The Great eBook of Employee Questions

1 | The Great eBook of Employee Questions 15FIVE.COM
The Great eBook of
EMPLOYEE QUESTIONS

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

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.

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.
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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

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.
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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.
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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

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.
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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

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
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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.
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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

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
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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.
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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

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.
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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

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
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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
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
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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 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.
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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
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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 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
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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
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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.

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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