The Great

eBook of
Employee
Questions
Introduction: The Power of Questions
Warren Berger, author of A More Beautiful Asking questions can improve business
Question explains that as children we ask more outcomes and even save hundreds of hours each
than 300 questions a day. As adults, that number week. The practice can boost team performance
plummets to merely a handful. Perhaps that’s and focus. But asking thought-provoking
because we are less curious, or because we have questions takes skill, and only the right questions
already gained fundamental knowledge on a will inspire creativity and yield the results that
diverse number of subjects. Unfortunately, I managers desire. Done well, this practice
believe that many of us are afraid to ask because inspires others to solve problems, and to think
of how we might be perceived. This is especially spontaneously and creatively.
true in competitive workplace environments and
when leaders are unresponsive. There is a saying in the legal world - Never ask a
question to which you do not already know the
Curiosity is vital for building thriving companies answer. I will modify that for the business context
and for fostering healthy relationships between - Never ask a question unless you know what you
co-workers. Good questions have the power are trying to achieve. A well-crafted question
to spark innovation, avoid fire-drills, and help can inspire and illuminate, and often brings co-
employees show-up as their best selves. workers closer together. Poorly worded questions
can create confusion and disconnection.
In business, we are often so results-focused
that we can discourage the disruptive thinking This eBook contains a list of over 50 questions
that leads to success. Asking questions lets us to help you build your culture, inspire progress,
take a second look at what we hold to be true increase morale, and a host of other desired
and what we view as false. When we ask business outcomes. We have also included top
questions, we begin to see that the “truth” is questions that thought leaders, entrepreneurs,
often based on subjective beliefs that can be and 15Five customers have used to create
reinvented or transformed. success with their teams.

When we focus more on answers than questions, Stay Curious!

we deprive everyone of an opportunity to grow.
Relationships suffer, because nothing makes
people feel more marginalized than telling DAVI D HAS S E LL
them your impressions about their experiences, F O U N D E R & C E O, 15 F I V E
feelings, or motivations. But asking a direct
question about another’s experience allows them
to feel more seen, heard, and fulfilled.

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Table of
Contents
I . Starter Questions
If you ask nothing else, ask these two questions.
They are vital for employee success.

II. Culture Building VII. Raising Morale

Merriam-Webster recently named “Culture” While often intangible, morale still has a
as the word of the year, which will tell you how powerful impact on the flow of the company.
important it is for your business. Here’s a handful of questions to promote
positive energy.
III. Managing Introverts
Some people are brilliant at what they do, VIII. Coaching Is the New Managing
but prefer limited interaction. Here are some Employees want to grow in their roles, and a
questions to enroll everyone in the conversation, manager’s job is to help them get there. Asking
without creating discomfort. questions helps people to start working on
solutions for themselves.
IV. Having Fun
At work? Are you kidding? Interjecting levity IX. Outside the Box
may seem like a waste of time, but think of it as Because innovation is the single most
a release valve to keep people performing at important determinant of success in today’s
their peak. competitive market.

V. Moving the Needle X. Making Meeting Time More Valuable

Having fun and creating a culture are important, Meeting time should be spent making
but so is getting sh*t done! These questions help decisions and taking action, so ask these
motivate team productivity. questions beforehand.

VI. Bringing Remote Teams Together XI. ABL (Always Be Learning)

Technology is making it easier than ever for Inspire personal and professional growth,
people to work from anywhere. Here’s how and help people to feel more knowledgeable,
questions can keep your team engaged competent, and fulfilled.
and connected.

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I. Starter Questions II. Culture Bending
If you ask nothing else, ask these two questions. Merriam-Webster recently named “Culture” as
They are vital for employee success. the word of the year, which will tell you how
important it is for your business.
What’s going well in your role, any wins
1
(big or small) this week? What are 5-10 qualities that you think
3
This is a great place to start. Employees are must-haves for new hires in terms
get to celebrate and even brag a little of culture fit?
about all the positive stuff that happened Finding a candidate who can do the work
that week by simply answering is one challenge, but hiring for culture-fit
that question. is arguably more important. Now you can
intelligently design an interview process
2 What challenges are you facing, where and to find out if people display
are you stuck? these qualities.
The quickest way to overcome challenges
and get unstuck is to say, “I’m stuck!” 4 What would an even more joyful
When we can identify where we’re stuck workplace culture look like to you?
and then bring someone else’s attention The concept of joy at work may seem
to the challenge at hand, we are in a foreign to some, especially those who
position to receive the coaching and constantly glorify “busy”. But joy can and
guidance that helps us think about the should go hand-in-hand with quality,
issue in a fresh new way. focused productivity.

What is one quality you see in a team

GENIUS QUESTION: How can we design your role 5
member that you’d like to cultivate in
to create what’s next in your career or your life?
your own habits and actions?
Employees have a fundamental human desire This question provides management
to continue to grow and evolve personally and with insights into desired qualities of
professionally. When managers support this employees who may be undercover
growth, employees become more engaged in their heroes. It also creates more team
work and feel more invested in the company. awareness and connection.

DAVI D HAS S E LL
F O U N D E R & C E O, 15 F IVE

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 Some of our values are Keep Things
GENIUS QUESTION: What sucks and what Simple and Commit to Customer Success
sucks less? and Delight. So when any employees face
a decision they can ask, “Am I over-
It gives people a safe space to report on what
complicating this? How would this impact
needs a fix or who needs help. Asking “what’s
our customers?”
ways gives lopsided answers. I learned this from
Charlie Kim, CEO of Next Jump.
How are you impacting the people
9
around you?
SIMON SINEK Why is it that the people with the
F O U N D E R /AUTH O R O F
START WITH WHY least self-awareness are usually the
most difficult to be around? This
question invites people to be aware
of their co-workers’ reactions and
What process can be fixed or improved? perceptions and ponder how they’re
6
Simple or complex, allowing your being experienced by others.
employees to speak up on process
empowers them and keeps them 10 If you could choose a colleague, team
constantly thinking of making things member, or exemplary professional to
better for everyone. coach you on a particular topic, who
would it be and why?
How can I be a better leader? LinkedIn is not just about looking for
7
This one will probably be the toughest a job. Have you ever reached out to
on your team, but the responses will also someone in your field and offered to take
be incredibly worthwhile. You will learn them to lunch for some valuable time you
what your employees perceive are core spend away from your desk. And if people
leadership values, and determine if they are clear on how to achieve their goals
are in sync with the values of management and start seeing results, they are less
and the company as a whole. likely to seek a new career path.

Which company value would you like to

8
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.

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 What’s something specific you
13
GENIUS QUESTION: What is it that you appreciate about [insert
think I don’t see about our culture? coworkers name]?
Introverts aren’t necessarily shy,
Anything I can do to break out of the they simply maintain their energy by
CEO bubble… spending time alone instead of having
it drained by others. In team
J O NATHAN R AYM O N D environments, introverts sometimes
FOUNDER OF REFOUND need a little nudge to consider others.

III. Managing GENIUS QUESTION: If you were running the

Introverts company, what would you be doing differently?

This question gives them an owner’s perspective.

If you ask nothing else, ask these two questions.
Managers/Leaders get their feedback on how
They are vital for employee success.
we could be doing a better job as a company
and how I could be doing a better job as CEO.
When do you thrive the most, when you It’s easier to answer than ‘how could I be doing a
11
collaborate with other team members or better job’ because that doesn’t feel as personal.
when you have time by yourself?
Introversion and shyness are often
confused with one another. Introverts DAVE K AS H E N
C E O O F WO R K L I F E
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 Was there a recent team discussion or
14
way that suits their personality. meeting where you did not get to share
your thoughts? Share them here now...
12 Who do you want to get to know better Introverts tend to need more time to
in the company? Tag them here for a think through an idea and they often get
coffee or virtual coffee date. interrupted or out-shouted by extroverts
No, you can’t just run to your desk and on the team. Asking this question in
put your headphones on. Let’s push your written form, with time to answer, allows
edges a bit so that we can create some managers to shine a light on their
cross-team camaraderie. hidden genius.

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IV. Having Fun 19
What’s your favorite prank?
Make it clear that these are not to be
At work? Are you kidding? Interjecting levity attempted while at work, unless you want
may seem like a waste of time, but think of it as your precious office electronics covered
a release valve to keep people performing at in shaving cream.
their peak.

GENIUS QUESTION: Where’s your fun meter at?

What are you listening to while working?
15
(Ignore if you don’t listen to music while
I ask this question at the beginning of my
working.)
leadership meetings and it’s always incredibly
Some people stay in flow by putting on
revealing. It tells you way more than if someone
some of their favorite tunes. Music choice
is having fun - it reveals how stressed they are,
can help to connect people on the team
how well we’re doing to create an environment in
on a more personal level. “Oh, you like
which people are loving their work, and sends the
Adele too?”
signal that yes, it’s ok to have fun!

16 When do you have the most fun at work?

After a rough or stressful week, asking S HAN E M E TCALF
this question can provide a much needed VP O F C U STO M E R S E RVI C E ,
15 F IVE
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.

17 What or who inspired you this week?

V. Moving the Needle
How? Having fun and creating a culture are important,
One definition of inspiration is “breathing but so is getting sh*t done! These questions help
in”. That’s how it feels when someone or motivate team productivity.
something gets us going.

Are there any key priorities you’re not

Wouldn’t it be amazing if… 20
18 making progress on? If so, what do you
We created a Dare to Dream board and
need to make progress?
collected some of our biggest, wildest
Questions like these offer the employee
and bold dreams about what we can
an opportunity to start considering the
accomplish as a company and put them
structure of how they work along with the
up on a white board for all to see. Try it on
substance of what they are producing.
your team!

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 What’s standing in the way of you
21
being more engaged and making more
GENIUS QUESTION: What’s holding you back
progress on a weekly/daily basis?
from accomplishing your tasks?
This is similar to the question above but
also includes engagement, which is often
I want to find what’s stopping progress and
more about how employees feel about
do everything in my power to eliminate those
their work or the company than an issue
roadblocks.
involving skill-sets, knowledge,
or systems.
R AN D F I S H K I N
What feature in our product would you WIZ AR D O F M OZ
22
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
If you had someone to delegate tasks
know what’s being asked for and what 26
that are NOT in your Zone of Genius (so
to prioritize.
you could increase the % of time in your
ZOG), what specific tasks and
On a scale of 1-10, how satisfied are
23 responsibilities would you delegate?
you with your own progress on your
A Zone of Genius is the group of skills
focus areas?
that allow people to add the most value.
Not only does this question give you the
manager a barometer for progress, but Dan Martell explains that anything that
it places the employee in a position to is high frequency and low value (outside
confront their own accountability. your ZOG) should be out-tasked.

When do you feel most productive? What would a 10% increase in your own
24 27
Let’s get scientific for a moment. personal productivity look like and how
Producing great work is fantastic, but could you achieve that?
understanding the recipe allows people
The first step to transformation is
to further optimize.
visualizing the change that you want
to have happen. The strategy (how can
25 What creates a sense of making
progress for you? you achieve that?) is also important, but
You are essentially asking the employee is not as effective without employees
to create benchmarks for themselves to stepping into more productive versions
hit on a daily or weekly basis. of themselves.

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 How have you improved your remote
29
working skills this month? Have you
GENIUS QUESTION: Is there anything you
identified any challenges?
need from me?
Remote work absolutely comes with its
own set of skills. Time management,
The job of the boss is to help and support
prioritization, consolidation,
their employees so they can do what they’re
collaboration and a whole slew of other
supposed to do.
“-ations”. Offer people a platform
to suggest a that helped them stay
RYAN H O LI DAY organized and productive from
AUTH O R O F TH E O B STAC L E
I S TH E WAY
a distance.

Are you out of the office or traveling in

30
the near future?
Many startups have flexible work

VI. Bringing Remote arrangements and unlimited vacation.

Everyone trusts that people will be
Teams Together available when needed and that they will
achieve the results for which they are
Technology is making it easier than ever for held accountable. But people still work
people to work from anywhere. Here’s how together on teams whose individual
questions can keep your team engaged members have to successfully pass the
and connected. baton on shared responsibilities and
team-wide goals. Everyone needs to know
What can help us improve daily if they will be running the race alone for 3
28
communication? or 4 days.
Based on research and our own internal
surveys, we know that communication is a What are your primary goals
31
major challenge for remote teams. And this quarter?
employees can be a great resource for People can be extremely busy and
ideas to make improvements. 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.

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VII. Raising Morale 34
What do you find most exciting about
work right now?
While often intangible, morale still has a powerful Work? Exciting? Yes! If it’s not, then this
impact on the flow of the company. Here’s a question opens up the floodgates to an
handful of questions to promote positive energy. important conversation that can shift
people into projects and roles that are
right for them.
What inspires you to succeed every day?
32
We can chalk challenges up to “having a
35 Of your accomplishments this week,
bad day” or we can be way more analytical.
which one are you most proud of
Create the realization that employees
and why?
can seek people or experiences that will
Taking pride in one’s work used to be far
influence their success.
more ubiquitous than it is today.
A faster paced world means that we often
What’s one personal goal that you’d
33 optimize for quantity over quality. This
feel comfortable sharing here that the
question reminds us of that great feeling
company as a whole can support you
of pride in a job well done.
in achieving?
Personal and professional goals do not
36 What is the most meaningful part
have to be at odds with one another. In
fact, when people feel fulfilled in both of your job?
realms, they bring more energy to work Daniel Pink compiled a wealth of
and not less. research to determine that we are
motivated by autonomy, mastery, and
purpose or meaning. This question
directs an employee’s focus to what is
GENIUS QUESTION: What do you want to be
most meaningful, thereby increasing
able to do in 6 months that you can’t do now?
their motivation.

I gain loyalty, alignment, challenging and

37 On a scale of 1 to 10, how happy
exciting for the team, which then drives
strategic and tactical decisions to align the are you? Why?
company behind the visions of the employees. When your team is happy, they not only
come up with better solutions, but their
satisfaction also helps to build a culture
B RYAN H O LI DAY of high performance and low turnover.
E X E C UTIVE C OAC H

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 Great leaders are aware of each
employee’s sweet-spot for challenges
GENIUS QUESTION: How are you feeling
and they step in with advice and coaching
about your workload today?
when needed.

I want to find out if they feel overwhelmed.

What could distract you next week from
‘Busy’ is an ok word, but as soon as they 39
making progress on your goals? How
indicate that they are overwhelmed it throws
could you minimize those distractions?
up a red flag. Anxiety equals a loss of focus
and generally really crappy work, so we want
While software makes us more efficient,
to make sure that they are confident in their
it can also pull us away from focused work
daily tasks.
(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
RE N E E WARRE N
that are more harmful than helpful.
F O U N D E R O F O N B OAR D LY

40 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,
VIII. Coaching is the time moves at an accelerated pace.

New Managing This question also widens the lense on

objectives so that people are focusing on
Employees want to grow in their roles, and a the now without losing sight of the not
manager’s job is to help them get there. Asking too distant future.
questions helps people to start working on
solutions for themselves. Anything in your work world that’s less
41
than stellar/causing frustration
or delays?
What challenges are you facing and how
38 Sometimes something peripheral can
can I help?
have a tremendous impact on getting
Every employee from entry level up
things done. It could be a noisy office
through the C-suite needs challenge.
space or IT issues. After a while,
Growth keeps your job and your life
employees might just “deal with it”
interesting. Sometimes, there is too
instead of enrolling someone who can
much challenge which leads to frustration
actually resolve the issues.
and eventually disengagement.

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42 Reflection: looking back on the week, From 1 to 10, how have your personal
45
is there anything that could have energy levels been? What would it take
gone better? to move that up a number?
Recollecting the details of a long week Employees who feel healthy and
of multitasking, meetings, getting to energetic get more done in less time.
inbox zero, and putting out fires can be They are also happier and more pleasant
difficult. Try adding entries to a work to be around. This question grows
journal at the end of every day so that awareness around low energy and
you can do a weekly post-mortem and because you ask for a suggestion to
optimize your workflow. improve, it actually places people on
the path towards making that change.
Are you crystal clear on your role and Employees often respond with ‘more
43
what you should be working on? If not, exercise’, ‘less coffee’, or ‘better diet’,
what aspects aren’t clear? and you can step in to support them.
Working hard and being busy doesn’t Follow up after a week or so and ask how
impress anyone, so you can stop running it’s going.
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 GENIUS QUESTION: What needs do you have

objectives does it contribute to? from me?

Are there any projects or issues that you 1) My job as a leader is to serve my team.
44
are worried about in either the short or Understanding their needs and identifying

long term? ways to meet them allows my team to operate

at an optimized level. 2) Mining for needs helps
They say that worrying is like praying for
to establish accountability
the things you don’t want. But we all have
on the team and a sense of who owns what. It
to consider the future, especially when
also opens up the conversation for what needs
we are unclear about how to create it in a
the team has of each other.
good way. Worry eats up much of our
energy that could be spent more
productively. Sharing what we are
DARRE N VI R AS SAM MY
worried about, or just getting it out
C O - F O U N D E R O F 34 STRO N G
of our minds and into a doc, frees up
that energy.

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IX. Outside of the Box 49 How do you describe our offering to
family and friends?
(Spark Innovation) A great two for one! Learn new messaging
that you haven’t thought of and help
Because innovation is the single most people refine those elevator pitches.
important determinant of success in today’s
competitive market.

GENIUS QUESTION: What are you excited

What would you change about our about? What’s important about it to you?
46 What do you want to make happen?
product if you had a magic wand?
We don’t always have to know how we can
It gets them present to what is right now, how
make things happen, we just have to be
they feel, what’s important, and what they
courageous enough to speak our ideas.
want to make happen. It also helps us trouble
Who knows, maybe someone else on the
shoot if they’re not excited about something
team can work their magic and pull that
nd possibly figure out a better way (or ditch if
rabbit out of the hat.
it’s perpetual).

47 Share an idea to improve any aspect of

your role or the company…
AN E S E CAVANAU G H
Some employees are exceptionally C R E ATO R O F TH E I E P M E TH O D
process oriented, and they may have an
idea for an optimization or improvement
that can benefit the team or the
entire organization.

48 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.

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X. Making Meeting 52
How are your meetings going? How can
we make them more productive?
Time More Valuable Precious time is often wasted bringing
people up to speed, when that
Meeting time should be spent making information could have been shared in
decisions and taking action, so ask these various other ways before the meeting.
questions beforehand. Streamlining your meetings means
limiting the number of people who need
What topics or questions do you want to to attend. They can spend that time
50
discuss in our next one-on-one meeting? working on priorities and you get the
most out of your payroll budget.
Pretty direct, huh? One-on-ones should
be used to build relationships, make
decisions, offer support, and dig deeper
into information you already have. XI. ABL (Always Be
Always ask questions and set the agenda
beforehand to have an informed and
Learning)
productive employee meeting.
Inspire personal and professional growth,
What decisions do we need to make, and help people to feel more knowledgeable,
51
and how will we make them? competent, and fulfilled.

Wasting time in meetings gets expensive

and gets on people’s nerves. Spend some
What book would you like to read
time before the meeting outlining what 53
(that you don’t already own) to further
needs to be discussed and how those
your professional development
decisions will be made. Will it be by
and satisfaction?
majority vote? Will the leader decide?
We are fast approaching an age when
formal education will not be nearly as
critical as figuring it out for yourself.
GENIUS QUESTION: How can I help? Free or inexpensive, yet highly valuable
information is everywhere. Also
I ask the question to promote collaboration,
democracy, and goodwill. everywhere is information that is
inaccurate, irrelevant, or difficult to
comprehend. So starting a conversation
S HAWN M U RPHY
CO-FOUNDER OF
about business books will allow the most
SWITC H &S H I F T valuable recommendations to rise to
the surface.

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 What’s one thing you learned this week? BONUS QUESTION: Are you clear about
54 56
This can be inside or outside of work, and what it takes to advance in your role at
it advances the values of learning and the company?
growth. It’s also a great barometer for People, and especially younger
employee satisfaction and morale. If employees, really want to move forward.
someone isn’t learning much, they They want to see the clear path that
could be bored, disengaged, frustrated, leads before them towards professional
or overworked. fulfillment. This often involves learning
new skills, obtaining expertise, or
What opportunities for learning and becoming a people manager. This
55
growth have you recently found or question starts the conversation about
created for yourself? What such advancement so that people are aware
opportunities do you see for your that this is on your radar, and so they
colleagues? know what is expected of them.
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.

GENIUS QUESTION: 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
AN D RE W D E UTS C H E R and allows them to prioritize their work and
VP O F B U S I N E S S D E VE LO P M E NT, connect to the larger mission or purpose of the
TH E E N E RGY P RO J E CT
company, or who they are supporting.

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Conclusion I am grateful that we have created a product
that the vast majority of our clients love. It
Ranging from simple to complex, questions allows them to add that degree of separation
are the most important business tool in your that entices honesty and candor. In the spirit of
management toolbox. While employees may candor, I will share that we periodically receive
be unwilling to share unsolicited feedback negative feedback from employees who use
(especially negative feedback), asking them our product, that the questions they ask have
often invites the answer. You can do this face- grown stale. No matter what method you use to
to-face, via email, or via employee feedback gather information and respond to employee
software. We have found that it is less concerns, triumphs, and ideas, always refresh the
intimidating to respond via software, even in questions you ask every few weeks. Employees
the most progressive and transparent will appreciate it, and appreciative employees are
company cultures. far more likely to tell you what you need to know.

About 15Five
15Five is a continuous performance management solution
that helps employees grow and develop, in just 15 minutes
each week. Through a lightweight weekly check-in, 15Five
delivers everything a manager needs to impact employee
performance, including continuous feedback, objectives
(OKR) tracking, recognition, 1-on-1s, and 360° reviews.

To learn more, visit www.15Five.com