Employee Onboarding for Startups - It Doesn't Have to Be Painful

Amanda Hallett
Employee Onboarding for Startups - It Doesn't Have to Be Painful

Steve just got the phone call from his candidate accepting the offer - cloud nine. Finally, the right candidate came along!

But after about 7 minutes, those warm and fuzzy feelings fade. Because he realizes that now come the dreaded next steps - Onboarding. Training. Legalese paperwork.

He wants to run and hide.

Why is this so painful? So avoided? Because we don’t take the time to create an onboarding plan. We don’t anticipate basic questions when someone is switching jobs. And we simply drop the ball because we aren’t organized and don’t delegate.

It’s that vicious cycle…you are buried and short-staffed, so you hire more employees to spread the work. But you’re so buried and short-staffed, you don’t have time to onboard or train them…and so on.

You may have a killer product, and growth strategy is looking good. But fact is, if you are disorganized with the first steps of bringing a new team member on board, it is a big turnoff. It sets the wrong tone, and can possibly affect how long he/she stays with you.

How does onboarding impact employee retention?

Retention starts the day that offer letter is signed! Many times if someone leaves a company, it’s not one thing but rather a culmination of little things over time - so don’t let a sloppy onboarding process play any part.

Employee Onboarding Statistics
Image Source: Broadsoft

So how do we break these bad habits, and set our new hire up for success? Let’s look below at a timeline that breaks up the different stages, as well as some helpful tools you can incorporate.

Employee onboarding timeline

  • The Lead Up (between offer and start date)
  • Start Date
  • First Two Weeks

The lead up (between offer and start date)

Your candidate accepted the offer…now what? Many of your existing inconsistencies likely stem from not having a standard onboarding procedure to follow. Crate.io has a great article around onboarding new employees, and provides some great insight.

Goals of a standard onboarding procedure:

  • Should be easy to set up and use
  • Should prompt interaction between people as opposed to just being a checklist you work on alone
  • Should be adaptable and easy to modify

Trello 101 - employee onboarding example

At Headway, we utilize Trello boards to create an easy, adaptable onboarding checklist. This allows us to create a template board that can be copied and personalized for each new hire (for inspiration, here is the onboarding checklist that Crate uses). The beauty is that you can create as many or as few lists as you need - bottom line is that it’s easy for a first time user to navigate. We utilize the following lists within our New Hire Board:

  • Pre-Onboarding
  • Everyone
  • Full Time
  • Developer
  • Designer
  • Marketing

Trello Onboarding

Now, lest we assume everyone is familiar with Trello, here is a Getting Started Guide to familiarize yourself with the tools and capabilities. Take a swing through here before you continue reading to make sure you know the difference between lists, cards, checklists, etc.


This list should include staple items that need to be completed or reviewed between the offer acceptance and the first day. Depending on your size/industry, you may have different compliance regulations to consider. Our list includes setting up new hire campaign emails, completing the Federal I-9, reviewing policies & benefits, and completing a questionnaire for swag!

Email setup

Before we begin any of the tasks below, we ensure the new hire has a company email provisioned, and create his/her profile in the company system - basically, make sure your new hire exists in whatever master list or HRIS system you are using.

We also kick off our new hire drip campaign. At Headway, we utilize Mail Chimp, allowing us to quickly create and edit templates. Our campaign includes:

  • A quick touch base from the leader sent shortly after the offer is accepted
  • A benefit overview email sent approximately 10 days before the start date
  • An official Welcome Email sent 5-7 days before the start date

Note: The last Welcome Email is not sent until the new hire’s Trello board is completed - so we make a note to come back and complete this task near the end of our process.

Federal I-9

The Federal I-9 is used for verifying the identity and employment authorization of individuals hired for employment in the United States (including citizens and non-citizens). Fair enough, right?

Section 1 (the portion the employee completes) is required to be completed on the employee’s first day of employment - i.e., the first day you start paying your new hire. So make sure if the first day is a travel day, it is completed same day. The employee can also complete this step before his/her first day of hire, if an offer has been extended/accepted.

The employee must also present acceptable documents as evidence of identity and employment authorization (i.e., Section 2, which is the portion the employer completes). You can learn more about that part here.

Policies & benefits

Is your handbook/company policy document up-to-date? New hires need to know expectations on vacation/time off, eligibility rules for benefits, etc. Many times confusion happens because the job description or offer letter only includes only high level descriptions. By laying everything out in detail, it ensures everyone is on the same page from day one.

Ah, benefits - a necessary evil when someone is coming on board to a new company. Here are some helpful tips to help get you organized:

  • Consider creating an in-house “Benefits” page to consolidate all the basic information for each individual plan you offer (i.e., what vendor you use, eligibility criteria, enrollment windows, and waiting periods). We utilize a Notion page that gives a glimpse of all our benefits to both new hires and current associates. This is a quick way to review high level information without having to dig through each plan’s Summary Plan Description (although those should be made available as well).
  • Push out an automatic email or create a Mail Chimp campaign to provide benefit information in advance to your new hire - these emails can be especially helpful since the new hire does not yet have access to your internal platforms. Include any benefit booklets/flyers available from your vendors - don’t make this harder than it needs to be! Direct new hires to the collateral already available rather than trying to create information from scratch.
  • Include a Trello card in their onboarding task list to have a short sit down with someone who can remind him/her where the Benefit policies are located, answer any high level questions, or direct the new hire to your broker or third party.

For any documents required for these steps, consider using electronic templates (we use Hello Sign). This creates a paper trail, and is much cleaner than sending attachments via email.

The communication during this “in-between time” sets the tone for the new hire’s first day. Set your candidate up for success - anticipate questions so he or she isn’t prying for information. Otherwise, you will get flooded with unnecessary emails titled “Quick Benefit Question” or “Time Off Clarification.”


We differentiate “Everyone” from “Full Time,” since there might be some tasks that a part time employee would still complete - such as computer setup, time tracking, and getting a portrait taken. We also combine similar tasks into one card, and include a checklist within that card - this is a cleaner process that employees can work through without being overwhelmed with separate cards for each task.

For instance, “Complete Account Registrations” includes 12 checklist items within that list (versus having separate cards for all 12 items).

Complete Account Registration Card

Full time

Full Time employees would still complete all the tasks under “Everyone”, in addition to the tasks in this list. There might be just a few items that fall here, such as Benefit enrollment or other responsibilities that are only given to full time employees.

Pro Tip - consolidate these two lists if the employee is coming on full time, eliminating an unnecessary list!

Designer Checklist


The remaining lists on the Trello board are broken out by role type - at Headway, a new hire would fall into the Developer, Designer, or Marketing category.

As the name implies, these lists are intended to capture any tasks that are role specific, such as different accounts that need to be set up, or launch pads into required trainings.

Start date

Whether you’ve nailed the lead up, or are just trying to keep your head above water, the impression of the first day really can cover a multitude of sins. While you do want to ensure the hard touches are there (accounts setup, paperwork completed), the soft touches really bring it home:

  • Be prepared to greet your new hire

    This might seem obvious, but be prepared when the new hire walks in the door - emphasize you are glad he/she is here. Give the appearance you are prepared for the day ahead (even if you’re not).

    If you have an unavoidable conflict during the time your new hire is set to arrive, delegate someone else in your office to greet the new hire and get the day started. There is nothing worse than the new hire walking in, only to realize no one is prepared to meet them (yikes). I have personally seen this happen - let’s just say it doesn’t set the right tone.

  • Have swag on their desk

    Nothing says “welcome” like a pile of new swag on your first day. You might shoot for the stars with t-shirts and coffee mugs, or keep it simple with a company notepad and stress ball. But having something there - whatever it is - sends a message that you are excited to have them! Here’s more inspiration on how to create a winning welcome kit.


  • Have a detailed agenda for the day

    So simple, yet so over-looked. Nothing says you forgot to plan ahead than saying, “O, go find Susie and do a sit in at her desk…for 6 hours.” Even if the list is simple, the very act of having one sets a good tone.

  • Arrange a team welcome lunch

    Maybe you already do this - but if you don’t, I strongly encourage you to start now. You can make it a big to-do and have the entire office go out somewhere, or keep it simple with pizza in the conference room. Once again, it’s not so much what you do - it’s that you actually do something to celebrate and welcome the new member on your team.

Set yourself up for success by creating an internal Trello list for these items too. It helps keep the people responsible for those soft touches accountable, since it’s a tangible task with a due date.

And one important thing to remember is that the new hire wants and values communication from you! Sometimes we shy away from detailed instructions or over communicating, so as not to give the impression we will be micro managers - but you don’t want your new hire to feel like he/she is on an island. Sometimes more is better, with a gradual move toward independence.

Week 1-2

Almost equally important as the first day is the first two weeks. If your new hire has a rockstar experience on day one, but then feels left out to dry after that, you’ve taken two steps backward.

Here are a few, simple things to incorporate into the new hire’s first couple weeks:

  • Schedule touch bases throughout the first week

    This is especially important for remote new hires, or if the new hire’s training is primarily spent with a peer. Having this time set aside provides an avenue for questions, and builds relationship from day one.

  • Paint the big picture

    Before you start getting into the weeds, give your new hire the big picture. What does this mean? Before you dive into the tactical, make sure you explain the why. Do you have a presentation that covers the company’s mission, core values, and approach to business? Get your new hire excited about joining the team before you throw him/her into the deep end.

    Painting the Big Picture

  • Overview biggest priorities

    The first few weeks at a new job can be information overload - you may have multiple projects that intersect, and several goals you are simultaneously working toward. How can the new hire start providing value right away? With no background on past projects or ongoing initiatives, this helps level set expectations and gives clear direction of how time should be prioritized.

“The way your employees feel is the way your customers will feel. And if your employees don’t feel valued, neither will your customers.” - Sybil F. Stershic

A plan makes it all possible

So what about Steve? You know, the leader who was overcome with dread at the looming idea of onboarding his upcoming new hire.

Let’s go back in time, and pretend his warm and fuzzy feelings did not fade. Why?

  1. He took the time to create a plan.
  2. He created Trello boards.
  3. He put together training objectives.
  4. He delegated tasks he knows will get lost in the shuffle if he tries to do it all himself.

All of a sudden, those feelings of dread are replaced with feelings of confidence and anticipation. And just like that, the onboarding experience helps set the state for the new hire’s successful transition to your team.

Onboarding Plan

If you think “I don’t have time to do all those things,” you can’t afford not to. Delegate things like account set ups and paperwork to someone on your team who is organized, and has the bandwidth. This frees you up for the soft touches that only you as the leader can do. But don’t just welcome someone to the team, then dish them off. While much of the training might involve more time spent with the new hire’s peers, make sure you are still the “face” to the onboarding experience.

Other ideas to consider

In addition to the ideas above, we’ve also found these other steps helpful when it comes to onboarding and team culture:

  • One on ones

    Set up weekly one on one’s with your new hire. They can be as long as an hour, or as short as 15 minutes. But having the time set aside provides a regular touch base to discuss projects, updates, concerns, and questions. Consider implementing this team-wide if this isn’t part of your culture already.

    One on Ones

  • Regular feedback tools

    Consider utilizing a platform that allows employees to provide timely, ongoing feedback. The questions for new employees vs. current employees will look different. Having that real time opportunity to gain feedback on the onboarding experience is incredibly valuable, and also sets the precedent for the employee to continue providing honest feedback as he/she advances. Here at Headway, we utilize Lead Honestly.

  • Assessments

    Does your company utilize any type of personality/emotional intelligence assessments? If you sigh when you hear this, stay with me. While past experiences or perceptions can sometimes cause business leaders to avoid utilizing these for their teams, the advantages can be invaluable - namely, if the assessments are done well and at the right time.

    • Consider implementing these in a new hire’s first week to understand how he/she approaches problem solving, deals with conflict, or works in a team environment.
    • By having your entire team complete these, you will gain greater insight to co-worker interaction and strengthen relationships among the group.

    At Headway, we use the DISC profile, EQ-i, and MCORE assessments. Another popular personality assessment is the Myers Briggs Type Indicator (MBTI). We then share and discuss the results within individual teams, so that everyone can incorporate that knowledge into their day to day interactions.

Where to go from here

Putting effort into onboarding updates can seem daunting, and even unnecessary - but it has been proven over and over that a well maintained process is proven to show greater engagement, retention and productivity. So create a plan. Implement. Delegate.

By doing so, your new hire can help you make even more of those killer products and take your growth to the next level.

Onboarding tools and resources mentioned

Here is the full list of tools and resources we linked throughout this article. Just in case you missed it somewhere along the line, we put them all together right here for you.

Tools and applications

Trello - Helps manage all of the to-dos!

Mailchimp - Create seamless email templates

Notion - The all-in-one workspace for note-taking, project management and task management

Hello Sign - Go paperless and streamline all of those important documents

Lead Honestly - Engage your employees with insightful and one-on-one assistance

DISC profile - behavior assessment tool which centers on four different personality traits (Dominance, Influence, Steadiness, and Conscientiousness)

EQ-i - Assess emotional intelligence with an intuitive model, custom reports, and easy online administration

MCORE - A quick assessment tool built to understand your employee’s unique motivations

Myers Briggs Type Indicator (MBTI) - Introspective questionnaire indicating differing psychological preferences in how people perceive the world around them and make decisions.

Online guides and resources

Getting Started Guide - Learn the basics of Trello

Article from Crate around onboarding new employees (plus their onboarding checklist)

Federal I-9 resources

How to create a winning welcome kit from Packlane

Other inspiration

To keep your juices flowing, here are some other places for onboarding inspiration:

10 Tips for Successfully Onboarding your New Hire - this article is filled with practical advice from Morag Barrett, founder of SkyeTeam.

Nobody Puts Onboarding in a Corner - in this short read, Sara Polllock reminds us that onboarding does not need to be a burden.

Onboarding Buyer’s Guide - available from Clear Company, this guide provides a place where you can take a deeper look at your timeline for potential changes.

Soapbox - use this online tool to create short informational videos. A visual of the Trello board can be helpful to see in advance, and puts a face to a name before the new hire even arrives! Win.


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