Graduating from the support team
In which we discuss some sad realities

As hard as it may be to believe, not everyone wants to stay in a customer engineering role for the rest of their career, or even for more than a few years! Yes, I know, shocking. I’ll give you a moment to recover. I mentioned this sad fact in passing a while back but this week let’s talk about the sad occasion when someone is ready to leave your team. Though a lot of teams don’t consider attrition before it happens, I think that’s a mistake. Instead, think very carefully, before the time comes, about where you can help your departing team members move next within your company.
Why?
To quote myself from the link above:
Once an engineer has done their time in the trenches, they may be ready to move onto a different role entirely. As a leader, you need to recognize that there are two ways this can happen: either within your company, or elsewhere. It’s far better to keep that accumulated knowledge and expertise, not to mention relationships with internal and external partners, within the company. While this process is likely to look different for every internal transfer, at least in a startup, it’s important to at least gesture in that direction so your team knows it’s an option.
Let’s dig into this a little more.
You can’t stave it off forever
In my years in the customer engineering field, I’ve encountered one, maybe two, support lifers. By that I mean people who have been doing technical support for a long time, are very good at it, and are perfectly content continuing to do it. If you’re lucky enough to have someone like that on your team, great! Hold tight to them. But most of your team won’t be like that. They’ll want new challenges, feel like they’re in a rut, or simply be tired of supporting your product in particular. You can do a lot to make sure life on your team is good, and your team members are compensated fairly through salary, bonuses, time off, and other perks … but that won’t keep people around forever. Eventually people will be ready for a change.
Better to keep them in the company if you can
Now, given that most or all of the people on your team are going to leave eventually, how would you rather it happen? Would you rather they leave the company entirely, or would you prefer to keep them in the company but in a different role, probably outside your team? Unless they’re a bad employee, you’d probably prefer the latter, right? They will have built up a tremendous amount of knowledge while on your team, and you don’t want to lose that entirely. They’ll bring insider support experience, and perspective, into their new team, and can advocate for your team’s needs from the outside. And when you need emergency assistance with support issues, your alumni are a pretrained talent pool! So let’s talk about how to make that happen.
How to do it
Set expectations early
A number of jobs ago, during the hiring process my future boss told me ‘All I ask from you is two years in this role. After that, I’ll do whatever it takes to get you moved into another job in the company, wherever you’re interested in going.’ I loved that honesty—it set clear expectations, as well as telling me that I could have a long tenure at that company without needing to worry that I’d be stuck in the same role forever. So ever since then, I’ve tried to make the same thing clear to my own employees: spend X time on the team (two years still feels like a good number to me), and we’ll find you a path to whatever team you want to join next.
After their first year or so, add a recurring line item to your 1:1 meetings with each employee to discuss their next move. What do they want to do more of? Do they want to stick with the team a while longer or are they ready to start thinking about moving on? How can you help them get there? On the flip side, if you know that what they want isn’t achievable in your current organization, it’s important to make that clear as well. (See You can’t stave it off forever above.) Whether your company isn’t going to have a relevant role open any time in the near future, or your employee is frankly not going to be successful in that job with your organization, you need to be clear with them so they can make their own decisions on whether to adjust their goals or seek to achieve them elsewhere.
Cross-training, revisited
Remember how I mentioned last week that cross-training goes both ways? While you’re figuring out how to get non-support staff trained in support, you should also be looking for opportunities to get your own team some experience in related fields: sales engineering, technical account management, and other customer-facing technical roles. While there are obvious benefits in terms of providing backup coverage, gaining new skills, and the like, that’s not the only reason it’s a good idea. When thinking in terms of your team members moving on, this kind of cross-training can open their eyes to the opportunities available within your company when they decide they’re ready to move on from a support engineering role.
Conducting cross-training with other teams isn't something you can unilaterally start, of course. To sell this kind of time-consuming activity to other team leadership, focus on how this cross-training can help them. Customer Success will get a chance to instill their own communications preferences on your engineers, to make sure everyone is speaking to customers in the same voice. Engineering can help your customer engineers improve their troubleshooting and debugging skills by giving them a deeper understanding of the product. If other team leaders understand the benefits to their own teams, they're more likely to give the green light.
Finding opportunities
This is where it gets tricky, because it involves things outside your own control: other leaders, other teams, and overall business needs and priorities. In brief: even if one of your support engineers would be great for role X, and they want to do role X, and they’ve done their time on your team so you support them moving to role X … there may not be a role X available in your organization. You have no control over that! But there are things you can do to improve your employees’ chances of finding a new home elsewhere in the company when they’re ready to move on from support.
Set expectations (again): Beyond your expectations for a support engineer while on your team, you need to make sure your team members have a realistic view of what other opportunities are available elsewhere in the company. Shadowing and cross-training can help open their eyes to what’s out there, but you need to always be sure you’re not raising their hopes unrealistically. If you know they have their heart set on (say) a product management role, but you happen to know that the Product team isn’t planning on expanding for at least another year, share that information! I don’t mean that you should break confidentiality if you know about upcoming layoffs or other confidential hiring decisions, of course, but do be very clear about the likelihood of your employee’s dream role being open in a timeframe that works for them.
Build relationships with other leaders: The best way to know ahead of time about another team’s staffing needs is to be in regular communication with that team’s leadership. The sooner you can ask them ‘Hey, Josie A on my team is interested in moving into product management—can we make that happen?’ the more likely you are to be able to work something out. Don’t wait until the last minute, either. If Josie is ready for a move, you should already know whether the Product team has room for her or not (and communicated it to her). In larger organizations, get close to the CFO and to the head of recruiting—you may have opportunities to learn about (and influence) hiring decisions months in advance!
Find skill-building opportunities within the support team: If Josie (I’ll pick on Josie again here) wants to go into product management, help her build those skills while still a member of your team. Look for places for her to collaborate with the Product team cross-functionally, give her responsibility for feature request management across the support team, find a mentor on the Product team to help her identify her skill gaps and offer suggestions for improvement. Give Josie every opportunity to prepare herself for her chosen role, as long as it doesn’t interfere with the job you’re paying her for today.
Given that nobody will be staying on your team forever, it is important that you spend some time with each of your employees to help prepare them for their next move. Ideally you’ll be able to help them find a new home elsewhere in the company, but even that doesn’t work out, you’ll be helping their future career and cementing your reputation as a stellar leader and developer of talent. In the end, that’s what you as an effective boss should be doing for them anyway.
Thanks for reading Andy's Support Notes 💻💥📝!