Rapidly Onboarding Teams Without Losing Context

Jul 15 · 9 min read

Context is expensive, no matter how you pay for it. But it’s worth it every time.

Previously, as a consultant who worked with businesses to create employee onboarding journeys that spanned into a new hire’s first year, I know that providing context to support productivity and culture is more expensive than just providing an org chart, a clean desk, and a t-shirt that fits. On the other hand, as a current hiring and product manager for a team that recently tripled its size while balancing competing priorities, I also know that providing context is expensive — just in other ways. With these two different backgrounds, and our hiring complete, I learned a few things about providing the deluxe onboarding journey to a rapidly growing team, while thin on time. If you are able to dedicate more resources to crafting an onboarding journey for your new team, or even a central strategy for your company, Alida Miranda-Wolff has a great, deep set of tips that may be more helpful. If you your new team needs to hit the ground running, here’s a few things I tried out that were helpful.

Before Week 1

Front Load on Your Interview Process

In my last post, I wrote about how doing proactive work before a team offsite can have an outsize impact on productivity during the trip. Perhaps not surprisingly, I’ve found the same benefits apply to onboarding. Looking back, there were a few things we did, and a few things I would do differently if I had to do it over gain.

Take Your Time

This seems counter to the startup value of speed, but it’s one of the best things I learned over the last few months. It’s understandable to want to fill your positions as quickly as possible, but rushing to hire is one of the most common hiring mistakes. Take your time to make a good decision. It will suck. You’ll be understaffed and doing jobs that are outside your comfort zone and don’t utilize your strengths for longer than is comfortable. You’ll just want the process to be over so you can actually make strides on the work that needs to be done. Keep going and keep interviewing. Hiring well is the work that needs to be done. It’s worth the wait when the right candidate presents themself.

Test for Autonomy

It’s particularly worth waiting for a self-directed candidate who can thrive in reasonably ambiguous settings. Previously, as a consultant, I saw many hiring managers share a common barrier to providing a robust and thorough onboarding journey: lack of time. While merely providing a clean desk and a welcome email is not acceptable and in fact a good way to lose talent, the best thing you can do to limit how much onboarding is needed by a new teammate is to hire for autonomy and comfort with reasonable ambiguity. What is reasonable is subjective, but note that lack of clarity in role and its execution is one of the leading reasons why folks leave teams.

The best method I’ve experienced to test for this is through short take-home exercises that have these characteristics:

They’re appropriately scoped:

Take-home exercises tend to disadvantage candidates in caretaker positions or those who need to work multiple jobs. We try to keep the scope of work limited so that a strong candidate can give a compelling submission after a few hours, and an aspiring candidate can give more time if they can and have the desire to.

They’re novel, but authentic:

Life-long learning is a popular phrase going around these days, so to test for it we ask candidates to learn something they likely don’t know, and then have them perform a small, authentic scope of work related to the role of the opening. For example, the Ember framework has, at the time of writings, a small developer community; candidates aren’t likely to be practitioners, making Ember novel. However, being able to learn its fundamentals and write a primer on Ember’s value and how to get started in the framework is an authentic scenario to roles on our team. Writing an Ember primer then is a novel, but unique scenario.

They’re authentic but not reusable:

This is a bonus and follow up to the last attribute, but important for the candidate experience. Keeping with the previous Ember example, output we get from the Ember assignment is authentic, but it’s not reusable, meaning, we don’t conceive of teaching it any time soon. By having candidates write a primer on Ember, we can evaluate their openness to learning new topics and their ability to create engaging material on that topic.

Unfortunately, take-home assignments have been abused by some companies to get free ideas and work from job candidates. By separating the content focus of assignments and our product just that much, we go the extra step to provide a positive candidate experience.

These assignments helped us find a talented group of new hires. Post-acceptance, there were a few other bonus things we did between their acceptance and start date that got things started on a good note:

Bonus: Offer Rest Time Before Starting

If you take your time to hire, you’ll definitely want a new teammate to start immediately, and they may feel obligated to do so. If your deadlines can swing it, however, consider offering your new teammate some time between positions to catch their breath. Starting a new job is a stressful life event; give them the time and space to adjust. You’ll be amazed by how a day or two can help someone truly start with a full tank.

Bonus: Set-up over Swag

A new hoodie with your logo emblazoned on the chest is a nice gesture. But you know what is likely to go further? Having all their stuff set up on day one. Everything, all the right permissions and settings and features enabled. A list of all the people they should reach out for help on house-clearing issues is icing on the proverbial cake.

Your First Sprint

Alright, you’ve finally made it to your new teammate’s first week. Aside from some of the essentials (welcome email with a first day itinerary, office tour, desk set up with all the fixings, etc.), there’s a few other things that shouldn’t be skipped over before new folks get plugged into production work.

Be Kind and Rewind

Even if you hired this new team to hit some ambitious and fast-approaching goals, be kind and rewind. No matter how fast you think you have to get someone into the game, try extending your patience that much further. If I learned anything from our recent hiring blitz it’s this:

the art of rapidly onboarding a new team amidst high company growth is moving as deliberately and intentionally as the immediacy of your customer’s needs allow.

In my case, our students need the most up to date, market-driven, high quality curriculum around. But they also need happy, holistic, and capable curriculum engineers for that to happen repeatedly. Time investment up front should pay off with more frequent and higher quality updates to the student experience.

For a helpful rewind, answer these questions:

  • Why are we here?
  • Where have we been?
  • Where are we now?
  • Where are we going?
  • Who are we working with?
  • Why are we here?

Why are we here?

Sure, why not get existential on day 1.

Some larger start-ups have a centralized program ran by HR that covers this material, but if not, absolutely cover it yourself. Even if they do, cover it again with your team’s perspective on it. Keep it simple. For my team, our mission is to provide a market-driven coding curriculum that’s trusted by the leading universities and their students. Show how your team’s mission fit into the company’s mission. Go a few layers deeper: how does each person on the team contribute to the team mission. For each layer of the Russian doll, what does it look like each is successful?

Where have we been?

Tell the backstory of your team’s work and how it’s evolved over time. Don’t skim on the lows of this journey, but be careful not to inculcate a negative perspective through your story. Knowing the history of your team’s work helps reveal what’s values and work to instill as the team grows.

Where are we now?

What’s the current state of your work? It should be clear how today is an extension of the past. Try to communicate this simply without diving into a project management tool yet.

Where are We Going:

In the near term, what is the team working on and why were these prioritized over other updates? The connection between these updates and the purpose should be made clear. Lastly, how do we know if updates are successful? If the purpose-update connection is clear, measurable OKRs or KPIs for each update will help cary buy-in transition to accountability.

Who are we working with?

Almost as important as solidifying why the business exists is concretely communicating how you solve a difficult customer problem and why it’s so acute. A customer journey that tells this spans from product awareness to product promotion and highlights how internal teams are involved throughout provides a wholistic view of the people new hires will be collaborating with. Knowing the connectors who will champion collaboration with your team is an extra step worth taking, setting up introductions with these stakeholders, if appropriate, goes the extra mile.

Performance Before Competence

Understanding why your company exists, and how your team, and each role in it, works to serve that larger purpose is paramount to any effective onboarding experience. From my personal experience, however, most of us are itching to get right into the work. We want to see what the day to day is really like and how we fare. It can be very calming…hopefully. Anticipating this, consider how you can get your new team or new employee performing authentic work before they’re necessarily competent. Consider the job as if it were a video game. What is level 1?

Recently, when a new group of engineers dedicated to our online program started on the same day, we planned their first sprint to focus on work that could tolerate slower execution and more coaching, but was something that would be put into production and also support a previous sprint. This scenario provided the new team a scope of work where we could follow our process very closely and get familiar with each other’s work styles, while also significantly contributing to work other teammates had done previously.

Just-in-Time Aids

As you co-build with your new hires, utilize tools that your new hires can use in the near future when you can no longer be as high-touch. Our team has a curriculum development process that we follow whenever we create new lessons for online and classroom learning. Nested within the larger parent document are several smaller worksheets that our engineers copy and complete before moving on to the next step. These nested worksheets build on ones that came previously, and become invaluable references when you finally get to the blank page.

While the first rule of agile is people over process, we’ve found that the blank page can make you go begging for process, especially as someone brand new to a team. Take the time to write down your team’s process and the deliverables along the way. If the process is effective, they’ll be used and updated without your involvement, and give your new teammates a needed sense of order.

Onboarding Plans

30–60–90 day onboarding plans are a staple of mature onboarding journeys. At rapidly growing companies, however, what 30–60 days out looks like can be difficult to nail down. For recent hires, we developed a Questions to Answer doc that guides 1:1s for a new hire’s first 12 weeks. When we meet each week, the new hire answers the question as they understand it and their manager adds to it or adjust it. Here’s a selection from a few weeks:

Week 1:

  • What is my role and how do you help me?

Week 3:

  • How do I know if I’m on the right track?

Week 5

  • What are my blind spots in the team, the product, the company?

Week 7

  • What should I start, stop, and continue doing?

This approach was a large time save, particularly in how it set a structure and agenda for the first several 1:1s and is flexible to change that’s expected.

Onboarding is Ongoing

Although I covered what we did during our first week, employee onboarding is more than your first week. Some companies consider onboarding as a journey during your first 6 months or even your first year at the company. Nonetheless, first impressions matter, and I think this first week really set the tone for us to get into the bulk of work in week 2, with in-the-moment feedback filling in the rest of our gaps.

Like I said earlier, context is expensive, but if it’s an investment you make upfront, both in interviewing and onboarding, it’s amazing what a new team can accomplish and the energy that ripples out. Best of luck if you’re growing a team now. It’s a tremendously fulfilling experience.

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EdTech Product Design & Management

The Startup

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