Beyond the Checklist: Building Belonging During Onboarding

Preboarding was paperwork. Now it’s on to the “watch and learn” stage of onboarding, where new hires sit on the sidelines and wait to fit in. They only want to do well at their jobs. The company checks in at regular intervals, just as the checklist says. 

However, this lack of belonging in the earliest days counts against companies. 

TL;DR

• Onboarding checklists often don’t include enough human interaction.
• Peer involvement is a must for building belonging during onboarding.
• Including people early in rituals makes them feel genuinely welcome.
• Some organizations include more AI in onboarding than new hires are comfortable with.

Why onboarding checklists prevent early belonging

Building belonging during onboarding is about being known, not told. Interacting, not performing. 

Checklists are about compliance and completion. Both the company and a new hire get a sense of finality from finishing forms and paperwork. The transactional framing inadvertently keeps us from building a stronger connection. The type of connection that helps us survive the bumps and snafus of fully acclimating over the first few months. 

Obviously, we still need checklists. Conforming (legal requirements, codes of conduct) is as important as authenticity (culture, identity) at work. But putting the checklist first and concluding it as a priority is a symbolic, unspoken shutting of the door.

Core strategy 1: Putting culture and connection up there with compliance

You’ve spaced out the form-filling and info dissemination to prevent overwhelm. This strategy leaves room for us to sprinkle some character into the process. What have you told your newbie about the culture, and would they agree with those claims a month later? 

Design multiple human touchpoints

Human interaction proves your company is what you said it is. You can say, “Our culture is radically honest and transparent.” A new hire who isn’t getting feedback or being asked what they think in the first weeks will feel excluded from the culture they were promised. 

Culture-specific activities right at the start aren’t the only (or even best) solution to this. It’s letting new hires personally discover or observe these qualities in the humans they work with. A few examples of how you might weave the human touch into your hybrid/remote onboarding:

• Short videos (with faces and voices) for welcomes or bite-sized knowledge sharing.
• Onboarding buddies who take the initiative to check in with them and want to answer questions or give a heads-up.
• Live call from a manager where they share why they think the new employee is a good fit, not the logistics of the job.
• Morning huddles a few times during the first weeks where everyone can ask questions, not just the new hire.

Make the first day about people instead of paperwork

If there’s just one day during the process when a new hire won’t be filling out a form, make it the first day. Use one or two of your human-touch ideas here, or pull from these examples and tips:

• Always make sure any questions a new hire has are answered quickly on that first day.
• Have peers or leadership tell stories about the founding of the company or notable events/memories. Do not use a slide deck.
• Have lunch together, virtually or physically. It’s not a meeting, so no updates or statuses. Informal discussion about interests, weekend plans, etc.
• Peer-created survival kit. Whether it’s a document, a chat thread, or a box bestowed upon them on-site, have the team share this. It can contain advice, resources, or small gifts that make someone feel wanted on the team.

Core strategy 2: Using AI in onboarding without erasing humans

It’s not like we all collectively decided that we don’t want to bother with onboarding tasks. It’s just that automation made it really easy, really fast. 

When first adopting AI in onboarding, we all figured it could do compliance stuff. We now had time and bandwidth to focus on making them feel welcomed as a person. But somewhere along the way that line got very blurry, so here’s your reminder.

Where AI in onboarding helps:

• Pre-filling forms
• Buddy scheduling
• Standard information delivery
• Personalized learning paths
• Basic queries (“Where is...?”)
• Auto-nudging paperwork

Where it doesn’t:

• Welcome messages from “the team”
• Cultural norms
• Introductions
• Emotional support
• Detailed feedback
• Negotiations
• HR discussions

In short, if an AI feels like a coworker or manager to a new hire, it’s over. Most people expect they’ll interact with AI on the job. When it starts to become a larger presence in the daily work environment, it influences culture and connection more than you do. 

Core strategy 3: Community tops the new remote onboarding best practices

Rituals replace “rules” on remote-first teams. By rules, we mean the social norms and expectations every workplace has that in-person hires learn by osmosis. Everyone’s sense of humor, what they celebrate and value, and even the best time to ping them. 

Engaging in digital rituals

If there’s anything a remote team does (especially if it’s informal or barely spoken), introduce a new hire to it right away. Some of the rituals we see async teams enjoy:

• Virtual taco showers to welcome new members. Instead of educating a new hire on how recognition is done, their peers just show them. Hires may have to ask, “What’s that?” once, and then never again. 
• Recognizing core values during the Friday wins meeting. This is more proof that the company represented itself accurately.
• Welcome threads with memes and GIFs. If casual or humorous interactions are part of team communication, new people need to feel as though they’re part of that right away.
• Recognizing their first (and smallest) wins in chat. A lot of people starting new jobs log off and review everything they missed or could have done better. Highlighting what went right takes the edge off.
• A peer-made virtual welcome whiteboard. Doodles, warnings, and well-wishes. Or a map of what they should know in the first week. The only requirement is that it’s inside baseball, not top-down info.
• Everyone shares their Work With Me guides. Do they always use that emoji? Am I bothering them? It truly is the small stuff making new members feel unsure or awkward. These standing docs eliminate a lot of that.

Measuring what’s working

The number one rule of remote rituals is that if it’s not landing, ditch it. This is a lot easier to follow through on when only 8% of your existing team shows up to your Zoom mixer. Here’s how to apply that to new remote hires and be sure onboarding is doing its job (making them feel like they belong).

1. Quick psychological safety check. Did they ask their peers questions in public channels? Did they admit to their manager that they didn’t know something? These are great signs. 

2. Relational depth. They may not be besties in the first two weeks, but are they participating in casual, non-work exchanges? Have they recognized a peer for their contributions the way others do?  

3. Realistic view of their role. What we thought we were hired to do and what we end up doing can differ. Did they need further, down-the-line clarification on how their share of the work impacts the company? Were they answering notifications in the middle of the night to seem hyper-available? 

These are early signs of stress, even if no one is directly putting pressure on them.

Building belonging during onboarding isn’t a bonus, it’s the goal.

A welcome from a manager doesn’t make you feel like you belong long-term. Training doesn’t, either. Checklists can introduce new hires to policies, but it’s the people they connect with who will ultimately make them care about your organization.

Praise and celebration can be part of casual, everyday connections with peer recognition. HeyTaco helps thousands of teams globally achieve this, weaving human connection and culture-strengthening digital rituals in one lightweight, lighthearted app.

"The team has gotten into the habit of assigning someone new every time a hire joins. 'Alright, who's teaching them about HeyTaco? Who's showing them how it works? Make sure they're set up right.'"

• A.J. Kissh, Outbound Sales Pro

See how it works for yourself, and bring every new hire out from the background and into belonging.