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The Great eBook of Employee Questions

70 phenomenal questions to ask your employees along with detailed explanations on why you should ask them. Build company culture, increase productivity, raise morale and bring your remote teams together, and achieve a host of other desired business outcomes. This edition includes a Genius Question Bank with questions designed by well-known entrepreneurs and thought leaders.

The Great eBook of Employee Questions

  1. 1. 1 | The Great eBook of Employee Questions 15FIVE.COM The Great eBook of EMPLOYEE QUESTIONS
  2. 2. 2 | The Great eBook of Employee Questions 15FIVE.COM INTRODUCTION: THE POWER OF QUESTIONS Warren Berger, author of A More Beautiful Question explains that as children we ask more than 300 questions a day. As adults, that number plummets to merely a handful. Perhaps that’s because we are less curious, or because we have already gained fundamental knowledge on a diverse number of subjects. Unfortunately, I believe that many of us are afraid to ask because of how we might be perceived. This is especially true in competitive workplace environments and when leaders are unresponsive. Curiosity is vital for building thriving companies and for fostering healthy relationships between co-workers. Good questions have the power to spark innovation, avoid fire-drills, and help employees show-up as their best selves. In business, we are often so results-focused that we can discourage the disruptive thinking that leads to success. Asking questions lets us take a second look at what we hold to be true and what we view as false. When we ask questions, we begin to see that the “truth” is often based on subjective beliefs that can be reinvented or transformed. When we focus more on answers than questions, we deprive everyone of an opportunity to grow. Relationships suffer, because nothing makes people feel more marginalized than telling them your impressions about their experiences, feelings, or motivations. But asking a direct question about another’s experience allows them to feel more seen, heard, and fulfilled. Asking questions can improve business outcomes and even save hundreds of hours each week. The practice can boost team performance and focus. But asking thought-provoking questions takes skill, and only the right questions will inspire creativity and yield the results that managers desire. Done well, this practice inspires others to solve problems, and to think spontaneously and creatively. There is a saying in the legal world - Never ask a question to which you do not already know the answer. I will modify that for the business context - Never ask a question unless you know what you are trying to achieve. A well-crafted question can inspire and illuminate, and often brings co-workers closer together. Poorly worded questions can create confusion and disconnection. This eBook contains a list of over 50 questions to help you build your culture, inspire progress, increase morale, and a host of other desired business outcomes. We have also included top questions that thought leaders, entrepreneurs, and 15Five customers have used to create success with their teams. Stay Curious! Founder & CEO, 15Five David Hassell
  3. 3. 3 | The Great eBook of Employee Questions 15FIVE.COM TABLE OF CONTENTS I . Starter Questions If you ask nothing else, ask these two questions. They are vital for employee success. II. Culture Building Merriam-Webster recently named “Culture” as the word of the year, which will tell you how important it is for your business. III. Managing Introverts Some people are brilliant at what they do, but prefer limited interaction. Here are some questions to enroll everyone in the conversation, without creating discomfort. IV. Having Fun At work? Are you kidding? Interjecting levity may seem like a waste of time, but think of it as a release valve to keep people performing at their peak. V. Moving the Needle Having fun and creating a culture are important, but so is getting sh*t done! These questions help motivate team productivity. VI. Bringing Remote Teams Together Technology is making it easier than ever for people to work from anywhere. Here’s how questions can keep your team engaged and connected. VII. Raising Morale While often intangible, morale still has a powerful impact on the flow of the company. Here’s a handful of questions to promote positive energy. VIII. Coaching Is the New Managing Employees want to grow in their roles, and a manager’s job is to help them get there. Asking questions helps people to start working on solutions for themselves. IX. Outside the Box Because innovation is the single most important determinant of success in today’s competitive market. X. Making Meeting Time More Valuable Meeting time should be spent making decisions and taking action, so ask these questions beforehand. XI. ABL (Always Be Learning) Inspire personal and professional growth, and help people to feel more knowledgeable, competent, and fulfilled.
  4. 4. 4 | The Great eBook of Employee Questions 15FIVE.COM I. STARTER QUESTIONS If you ask nothing else, ask these two questions. They are vital for employee success. What challenges are you facing, where are you stuck? The quickest way to overcome challenges and get unstuck is to say, “I’m stuck!” When we can identify where we’re stuck and then bring someone else’s attention to the challenge at hand, we are in a position to receive the coaching and guidance that helps us think about the issue in a fresh new way. What’s going well in your role, any wins (big or small) this week? This is a great place to start. Employees get to celebrate and even brag a little about all the positive stuff that happened that week by simply answering that question. 1 2 DAVID HASSELL Founder & CEO of 15Five How can we design your role to create what’s next in your career or your life? Employees have a fundamental human desire to continue to grow and evolve personally and professionally. When managers support this growth, employees become more engaged in their work and feel more invested in the company. ?GENIUS QUESTION
  5. 5. 5 | The Great eBook of Employee Questions 15FIVE.COM What are 5-10 qualities that you think are must-haves for new hires in terms of culture fit? Finding a candidate who can do the work is one challenge, but hiring for culture-fit is arguably more important. Now you can intelligently design an interview process and to find out if people display these qualities. What would an even more joyful workplace culture look like to you? The concept of joy at work may seem foreign to some, especially those who constantly glorify “busy”. But joy can and should go hand-in-hand with quality, focused productivity. What is one quality you see in a team member that you’d like to cultivate in your own habits and actions? This question provides management with insights into desired qualities of employees who may be undercover heroes. It also creates more team awareness and connection. What process can be fixed or improved? Simple or complex, allowing your employees to speak up on process empowers them and keeps them constantly thinking of making things better for everyone. 3 II. CULTURE BUILDING Merriam-Webster recently named “Culture” as the word of the year, which will tell you how important it is for your business. 4 5 6 SIMON SINEK Founder/Author of Start With Why What sucks and what sucks less? It gives people a safe space to report on what needs a fix or who needs help. Asking “what’s working and what’s not” always gives lopsided answers. I learned this from Charlie Kim, CEO of Next Jump. ?GENIUS QUESTION
  6. 6. 6 | The Great eBook of Employee Questions 15FIVE.COM How can I be a better leader? This one will probably be the toughest on your team, but the responses will also be incredibly worthwhile. You will learn what your employees perceive are core leadership values, and determine if they are in sync with the values of management and the company as a whole. Which company value would you like to have a new high mark in? (as in, which do you feel you aren’t living to its potential?) Company values are the compass by which autonomous employees steer, and this question keeps the values top of mind. Some of our values are Keep Things Simple and Commit to Customer Success and Delight. So when any employees face a decision they can ask, “Am I over-complicating this? How would this impact our customers?” How are you impacting the people around you? Why is it that the people with the least self-awareness are usually the most difficult to be around? This question invites people to be aware of their co-workers’ reactions and perceptions and ponder how they’re being experienced by others. If you could choose a colleague, team member, or exemplary professional to coach you on a particular topic, who would it be and why? LinkedIn is not just about looking for a job. Have you ever reached out to someone in your field and offered to take them to lunch for some advice? That hour could be the most valuable time you spend away from your desk. And if people are clear on how to achieve their goals and start seeing results, they are less likely to seek a new career path. 7 8 9 10 JONATHAN RAYMOND, Founder of Refound What is it that you think I don’t see about our culture? Anything I can do to break out of the CEO bubble… ?GENIUS QUESTION
  7. 7. 7 | The Great eBook of Employee Questions 15FIVE.COM When do you thrive the most, when you collaborate with other team members or when you have time by yourself? Introversion and shyness are often confused with one another. Introverts are not necessarily shy, they often have a preference for space to develop their own ideas. Managers can use this question as a litmus test and then harness the power of each employee by engaging them in a way that suits their personality. Who do you want to get to know better in the company? Tag them here for a coffee or virtual coffee date. No, you can’t just run to your desk and put your headphones on. Let’s push your edges a bit so that we can create some cross-team camaraderie. What’s something specific you appreciate about [insert co- workers name]? Introverts aren’t necessarily shy, they simply maintain their energy by spending time alone instead of having it drained by others. In team environments, introverts sometimes need a little nudge to consider others. Was there a recent team discussion or meeting where you did not get to share your thoughts? Share them here now... Introverts tend to need more time to think through an idea and they often get interrupted or out-shouted by extroverts on the team. Asking this question in written form, with time to answer, allows managers to shine a light on their hidden genius. III. MANAGING INTROVERTS Some people are brilliant at what they do, but prefer limited interaction. Here are some questions to enroll everyone in the conversation, without creating discomfort. DAVE KASHEN CEO of Worklife If you were running the company, what would you be doing differently? This question gives them an owner’s perspective. Managers/Leaders get their feedback on how we could be doing a better job as a company and how I could be doing a better job as CEO. It’s easier to answer than ‘how could I be doing a better job’ because that doesn’t feel as personal. ?GENIUS QUESTION 11 12 13 14
  8. 8. 8 | The Great eBook of Employee Questions 15FIVE.COM What are you listening to while working? (Ignore if you don’t listen to music while working.) Some people stay in flow by putting on some of their favorite tunes. Music choice can help to connect people on the team on a more personal level. “Oh, you like Adele too?” When do you have the most fun at work? After a rough or stressful week, asking this question can provide a much needed reminder that people do indeed have a good time at the office. If the answer is “never”, it’s time to presence the importance of downtime. What or who inspired you this week? How? One definition of inspiration is “breathing in”. That’s how it feels when someone or something gets us going. Wouldn’t it be amazing if… We created a Dare to Dream board and collected some of our biggest, wildest and bold dreams about what we can accomplish as a company and put them up on a white board for all to see. Try it on your team! What’s your favorite prank? Make it clear that these are not to be attempted while at work, unless you want your precious office electronics covered in shaving cream. IV. HAVING FUN At work? Are you kidding? Interjecting levity may seem like a waste of time, but think of it as a release valve to keep people performing at their peak. 15 16 17 18 19 SHANE METCALF VP of Customer Success, 15Five Where’s your fun meter at? I ask this question at the beginning of my leadership meetings and it’s always incredibly revealing. It tells you way more than if someone is having fun - it reveals how stressed they are, how well we’re doing to create an environment in which people are loving their work, and sends the signal that yes, it’s ok to have fun! ?GENIUS QUESTION
  9. 9. 9 | The Great eBook of Employee Questions 15FIVE.COM Are there any key priorities you’re not making progress on? If so, what do you need to make progress? Questions like these offer the employee an opportunity to start considering the structure of how they work along with the substance of what they are producing. What’s standing in the way of you being more engaged and making more progress on a weekly/daily basis? This is similar to the question above but also includes engagement, which is often more about how employees feel about their work or the company than an issue involving skill-sets, knowledge, or systems. What feature in our product would you most like to see fast tracked/developed? This is a great one for public-facing employees, the ones who work most closely with your customers. They know what’s being asked for and what to prioritize. On a scale of 1-10, how satisfied are you with your own progress on your focus areas? Not only does this question give you the manager a barometer for progress, but it places the employee in a position to confront their own accountability. V. MOVING THE NEEDLE Having fun and creating a culture are important, but so is getting sh*t done! These questions help motivate team productivity. RAND FISHKIN Wizard of Moz What’s holding you back from accomplishing your tasks? I want to find what’s stopping progress and do everything in my power to eliminate those roadblocks. ?GENIUS QUESTION 20 21 22 23
  10. 10. 10 | The Great eBook of Employee Questions 15FIVE.COM When do you feel most productive? Let’s get scientific for a moment. Producing great work is fantastic, but understanding the recipe allows people to further optimize. What creates a sense of making progress for you? You are essentially asking the employee to create benchmarks for themselves to hit on a daily or weekly basis. If you had someone to delegate tasks that are NOT in your Zone of Genius (so you could increase the % of time in your ZOG), what specific tasks and responsibilities would you delegate? A Zone of Genius is the group of skills that allow people to add the most value. Dan Martell explains that anything that is high frequency and low value (outside your ZOG) should be out-tasked. What would a 10% increase in your own personal productivity look like and how could you achieve that? The first step to transformation is visualizing the change that you want to have happen. The strategy (how can you achieve that?) is also important, but is not as effective without employees stepping into more productive versions of themselves. 24 25 26 27 RYAN HOLIDAY Author of The Obstacle Is The Way Is there anything you need from me? The job of the boss is to help and support their employees so they can do what they’re supposed to do. ?GENIUS QUESTION
  11. 11. 11 | The Great eBook of Employee Questions 15FIVE.COM What can help us improve daily communication? Based on research and our own internal surveys, we know that communication is a major challenge for remote teams. And employees can be a great resource for ideas to make improvements. How have you improved your remote working skills this month? Have you identified any challenges? Remote work absolutely comes with its own set of skills. Time management, prioritization, consolidation, collaboration and a whole slew of other “-ations”. Offer people a platform to suggest a new technology or a system that helped them stay organized and productive from a distance. Are you out of the office or traveling in the near future? Many startups have flexible work arrangements and unlimited vacation. Everyone trusts that people will be available when needed and that they will achieve the results for which they are held accountable. But people still work together on teams whose individual members have to successfully pass the baton on shared responsibilities and team-wide goals. Everyone needs to know if they will be running the race alone for 3 or 4 days. What are your primary goals this quarter? People can be extremely busy and still contribute very little to overall company goals. Asking this question lets you know how effective your internal communications really are and how aligned people stay when they work from home. VI. BRINGING REMOTE TEAMS TOGETHER Technology is making it easier than ever for people to work from anywhere. Here’s how questions can keep your team engaged and connected. 28 29 30 31 BRYAN FRANKLIN Executive Coach What do you want to be able to do in 6 months that you can’t do now? I gain loyalty, alignment, and visibility into what is challenging and exciting for the team, which then drives strategic and tactical decisions to align the company behind the visions of the employees. ?GENIUS QUESTION
  12. 12. 12 | The Great eBook of Employee Questions 15FIVE.COM What inspires you to succeed every day? We can chalk challenges up to “having a bad day” or we can be way more analytical. Create the realization that employees can seek people or experiences that will influence their success. What’s one personal goal that you’d feel comfortable sharing here that the company as a whole can support you in achieving? Personal and professional goals do not have to be at odds with one another. In fact, when people feel fulfilled in both realms, they bring more energy to work and not less. What do you find most exciting about work right now? Work? Exciting? Yes! If it’s not, then this question opens up the floodgates to an important conversation that can shift people into projects and roles that are right for them. Of your accomplishments this week, which one are you most proud of and why? Taking pride in one’s work used to be far more ubiquitous than it is today. A faster paced world means that we often optimize for quantity over quality. This question reminds us of that great feeling of pride in a job well done. What is the most meaningful part of your job? Daniel Pink compiled a wealth of research to determine that we are motivated by autonomy, mastery, and purpose or meaning. This question directs an employee’s focus to what is most meaningful, thereby increasing their motivation. On a scale of 1 to 10, how happy are you? Why? When your team is happy, they not only come up with better solutions, but their satisfaction also helps to build a culture of high performance and low turnover. VII. RAISING MORALE While often intangible, morale still has a powerful impact on the flow of the company. Here’s a handful of questions to promote positive energy. RENEE WARREN Founder of Onboardly How are you feeling about your workload today? I want to find out if they feel overwhelmed. ‘Busy’ is an ok word, but as soon as they indicate that they are overwhelmed it throws up a red flag. Anxiety equals a loss of focus and generally really crappy work, so we want to make sure that they are confident in their daily tasks. ?GENIUS QUESTION 32 33 34 35 36 37
  13. 13. 13 | The Great eBook of Employee Questions 15FIVE.COM What challenges are you facing and how can I help? Every employee from entry level up through the C-suite needs challenge. Growth keeps your job and your life interesting. Sometimes, there is too much challenge which leads to frustration and eventually disengagement. Great leaders are aware of each employee’s sweet-spot for challenges and they step in with advice and coaching when needed. What could distract you next week from making progress on your goals? How could you minimize those distractions? While software makes us more efficient, it can also pull us away from focused work (I’m looking at you email and Facebook). These behaviors become habitual and eventually invisible to us. This question brings awareness back to the activities that are more harmful than helpful. What do you need help with? This week? This month? Remember when a week was 7 days and a month was 30 or 31? In business, time moves at an accelerated pace. This question also widens the lense on objectives so that people are focusing on the now without losing sight of the not too distant future. Anything in your work world that’s less than stellar/causing frustration or delays? Sometimes something peripheral can have a tremendous impact on getting things done. It could be a noisy office space or IT issues. After a while, employees might just “deal with it” instead of enrolling someone who can actually resolve the issues. VIII. COACHING IS THE NEW MANAGING Employees want to grow in their roles, and a manager’s job is to help them get there. Asking questions helps people to start working on solutions for themselves. DARREN VIRASSAMMY Co-founder of 34 Strong What needs do you have from me? 1) My job as a leader is to serve my team. Understanding their needs and identifying ways to meet them allows my team to operate at an optimized level. 2) Mining for needs helps to establish accountability on the team and a sense of who owns what. It also opens up the conversation for what needs the team has of each other. ?GENIUS QUESTION 38 39 40 41
  14. 14. 14 | The Great eBook of Employee Questions 15FIVE.COM Reflection: looking back on the week, is there anything that could have gone better? Recollecting the details of a long week of multitasking, meetings, getting to inbox zero, and putting out fires can be difficult. Try adding entries to a work journal at the end of every day so that you can do a weekly post-mortem and optimize your workflow. Are you crystal clear on your role and what you should be working on? If not, what aspects aren’t clear? Working hard and being busy doesn’t impress anyone, so you can stop running around the office with a furrowed brow. For any given task an employee should be able to answer what exactly they are doing and why. What team and company objectives does it contribute to? Are there any projects or issues that you are worried about in either the short or long term? They say that worrying is like praying for the things you don’t want. But we all have to consider the future, especially when we are unclear about how to create it in a good way. Worry eats up much of our energy that could be spent more productively. Sharing what we are worried about, or just getting it out of our minds and into a doc, frees up that energy. From 1 to 10, how have your personal energy levels been? What would it take to move that up a number? Employees who feel healthy and energetic get more done in less time. They are also happier and more pleasant to be around. This question grows awareness around low energy and because you ask for a suggestion to improve, it actually places people on the path towards making that change. Employees often respond with ‘more exercise’, ‘less coffee’, or ‘better diet’, and you can step in to support them. Follow up after a week or so and ask how it’s going. 42 43 44 45
  15. 15. 15 | The Great eBook of Employee Questions 15FIVE.COM What would you change about our product if you had a magic wand? We don’t always have to know how we can make things happen, we just have to be courageous enough to speak our ideas. Who knows, maybe someone else on the team can work their magic and pull that rabbit out of the hat. Share an idea to improve any aspect of your role or the company… Some employees are exceptionally process oriented, and they may have an idea for an optimization or improvement that can benefit the team or the entire organization. How can we become the company that would put us out of business? In a highly competitive marketplace, one brilliant innovation can put you ahead of others vying for the same market-share. Front-line employees often have the greatest insights but don’t share those ideas because they consider them to be obvious. Asking this question emboldens people to share their ideas. How do you describe our offering to family and friends? A great two for one! Learn new messaging that you haven’t thought of and help people refine those elevator pitches. IX. OUTSIDE THE BOX (SPARK INNOVATION) Because innovation is the single most important determinant of success in today’s competitive market. ANESE CAVANAUGH Creator of the IEP Method What are you excited about? What’s important about it to you? What do you want to make happen? It gets them present to what is right now, how they feel, what’s important, and what they want to make happen. It also helps us trouble shoot if they’re not excited about something and possibly figure out a better way (or ditch if it’s perpetual). ?GENIUS QUESTION 46 47 48 49
  16. 16. 16 | The Great eBook of Employee Questions 15FIVE.COM What topics or questions do you want to discuss in our next one-on-one meeting? Pretty direct, huh? One-on-ones should be used to build relationships, make decisions, offer support, and dig deeper into information you already have. Always ask questions and set the agenda beforehand to have an informed and productive employee meeting. What decisions do we need to make, and how will we make them? Wasting time in meetings gets expensive and gets on people’s nerves. Spend some time before the meeting outlining what needs to be discussed and how those decisions will be made. Will it be by majority vote? Will the leader decide? How are your meetings going? How can we make them more productive? Precious time is often wasted bringing people up to speed, when that information could have been shared in various other ways before the meeting. Streamlining your meetings means limiting the number of people who need to attend. They can spend that time working on priorities and you get the most out of your payroll budget. X. MAKING MEETING TIME MORE VALUABLE Meeting time should be spent making decisions and taking action, so ask these questions beforehand. SHAWN MURPHY, Co-founder of Switch&Shift How can I help? I ask the question to promote collaboration, democracy, and goodwill. ?GENIUS QUESTION 50 51 52
  17. 17. 17 | The Great eBook of Employee Questions 15FIVE.COM What book would you like to read (that you don’t already own) to further your professional development and satisfaction? We are fast approaching an age when formal education will not be nearly as critical as figuring it out for yourself. Free or inexpensive, yet highly valuable information is everywhere. Also everywhere is information that is inaccurate, irrelevant, or difficult to comprehend. So starting a conversation about business books will allow the most valuable recommendations to rise to the surface. What’s one thing you learned this week? This can be inside or outside of work, and it advances the values of learning and growth. It’s also a great barometer for employee satisfaction and morale. If someone isn’t learning much, they could be bored, disengaged, frustrated, or overworked. What opportunities for learning and growth have you recently found or created for yourself? What such opportunities do you see for your colleagues? Much like the question above, but this iteration shifts the attention onto the team. Co-workers engage with one another during lunches and happy hours, and sometimes those conversations are about life goals, and learning experiences. Help out a colleague by shining a light on something they want for their personal and professional development. XI. ABL (ALWAYS BE LEARNING) Inspire personal and professional growth, and help people to feel more knowledgeable, competent, and fulfilled. ANDREW DEUTSCHER VP of Business Development, The Energy Project What is the reason why? Our thoughts and emotions are a function of the quality of our questions, both internally and externally. If I remind people why they are doing something then it gives them more equity and allows them to prioritize their work and connect to the larger mission or purpose of the company, or who they are supporting. ?GENIUS QUESTION 53 54 55 BONUS QUESTION Are you clear about what it takes to advance in your role at the company? People, and especially younger employees, really want to move forward. They want to see the clear path that leads before them towards professional fulfillment. This often involves learning new skills, obtaining expertise, or becoming a people manager. This question starts the conversation about advancement so that people are aware that this is on your radar, and so they know what is expected of them.
  18. 18. 18 | The Great eBook of Employee Questions 15FIVE.COM CONCLUSION Ranging from simple to complex, questions are the most important business tool in your management toolbox. While employees may be unwilling to share unsolicited feedback (especially negative feedback), asking them often invites the answer. You can do this face-to-face, via email, or via employee feedback software. We have found that it is less intimidating to respond via software, even in the most progressive and transparent company cultures. I am grateful that we have created a product that the vast majority of our clients love. It allows them to add that degree of separation that entices honesty and candor. In the spirit of candor, I will share that we periodically receive negative feedback from employees who use our product, that the questions they ask have grown stale. No matter what method you use to gather information and respond to employee concerns, triumphs, and ideas, always refresh the questions you ask every few weeks. Employees will appreciate it, and appreciative employees are far more likely to tell you what you need to know. 15Five provides web-based performance management software that improves employee engagement through a lightweight weekly check-in. This practice strengthens relationships, offers detailed visibility for company leaders, and creates an opportunity for employees to share triumphs, challenges, and innovative ideas. 15Five.com

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