the great ebook of employee questions

1 | The Great eBook of Employee Questions 15FIVECOM

The Great eBook of EMPLOYEE QUESTIONS


INTRODUCTION THE POWER OF QUESTIONSWarren 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 thatrsquos 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 ldquotruthrdquo 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 anotherrsquos 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 amp CEO 15FiveDavid Hassell


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 ldquoCulturerdquo 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 sht 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 Herersquos 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 Herersquos a handful of questions to promote positive energy

VIII Coaching Is the New Managing

Employees want to grow in their roles and a managerrsquos 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 todayrsquos 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


I STARTER QUESTIONSIf you ask nothing else ask these two questions They are vital for employee success

What challenges are you facing where are you stuckThe quickest way to overcome challenges and get unstuck is

to say ldquoIrsquom stuckrdquo When we can identify where wersquore stuck and then bring someone elsersquos 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

Whatrsquos 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

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2

DAVID HASSELLFounder amp CEO of 15Five

How can we design your role to create whatrsquos next in your career or your lifeEmployees 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


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 ldquobusyrdquo But joy can and should go hand-in-hand with quality focused productivity

What is one quality you see in a team member that yoursquod 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 BUILDINGMerriam-Webster recently named ldquoCulturerdquo as the word of the year which will tell you how important it is for your business

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5

6

SIMON SINEKFounderAuthor of Start With Why

What sucks and what sucks lessIt gives people a safe space to report on what needs a fix or who needs help Asking ldquowhatrsquos working and whatrsquos notrdquo always gives lopsided answers I learned this from Charlie Kim CEO of Next Jump

GENIUS QUESTION


How can I be a better leaderThis 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 arenrsquot 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 ldquoAm I over-complicating this How would this impact our customersrdquo

How are you impacting the people around youWhy 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-workersrsquo reactions and perceptions and ponder how theyrsquore 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 whyLinkedIn 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

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JONATHAN RAYMOND Founder of Refound

What is it that you think I donrsquot see about our culture

Anything I can do to break out of the CEO bubblehellip

GENIUS QUESTION


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 canrsquot just run to your desk and put your headphones on Letrsquos push your edges a bit so that we can create some cross-team camaraderie

Whatrsquos something specific you appreciate about [insert co-workers name]

Introverts arenrsquot 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 INTROVERTSSome 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 KASHENCEO of Worklife

If you were running the company what would you be doing differentlyThis question gives them an ownerrsquos perspective ManagersLeaders 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 Itrsquos easier to answer than lsquohow could I be doing a better jobrsquo because that doesnrsquot feel as personal

GENIUS QUESTION

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12

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What are you listening to while working (Ignore if you donrsquot 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 ldquoOh you like Adele toordquo

When do you have the most fun at workAfter 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 ldquoneverrdquo itrsquos time to presence the importance of downtime

What or who inspired you this week HowOne definition of inspiration is ldquobreathing inrdquo Thatrsquos how it feels

when someone or something gets us going

Wouldnrsquot it be amazing ifhellip 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

Whatrsquos 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

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SHANE METCALFVP of Customer Success 15Five

Wherersquos your fun meter atI ask this question at the beginning of my leadership meetings and itrsquos always incredibly revealing It tells you way more than if someone is having fun - it reveals how stressed they are how well wersquore doing to create an environment in which people are loving their work and sends the signal that yes itrsquos ok to have fun

GENIUS QUESTION


Are there any key priorities yoursquore 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

Whatrsquos standing in the way of you being more engaged and making more progress on a weeklydaily 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 trackeddeveloped

This is a great one for public-facing employees the ones who work most closely with your customers They know whatrsquos 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 NEEDLEHaving fun and creating a culture are important but so is getting sht done These questions help motivate team productivity

RAND FISHKINWizard of Moz

Whatrsquos holding you back from accomplishing your tasksI want to find whatrsquos stopping progress and do everything in my power to eliminate those roadblocks

GENIUS QUESTION

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When do you feel most productiveLetrsquos 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 youYou 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 delegateA 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

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RYAN HOLIDAYAuthor of The Obstacle Is The Way

Is there anything you need from meThe job of the boss is to help and support their employees so they can do what theyrsquore supposed to do

GENIUS QUESTION


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 ldquo-ationsrdquo 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 futureMany 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 quarterPeople 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 TOGETHERTechnology is making it easier than ever for people to work from anywhere Herersquos how questions can keep your team engaged and connected

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BRYAN FRANKLIN Executive Coach

What do you want to be able to do in 6 months that you canrsquot 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


What inspires you to succeed every day We can chalk challenges up to ldquohaving a bad dayrdquo or we can be

way more analytical Create the realization that employees can seek people or experiences that will influence their success

Whatrsquos one personal goal that yoursquod feel comfortable sharing here that the company as a whole can support you in

achievingPersonal 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 itrsquos 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 onersquos 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 jobDaniel Pink compiled a wealth of research to determine that

we are motivated by autonomy mastery and purpose or meaning This question directs an employeersquos 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 MORALEWhile often intangible morale still has a powerful impact on the flow of the company Herersquos a handful of questions to promote positive energy

RENEE WARRENFounder of Onboardly

How are you feeling about your workload todayI want to find out if they feel overwhelmed lsquoBusyrsquo 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

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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 employeersquos 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 (Irsquom 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 monthRemember 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 thatrsquos less than stellarcausing 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 ldquodeal with itrdquo instead of enrolling someone who can actually resolve the issues

VIII COACHING IS THE NEW MANAGINGEmployees want to grow in their roles and a managerrsquos job is to help them get there Asking questions helps people to start working on solutions for themselves

DARREN VIRASSAMMYCo-founder of 34 Strong

What needs do you have from me1) 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

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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 arenrsquot clear

Working hard and being busy doesnrsquot 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 donrsquot 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 lsquomore exercisersquo lsquoless coffeersquo or lsquobetter dietrsquo and you can step in to support them Follow up after a week or so and ask how itrsquos going

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What would you change about our product if you had a magic wand

We donrsquot 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 companyhellipSome 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 donrsquot 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 havenrsquot

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 todayrsquos competitive market

ANESE CAVANAUGHCreator of the IEP Method

What are you excited about Whatrsquos important about it to you What do you want to make happenIt gets them present to what is right now how they feel whatrsquos important and what they want to make happen It also helps us trouble shoot if theyrsquore not excited about something and possibly figure out a better way (or ditch if itrsquos perpetual)

GENIUS QUESTION

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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 peoplersquos 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 VALUABLEMeeting time should be spent making decisions and taking action so ask these questions beforehand

SHAWN MURPHYCo-founder of SwitchampShift

How can I helpI ask the question to promote collaboration democracy and goodwill

GENIUS QUESTION

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What book would you like to read (that you donrsquot already own) to further your professional development and

satisfactionWe 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

Whatrsquos one thing you learned this weekThis can be inside or outside of work and it advances the

values of learning and growth Itrsquos also a great barometer for employee satisfaction and morale If someone isnrsquot 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 colleaguesMuch 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 DEUTSCHERVP of Business Development The Energy Project

What is the reason whyOur 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

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BONUS QUESTIONAre 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


CONCLUSIONRanging 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 15Fivecom


INTRODUCTION THE POWER OF QUESTIONSWarren 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 thatrsquos 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 ldquotruthrdquo 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 anotherrsquos 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 amp CEO 15FiveDavid Hassell




II Culture Building




IV Having Fun


V Moving the Needle




VII Raising Morale




IX Outside the Box












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II Culture Building




IV Having Fun


V Moving the Needle




VII Raising Morale




IX Outside the Box












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Leadership & Management