Never underestimate the power of a simple check-in. It might seem like a small gesture, but check-ins are an essential element of strong communication and can be a source of employee empowerment. While regular check-ins are valuable in all sorts of relationships, when you’re building a business, checking in with your employees not only improves morale but can also drive growth, retention, and long-term success.

1. Practice healthy communication.

These communication themes can impact a range of outputs, from efficiency to engagement and retention.

Positive: “How’s that report on widget theory coming along—any support I can provide?”
Neutral: “Do you have that report on widget theory finished?”
Negative: “Where’s the widget theory report I asked for yesterday?”

While all of these questions are driving toward the same topic, the outcomes of those question styles will differ dramatically. Not surprisingly, good check-in outcomes rely on good check-in questions.

2. DO check in, DON’T micromanage.

While a check-in can be helpful and motivating, micromanagement is often de-motivating and hinders progress. Without thoughtful framing, a well-meaning check-in question could be perceived as micromanagement. For anyone who has worked under a micromanager, you know precisely how much it can erode trust and respect.

3. Optimize check-in cadence, context, and cause.

Understanding these three key elements is critical to making your check-ins mutually beneficial.

Cadence helps define the value of both the question and answer. If the answer isn’t likely to change since the last check-in, the cadence is too short. Anyone who has been on a long car ride with kids has likely heard, “Are we there yet?” countless times. The more a question is asked, the less valuable it gets.

On the flip side, you can miss a lot of important information if you wait too long between check-ins. If you’re asking how happy your employees are once a year, you’ve almost surely missed opportunities to provide support and guidance.

There’s no perfect cadence for all check-ins or all employees. The key is simply paying attention. Find a cadence that aligns with your mutual goals and adjust as needed.

Context aligns your check-in to the topic at hand, setting your recipient up to give the most relevant and useful response. If you schedule a meeting to ask someone who’s in the midst of a time crunch how connected they feel to their remote peers, that’s an example of poor context. Whereas checking your employee’s calendar in advance and scheduling your meeting with their time in mind sets the stage for a more valuable check-in.

Cause defines the level of discretionary effort and cooperation you’re likely to experience.

If you’re checking in because you want to provide support during a difficult time or on a challenging pursuit, there’s a greater chance you’ll get candid and helpful responses. However, if your check-in exists purely to serve your own interests, it’s less likely to inspire the same discretionary effort.

4. Find your balance.

A successful check-in strategy hinges on the balance of individual and shared benefits. This simple litmus test can help you find that balance.

Are these questions:

Asked often enough?
Asked too often?

Is this check-in:

Contextual to the situation?
Relevant to the recipient?

Is this check-in:

For my benefit?
For my employee’s benefit?
For our mutual benefit?

5. Know your data needs.

A successful check-in starts with formatting the questions in a way that helps your employees give meaningful answers. Next, you need to determine what kind of data you’re hoping to capture.

Quantitative Data - Data that can easily be quantified, codified, and viewed in aggregate. Quantitative answers are usually much faster and take less mental bandwidth to give.
Qualitative Data - Data that cannot easily be quantified and typically require more time and thought.

To determine what type of data you need, check in with yourself as you’re forming questions:

“What do I need to learn from this check-in?”
“Why do I need to learn that?”
“What will I do with the knowledge?”

6. Standardize your check-in formats.

The number of formats you can ask a question in are almost unlimited, but to standardize the answers, these are some of the most popular and easy-to-digest options:

Open-ended: Do you feel appreciated?
Multiple choice: What makes you feel appreciated?
- a) Positive feedback from my boss
- b) Positive feedback from my peers
- c) Raises/bonuses
- d) All of the above
Multi-select: What would make you feel more appreciated?
- ☑ More schedule flexibility
- ☑ More praise
- ☑ Better benefits
Numeric range: On a scale of 1-10 with 1 being not at all, and 10 being extremely, how appreciated do you feel?
- 1 | 2 | 3 | 4 | 5 | 6 | 7 | 8 | 9 | 10
Descriptive range: I feel appreciated:
- always
- sometimes
- never
Illustrative/emoji range: Thinking about how I’m appreciated at work makes me feel:
- 😃🙂😐😕☹️😫

If you’re looking for a laser-focused answer, then it’s only logical to ask it in a quantitative format, such as the 1-10 scale. But that data can only tell you if there’s a problem - not why. That’s where qualitative follow-up questions come in.

For example, if your goal is improving your team’s remote work experience, follow your 1-10 scale with an open-ended question: “What’s one thing that would improve your remote work setup?” This allows you to see that there’s a problem and start working toward a solution.

7. Structure your questions to better answers.

The trick to getting a useful answer without burdening your audience is to narrow the response range. You want to narrow the range enough that it makes the question easy to answer, but not so much that you lose the depth needed to move forward.

If you ask a series of open-ended questions, you may find that your employee struggles to answer in good time (or at all). Again, balance—between the type of info you need and the burden it requires—is the key.

Just remember, whether you’re the CEO or just starting out, we all simply want to be heard. Doing a little work on the front-end to ensure you’re giving your team the best possible employee experience can go a long way in growing your business.

"A successful check-in strategy hinges on the balance of individual and shared benefits."

About the author: Audra Aulabaugh is the head of people operations at Polly. Over her people-focused career, Audra has built talent acquisition and people experience frameworks to support a variety of tech companies at various stages of growth and scale. She is passionate about people and creating experiences that allow them to shine and do their best work.

Featured image: Smith House Photo