Our 6 Must Reads for Onboarding Tactics That Help New Hires Succeed (and Stay)
People & Culture

Our 6 Must Reads for Onboarding Tactics That Help New Hires Succeed (and Stay)

Onboarding is so much more than the standard-issue IT set-up: It's the foundation for how new hires settle into their roles and their future at the company. We gathered perspectives on how to prime your newest employees for success.

Hiring managers and founders spend so much time and energy on recruiting, evaluating and closing talented candidates. And while it might have taken creative hiring tactics and an extended timeline to get star candidates to sign on the dotted line, in many ways, the real journey is only beginning. New hires' first days and weeks are what will determine whether they’ll stick around for the long run. But all too often, startups underinvest in onboarding, or ignore it entirely, hoping that “trial by fire” will be a reliable teacher.

We’ve found that having a supportive system in place is crucial. The whirlwind of emotions that come with starting a new job are intensified at rapidly-scaling startups; whether a new team member feels encouraged and excited, or excluded and bewildered by a startup’s breakneck pace, is determined at the very beginning. And those first few weeks set the foundation for how new hires settle into your culture, their roles and their long-term prospects at your company.

In other words, onboarding is so much more than the standard-issue IT set-up and friendly pointers for working the coffee machine. To help break down the essential ingredients of an excellent onboarding process, we gathered perspectives on onboarding from the Review’s most seasoned operators to help you maximize the impact of those decisive first interactions.

Their tactical advice spans a template for the ideal Day One timeline, to how startups can concretize the conversation on culture. It also considers the effects of onboarding that persist long after the logistical nitty-gritty tasks have been checked off, discussing how startups can use onboarding as an opportunity to nip factions in the bud and deepen new hires’ understanding of the industry.

We hope their wisdom inspires you to make the most out of your new hires’ first few days — and helps you ensure that your scaling startup remains a compelling, close-knit and rewarding place to work.

1. Don’t fall into these two startup onboarding traps.

When people ask 15-year HR veteran Carly Guthrie about how she thinks startups should fix their broken employee onboarding processes, she likes to open up with a joke:

You’re greeted at the pearly gates to heaven by St. Peter who asks where you’d like to spend eternity. “Well, heaven of course!” you say. Peter replies: “You have to check out hell just to see what you think before you commit.” Disappointed, you shrug but agree. And to your surprise, when the elevator doors open into hell, you see golden beaches, golf courses, gorgeous people mingling with colorful drinks. It’s not what you expected, but maybe heaven is even better, you think. So you take the elevator back up, but all you find there is a bunch of dull harp-playing on clouds. There doesn’t even seem to be anything great to eat.

You go back to Peter: “I didn’t think I'd ever say this, but I think I’d rather go to hell,” you say. “So it shall be,” he says, and you head back down to start your new afterlife. Only this time, when the doors open, you’re met with fire, brimstone and flowing lava. “What is this?” you yell. “Where’s the beach? What happened?” Your welcoming committee stares at you blankly: “Oh,” they say. “Yesterday we were recruiting you. Today, you’re staffed.”

Guthrie, now the Director of Human Resources at Heath Ceramics, says that despite a startup’s best intentions, this bait-and-switch happens all the time to new employees. And when it does, no one benefits. She shares two common myths that are preventing startups from investing in onboarding, and how startups can overcome them to set up their employees for success.

Myth #1: Hiring is more important than onboarding.

“There’s this dark alley knife fight for the best talent in the tech industry right now,” says Guthrie. “Everyone is so focused on getting the best people in the door, it eats up all this bandwidth and sucks the life out of them, but as soon as they win the battle and get someone to sign, they drop the ball.”

There’s this dangerous mentality of simply getting butts in seats with little thought paid to the onboarding process or the new hire’s early experience. “Everyone wants to feel cherished, especially after being so vigorously pursued,” she says. “People who are this talented get calls from recruiters all the time, and if they suddenly realize that they’re just a number or a cog in the wheel to you now, they have other options.”

It’s also important for early-stage startups to be thinking about HR, even if founders or hiring managers still shoulder the primarily responsible for hiring. “You don’t need to have an in-house HR person or department,” says Guthrie. Rather, it’s all about the process, which should be developed as early in your company’s life as possible, and having someone to execute it. “Even if you’re working with an HR person on contract or part-time, you want to start early,” she says. “It’s a lot easier to build trust and understanding with an HR person when you’re talking about defining culture and onboarding. The last thing you want to do is bring them in when you’re already in hot water."

For example, it’s very challenging for someone to help you navigate firing someone if they just met you and are coming into the organization cold. No company escapes the need to have tough conversations like this. If you run a company or manage people, you’ll inevitably need to address low performance or the possibility of letting someone go. “It’s incredibly hard to do those things solo without a sounding board, especially a sounding board you can trust to give their honest opinion,” says Guthrie. That’s a major reason you should seek out a constructive HR relationship early, while you’re still small.

“If you’re at a really early-stage startup, you definitely don’t need someone full-time, but someone at the company should wear this hat. I would recommend looking for someone with HR experience who can also do office manager work rather than the other way around,” she says.

Carly Guthrie, Director of Human Resources at Heath Ceramics

Myth #2: Your startup is too “lean” for onboarding.

“A lot of companies hide behind this excuse: ‘Well, we’re a scrappy startup and moving so fast that we don’t have a lot of time to do things like put Chrome on a new hire’s computer or set up someone's desk,’” Guthrie says. “It might be something that simple, but it sends the message that you can’t be bothered, that you’re not into the finer details, that you’re about broad-strokes, and most dangerously, that they shouldn’t trouble you to ask questions. What does this tell people about how to treat your company's product or users when they see a bug or something wrong?”

Sloppy onboarding turns into sloppy culture.

“If you accept the fact that people are too busy to give new employees a good experience, that attitude will perpetuate every time you bring someone new on,” she says.

Being busy with a tiny startup is no excuse, Guthrie says. “You’re not too busy. You just spent all this time, energy and money getting this new person to join. Blowing it is going to cost you even more when you have to start the hiring process again from scratch. Don’t make someone feel like you’re too busy to make them feel good about choosing to work with your company.”

Your goal should always be to make people believe on a gut level that your organization is so amazing that they couldn’t possibly work anywhere else. Building that attitude starts immediately once an offer letter is signed. And if you do it right, when the phone rings, and it’s a recruiter on the end of the line offering the next big thing, they’ll say, “Sorry, I’m happy where I am.”

Day One is your chance to be who you said you were in the recruiting process.

Read more of Guthrie’s observations and advice on why employee onboarding at startups is broken (and how to fix it.)

2. Craft the perfectly over-scheduled Day One timeline.

Back when Percolate doubled its headcount from 30 to 60 employees over the course of months, Noah Brier knew he had to keep a steady hand on the reins. If he wanted Percolate to scale sustainably, he had to devise a way to nurture the company’s growth, all while integrating and motivating his newest employees. To him, that meant designing a thoughtful onboarding strategy.

Here, Brier shares the detailed blueprint that he came up with during Percolate’s early days, outlining onboarding prep through the end of a new hire’s crucial first day of the office.


The Friday before the new hire starts, they get access to their email and an overstuffed calendar. “I know there are different schools of thought about onboarding schedules. Generally, we try to over-schedule instead of under-schedule for new employees,” says Brier. “In my own personal experience, it’s a weird feeling to show up on the first day and not having any work or idea of what to do. So we fill those days as much as possible.”

Default to filling new hires’ calendars. Don’t leave them with the feeling that you’re surprised that they showed up.

Here’s more key information that new hires receive to prepare them for their first week:

  • Practical instructions, including email login, arrival time and FAQs
  • Email introduction to a “Percolator,” an employee who will reach out to welcome the new hire and act as another point person for questions and guidance
  • People Ops onboarding calendar, which outlines the first two days of meetings and Asana tasks for their first week.


New digs Percolate sets up the desks of new hires so that there’s no need to search for supplies. Standard-issue items, such as a computer, monitor, notebook and pens, are laid out. “You walk in the door and you've got a desk full of everything that you need to get started,” says Brier. “One of the things that I've seen done poorly is when new hires need to wait until 2 o'clock to get their laptop. Obviously, that's the first thing everybody wants to set up and get going.”


Not every company does professional headshots, but it’s an important detail to Percolate. “It’s something we do and people seem to really appreciate it. We have a photographer who takes headshots for everybody,” says Brier. “It’s important to be a part of a community, and one key to achieving that is appearing to be part of the tribe. So, if you go view a few Percolate employees’ LinkedIn pages, you’ll find they share a very similar headshot.”

Day One Document

For six months in 2013, half the people at Percolate had not heard Brier speak about its values and lay out the year’s kick-off plan. He fixed this by writing everything down. Nothing scales better or faster than words. Plus, documentation is a ready resource, while people aren’t always available.

Six months after founding Percolate, Brier wrote the original version of Percolate’s detailed documentation of the culture of the company. It lives in Google Docs and has evolved in the hands of his employees. “There's a lot going on, and it’s as defined by what it is as by what it isn’t. It is not your HR read-through of your benefits,” says Brier. “It’s our living, breathing document that covers all aspects of our culture, from where the company comes from to our point of view on meetings. Mostly it’s about our culture, ideas and methodology. We try to focus on explanations, not rules.”

The document itself is a living artifact of one of Percolate’s founding values. “The Day One Document is a prime example of our belief in writing everything down,” he says. “The key to designing a thorough onboarding program that gets new people acquainted quickly is over-documenting everything. We find that words scale well. Plus, documentation is a ready resource that new hires can refer to before asking other colleagues, which is essential if you’re a founder. With a document like this, your team can asynchronously learn and engage.”

A Living Archive of “Introduce Yourself” Emails. As outlined in the Day One Document, a hire sends an “Introduce Yourself” email at the end of the first day. It’s a scripted greeting to the company from the new hire sharing a bit of background and trivia. “Everyone who starts with the company sends one out. It also includes a photo and a link to three questions on Barista, Percolate’s internal Q&A platform. The idea is that it’s not about just giving information, but starting an exchange with your new team,” says Brier.

The “Introduce Yourself” emails live on as an archive of — and inspiration for — every introduction sent by a new hire. “People go back and read them, for guidance, perspective or pure entertainment,” says Brier. “Early on, we encouraged people to share embarrassing photos for fun, but when we hit about 150 people, we thought it wise to move away from that prompt. So, we told people to include any snapshot, but embarrassing photos kept coming. Apparently, everyone was inspired by the old way. It works pretty well as a nice way for people to get to know each other through these offbeat stories.”

Read more about Brier’s tested strategy for creating a tight, impactful onboarding timeline, from the day the offer letter is signed to the end of the first week.

3. Infuse your onboarding with puns, personality and executive priority.

Since 2010, the year that Dave Gilboa and Neil Blumenthal hired their first official employee for Warby Parker, one belief has remained constant: the co-founders’ conviction that creating an extraordinary employee life cycle is just as important as developing a killer product.

“One thing I’ve always found surprising and unfortunate is that as companies get bigger and have more money and more ability to invest in the employee experience, they actually become worse places to work,” says Gilboa. “That terrifies us.”

At the start of onboarding, new hires should feel immediately like a part of a company’s distinct culture. “You have to make people feel special and welcome from the very first moment they step into your organization,” says Gilboa.

Warby Parker co-founders Neil Blumenthal and Dave Gilboa

Here, Gilboa shares three tactics that guide Warby Parker’s playful approach to onboarding.

Put together welcome packets that pop.

Warby Parker’s welcome packet includes standard-issue fare like an office map and style guide, but also something unexpected: A copy of Jack Kerouac’s Dharma Bums. “The name Warby Parker came from two early Kerouac characters,” Gilboa says. “We want to make that heritage part of the employee experience from the very first day. It’s something utterly unique to us that will always stand out.”

Help new employees become the most approachable people in the office.

Being new can suck. You feel like you have to prove your value right away. Everyone around you has some degree of shared history, inside jokes, and institutional knowledge. To help your new employees break the ice, you want to take the pressure off their shoulders and make it easy for your existing team to induct them into the culture and conversation.

Warby Parker does this in a few ways. The first is a quirky variation of something often done at large companies, but seldom at their smaller counterparts. They designed a custom helium balloon that features an illustration of a steak with a pair of glasses on. It reads, “Nice to meat you!” These balloons are affixed to every newcomer’s desk for their first couple weeks. Other employees are conditioned to treat the balloons as beacons so they’ll introduce themselves and strike up conversations with newbies.

New employees are also asked to introduce themselves during all hands meetings, so that they can seed commonalities and inside jokes in front of the rest of the company. As part of this intro, they’re asked to share a fun fact about themselves. “They’ve ranged from someone who held Michael Jackson’s baby to a 5’ tall woman who announced she had the colon of a 6’ tall man,” says Gilboa.

By asking folks to share something memorable (and occasionally bizarre), you can help them become more recognizable to their colleagues and equip everyone with a hook to get to know each other better and strike up conversation around the office. People don’t do this for themselves as proactively as you think they will. You need to build it into their first days on the job to make them as approachable as they’d like to be — without putting the onus on them to forge a bunch of connections on their own.

Make training an executive priority.

Far too many companies delegate new employee onboarding and training to junior staff or the human resources team. Some even outsource it. But Gilboa says that good leaders don’t even dream of relinquishing this crucial task. “We think it’s vital for the most senior people at the company to be involved in this process, including me and my co-founder,” he says.

The presentations might seem repetitive after a while, or below the C-suite’s pay grade, but having them drive onboarding sends a strong message that new employees are extremely valuable to the company. Beyond that, a startup’s leadership team tends to have all the important institutional knowledge at their fingertips — from the origin story to governance structure.

When company values are articulated, explained in detail and reinforced (ideally with examples) by a founder, they carry far more weight than they might when simply written on a piece of paper or a poster on the wall.

Read more about how Warby Parker’s co-founders have made every point in its employee life cycle extraordinary.

4. Culture isn’t one conversation — it’s a history curriculum.

Back when Atrium co-founder Peter Kazanjy was building the initial sales team for TalentBin, he was struck by the high opportunity cost of poor employee onboarding. Here’s the algebra behind it: Well-trained sales reps produce happy customers. Because happy customers recur and refer others, missed or dissatisfied customers (consequences of ineffective sales reps) rob the company of tremendous future value.

He contends that once you’ve pulled the trigger and hired salespeople you like, your entire focus needs to fully ramp productivity as quickly as possible. The best weapon against these losses, he realized, was an ironclad onboarding program that would equip new hires with all of the resources they’d need to land and close business.

In a small slice of his rigorous framework for onboarding, Kazanjy emphasizes the importance of concretizing culture during the onboarding process. While he’s wearing his sales hat in the section that follows, his onboarding advice has value for all roles, not just sales. For Kazanjy, it’s important to make sure culture isn’t just one conversation. “It's how you demonstrate the way your company executes, what’s celebrated and what’s censured. Kick it off early in onboarding with a proactive, explicit discussion of what your sales org values and what's not okay,” he says.

Here are three tenets that Kazanjy presented upfront during onboarding at TalentBin:

  • You don't have to be an engineer to operate with an engineering mindset. “This is a value we wanted the sales team and everyone in the company to embody and carry on, encouraging them to identify constraints, propose solutions, test them, rinse and repeat,” says Kazanjy.
  • We are all the product managers of our sales organization. “We wanted people to behave like product managers so they would constantly be thinking about ways to improve our workflows,” he says. “We actually called different aspects of our sales process ‘features’ and asked for people to speak their mind on which features should be iterated on, killed or added.”
  • Intellectual honesty is paramount. “The company itself was born out of an initial failed product. We had to pivot our way to product/market fit. But that never could have happened if we hadn't been brutally honest in our self assessments. You have to be willing to declare failure before you can improve, and we wanted continuous improvement,” he says.

These are the types of cultural touchstones you want to relay to new hires immediately, no matter their role in the company. They should be couched as foundational and unflinching. Having these tenets in place will help you hire, and will make it easy to spot which new employees are really inspired by them.

Finally, every culture curriculum should include a history lesson in your company. “A robust review of your company's path are important for cultural onboarding and provide a key opportunity to underscore major themes in how you like people to work,” says Kazanjy.

Frame your culture in terms of company history. “This is where we started, and this is how we got here. This is where we are, and this is where we're going.”

Read about Kazanjy’s rigorous onboarding process can help B2B startups build the best-prepared sales teams.

5. Fight factions from the first day.

David Loftesness and Alexander Grosse have lived through the brilliant and bleak moments of scaling teams. Between the two of them, they’ve held engineering leadership roles at Twitter, SoundCloud, Amazon/A9, issuu and Nokia. (Today, Loftesness is Head of Engineering at eero, and Grosse is VP of Engineering at BCG Digital Ventures.) Throughout their careers, they’ve led engineering through during periods when hot products demanded that their companies stretch in new ways, and fast.

Both have seen onboarding play a crucial role as startups scale through hypergrowth, helping new employees feel supported and aligned toward a greater goal. Practically speaking, onboarding is when new employees have the time to learn about the company and meet colleagues they might not otherwise encounter.

“This is the time to introduce them to each function — the data team, the tools team, the sales team, the product team, you name it — before they get buried in their day-to-day work,” says Loftesness. “Fostering an understanding of what each team does, what their challenges are, the basic act of putting names to faces after a meaningful interaction, is a great way to sidestep factions down the road.”

The specifics and demands of your business will dictate how much time you can spend on this interdepartmental “get-to-know-you.” But even a few half-hour meetings with colleagues in various departments can make a big difference. On the other end of the spectrum, formalized, week-long (or longer) rotations on different teams can establish even stronger bonds. Here’s how a few companies have navigated onboarding:

  • eero launched a ‘shadowing program,’ where new colleagues from other departments get a day-in-the-life view of your job,” says Loftesness. “The sales team, for example, actually takes engineers, CX reps and managers out to a Best Buy, walking them through their retail training program. They see first-hand the end caps and how the product is positioned. They get to really experience the life of the sales team.”
  • At Amazon, where customer satisfaction is paramount, Loftesness, like all managers of a certain seniority, was required to spend several days training as a customer service rep. “The ‘Customer Connection’ training was an eye-opener, I’ve got to say. It was incredibly motivating, too. The problems you thought your team needed to focus on would shift when you actually saw what real customers’ frustrations were, and where there were opportunities to make them happier,” he says.
  • Issuu went one step further than shadowing. It actually delayed team assignments for engineers until they’ve completed a robust onboarding process. First, new hires spend a week with every team. “After those five weeks, I usually sit together with the new engineer and maybe two team leads, and we decide on a team for their placement. It’s always a compromise between business needs and the personal preference of the engineer,” says Grosse. “In some ways, this onboarding process is an extension of our hiring process: it only suits engineers who we want to attract — those who are open to a broad range of challenges. But regardless, it encourages deeper engagement in the onboarding process. When you assign the team before onboarding, new hires have less patience. Understandably, they want to contribute to their team and be successful. If they don’t know who their team is, they usually are more curious about the company, asking: ‘Hey, what’s here, what’s there, what’s interesting? Where can I contribute?’”

Once you grow beyond five or six teams, or start hiring employees at a faster clip, a rotation-based onboarding process may be impossible to scale due to the sheer number of teams. But while growth complicates certain onboarding practices, it facilitates others.

“At a certain scale, you're growing so fast that you might have five to 10 or more employees starting in a given week. Take advantage of these new hire cohorts and help them to bond like a freshman class at college. Even without team rotations, they can use these personal connections to learn more about other teams. It’s a particularly effective way to formalize onboarding without sacrificing rigor,” says Loftesness. “Plus, those cohorts will likely end up in different departments, and they will form and facilitate connections and empathy. When people have friends in other parts of the company, that can be a really useful way of knitting those teams together over time.”

Make room in your onboarding process for informational check-ins with key cultural gatekeepers, too. “Get new hires in a room with your veteran employees, for example, to maintain a thread to your earliest days. Encourage them to share stories, both difficult failures and energizing successes. This can give the new folks some perspective of what the old-timers went through to get the company to where it is today,” says Loftesness.

“At Twitter, it was really common for a newbie to come in, look at some cruddy Ruby code in the Monorail and think, ‘Oh my god, what were these people doing?’ But once you’ve heard the origin story for that bit of code, how it saved the day at two in the morning, just before the Grammys, when the site was about to fall over, you’ll have a lot more empathy for what the old guard went through. That kind of shared understanding creates cohesion across different generations of employees, a connection that will only become more vital as your company grows,” he says.

Read more from Loftesness and Grosse here, on how startups can scale sustainably without factions, here.

6. Onboard new hires into your industry, not just your institution.

You probably know the basic elements of good onboarding: integrating new hires into their team, introducing them to people who will have helpful institutional knowledge, sharing your company’s values.

Meg Makalou challenges startups to take their onboarding a step further. She’s a human resources leader for startups big and small, from a four-year stint as Zynga’s Vice President of HR during a period of hypergrowth to her current role as chief people officer for The Climate Corporation and the People Ops Expert-in-Residence for First Round’s companies. She’s confronted every type of employee performance problem and has navigated some of the gnarliest HR conversations with patience, clarity and grace.

Meg Makalou, Chief People Officer for The Climate Corporation

In Makalou’s eyes, onboarding is a way of not only nipping potential performance problems at the bud, but fostering a culture of authenticity — a critical precursor to the agility successful startups demand.

“Don’t miss the opportunity to develop, right out of the gate, each new hire’s business acumen about what exactly the company does. It helps put everything else into context,” she says.

In other words, onboarding isn’t just making sure that the tech is set up. It should be a holistic process that provides a new hire with macro-level insight about where they fit in a larger ecosystem.

So often, startups focus on making onboarding narrowly about sharing institutional — not industry — knowledge. On the other hand, if you give new hires context within an industry, you’ll impart them with greater imagination and impact.

At The Climate Corporation, for example, industry-level education takes the form of an immersive two-day class on the basics of agriculture. The average software engineer knows little to nothing about growing crops. But once they’ve gone through the exercise of running an imaginary farm—from buying a tractor to dealing with uncooperative weather—they are much better positioned to develop the products their end users need.

In other spaces, your training might be even simpler. Makalou was previously an HR manager for Andale, which developed auction-management tools for eBay sellers. “Munjal Shah, the CEO at the time, knew that people needed to get what we were doing as a company right off the bat, so he required that everyone sell something on eBay. It could be things that we had in the office. You didn't have to go find items to sell, but you had to experience being a seller on eBay. You had to experience, firsthand, what that feels like and what that requires.”

Read more about Makalou’s tactics for handling the thorniest HR conversations here.

Photography by Bonnie Rae Mills. Image by iStock / Getty Images /Rost-9D.