George Dickson - January 29, 2020 -
13 Min Read

12 Questions to Ask Employees in Your Monthly Meetings

Successful leaders and organizations recognize the irreplaceable value of employee feedback and insights -- but it’s not always clear what to look for, how and when to gather those insights, or how to apply what you’ve gathered.

Don’t worry -- that’s what this guide is all about. 

We got a lot of positive feedback from the community on this guide, so we updated and expanded it with even more useful info.

Let's break down some of the most important elements to evaluate with your team, outline the best ways to build them into your daily employee experience, and apply your learnings toward meaningful outcomes.

What do you need to do?

Timely, contextual, and omnidirectional feedback loops are the key to building the kind of institutional knowledge that can alter the trajectory of a company’s culture, team morale, productivity levels, and overall employee engagement.

Why is that so important to get right?

Research shows that a dismal 15% of workers around the world feel engaged with their job. Look around you: that means you’ve probably got one, maybe two actively engaged employees in your line of sight, and that’s an optimistic estimate.

OK, but why does that matter?

Employee engagement has a dramatic impact on your organization’s bottom line. A Gallup study of 32,000 employees across 30 countries found that engagement has a significant impact on everything from productivity to inventory shrinkage and even earnings per share.

Research by Bain & Company found that "over seven years, companies with highly engaged workers grew revenues two and a half times as much as those with low engagement levels."

Despite its myriad benefits, the types of dialogues that lead to sustainable engagement don’t happen on their own, or as often as they should. Communication is one of the most significant factors in building sustainable engagement, and most organizations struggle with it.

Solid communication is more important now than ever.

Although communicating effectively with your team has always been a crucial component of a leader's skill set, developing strong feedback loops is more important than ever. With millions of employees working from home for the foreseeable future, many tried and true methods of communication are no longer available.

But I’m a great communicator, so I can stop reading, right? 

Don’t count on it. Most of us in leadership positions vastly overestimate the breadth and depth of our communication skills. Research from TINYpulse found communication to be one of the top influential factors for employee engagement; however, that influence worked both positively and negatively.

Most employees get very few opportunities to share or receive feedback, if they get them at all. Thankfully, many modern organizations are moving away from performance management strategies that rely solely on annual reviews as a feedback channel toward more effective, real-time feedback loops.

If annual reviews are on the way out, then what’s next? What should you be building your feedback loops around, and what should the cadence be?

Ideally, you’re gathering this feedback in the context of the work itself so the information is reliably fresh and relevant. With that information in hand, your scheduled check-ins are more productive, and the topics you discuss are more meaningful. 

That sort of system might sound hard to orchestrate, but it doesn’t have to be. Technology and creativity are your best friends here.

For example: an engineering manager might install a feedback loop that delivers an automated survey in Slack or Microsoft Teams after an issue closes in GitHub or JIRA, asking some key questions about the issue, like “Did you have easy access to the resources you needed to resolve this issue?” or “How well was this issue documented?”

Want to set up some contextual feedback loops of your own? We’ll show you how!

   Request a Demo

Supplemented with contextual information in advance, your scheduled face-to-face discussions with reports and peers will be richer, more strategic, and far more useful overall.

So let’s get to the heart of the matter: what are some good topics you should be discussing during those meetings?

It truly depends on your organization, what you’re working on, and what kind of relationship you’ve built with your team, but the following questions are pretty universally useful.

1. What was your biggest accomplishment this month?

We all like to congratulate ourselves once in a while, and recognizing accomplishments can go a long way toward helping stem the tide of disengagement spreading among full-time workers. This question builds on a sense of progress, while giving employees a chance to celebrate a job well done.
It’s also an opportunity to reflect on values in a meaningful way -- keying in on what they value most in their own accomplishments, and exploring how those accomplishments align with broader organizational values.

You also gain a sense of what types of work intrinsically motivates each member of your team. They’ll almost always be different from one another, and often different from your expectations.

It might be a surprise to learn that completing a large project wasn’t the highlight of someone’s month, but the collaborative process that led to the creation and development of new ideas.

2. What’s the biggest challenge you faced this month?

Asking about the challenges your team faced this month is the perfect follow-up to the first question. The resulting answers allow you to understand any struggles that may have slipped off your radar, or never caused a blip to begin with.

From faulty software to missed deliveries, employees function at their best when any issues are swiftly resolved. Your awareness and response to these matters not only makes you a responsible leader, but it fosters the trust and open channels of communication needed for a better company culture.

That trust is also a key factor in inspiring employee engagement. Research from ADP found that “A worker is 12 times more likely to be Fully Engaged if he or she trusts the team leader.”

Another good reason to ask about the challenges faced: it can lead directly to solutions that impact a much greater audience.

Questions like these posed in a trusting and transparent environment often lead to a resourceful and productive exchange. By better understanding the challenges your team faces, you’re more equipped to solve them and clear the way for your team to do the best work of their career.

3. What resources would help you succeed in your role?

A resource could be anything from a standing desk or quiet workplace, to software, or a more effective means of communication. 

A recent workforce study found 75% of US workers believe they don’t have access to efficiency-boosting technology. Whatever the answer happens to be, you’ll receive actionable information, which can be turned into positive change. 

The crucial element here is to follow up on the responses you receive. Even if it’s just to say that you’re not able to provide a particular asset, explaining why turns what would have been a frustrating one-way street into a productive and mutually beneficial dialogue.

The primary purpose of this topic is to understand the realistic changes that you can make to facilitate the success of your employees—information we all too often overlook.

4. On a scale of 1-10, how safe do you feel sharing new ideas?

Stacking a team with high performing individuals won’t necessarily produce a higher performing team.

So what does?

Research at Google confirmed that psychological safety – not core competencies, individual performance, or seniority – was the strongest predictor of a team’s success. In fact, of the five key dynamics that set successful teams apart from other teams, Google researchers found that “Psychological safety was far and away the most important of the five dynamics we found -- it’s the underpinning of the other four. “

If you’re working to improve performance, start with a foundation of trust and safety. Fostering an environment where team members feel safe to share ideas and, inevitably, sometimes fail will produce a more productive, innovative team.

5. What’s something we can improve as a company?

Each team member has a unique interpretation of their role within a company, as well as what they think the company could be doing to achieve better results. If they don’t, that’s an important data point (and talking point) in itself.

Tap into your team’s insights on a consistent basis and you’ll reliably receive valuable information. Employees with a vested interest in their organization’s success will respect and often actively support your efforts to continually improve it in any way possible. Employees who feel their voices are heard are also “4.6 times more likely to feel empowered to perform their best work.”

In addition to where you ask questions like these, how you ask them can be just as important. Some questions are inherently sensitive and best posed anonymously.
Providing your team that layer of safety helps ensure honest and candid responses about what your company or department could be doing differently, and with real-time results allow for quicker course corrections.

6. How can I improve as a resource for you?

This question is the bedrock of collaborative leadership. It requires more trust (and self-confidence) than the other questions mentioned above, as employees will be reluctant to answer honestly at the risk of upsetting their boss and triggering some form of subtle (or obvious) retaliation.

However, if you’re doing a good job of building an environment of psychological safety for your team, this sort of question will feel natural and welcome. When employees are empowered to open up, you might be surprised to learn what they have to say.

Questions like these also help foster a sense of ownership over the direction their work takes them, and reinforces that their opinions are truly valued at every level.
As Mark Tarallo explains in a recent article for the Society for Human Resource Management (SHRM):

“If serving staff is the bedrock principle of servant leadership, two core practices toward achieving that goal are close listening and searching questions.“

The better you get at asking and responding to these kinds of questions, the better you’ll be able to serve your team.

7. How’s everything going?

Just leave it at that and let them decide where it leads. You might receive a basic affirmative response, like “great,” but if things aren’t “great,” this is your chance to learn about an aspect of their experience you may not have anticipated. 

Open-ended questions also provide an opportunity to build a more human connection between you and your team. Are they struggling with the loss of a loved one, moving across the city, or juggling a full-time job with school or children?

Those are all crucial pieces of information for you to have, in order to provide them with the best possible working environment. Professionalism is important, so make sure you’re still setting appropriate boundaries. Checking in with employees and showing genuine human concern and empathy demonstrates your authenticity as a facilitator of their growth and success.

8. Are you blocked on anything?

If you’re not asking your team about blockers, you should be, and today’s a great day to start.

It’s hard to embrace accountability for a task if you don’t have the resources you need to complete it. It’s similarly difficult to complete a task you can’t reach behind a major blocker.

This isn’t about a failure to accept accountability; there are many things that can hold up an entire project, and they’re often not within an employee’s power to change or fix. Few things are more frustrating than missing deadlines and getting pressured by leaders because of a bottleneck you have no power or influence to bypass.

There will be times when you’re powerless to alleviate a blocker, but those aren’t the majority. It may be something as easy as a quick message to one of your colleagues in a different department standing between your direct report and their successful completion of a task (or series of tasks).

9. What’s something a colleague did recently that made a positive impact?

78 percent of employees surveyed in a recent study said that “being recognized motivates them in their job.” One of the easiest ways to ensure that happens is to empower employees to share examples of contributions their peers made that are worth celebrating.

Close colleagues will invariably be exposed to more examples of great work that deserve applause and recognition. It’s not practical (or even possible, really) for a manager to personally witness, recognize, and reward every contribution a member of their team makes.

This is why it’s so important to ask about it.

If you build a culture of appreciation within your team, it won’t be hard for each member to think of a valuable contribution someone made. Once you’ve developed a habit of noticing these things, they become visible everywhere.

10. What should I Start/Stop/Continue doing?

There’s a subtle, but important difference between asking this and asking “How can I improve as a resource for you?” This question is more specific and tactical, by design.

A lot of things you do every day impact employees in both large and small ways. That impact can be positive, neutral, or negative, and sometimes the only way to find out is to ask.

Employees who work closely with you (especially direct reports) notice things you could do better -- believe me, they notice. The key is to embrace the humility it takes to accept that, and ask for help honing your skills.

The start/stop/continue format works well for many leaders in this regard -- it’s simple, but it gets at key issues quickly and often candidly.

In order to get the types of feedback you need to improve as a leader, it’s paramount that you’ve established an environment of trust and transparency among your team. Without that sense of safety, it’ll be nearly impossible for employees to answer honestly without feeling as though there might be negative consequences associated with their answer, regardless of its tone or direction.

Conversely, having built an environment of safety and trust, you’ll be surprised at the many ways you can improve through the benefit of another person’s perspective.

It works like this:

  • What should I stop doing?
    • This question is rooted in the past, but it’s crucial for the present. You can’t undo an action, but you can end its repetition. There might be something as small as the way you’re scheduling meetings, or delivering feedback on projects. The only way to find out is to ask.
  • What should I continue doing?
    • This question is rooted in the present, but it’s crucial for the future. This is where you learn what you’ve been doing that makes a consistently positive impact on your team, and what you should probably lean into moving forward.
  • What should I start doing?
    • This question is rooted in the future, and it’s crucial for your ongoing success as a leader. It can be overwhelming to consider all the possible actions you might take to make a positive impact. That’s why it’s so useful to gather some feedback on this topic. Let your team help narrow down the field, so you can start taking action confidently sooner.

11. Which of our core values do you identify most closely with?

Authentic, powerful core values are a driving force. Understanding how they fit within your daily work can be an extraordinary source of intrinsic motivation. They're so important in the minds of organizational leadership that 90 percent of American companies report that they have a set of clearly defined corporate values.

But here's the problem: a small minority of employees (including those in leadership) know their organization's core values well enough to recite them.

How can you align with something that barely exists?

Asking questions that reference and relate to core values actively helps employees to build that connection between the values of their organization, and the sum of their contributions to it.

So what are your core values?

As someone in a leadership position, if you can’t articulate your organizational or team values (without sneaking over to your website's "About us" or "Careers" page) it’s high time to re-evaluate them, or re-evaluate your own alignment with them.

If your direct reports have difficulty with this question, that’s often a sign they haven’t internalized them to the degree that they see them in their work. As a leader, it's your responsibility to build and maintain that alignment, so take this as an opportunity to do that, and forge a more successful working relationship.

12. Of these three outside mentors I could introduce you to, which would you be most excited to meet?

Are you helping your direct reports grow and excel in their career? If you’re not, it’s to your own detriment, and that of your organization.

It might seem as though this type of thing is ‘above and beyond’ your job description -- after all, most managers have a great deal of their own work, metrics, results, and high-level goals they’re responsible for; however, it’s imperative to understand that as a leader, the performance and professional growth of your team is the most important lever you have to achieve those goals.

Actions you take to help your team grow not only provide the benefit of a more skilled or equipped team, they also foster engagement, intrinsic motivation, esteem, and confidence. 

These efforts can also be a meaningful factor in attracting and retaining employees long-term. 91 percent of Generation Z employees view professional development and employee engagement as leading factors when they’re picking a company to work for.

Better still, you (as a representative of organizational leadership) are visibly investing discretionary effort toward their continued growth and success, which can help inspire a reciprocative investment of the same sort of effort on their part.

In essence, the more time and effort you dedicate to building up the people around you, the higher you’ll all reach together.

Ask Better Questions Consistently, Get Better Results Reliably

Asking actionable questions on a regular basis is an excellent way to improve employee engagement, boost productivity, and establish stronger relationships with each member of your team. 

At its core, asking questions opens a channel of communication that can strengthen the environment of an office, and strengthen the organization it serves.

George Dickson

Written by George Dickson

Lives to learn and build cool things with good people.