Employee Onboarding at Startups Is Broken – Here’s How to Fix It
People & Culture

Employee Onboarding at Startups Is Broken – Here’s How to Fix It

Carly Guthrie has helped onboard new employees in startup offices and crowded restaurants. Here's what she learned from hard-won experience.

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.”

This is Carly Guthrie's one HR joke. And after working in the business for over 15 years across a variety of industries, she says it rings true all too often. Today, she helps companies build HR organizations as a consultant and says this bait-and-switch happens all the time to new employees, sometimes despite the company’s best intentions. And when it does, no one benefits. In this exclusive interview, she lays out a plan for onboarding that sets everyone up for success.


“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. Two things can set the tone of tenure:“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.”

“You need to weaponize your HR process to not only get the best talent, but keep them.”

According to Guthrie, a fully-weaponized HR approach is a tool you use to your benefit, not something that's an afterthought. It's coherent, consistent, culturally aligned and owned by someone in particular —whether it’s a consultant, office manager, or head of HR.


“To really optimize someone’s first experience with their work environment, you need to be thoughtful about how to improve the onboarding process and provide hospitality,” says Guthrie. “First days are an opportunity to tell the story of who you are and what you want to accomplish, and have that stick with every single person who joins your organization. You want to take the opportunity to validate their decision to join.”

This doesn’t mean you have to have an in-house HR person or department. 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.”


“From a sheer tactical standpoint, you’re never going to have the same opportunity to impact people that you do on their first day,” says Guthrie. “Everyone’s feeling great and psyched to be there, they’re willing to sign their lives away. You have to be organized enough to make them feel even more awesome and reaffirm their choices.”

“Day one is your chance to be who you said you were in the recruiting process.”

You don’t want to be fake about this. When asked about their culture, a lot of companies will say something like, “Oh yeah, we like go bowling and hang out all the time like friends...” But that all starts to sound the same. By being a bit different, you have the chance to really set your startup apart.

“Create an experience where someone walks in on their first day and everyone is already expecting them. Everyone already knows their name and what they're there to do. Everyone is super welcoming and understanding of the fact that meeting so many new people is overwhelming,” says Guthrie. “Don’t make them wonder where and how they’ll eat lunch. Remove all of those small obstacles that cause first-day nerves. All of this shows a level of thoughtfulness that many organizations fail to accomplish.”

Before getting into tech, Guthrie managed HR for the Thomas Keller Restaurant Group, owner of elite California restaurant The French Laundry— and their success is no secret. “They are incredibly, incredibly thoughtful about every detail of a guest's dining experience,” she says. “Ahead of time, they'll have already considered food allergies and preferences, even menu items you might have tried previously. It’s a level of care and attention that often gets lost in modern times, but it goes a really long way toward making things special, memorable.”

You don’t have to have all of the answers about your culture, or even what a new hire can expect down the line, she says. But by showing up and being willing to think through and act on the small things, you distinguish yourself and build trust.


(Rules for managers.)

Rule #1: Never have someone start their first day at 9 a.m.— have them come at 11. “That gives you a chance to get in, have your coffee, get through your email, and doublecheck that everything is set up for them to arrive,” she says. “By the time it's 11 a.m., you can give them your full attention, help them get the paperwork out of the way, and introduce them to the team.”

Rule #2: Don’t outsource a welcome. “It’s always better for someone’s manager to be the one to show them around and make introductions,” says Guthrie. That said, everyone should know the new person is starting and should proactively walk up to greet them as well. These introductions should serve a purpose. Everyone should know to say, “Hi, my name is Joe. I work in product and am responsible for X.” (Not just “I’m Joe, I sit over there.”) You want to give your new hire pieces of a puzzle that will fit together quickly so that they understand the team and how they work together.

Rule #3: Keep the first day light. “Very few people get a good night’s sleep before starting a new job, so be respectful of that. You can have some meetings planned, but remember there’s a lot of information coming at that person and it’s hard. Even the most confident, ‘I’ll dive right in’ person is still learning a bunch of new names and faces. Set the expectation: 'This first week you should not be here past 5 p.m. Your job is to be a big sponge, and we want you to have time to reflect and recharge before coming back every day.'”

Even if you talked about long, grueling hours during the interview process and the candidate agreed to them — even if you said, “We literally never go home, we have no lives” — don’t make that the case the first week. “People pick up on so many written, verbal and unspoken cues when they start a new job. Be sensitive to the sensory overload.”

Rule #4: Clue them in on the vernacular. Every company has its own secret language, especially if people have been working together for a while. It’s made up of inside jokes and shorthand that can be intimidating and even alienating for someone new. “When I directed HR at Readyforce, we worked with so many hilarious people, we had all of these jokes with each other. So part of our onboarding was literally looping people in on insider stuff, saying things like, ‘Oh, when so-and-so says this, this is what she means...’” Figure out what those things are at your company, and make them inclusive in your onboarding. Don’t let them make a new hire feel like an outsider.


“Number one, be who you said you were during the recruiting process,” Guthrie says. “Let people make a conscious and accurate decision for themselves. Don’t tell them the hours aren’t that bad if they are. Don’t tell them you all hang out all the time if you don’t.”

Beyond that, there are a number of logistical steps you can take to make someone even more enthusiastic, excited and dedicated coming in than they were already.

“Make sure their desk is set up and that they have all the tools they need — and go the extra mile. It’s one thing to have a computer waiting for you. It’s another to have Chrome and everything they will need already installed,” she says. “There should be a welcome note, ideally handwritten by their manager, and some nice SWAG. People are excited on their first day. They’ll want to start repping your brand.”

Again, this is where a little extra goes a long way. “Really great companies don’t only provide SWAG for the new employee (even better, in the right size), but also for their partner and kids if they have them. If you’re a manager and you don’t know what the situation is, simply ask: ‘Do you have anyone else we can get things for?’ Maybe their dad is super excited about the job and would want a T-shirt. Making that happen is incredibly thoughtful, and T-shirts cost nothing in the grand scheme.”

“The good will that a great welcome experience generates is priceless.”

“Remember, when someone joins your organization, it’s not just them that’s working there. Especially if they work long hours that can impact their entire family.”

To create great beginnings, you have to play a couple moves ahead. You should know who is taking the person to lunch and what their entire schedule looks like for their first week. “You should have all of this written down for them, with any meetings already on their calendar,” says Guthrie. “Tell them, ‘I want you to just take everything in and meet as many people as possible, so I’ve set up these meetings, and here’s a little blurb about the people involved and why this is important.”

Finally, as a manager, be constantly available and interruptible in the first several weeks. “Tell your new hire to keep a list of questions that can be addressed during a regular, pre-scheduled meeting once a week, but that you’re also always available to answer anything urgent.” She recommends starting a shared Google Doc where the new hire can write all of their questions. That way managers can see what’s on their mind.

“To make people feel really cared for, you can’t just be thinking about today or tomorrow. You should know what the first six weeks will look like before they even get there. What do you want them to accomplish in the first 90 days? You should already have this in mind so that if they aren’t a perfect fit, you know by that 90th day, not the 900th day.”


“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, andmost 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.”

You say you’re too busy. You work at a tiny startup after all. But that’s 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.”