Hiring & Teams 14 guests | 14 insights

Onboarding New Hires

Onboarding is where the promise of hiring gets fulfilled or broken. The first 90 days determine whether a new hire becomes a high performer or a regretted decision. Great onboarding creates belonging, clarity on success, and early wins that build momentum and credibility.

The Guide

6 key steps synthesized from 14 experts.

1

Define success at 90 days, 1 year, and 2 years before they start

Before the hire even begins, document exactly what 'crushing it' looks like at each milestone. This creates a shared understanding of expectations and gives the new hire a clear target to aim for from day one.

Featured guest perspectives
"The 90 day plan is something that's overused but so necessary, and that's just the tip of the iceberg. So that component and then, okay, a year from now, what should this person be doing? Two years from now?"
— Lauren Ipsen
"How do I ramp them up as quickly as possible... make sure it's clear what success looks like in their first 90 days? And then how do I help them secure early wins essentially?"
— Melissa Tan
2

Create immediate belonging through pairing

New hires shouldn't spend their first day alone. Assign a 'first pair' partner who works alongside them immediately. This creates social integration, accelerates learning through collaboration, and prevents the isolation that leads to early attrition.

Featured guest perspectives
"So the tip with one by one is when someone joins, help them feel a sense of belonging, and you can do that through not having their first day be them sitting over there alone. You could have someone have a first pair."
— Heidi Helfand
3

Conduct a listening tour before taking action

For senior hires especially, the first 30 days should be about diagnosis, not prescription. Meet as many stakeholders as possible, understand the current state, and summarize findings before proposing changes. This builds trust and prevents costly missteps.

Featured guest perspectives
"Conduct a 'listening tour' in the first 30 days, meeting as many stakeholders as possible. Summarize findings into a 'state of the union' to show the team they have been heard. Align on vision in the second 30 days and move to full execution by day 90."
— Deb Liu
4

Engineer early wins for visibility

Identify low-hanging fruit projects that let the new hire demonstrate value quickly. Create opportunities for them to present their work to leadership early. These wins build internal credibility and momentum that compound over time.

Featured guest perspectives
"So I often will suggest, 'Hey, you should do this presentation. It's a great way to get visibility early in your journey here.'"
— Melissa Tan
5

Teach golden rituals by the first Friday

Great companies have a small number of core rituals that define how work gets done. Every new hire should know these rituals by name and be able to participate in them within their first week. This accelerates cultural integration faster than any handbook.

Featured guest perspectives
"Great companies has a very small list of golden rituals. And there are three rules of golden rituals. Number one, they're named. Number two, every employee knows them by their first Friday and, number three, they're templated."
— Shishir Mehrotra
6

Be honest about chaos and avoid over-promising

Don't promise stability, specific titles, or never hiring over someone. These 'letter bombs' explode later when reality doesn't match expectations. Be upfront about the ambiguity and change inherent in scaling environments.

Featured guest perspectives
"Do not promise things that you can't control... being honest and upfront about who you are as a company, about what you're able to promise, all of that is actually... it's very hard work but it's so important."
— Molly Graham

Common Mistakes

  • Leaving new hires to figure things out alone on their first day
  • Promising stability or specific career paths you can't guarantee
  • Skipping the listening tour and jumping straight to execution
  • Failing to define clear success criteria before the hire starts

Signs You're Doing It Well

  • New hires can articulate the company's core rituals and values within their first week
  • 90-day reviews show progress aligned with pre-defined success criteria
  • New hires report feeling welcomed and clear on expectations

All Guest Perspectives

Deep dive into what all 14 guests shared about onboarding new hires.

Brandon Chu 1 quote
Listen to episode →
"one amazing, and just the context, I'm really old at Shopify now... people that would join my team already knew how I thought. It was pretty onboarded a lot of the PMs that would join my team because obviously, they're going to look for who their leads is and Google that a bit"
Tactical:
  • Write about your management and product philosophy to help new hires ramp up before their first day
View all skills from Brandon Chu →
Deb Liu 1 quote
Listen to episode →
"I created, it's actually when I joined Ancestry... I decided I was going to adapt all of those things into a summary and then I was going to try it real time in my blog... it's focused on listening and learning first and then doing. So that's the crux of it, which is in those 90-days it's like you got to get used to the environment. You want to have some impact at the start. You want to have a couple quick wins, but you want to understand the lay of the land and you want to listen."
Tactical:
  • Conduct a 'listening tour' in the first 30 days, meeting as many stakeholders as possible
  • Summarize findings into a 'state of the union' to show the team they have been heard
  • Align on vision in the second 30 days and move to full execution by day 90
View all skills from Deb Liu →
Heidi Helfand 1 quote
Listen to episode →
"So the tip with one by one is when someone joins, help them feel a sense of belonging, and you can do that through not having their first day be them sitting over there alone. You could have someone have a first pair."
Tactical:
  • Ensure new hires are not left to work alone on their first day
  • Assign a 'first pair' partner to work with the new hire immediately
  • Encourage new hires to share their personal stories to increase retention and connection
View all skills from Heidi Helfand →
Kenneth Berger 1 quote
Listen to episode →
"I recommend to a lot of founders for maybe their first 10 or 15, or 20 employees of just have a relationship design conversation with each of them when they're first hired."
Tactical:
  • Conduct a 'relationship design' conversation during the first few weeks
  • Collaboratively figure out the best way to work together given the specific roles and personalities involved
View all skills from Kenneth Berger →
Lauren Ipsen 1 quote
Listen to episode →
"The 90 day plan is something that's overused but so necessary, and that's just the tip of the iceberg. So that component and then, okay, a year from now, what should this person be doing? Two years from now?"
Tactical:
  • Define what 'crushing it' looks like at the 90-day, 1-year, and 2-year marks before starting the search.
View all skills from Lauren Ipsen →
Melissa Tan 1 quote
Listen to episode →
"How do I ramp them up as quickly as possible... make sure it's clear what success looks like in their first 90 days? And then how do I help them secure early wins essentially? So I often will suggest, 'Hey, you should do this presentation. It's a great way to get visibility early in your journey here.'"
Tactical:
  • Define specific success criteria for the first 90 days
  • Identify 'low-hanging fruit' projects for the new hire to tackle immediately
  • Create opportunities for new hires to present their work to leadership early on
View all skills from Melissa Tan →
Mike Krieger 1 quote
Listen to episode →
"I actually hadn't joined a company since my first internship in college basically. And I was like, 'Oh, how do I onboard myself? How do I get myself up to speed? How do I balance making sweeping changes versus understanding what's not broken about it overall?'"
Tactical:
  • Focus on identifying 'founder-type' engineers who can drive high-impact projects independently.
  • Avoid over-indexing on headcount early; instead, find key senior leaders who can shape product strategy.
View all skills from Mike Krieger →
Molly Graham 1 quote
Listen to episode →
"Do not promise things that you can't control... being honest and upfront about who you are as a company, about what you're able to promise, all of that is actually... it's very hard work but it's so important."
Tactical:
  • Avoid promising things like stability, specific titles, or never hiring over someone.
  • Be honest about the ambiguity and chaos of a scaling environment during the recruitment process.
View all skills from Molly Graham →
Nikita Miller 1 quote
Listen to episode →
"I think that in-person onboarding for new folks is really important for everyone. For any new person to an organization, I think how we work culturally, having a contact that you can reach out to, all of that I think is really crucial."
Tactical:
  • Aim for one week of in-person onboarding for new hires
  • Ensure new hires have a specific cultural contact or 'buddy' to reach out to
View all skills from Nikita Miller →
Roger Martin 1 quote
Listen to episode →
"You have to have a different way of recruiting, a different way of onboarding, a different way of career development. And if you do all of those things, you end up with a 10% turnover rate, so that your people are there 10 years on average, and you can then get them trained up to deliver that kind of service."
Tactical:
  • Align onboarding and training specifically to the 'how to win' choice (e.g., specialized service).
  • Focus on reducing turnover to build the long-term expertise required for a differentiated brand.
View all skills from Roger Martin →
Shishir Mehrotra 1 quote
Listen to episode →
"Great companies has a very small list of golden rituals. And there are three rules of golden rituals. Number one, they're named. Number two, every employee knows them by their first Friday and, number three, they're templated."
Tactical:
  • Ensure every new hire knows the company's 'golden rituals' by their first Friday.
  • Include core rituals in the new hire onboarding curriculum.
View all skills from Shishir Mehrotra →
Tomer Cohen 1 quote
Listen to episode →
"Starting January, we're going to start having our APB program and they're going to come into LinkedIn. We're going to teach them how to code, design and PM at LinkedIn. They're going to go through a pretty rigorous training process, and then they're going to join those pods."
Tactical:
  • Replace traditional APM programs with 'Associate Product Builder' tracks
  • Provide rigorous cross-functional training in coding, design, and PM skills for new hires
View all skills from Tomer Cohen →
Scott Wu 1 quote
Listen to episode →
"One of the fun use cases that we've seen actually with folks is they'll often actually get Devin's help to onboard new engineers on the team. When you're new and you're joining, there's obviously a lot of questions that you have about the code base... It's nice to just be able to ask Devin and to go through Devin's wiki and to understand these internal representations."
Tactical:
  • Use AI to index the codebase and create an interactive wiki for new engineers
  • Encourage new hires to use AI tools to explore internal representations and system architecture during their first weeks
View all skills from Scott Wu →
Timothy Davis 1 quote
Listen to episode →
"I want to try and make that 45 days, if not 30... giving them responsibility early on for something... 'Here's everything we did last additions. This is the results. These are your responsibilities, these are the expectations. Go.'"
Tactical:
  • Use an 'ops cadence' spreadsheet to define exactly how often tasks (weekly, bi-weekly, monthly) should be performed
  • Assign a specific campaign or project ownership within the first few weeks to drive immediate impact
  • Conduct 'over-the-shoulder' screen-sharing sessions to demonstrate efficient workflows
View all skills from Timothy Davis →

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