why your customers love you: (They do love you, right? If not, maybe disregard this part. Or do better.) One of the best ways to drive home the importance of good support is to see the results firsthand. Satisfied customers, resolved incidents, explosive customer situations successfully defused will do more to display the value that your support organization brings to the company than a hundred presentations.
Thanks for reading Andy's Support Notes 💻💥📝!