Mentorship & Onboarding: building a more inclusive work culture, hiring better and ramping up new employees faster

Sound too good to be true? Well… be warned: while the rewards are significant, this is hard to get right and there’s no single way, either (skip ahead to the end for examples of two companies implementing their own versions of these practices).

Real change requires a lot of up-front investment and self-reflection, and regular review/iteration of your resulting documentation. Few teams feel they have time for this, especially if they already struggle to find time for other important tasks like documentation and long-term planning. Sorry/not sorry; it’s just one of those things teams must make time for if inclusion, effective hiring and onboarding are a priority (and they should be). It’s easier to change when your company is smaller, but never too late to get started!

Credit reel (up front so you read it): I want to nod heads to the thoughtful engineering mentors and managers (primarily Jonathan Maltz and Brad Barry, but also Scott Triglia, Fred Hatfull, Phil Zukin, Srivatsan Sridharan, Jenni Snyder, and many others) with whom I’ve shared lots of coffee and walks on these topics over several years. I won’t speak for them or their opinions, but our conversations have certainly influenced mine. I’m also influenced by all the incredibly articulate voices in the hiring, equity, belonging & inclusion spaces, including but certainly not limited to the data-oriented minds at interviewing.io, KR Liu whose talks on accessibility have been so insightful, Aubrey Blanche’s Smart Opinions on Everything (but especially intersectionality and belonging), the teams at TechSF and Techtonica slowing displacement with apprenticeships, and the amazing folks at Tech Inclusion and Project Include who introduced me to so many more.

Anyway, the tl;dr keys to the castle are this:

1. develop a good understanding of what it means to be a positive contributor to your team.
2. document it in excruciating detail with every skill, language, tool, or other proficiencies required to do the job effectively.
3. explicitly plan for a new hire’s first few months.
4. profit.

I’ll elaborate:

1. Clearly define “effective individual contributor” on your team

If your team does nothing else but have a deep understanding of what makes an effective individual contributor on your team, you will probably get better at interviewing, mentoring, and managing new hires without much further effort (that doesn’t mean you shouldn’t try!).

This definition needs to be specific to your team (even down to sub-teams, if applicable) and should include all the languages, tools, technologies, skills, and values your team needs to do your job. Do this as a team and keep the brainstorming results as a living document to revisit regularly as your team evolves. The frequency will depend on the pace of your team‘s growth, but at least as often as you might consider new long-term goals.

• Reflect honestly and thoroughly on: what everyone on your team knew when they started, and what they’ve learned/how they’ve grown (technical and not, at work and outside of it — at conferences/workshops, coursework, self-study, etc). These shouldn’t be the only criteria you use to define effective contributors on your team, but a common tendency is to inch the hiring bar ever-higher as a team’s members stay longer/learn more, often expecting new members to magically arrive at the same level. That’s completely valid if your recruiting team also adjusts the job description/title/salary in your hiring process, but exclusionary if you don’t (especially if you claim it’s still entry-level).
• Decide what a new team member must know when they start — and at what proficiency level — and what they can learn on the job (either on their own, with help from mentors, or outsourced with your company’s education budget). This will likely change the most frequently as your team and product (and tools!) evolve.
• Consider any team goals or process improvements on the docket and how your new hires might be the best agents for implementing them. New hires arrive without the baggage of old processes that you’ve wanted to improve, so building good habits is easier for them. Under the right circumstances (namely, the team responding positively), empowering new hires to implement new processes can be a great engagement tool to keep them motivated when they aren’t contributing 100% yet.

2. Document your definition and the list(s) of skills needed

There’s no ‘correct’ format except one that is clear to brand new members of your team and those who will help onboard that new employee. Use the information brainstormed earlier to:

Create your team’s knowledge appendix. Chances are, your team has Opinions about the best resources they’ve found to learn the tools and languages of their trade. Don’t assume the sources of that info are ubiquitous or easily/freely accessible. Put those Opinions to work in an editable, consistently-formatted archive of links (include a short blurb: credit the recommenders, briefly describe how it’s applicable to the team’s work, and mention which are free and which your company will pay for). If some aren’t available online, buy books for employees to borrow at any time. Encourage new employees to add any resources they find/found useful to this list.

• Note: some teams send this appendix to new employees in advance of their onboarding and I discourage it for a few reasons: 1) incoming employees won’t be paid for time spent studying before they start, 2) sending it in advance can cause unnecessary worry over whether the company really means it when they say “don’t dig into this yet,” and 3) even though the resources are likely available publicly, it may be risky/against your company’s trade secret or HR policies to share which tools/languages your team uses in detail before an employee is paid to protect that information or understand its context. It’s generally fine to share some information upon request, but save the big docs for the onboarding process.

Create your team’s onboarding timeline/guidebook/milestone list. Whatever you want to call it, this should be as specific as possible and, again, will probably change as your tools change and with new hire input. But! It shouldn’t change so often or so dramatically that a new hire can’t keep their bearings.

• This document should be a concrete rubric that shows how a new hire is doing during their first few months — if they are struggling, ideally they’ll know what they need to do/learn to catch up, and if they’re bored or excelling, they have written guidance on what to tackle next. It can also reassure nervous on-track new hires that they’re doing perfectly fine. Mentors may also find this reduces their mental workload, and managers can refer to it as evidence in performance management cases. It’s also a good way for teams to keep unconscious bias in check— I’ve read loads of performance feedback that vaguely stated a recent hire wasn’t doing “as expected” at midpoint performance evaluations, but also failed to define those expectations clearly to themselves or the new hire (and was probably not self-aware about any possible mitigating circumstances that caused reasonable, if unstated, expectations not to be met). This doesn’t mean there is bias, but we also can’t rule it out if a team isn’t transparent about their expectations.
• A Note on Time & Accessibility: Do be sensitive to the impact of time-bound objectives on some new hires, especially those different from whatever your team has experienced to date. Sometimes employees with disabilities or other limitations (even temporary, like needing to leave early to catch a certain bus until they relocate) may require additional consideration. But don’t assume their needs for them, or assume they have none— review/agree to a reasonable timeline for these onboarding objectives as part of the manager and new hire’s first conversations, and keep checking in to make sure those objectives are still reasonable as they onboard.

The format can also be whatever is clear/useful to the team, as long as it is easy for people outside your team to understand:

• For example: “Week 1 objectives: 1) learn the names of mentor, manager. Stretch goal: learn the names of everyone else on the team, 2) set up computer/get all software installed [list provided, plus freedom to install any other software or accessibility tools they may need], 3) attend benefits/company HR orientation, 4) go to lunch with team or team members at least once, 5) learn one person’s name/role outside of the team, 6) read through team onboarding documentation and confirm timeline with manager, 7) review instructions for first ticket/task with mentor. 8) sit in on regular team meetings, 9) get benefits set up, 10) learn company secrets.”

Make sure the guide thoroughly covers the first three months (be honest about how long even minor tasks can take at that early stage of onboarding with a million hurdles and distractions). Your mileage may vary, but once you’ve made it past the first 4-5 weeks you can probably move into longer chunks of time between milestone lists. It can also be a helpful introduction to larger career milestone or continuous learning conversations.

3. Plan ahead for your new hires.

Every time your team plans for the future (on whatever cycle — monthly, quarterly, annual, whatever), include future new hires. Do you expect any in that upcoming quarter? If so (even if not — unexpected needs come up!):

1. Expect the mentor(s) to have slower progress on regular projects than usual*, just as you would for their time off, company events, trainings, holidays, interviewing, and other meetings during that time.
2. Earmark a few real projects (or comparable units of work) that may help new hire(s) integrate into the team. These should start simply and get incrementally difficult as the new hire learns your systems. For a software role, this can be a project that fixes a pesky typo, or another bit of tech debt that exposes them to the team’s main code base and lifecycle, or a larger project they’ll own for their first quarter (but which is broken into manageable pieces and guided by their mentor).

*Note: Many managers tell me they struggle to give up time for mentors to temporarily be “less productive.” Let me be perfectly clear: mentoring is a critically important part of a team member’s job when they have accepted that responsibility. It is also a positive engagement/retention opportunity, broadens collaborative skills beyond individual contribution, and gets your new hires up to speed faster. Time spent mentoring is productive and an investment in your entire team’s health and long-term productivity. Expecting individual output to remain the same (explicitly or implicitly) while mentoring a new hire burns them out and sets the mentee up for failure.

That said, some teams aren’t ready yet to support a full mentorship model. Another option I’ve seen work well on some teams is to spread onboarding mentorship responsibilities around several or more willing/able participants, which can reduce both the overall “productivity” loss and pressure on a single mentor — this is effective when planned to ensure the new hire has a consistent experience learning from each subject-matter expert in their part of the team. It also has other benefits: lets new hires get acquainted with more team members sooner, gives inexperienced mentors opportunities to build skills and engagement with less risk, and hedges against long-term harm from any not-great experiences with a single mentor (like a mentor taking vacation during the first month of their new hire’s start date… that’s a bad idea, avoid it!).

Whichever method you choose, plan ahead — and don’t let the new hire be the ball you drop when things change.

4. Profit.

OK, maybe this was misleading… by “profit,” I mostly mean “improve outcomes,” though some benefits do include cost savings that may tangentially improve profit depending on your business, and certainly a lot of data shows more diverse workplaces do profit more than others.

All of these ideas are interconnected as part of a company’s greater ecosystem. It’s hard to say you’ll move the needle in one or two areas if others are lacking, and it may be hard to buy into long-term benefits if your company is heavily short-term focused or has more room for improvement.

But especially when unemployment is low, an inclusive/welcoming work culture is critically important to candidates considering multiple offers or existing employees considering new opportunities. It’s risky not to invest in improving these outcomes and it’s also far less painful to change when teams are smaller!

• Hiring: interviewing is imperfect, but having a rock-solid and specific awareness of what makes contributors effective on your team means you fundamentally better-understand your team’s needs. That will make it clearer to evaluate objectively 1) if a candidate can contribute existing team skills, values, etc at the same or comparable level, 2) if they can contribute new skills or experience your team currently lacks, 3) if they demonstrate potential to learn existing team skills or new ones. This may sound like what your hiring process is already aiming for, but it will get much easier with more self-awareness — and once you reap retention benefits you’ll spend less on hiring overall.
• Faster/better onboarding: When new team members get up to speed more quickly, your team reaches full steam more quickly. Even if it takes the same amount of (or a little longer) linear time compared to whatever you were doing before, I’ll wager with structured onboarding you’ll discover your new hires have a deeper understanding of the company’s business needs and become more proactive contributors sooner. You’ll also notice red flags earlier — maybe you’ve heard “bad hires are expensive” and this is true both because you need to replace them and they may cause damage (losing other team members, reducing team productivity, or introducing toxic behavior that drives down morale). You’ll find fewer “bad hires” because you got better at interviewing (right?) and you may be able to correct performance issues identified early enough with additional support (or decide that person needs to go sooner)— and that saves $$, too.
• Culture: You won’t solve culture 100% here, but you might find improvement. As recruiting teams mature to hire more candidates from diverse backgrounds, the rest of the company needs to help those new hires belong. Setting them up for success with clear expectations and explicit support will benefit all new hires, but especially those who are new to their roles or the industry itself. When I surveyed hundreds of recent hires (of all backgrounds) about their experiences in the first month or so of work, overwhelmingly their response was a version of “I didn’t know what I struggled with was OK or normal. I was told to ask questions, but I didn’t feel like mine were worth asking or my team seemed too busy.” This affects all new hires, but disproportionately impacts those from underrepresented backgrounds. Saying you welcome questions is one thing, but it’s another to embody that from Day 1. Beyond the documentation and weekly objectives I described earlier, assume competency and prepare for a new hire’s (totally normal) performance anxiety/impostor syndrome by normalizing questions and setting boundaries on interruptions so they know when or how to ask. Answering questions can often unblock someone quickly enough to meet or exceed performance targets. Having an open, inclusive attitude around curiosity improves productivity for everyone. Better onboarding experiences can set new hires and their teams up to stay longer, which also promotes a more stable work culture.
• Senior team member retention: Mentoring is much bigger than being a new hire’s onboarding point-person, but guiding the first few months of someone’s time at a company is a unique opportunity and responsibility to set the tone and influence best practices on that team. Take advantage of the “honeymoon” period of a new hire’s first months and invest in the best possible first impression you can give them — the mentorship of a respected, knowledgable team member. Mentors may find they learn a lot from the new hire, and this can be an engaging way to grow and retain more senior members of your team. Over time, new hires who had a positive mentorship experience usually grow into excellent mentors themselves.

Sounds great, but does anyone do this in practice?

Yes! I’m sure there are more examples, but here are two different approaches that implement many of the same concepts I’ve described. Both are engineering-focused, but I think can be applicable to any team.

• Team-level: Jonathan Maltz gave this 2017 talk on mentorship and amplifying team impact through the lens of a Yelp Android development team. His team’s success implementing these ideals was a solid reassurance to me that we were onto something.
• Company-wide: On the more comprehensive end of the spectrum, take a gander at Jen Gilbert’s promising tech learning/onboarding program at Lyft. What’s exciting about this to me (from what I can glean in the article, which is currently the only knowledge I have of it) is how seamlessly onboarding and continuous learning are integrated. It takes quite a bit of effort, expense and commitment to implement this depth of programming but it’s likely quite effective to attract and retain talent long-term — and that’s probably far cheaper than replacing departing talent all the time.

Whew, that was a lot, so I’ll stop here. At the very least, I hope this was a helpful starting place for insightful conversations on making a better world inside your own company (so your teams can make a better world outside of it).

Feel free to reach out if you’d like to say hi, have a comment, or want to pay me to work on this stuff at your company.

About me: I used to be a technical recruiter and intern program manager at Yelp. Over years of reviewing evaluations and talking with candidates/interviewers/interns/mentors/managers, I noticed a sizable gap between how tech companies describe and execute employee experiences, from hiring processes through their last day. This gap means candidates and employees often succeed despite (not because of) the employer’s efforts — and this is hugely problematic if we hope to make real change in equal opportunity hiring.

I mediate between these worlds to narrow those gaps — by helping software engineering candidates find their best roles and prepare more effectively, and helping employers optimize their interview processes and employee engagement.

I’m based in San Francisco and a sucker for public transit, tasty cheese, fun facts and juicy novels. I’m on Twitter @keeterooni and LinkedIn.