10 Questions You Should Ask Your Remote Employees To Keep Them Engaged

March 31, 2020

This post was written by Baili Bigham at 15Five

Building and maintaining a strong company culture can be difficult when you only see your team for several minutes each week and can be especially challenging if these moments aren’t optimized to be high-impact conversations. One of the easiest ways to combat this common challenge with your remote employees is by asking the right questions. 

Questions are how people form deeper bonds and build mutual trust. By digging deeper and asking questions that are purposeful and at the right frequency, you can establish a better team structure and cohesion that helps to turn your imaginary office into something tangible. This practice allows company leaders to connect their teams and makes room for a highly engaged workforce, even from a distance.

Here are ten questions designed to help you maintain a resilient culture and support your remote employees and teams wherever they decide to work.

1. How are you feeling, and what’s your energy level?

This one may seem obvious, but when everyone works in the same physical space, managers can easily stop by their employee’s desk and check-in with them. Even nonverbals can give insight into how your people are feeling, but it’s not as easy to pick up on these feeling states and energy levels over a slack message or email.

At 15Five, we use the practice of Intentional Energetic Presence, or IEP. This can be easily adapted in daily practices, like at the beginning of meetings, and the goal is to be open and honest about how present you are at that moment. You can share your IEP level using a scale of 1 to 10, with 1 representing the lowest energy level and disengagement, and 10 being the highest, most present energy level.

Asking this question often let’s your people know that you care about them as humans, not just as employees. 

2. What challenges are you facing? What wins—big or small did you have last week?

This two-part question is no stranger to remote or in-office employees at 15Five. We often ask this because it’s important to find out what’s not working well so we can catch issues before they grow and become out of hand, but most importantly, this question helps you learn what’s going well.

Allowing your remote employees to share both big and small wins is an important opportunity for you to recognize their hard work. Each experience of receiving thanks or appreciation brings with it a brief moment of emotion that will contribute to a sustained sense of positivity. Plus, asking this question regularly lets you celebrate the positives more often and remedy the negatives more swiftly—an important characteristic of any agile business.

3. What do you think could help us to improve daily communication?

Every person is different, and therefore, prefers different ways of communicating. Learning these preferences of your remote employees can help make your 1-on-1 meetings more impactful because it isn’t perceived as a stretch or disruption. For example, improving daily communications could mean setting up quick, virtual stand-up meetings in the mornings to go over what’s on the agenda for that day, or it may mean something completely different, like blocking certain parts of the day so your employee can stay in flow.

4. What part of your role is the most energizing, draining, and purposeful?

Part of being an effective coach for your employees is learning about their unique strengths and abilities. An easy way to do this is by making it a habit to ask what parts of their day they find gives them the most energy and excitement so you can understand what’s driving their performance, what they find difficult or draining to find out what’s hindering their growth, and what type of work they find is most meaningful to learn what they’re passionate about.

As remote employees develop in their own career paths, they will naturally be given tasks that they can be trusted to execute well on, but the kicker here is that they may not particularly find joy or enjoyment in doing those assignments. A manager may never know this without explicitly asking. This question can help you find out what specific practices are truly driving their overall performance and fueling their motivation so that you can curate more opportunities like them.

5. What skill would you like to develop or improve?

Fortunately, today’s employees don’t have to stick to predetermined career ladders because there is more flexibility to pave their own paths for career growth. As the progression of technology speeds up, new pathways for personal development in the workplace begin to take shape, but for those working remotely, they may not be aware of the resources that may be available to them.

Employees have a deep desire to grow their skillsets, personally and professionally, and it’s the job of their manager to help them do it. Create the space to learn more about your remote employee’s interest and empower them to grow and develop alongside the company, rather than apart. 

Furthermore, upskilling adds to an employee’s wheelhouse and replaces outdated methods that may be hindering your company, because your workforce may be moving backward just by standing still. 

6. Are you crystal clear on your role and what you should be working on? If not, what aspects aren’t clear?

Role clarity paves the way for psychological safety in the workplace. Without this direction, employees will work towards a path they can only assume is correct. Oftentimes, these insinuations turn into misalignment, and employee development can be slowed down significantly, especially for remote employees who are more prone to feeling isolated if they don’t have a strong connection with their manager.

Check in with your employees by asking this question regularly and help them define what success looks like for their role so they can continually strive for it. 

7. When do you thrive the most—when you collaborate with other team members or when you have time by yourself?

Not every employee has the personality type that allows them to easily speak up when they have something they’d like to say, but as a manager, it’s your responsibility to help your remote employees feel like they have a voice. If your employee tends to be more introverted, they often have a preference for space to develop their own ideas. Managers can use this question to learn about their employee’s collaboration style and use this information to create more cohesive relationships between them and their team.

8. What’s one personal goal that you’d feel comfortable sharing that the company can support you in achieving?

Productive employees will often do whatever it takes to get the job done, often going above and beyond. Although this can be viewed as a good way to work, it may not be the most optimized route to take. Not every task should be aimed to fulfill a business objective—in order to grow, employees must also focus on personal development. 

But, personal and professional goals don’t have to be at odds with one another. It may seem strange for a manager to support a personal goal, but those are the type of experiences that create strong work relationships and deeper levels of commitment, especially among dispersed employees. In fact, when people feel fulfilled in both realms, they bring more energy to work and not less.

9. What has communication been like with team leaders, managers, and directors?

Genuine conversations and consistent human connection have the power to bridge gaps, whether they are educational, generational, or hierarchical. But if your organization doesn’t offer mediums like conversation forums and company-wide survey prompts to encourage remote employees to give feedback and connect, it may be challenging for them to have open communication. Continuously supporting your employees to get out of their comfort zone can help your teams avoid silos. 

10. What do you do to take breaks and recharge throughout the day?

Working remotely comes with many perks, but it also comes with it’s own set of challenges. Specifically, it can be difficult to separate work and personal time if both happen in the same place. Check in with your remote employees and help them set boundaries between these moments. By asking this question, you can ensure they are taking these much needed breaks throughout the day and aren’t overextending themselves, which can quickly lead to burnout.

Ask this question to gauge how your remote employees are collaborating across the organization so you can better support their efforts in stepping outside of their normal conversations and fostering new connections.

Today, many companies are beginning to shift more towards remote work, some for the very first time. For those who might be nervous about this transition, use these eight questions in your 1-on-1s to facilitate more meaningful conversations and continue building a strong connection with your remote employees and teams.

Baili Bigham is the Content Manager at 15Five, continuous performance management software that includes weekly check-ins, OKR tracking, peer recognition, 1-on-1s, and 360° reviews. When Baili isn’t writing, you can find her binge-reading a new book or strategizing ways to pet every dog in San Francisco. Follow her on 

March 31, 2020
Hilton Thompson