Improve Employee Retention by Adding One-on-Ones to Your Onboarding Checklist

Cover image for onboarding checklist blog post

For managers, the first 90 days of a new hire’s employment are a singular opportunity to secure their buy-in to your company’s values and culture. Yet often, employees never even make it to the end of onboarding.

According to a Jobvite survey, 30% of employees have quit a job in the first 90 days.

Clearly, managers need to identify and address the most common issues causing employees to jump ship and make sure that new hires leave onboarding prepared for success. But that’s difficult if your only tool is an employee onboarding checklist you only use during a new hire’s first few days at work.

To ensure your employee is equipped to not only stick around but thrive after onboarding, start holding one-on-one meetings with them their first week, throughout their first 90 day, and beyond.

There are some topics you need to address right away, and others that you need to bring up later, as a new hire gets more comfortable and has a better sense of what they need. In this piece, we’ll go over the most common onboarding issues for employees, and how managers can get ahead of them at 30, 60, and 90 days.

Clarifying Expectations

The Jobvite survey mentioned above found that the number one reason new hires leave in the first three months is that their “day-to-day role wasn’t what they expected.” This expectations gap has been observed in other studies as well; in a Bamboo HR survey, 23% of respondents said they might not have quit had they had clear guidelines about what their responsibilities were.

The number one reason new hires leave in the first three months is that their “day-to-day role wasn’t what they expected.”

To provide this clarity, you need to touch-base and discuss expectations, both theirs and yours, every month. If there are areas where an employee’s new role doesn’t fit with the job description, this is the time to get in front of those problems and address them head on. It might mean this new hire really would be happier somewhere else, or it might mean you can tailor their role to their skill set.

First month of onboarding checklist

During the first month of onboarding, set short-, medium-, and long-term goals, defining when an employee is supposed to be proficient at the various aspects of their job. There are things you need them to pick up quickly (like a familiarity with internal tools), and things they will learn gradually (like a fine-grained expertise about customers), but new employees won’t know what to prioritize unless you tell them.

In your first one-on-one meeting, go over onboarding materials that lay out detailed expectations for the next three months (at a minimum). Lay out what they are expected to know, and when. If an employee’s role is wildly divergent from their expectations, both you and they should figure that out ASAP to determine if adjustments can be made, or if this is just a bad fit.

At every juncture, slow down and ask if the new hire understands what is being asked of them. Remember, everything is new to this person, from the finer points of the employee handbook to the location of the break room, so don’t expect everything you’re saying to stick the first time.

Lastly, ask if they know who to talk to if they get stuck–whether that’s a more experienced colleague or human resources–and if they feel comfortable seeking that assistance.

Second month of onboarding checklist

No matter how effective your first month of onboarding is, a new employee won’t be able to absorb everything you’re asking them to learn, so this is your chance to make sure nothing major has fallen through the cracks.

Review the areas an employee is supposed to be proficient in at this juncture. Ask what they understand, and what they’re still unclear about. Provide resources and support to address problem areas.

Ask employees if they’re still getting stuck often, or they’re starting to be able to complete tasks on their own.

Third month of onboarding checklist

By this point, an employee should have gotten a sense of what their responsibilities are and have an idea of how happy they’re likely to be at this job. If there’s a mismatch that’s threatening their commitment (for example, an introverted, data-driven person being assigned a lot of customer-facing duties), it’s a chance to make adjustments. 

Ask the following questions:

  • “Does the work you’re doing meet with your skillsets? Are there other areas of the company you think would be a better match?”
  • “Do you see opportunities for learning and growth here? What do you hope to learn in the next three months/six months/a year?”
  • “Does your role here match the job description you had when you accepted the position? If not, what areas are you finding particularly challenging?”
Would you like to boost productivity, increase trust and have a healthier, happier team?

Download your FREE 1:1 guide now!

(Really) Getting to Know You

Aligning with your new hire on expectations is vital to keep them from quitting during employee onboarding, but retention is only half the battle. The other half is actively setting a new hire up for success from their first day, and that requires learning what each individual needs in order to thrive. Of course, a new hire might find it difficult to advocate for themselves on day one, so these questions also need to evolve over the first three months.

First month of onboarding checklist

Ask questions about their work style so that you know how to support them. Different employees thrive in different environments, and you want to create the circumstances that bring out the best in each individual.

Ask the following questions:

  • “What is your learning style? Do you learn by doing or do you like to have detailed walkthroughs before you attempt something yourself?”
  • “What time of day are you most productive? Do you like to have uninterrupted focus time in the morning, for example?”

You should also take the time to ask “How are you?” As we’ve discussed before, this question is a powerful tool if you ask it with intention, and communicate with your tone and body language that you care about the answer.

Second month of onboarding checklist

Ask more personal questions, which they should feel more comfortable answering at this juncture, and which will establish your investment in them as a person. (And for more ideas on how to approach these questions, check out our blog on the subject.)

Ask about their hobbies outside of work, their pets, where they’re from. Building a rapport and learning an employee’s sense of humor is crucial to relating to each other as human beings, and opening up genuine communication.

Introduce your company’s core values and ask which ones a new hire sees as growth areas. Would they like to become better communicators? Are they interested in building leadership skills?

Third month of onboarding checklist

Dig deep into what you as a manager can do to support this employee, building on what you already know about them. Hopefully, by now they’ll be comfortable enough to give honest answers even to challenging questions.

Ask the following questions:

  • “What is your relationship to praise and criticism? Are you sensitive to one or the other? How do you like each to be communicated?”
  • “What can I start or stop doing that would help you succeed? Do you want more frequent check-ins? Fewer?”
  • “If you’re struggling with an assignment, how do you deal with it? Do you dig in and try and solve it yourself? Do you ask for help? What should I be looking out for?”

Learning Your Own Blind Spots

The Jobvite survey found that, after the expectation issue, company culture ranks high on the list of reasons why new hires leave, with 32% citing it as a motivator. Everything you do—from your welcome email to the office layout to the way you deliver praise and criticism—communicates a message about your company’s culture, and it’s important to put your best foot forward while a new employee is onboarding. But onboarding is also an excellent opportunity to learn about your culture’s weak spots from a new person with a fresh perspective. Asking about these issues will not only make a new hire feel like their opinion is valued, it’ll help you build the kind of workplace where turnover isn’t an issue.

First month of onboarding checklist

The most important thing for the first month is to make a new hire feel connected and supported, not just dropped in the deep end and left to fend for themselves.

Ask if they’ve had a chance to get to know the rest of the team yet. If the answer is “no, everyone has been huddled over their own work,” you should make some time for some low-pressure, team-wide conversations.

It’s also a good idea to ask who on the team has been particularly helpful in getting your new hire settled. That’s useful information for you to have, and it will also prompt your new hire to pause and reflect on positive interactions they’ve had at the company.

Second month of onboarding checklist

This is the perfect time to actively solicit feedback from a new hire about their impressions of the workplace’s shortcomings. These are the things you’ve gotten used to but which are causing turnover.

Ask the following questions:

  • “What about our work processes doesn’t make sense to you?”
  • “How would you describe our overall culture in a few words? Warm? Relaxed? Demanding?”
  • “How could we improve our communication between team members? Are the communication channels we have meeting your needs when you have a question or want to raise an issue?”

Third month of onboarding checklist

Employees coming out of onboarding are the only people who can give you an accurate picture of the onboarding process itself, and you should continually refine your procedures based on their feedback.

Ask the following questions:

  • “How would you rate your onboarding experience? How does it compare to onboarding at previous jobs?”
  • “Do you have any ideas for how we could improve our onboarding program? What could we have explained better? What did you find most stressful?”

Beyond Retention to Inspiration

Think about your most inspiring manager, mentor, or teacher. They didn’t just prod you along in the right direction, they harnessed your passion, and made you want to give them your best.

The only way to bring that kind of dedication out in a new hire is by modeling it yourself, starting with these critical first impressions. Having strategic one-to-one conversations during a new hire’s first 90 days is a powerful way to ensure you’re not losing top talent to a bad onboarding process. But it’s also the process by which you make good employees: people who are motivated, supported, and fully engaged.

Download your FREE Ultimate Guide to 1:1s

Learn how to have productive and meaningful conversations and boost productivity, increase trust and have a healthier, happier team! 

Subscribe below to get future posts from Michael