15five Questions Ebook
15five Questions Ebook
15five Questions Ebook
EMPLOYEE QUESTIONS
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 anothers
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!
David Hassell
Founder & CEO, 15Five
Whats going well in your role, any wins (big or small) this
1
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.
DAVID HASSELL
Founder & CEO
of 15Five
What challenges are you facing, where are you stuck?
?
2
The quickest way to overcome challenges and get unstuck is
GENIUS QUESTION to say, Im stuck! When we can identify where were stuck and then
bring someone elses attention to the challenge at hand, we are in
a position to receive the coaching and guidance that helps us think
How can we design your
about the issue in a fresh new way.
role to create whats 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.
What are 5-10 qualities that you think are must-haves for new
3
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.
SIMON SINEK
Founder/Author of
Start With Why
What would an even more joyful workplace culture look like to
?
4
you?
GENIUS QUESTION 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
What sucks and with quality, focused productivity.
what sucks less?
It gives people a safe
space to report on what What is one quality you see in a team member that youd like
5
needs a fix or who needs to cultivate in your own habits and actions?
help. Asking whats This question provides management with insights into desired qualities
working and whats not of employees who may be undercover heroes. It also creates more
always gives lopsided team awareness and connection.
answers. I learned
What process can be fixed or improved?
this from Charlie Kim, 6
CEO of Next Jump. Simple or complex, allowing your employees to speak up on
process empowers them and keeps them constantly thinking of
making things better for everyone.
GENIUS
? QUESTION
GENIUS
? QUESTION 12
Who do you want to get to know better in the company? Tag
them here for a coffee or virtual coffee date.
No, you cant just run to your desk and put your headphones on.
If you were running the
Lets push your edges a bit so that we can create some cross-team
company, what would
camaraderie.
you be doing differently?
This question gives them
an owners perspective.
Whats something specific you appreciate about [insert co-
Managers/Leaders get their 13
workers name]?
feedback on how we could
Introverts arent necessarily shy, they simply maintain their energy by
be doing a better job as a
spending time alone instead of having it drained by others. In team
company and how I could
environments, introverts sometimes need a little nudge to consider others.
be doing a better job as
CEO. Its easier to answer
than how could I be doing
Was there a recent team discussion or meeting where you did
a better job because that 14
not get to share your thoughts? Share them here now...
doesnt feel as personal.
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.
SHANE METCALF
VP of Customer Success,
15Five When do you have the most fun at work?
16
?
After a rough or stressful week, asking this question can provide
GENIUS QUESTION a much needed reminder that people do indeed have a good time at
the office. If the answer is never, its time to presence the importance
of downtime.
Wheres your fun
meter at?
I ask this question at the What or who inspired you this week? How?
17
beginning of my leadership One definition of inspiration is breathing in. Thats how it feels
meetings and its always when someone or something gets us going.
incredibly revealing. It
tells you way more than if
someone is having fun - it Wouldnt it be amazing if
18
reveals how stressed they We created a Dare to Dream board and collected some of our
are, how well were doing biggest, wildest and bold dreams about what we can accomplish as
to create an environment a company and put them up on a white board for all to see. Try it on
in which people are your team!
loving their work, and
sends the signal that
yes, its ok to have fun! Whats your favorite prank?
19
Make it clear that these are not to be attempted while at work, unless
you want your precious office electronics covered in shaving cream.
Are there any key priorities youre not making progress on? If
20
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.
RAND FISHKIN
Wizard of Moz
Whats standing in the way of you being more engaged and
21
?
making more progress on a weekly/daily basis?
GENIUS QUESTION 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.
Whats holding you back
from accomplishing
your tasks?
What feature in our product would you most like to see fast
I want to find whats 22
tracked/developed?
stopping progress and do
This is a great one for public-facing employees, the ones who work
everything in my power to
most closely with your customers. They know whats being asked for
eliminate those roadblocks.
and what to prioritize.
GENIUS
? QUESTION
26
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?
Is there anything you
A Zone of Genius is the group of skills that allow people to add the
need from me?
most value. Dan Martell explains that anything that is high frequency
The job of the boss is
and low value (outside your ZOG) should be out-tasked.
to help and support
their employees so they
can do what theyre
What would a 10% increase in your own personal productivity
supposed to do. 27
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.
BRYAN FRANKLIN How have you improved your remote working skills this
Executive Coach 29
month? Have you identified any challenges?
?
Remote work absolutely comes with its own set of skills. Time
management, prioritization, consolidation, collaboration and a
GENIUS QUESTION
whole slew of other -ations. Offer people a platform to suggest a
new technology or a system that helped them stay organized and
What do you want to be able productive from a distance.
to do in 6 months that you
cant do now?
I gain loyalty, alignment, 30 Are you out of the office or traveling in the near future?
and visibility into what is Many startups have flexible work arrangements and unlimited
challenging and exciting for vacation. Everyone trusts that people will be available when
the team, which then drives needed and that they will achieve the results for which they are
strategic and tactical decisions held accountable. But people still work together on teams whose
to align the company behind individual members have to successfully pass the baton on shared
the visions of the employees. responsibilities and team-wide goals. Everyone needs to know if they
will be running the race alone for 3 or 4 days.
RENEE WARREN
Whats one personal goal that youd feel comfortable sharing
Founder of Onboardly 33
?
here that the company as a whole can support you in
achieving?
GENIUS QUESTION
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
How are you feeling about
more energy to work and not less.
your workload today?
I want to find out if they
feel overwhelmed. Busy
What do you find most exciting about work right now?
is an ok word, but as soon 34
Work? Exciting? Yes! If its not, then this question opens up the
as they indicate that they
floodgates to an important conversation that can shift people into
are overwhelmed it throws
projects and roles that are right for them.
up a red flag. Anxiety
equals a loss of focus and
generally really crappy
Of your accomplishments this week, which one are you most
work, so we want to make 35
proud of and why?
sure that they are confident
Taking pride in ones work used to be far more ubiquitous than it is
in their daily tasks.
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.
GENIUS
? QUESTION
39
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
What needs do you
from focused work (Im looking at you email and Facebook). These
have from me?
behaviors become habitual and eventually invisible to us. This
1) My job as a leader
question brings awareness back to the activities that are more harmful
is to serve my team.
than helpful.
Understanding their
needs and identifying
ways to meet them allows
What do you need help with? This week? This month?
my team to operate at 40
Remember when a week was 7 days and a month was 30 or 31?
an optimized level. 2)
In business, time moves at an accelerated pace. This question also
Mining for needs helps to
widens the lense on objectives so that people are focusing on the
establish accountability
now without losing sight of the not too distant future.
on the team and a sense
of who owns what. It also
opens up the conversation
41 Anything in your work world thats less than stellar/causing
for what needs the team
frustration or delays?
has of each other.
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.
Are you crystal clear on your role and what you should be
43
working on? If not, what aspects arent clear?
Working hard and being busy doesnt 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
44
either the short or long term?
They say that worrying is like praying for the things you dont 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.
What would you change about our product if you had a magic
46
wand?
We dont 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.
ANESE CAVANAUGH
Creator of the IEP Method
GENIUS
? QUESTION
GENIUS
? QUESTION
How are your meetings going? How can we make them more
52
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.
What book would you like to read (that you dont already
53
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
ANDREW DEUTSCHER
information that is inaccurate, irrelevant, or difficult to comprehend.
VP of Business Development,
So starting a conversation about business books will allow the most
The Energy Project
valuable recommendations to rise to the surface.
GENIUS
? QUESTION
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.
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.