Your First 50 Days PDF

Your First
50 Days
Your First
50 Days
Actionable Tips for Evolving
from Manager to Leader
Written and edited by Butterfly.ai

Chapter 1
6 Shifting your mindset
Chapter 2
32 Leading from within
Chapter 3
56 Focusing on talent
development
Chapter 4
81 Establishing a healthy
& productive culture
Chapter 5
106 Growing as a leader
Butterfly: Your First 50 Days 3

Introduction
Your new job description might
say “manager.” But are you ready to
be a leader?
When we first became managers, we were a bit lost. There was

no guide, and we didn’t know which of the thousands of Forbes
and Harvard Business Review articles to read first. There
were a lot of materials out there, but none of them seemed
to be written for us. Now that we’re managers ourselves,
we wanted to share some of our wisdom with all of you.
So, here we are. Congratulations! You’ve just been promoted.

Clearly, you are awesome at your job—and what’s more, the
leadership at your organization believes in you enough to
put you in charge of the development of other people.
“Your First 50 Days” is the book we wished we had when

we first became managers. To inform this guide, we
interviewed dozens of leadership experts and layered in our
own experiences. We then took all of these great insights and
distilled them into something you might actually have time
to read, hence why we slashed the typical 100-day plan to 50.

Becoming a manager is more than just a title change on
LinkedIn; it’s an important career milestone.
It’s something you should be proud of, and also something

you should take seriously. If you’re reading this book, you’re
already taking the most important first step to becoming a
great manager, which is having an insatiable curiosity and
a desire to learn about leadership as an ongoing craft.
Nobody knows everything there is to know, and if they

say they do, they’re lying. The key is to open yourself up to
constant learning and listening from Day 1. If you do this,
you’ll be on your way to becoming a stronger leader.
So, what do you say, are you ready to hatch out of your shell
and become the leader you always knew you could be?
Let’s get started!

Chapter 1
Shifting
your mindset
You did it! You’re a manager.
Did you update your LinkedIn headline? Great.
Now that we got that out of the way, it’s time to roll up your
sleeves and get to work.
We know it’s only Day 1, but believe us, being a manager is

hard work. It also doesn’t come naturally to most, but there
is good news: with the right foundation, you’ll be on your
way to becoming a great leader.

DAY 1
Assess the situation

Now, before you go into full TED Talk mode at your next
team meeting, our first piece of advice is to pause, breathe
and assess the situation.
Take an audit of what tools and resources you have available,

and which you do not. If you work at a large company, you
likely have an army of experienced and dependable human
resources professionals there to guide you as you ease into
your managerial duties. But if you’re at a smaller company
or a startup, it’s you against the world, kid.

Some important questions to consider:
What does your company’s HR team look like?

Who are the key people to get to know?
What are the key processes you should be familiar with when
it comes to management training and team development?
When are performance reviews?

What’s the process as a manager?
How are bonuses paid out?

What is the manager’s role in that process?
What is the process for when an employee is failing to

meet their objectives?

DAY 2
Audit your team

Whether you were promoted up from within a team or are
starting a brand new job as a team lead, you’ll want to get
acquainted with the personalities on your team, as well
as their dynamics with each other. Don’t wait to schedule
one-on-ones with each team member to get a sense for their
overall engagement and job satisfaction. Set the tone early
by transparently and candidly getting to know them
as individuals.
What motivates them, what frustrates them and where do

they see their career going in the future? Our No. 1 piece of
advice for these early conversations: Clearly communicate
to your team members that you’ve got their back from Day 1.
Establish a foundation of transparency and trust early on
that will carry on through your relationship.

Here are some things to explore during
these GTK (get-to-know) meetings:
Career journey: How did you get to this job?
What is your favorite thing about your job now?
What do you wish there were more of?
How do you feel about senior leadership?
How do you feel about the team’s overall dynamics?
How do you feel about the office environment?
What are your personal career goals and how can I help
create a plan to get there?

PRO-TIP
Tiffany Pham, CEO & Founder of

Mogul, says she prefers to schedule
one-on-ones with her team members
outside of the office. “I never eat
alone,” she tells us. By getting your
team members out of the cube and into
a more relaxed setting, you’ll learn more
about them and how their work and
their lives intersect.
DAY 3
Identify a
management mentor
You can read blogs and advice books (like this one) until you’re
blue in the face, but know this: The single best way to become
a better leader is to watch a great leader in action. Whether
your company is 10 people or 10,000 people, strong leaders
will stand out. Identify a leader that matches with your own
leadership style or personality, and invite them to coffee to
propose a mentorship relationship to them.
When setting up these meetings, avoid vague phrasing such

as, “I’d like to pick your brain.” Explain exactly what you
hope to benefit from the relationship, and set expectations
for the mentor so they know exactly. For example, perhaps
you schedule a standing 20-minute coffee break, where you
stroll out of the office and tackle one question or topic at a
time. This makes the ask much more manageable for your
mentor, and also gives you a framework for guiding
actionable conversations.

Some topics to address with your
management mentor:
What do you wish you knew when you first became

a manager that you know now?
What is your advice for giving tough feedback?
How should I celebrate wins within my team?
What’s the best way to motivate the range of personality

types on my team?
How can I better collect feedback on my management

style from the team?
How can I lead by example when it comes to

work/life balance?

DAY 4
Establish a
delegation strategy
If you’re new to managing a team, you might think delegation
is simply a matter of forwarding along emails, or assigning
tasks that you might not want to do. If you’ve had a bad
manager at any point in your career, no doubt you’ve been
on the other side of this equation.
Effective management is as much about about scaling

your talents across your direct report or team as it is about
developing that person in their own role.
Effective delegation involves pairing the right individual with

the right tasks, and creating a framework for which types of
tasks you delegate to whom. One of the most important pieces
of delegation involves providing context—that is, clearly
communicating to your team what the objective of the task
is and why it’s important to the team or company mission.

Here are some additional best practices
to consider:
How you communicate the tasks you delegate will set

the tone for the project ahead. Phrases like, “I would like
you to own this project end-to-end,” and “Handle this ASAP,”
will have drastically different effects on your team.
Providing support and micromanaging are two very

different things. Offer help or step in as needed, but create
timelines that allow your team to learn and do with some
breathing room for bumps along the way.
Give feedback. After a task or project has been completed,

give praise for the positive and offer up ways to improve
if critical feedback is needed. Always close the loop
on the conversation.

DAY 5
Implement time
management hacks
Within the first week of being a manager, you’ll notice that
the hours seem to slip by quicker than they used to. At many
companies, managers operate as player-coaches, tasked with
their own responsibilities while also being in charge of the
performance and ongoing development of their teams.
With more on your plate, efficiency will become exceedingly

important to maintaining a healthy work/life balance.
A ten-second Google search will yield hundreds, if not

thousands, of time management tips and trips. As a manager,
it’s on you to develop processes that work for you and your
unique work habits.

Here are some hacks to test out in your
first few weeks:
Know your ‘Top Three’: Each morning, write down the top
three priorities you want to advance on that day. Set clear
and realistic milestones and hold yourself accountable.
Block your calendar: Instead of creating to-do lists,

block windows in your calendar to complete specific
task or projects within a given window. This is called
calendar-blocking.
Stop multitasking: Interruptions are the enemy of

efficiency. Establish discrete windows for checking email
and hold “Office Hours” so your team knows when you’re
available for questions (and when you need to focus your
attention elsewhere.)
Prioritize and say, “No.” Savvy managers know how to

rank the projects that are most important to the team and
company objectives. They also know when to say, “No,”
or push things off to a later date.

DAY 6
Formalize
feedback loops
Giving and receiving feedback is one of the easiest ways
to create stronger relationships with your teams. The real-
time nature of work means that communication has become
instantaneous and ongoing, and yet most companies still
rely on annual reviews or infrequent employee engagement
surveys. By the time managers receive the data, it’s no longer
timely nor actionable.
Whether you rely on technology to collect and give team

feedback or not. The most important step to take is to
formalize feedback loops early. Set the tone in your first
week of becoming a manager that you welcome open and
transparent communication. Clearly communicate to teams
how and when they can provide feedback to their manager.

Here are some thought-starters
for formalizing feedback:
At the end of weekly team meetings, make it habit to ask

how your team is feeling. This can be as easy as asking
each person to share how they’re feeling at the end
of their individual updates.
Always acknowledge feedback. If an idea isn’t actionable,

explain why. If someone poses an idea that would benefit the
team and/or company, take action as a manager to push
it along, and share the success with the team.
Use technologies like Butterfly to automate team feedback

at regular intervals (weekly or biweekly) and train teams
to get into the habit of giving feedback. Discuss the data
gleaned transparently as a group to socialize the importance
of feedback in the big picture.

PRO-TIP
Holding regular Butterfly meetings will

reinforce the importance of feedback
to your team, and give people a platform
for voicing their opinion on the key
drivers that affect their engagement
and happiness at work.
DAY 7
Put the team first,

you second
A common pain point for new managers is the pressure
of having other individuals dependent on them for success.
While your team is ultimately supporting the priorities
you set as the team leader, your support of them is perhaps
even more important.
You might be familiar with the term “servant leadership,”

coined by Robert K. Greenleaf in 1970. Within this philosophy,
managers focus on team development as their No. 1
priority, tirelessly working to “serve” their teams in this
capacity. Servant leadership requires a tangible presence
of the manager in the lives of their team members,
one that emphasizes support and guidance as opposed
to micromanagement.

Here are some quick ways to exert
yourself as a servant-leader:
Be an active listener. Give your team members a platform

for providing feedback, and make that feedback actionable.
Demonstrate empathy. Make it a point to gauge how

your team members are feeling not just at work, but in
their lives more holistically.
Work on your self-awareness. Understanding your

own strengths and weaknesses will allow you to serve
your team better.

PRO-TIP
“Self-awareness is an innate quality,

but it can be gained through time and
through coaching. The best managers
have it, and the worst do not. Seventy
percent of the workforce is disengaged
to varying degrees, and that’s an
indictment on management.”
Victor Lipman
Leadership Expert & author of The Type B Manager
DAY 8
Embrace the
new dynamic
One of the early missteps a new manager can make is to
let their newfound “power” get to their head. Becoming a
manager is a responsibility that comes with challenges, but
also exciting opportunities to help develop yourself and those
around you. Your attitude toward this new responsibility will
ultimately set the tone for your entire management career.
A recent study from the Harvard Business Review found

that most people who are “rookies” in their roles are
“surprisingly strong performers in terms of both innovation
speed.” The one category of people the research didn’t apply
to was new managers. Why? Rookies in other roles proved
more likely to listen, ask for help, test-and-learn, and eagerly
receive feedback. Managers–not so much. This group seemed
to double-down on what got them promoted in the first
place (e.g. focusing on themselves/their own asks), instead
of empowering their teams.

The big takeaway:
Approach management as you would
taking on any other new skill:
Listen and get feedback: Formalize feedback loops

with your team to help optimize your approach.
Seek guidance (see Day 3: Identify a management mentor)
Experiment: Be flexible in your approach early on and

make adjustments as needed.

DAY 9
Set a self-training plan

Becoming a better leader doesn’t happen overnight.
You’ll find that as a manager, there is always more to learn
and there always places to improve. Marathon runners don’t
complete one or two training runs before the big day.
They establish a daily plan with milestones that will get

them to their ultimate goal over time. Similarly, developing
as a leader is a gradual process that unfolds over time.
And unlike a marathon, the finish line is a moving target.

Listen and subscribe to relevant leadership blogs and
publications. The Harvard Business Review, Forbes and
Workforce are great places to start. Follow your favorite
leadership experts on LinkedIn, Medium or Twitter.
Get feedback: Formalize feedback loops with your team

to help optimize your approach.
Set aside time to take stock of your progress as a manager.

After check-ins with your team, take note of their feedback
and prescribe areas to focus on.

make adjustments as needed. Set one manager goal per
month and focus your growth on that topic. For example,
you might devote one month to improving communication,
and the next to motivation.
Keep mentor meetings active and on the calendar.

Write down questions or challenges you have in Evernote
or a simple document, so that when you have time to meet
with your mentor, you are prepared.

DAY 10
Review your progress

Remember that point we made about self-awareness?
The thing about being self-aware is that it doesn’t come
naturally to most people. Keep yourself honest by
scheduling time for reflection.
We can start by auditing the first few

lessons of this chapter:
Listen and get feedback: Formalize feedback loops

with your team to help optimize your approach.
Seek guidance (see Day 3: Identify a management mentor)

make adjustments as needed.
Are you effectively managing your time?
Are you putting your team first, and you second?
Are you embracing your new responsibilities as a leader?
Have you scheduled time to advance your leadership

training over time?
Are you delegating within a framework, and providing context?

PRO-TIP
“The first step to even being able to

recognize other people’s stress is to
practice self-awareness yourself.
When you’re mindful, you tend to
understand how others might be feeling
faster, because you pay attention more.
Being in the present moment is the key
to emotional intelligence for managers.”
Joe Burton
Founder & CEO, Whil Concepts
Chapter 2
Leading
from within
You’re probably familiar with the common airline
instructions to put your own oxygen mask on first before
assisting others. The idea is that you can’t help other people
unless you take care of yourself first. While this might
seem selfish and somewhat nonsensical in the context of
management, experts agree that leaders are built from within.
Although the outputs of your leadership skills might manifest
in the development of the people, business and culture that
surrounds you, your journey as a manager is ultimately
a personal one. It begins and ends with you.
Once you’ve shifted your mindset from that of an individual

contributor to a manager, the next step is to turn inward to
identify your strengths and weaknesses, as well as your own
personal management style. Compare the jovial exuberance
of Richard Branson to the thoughtful reticience of Mark
Zuckerberg, and you’ll quickly see that leadership comes in
many forms. It’s all about finding the style that works for you.

PRO-TIP
“The respect you give others is

a dramatic reflection of the respect
you give yourself.”
Robin Sharma
Bestselling Author & Leadership Expert
DAY 11
Learn to lead
by example
We’ve all heard the adage, “Actions speak louder than
words,” and it’s especially true in the context of leadership.
A manager who instructs her team members to be at their
desks in the office by 9 a.m. each day will garner more
respect if she follows her own rules.
Similarly, a manager who can take responsibility for a misstep

will be more admired than one who routinely passes the buck.
Respect and having a management title don’t automatically

go hand-in-hand. Respect must be earned, and the best way
for a leader to do so is to lead with their actions.

Here are some easy ways to lead
by example:
Roll up your sleeves. Is your team consistently putting

in late nights at the office to wrap up a critical project?
Offer to stay with them and help, if only for one evening.
The gesture shows you’re a manager and a team player.
Respect the chain of command. Avoid speaking

negatively of your own managers in front of your team,
as this sets a precedent for a “trash-talking” team culture.
Be proactive, not reactive. Great leaders are thoughtful

in the way they respond to conflict or challenge. If you find
yourself at a critical moment, take a breath and be deliberate
and thoughtful in your next steps. Be proactive in how you
plan to rectify the situation.

DAY 12
Practice empathy
Empathy is the ability to understand, or share in, the position
of someone else. With management, empathy materializes as
not only understanding someone’s position, but also weighing
it when it comes to decision-making.
Speaker Simon Sinek, millennial leadership expert, writes

about the importance of empathy to leadership in his book
Leaders Eat Last: Why Some Teams Pull Together and Others
Don’t. In an interview with SUCCESS magazine, he points out
that treating people with empathy can have a “compounding
and reciprocal effect.” Science backs this up: A 2009 study
found that even small acts of kindness trigger a release of
oxytocin in the brain.

Some simple ways to demonstrate
empathy include:
Ask how you can help. Drive home that you have your
team’s back and you’re there for them. The simply act of
saying, “Do you have what you need? How can I help?”
demonstrates that you are aligned with your team and
there to support.
Ask your team about their weekend plans,

and demonstrate a genuine interest in their health
and wellbeing outside of the office.
Get to know what employees are passionate about

outside of the established parameters of their role.
Infuse their personal passions into the role if and
where it makes sense.
Award an employee who has been consistently logging

extra hours with a personal gift, such as a pair of tickets
to the next home game for their favorite team.

DAY 13
Set boundaries
It’s natural to want to be liked. New managers in
particular struggle with navigating the tricky balance
between likeability and respect.
With millennials rising through the ranks faster than older

generations (one study found them have at least four direct
reports, on average), it’s increasingly common for managers
to be at the same age if not life stage as their direct reports.
The blurred lines between “work” and “life” means that

new managers can find themselves at happy hour with their
team in one moment, and leading a serious discussion with
them in another one.

PRO-TIP
“Common mistakes new managers

make are to try to be everyone’s friend,
or conversely, come on too strong and
exert their newfound authority without
too much thought or discrimination,
Either will get you into trouble.”
Victor Lipman
Leadership Expert & author of The Type B Manager
DAY 14
Balance confidence
with authenticity
Great leaders demonstrate a blend of self-confidence and
authenticity that together engender trust from their teams.
Confidence is critical in leaders, as it helps them make more
sound decisions and motivate teams to rally around those
decisions. Authenticity is equally important, as it invites your
team to provide feedback that will ultimately help you do
your job better.
Many new managers struggle with self-confidence in the context

of their new roles. Managers who lack confidence are more likely
to hastily make decisions and lose the support of their teams.
Being chosen to lead, even if it’s your first time doing so, means
that your organization believes you are capable of taking on the
responsibilities of the role. Act like it! As self-confidence grows,
keep yourself grounded by being an authentic figure in the
eyes of your team. If you make a misstep, own it. Demonstrate
empathy with respect to the challenges of your team members
and offer support as a servant-leader along the way. Finally,
reiterate that feedback is critical to the success of the team.

PRO-TIP
“The most dangerous leadership myth

is that leaders are born—that there is
a genetic factor to leadership. That’s
nonsense; in fact, the opposite is true.
Leaders are made rather than born.”
Warren Bennis
Organizational Consultant
DAY 15
Define your personal

management style
Although the characters of some of our favorite films and
TV shows would indicate otherwise, there is no single
“manager” type. Leaders come in all forms: introverts,
extroverts, Type As, Type Bs, etc. The key to unlocking
your management potential is to recognize your personal
management style early on, and build from there.
Victor Lipman, leadership expert and author of “The Type

B Manager: Leading Successfully in a Type A World” writes
in the Harvard Business Review, “When it comes to talent
assessment, it seems we tend to make decisions with blinders
on, defaulting to an expected model of high-stress, high-
intensity leadership.” The correct way to judge leaders,
he argues, is by results—and not by stereotypical behaviors.

Take an audit of your own style, keeping in mind that most
of us are a mix of Type A and Type B. Identify situations where
each side of your management personality tends to come out.
If you’re a high-stress (Type A) manager, be aware of

circumstances where you might improve your soft skills or
demonstrate empathy to your team. This will complement
your direct demeanor.
If you’re a low-stress (Type B) manager, keep in mind that

you should strive to balance this style with a results-oriented
leadership style in order to hold your team accountable.

DAY 16
Find your North Star

as a leader
Just as your organization likely has a mission statement and
set of guiding principles, team leaders should also have their
own North Stars that they aspire to work toward as managers.
Here’s an example from Denise Morrison, CEO of Campbell
Soup Company: “To serve as a leader, live a balanced life, and
apply ethical principles to make a significant difference.”
Amanda Steinberg, CEO of DailyWorth.com, aligns her

personal mission with the ultimate ambition of the company
she leads: “To use my gifts of intelligence, charisma, and serial
optimism to cultivate the self-worth and net-worth of women
around the world.” Take a five minutes today to jot down
your own personal mission statement, keeping in mind
that it might change over time.

Some tips for thinking about your
personal mission statement:
What is the big idea your company or team is

trying to solve? How can you apply this big idea to the
culture of the team?
Whom do you admire when it comes to leadership?

Think about what, specifically, you admire about their
leadership styles. Write down those traits and use them
to guide you.
From your mission statement, identify three to five ways

you can help bring that mission to life within your team.
Make sure there points are specific and actionable.
Finally, determine KPIs. How will you know you are

effectively following this mission? You might use technology
(like Butterfly) to gather feedback from the team, or ask
employees for their thoughts during in-person checks,
both formal and informal.

DAY 17
Identify your
weaknesses
Remember that section on self-awareness? Confidence
in known strengths is a beautiful thing, as it demonstrates
authority and builds trust—but the same can’t be said for
weaknesses. As a manager, it’s on you to reflect and collect
feedback to help identify what you’re not good at, so you
can either minimize or improve gaps over time.
For example, as a manager you might realize that keeping

track of details is not your forte. In the short term, you can
minimize this weakness by asking a team member with
complementary skills around organization to help project
manage core team tasks. In the long-term, you can improve
this weakness by identifying tools and process that will
help you become more organized.

Here are some ways to explore
your weaknesses:
Ask close friends, family and mentors for their candid

thoughts. Guide the conversation by starting with a
specific question: “When we worked on Project X,
what’s one thing I could have done better?”
Take a personality assessment. Many organizations

administer DiSC® or similar personality tests. While these
should not be taken literally, they can be used directionally
to identify potential gaps in your aptitude as a leader.
Invite ongoing feedback from your team and explore

trends over time. Does your team consistently cite
“miscommunication” as a frustration? Perhaps you need
work toward becoming a better communicator. For this
type of feedback, anonymizing team responses will give
way for more transparent (and more powerful) insights.

DAY 18
Create a personal
management plan
It’s time to outline the steps you’ll need to take to develop
your leadership skills around your North Star.
Start by referring back to the weaknesses you’ve identified

from conversations with your inner circle or team members
and isolate the most critical areas of improvement. Next,
frame each weakness as a tangible goal. For each goal,
identify the skills or behaviors you will need to acquire
or develop to get there.
Then, set a strategy—or means for effecting change—and a

timeline for when you plan to assess progress. For example, if
you are weak at public speaking, you might consider taking a
series of improv classes and volunteering to lead two internal
workshops prior to assessing progress in three months.

Weakness I am not a confident public speaker
Skills Oral communication

& speech-making
Controlling non-verbal cues

(gestures)
Storytelling, improvisation
& off-script presenting
Goal More effectively communicate in

front of large groups, in order to
better inform and motivate my
team, as well as build influence.
Strategy Enroll in six-week improv program
Study ten TED Talks; implement

what works
Lead two internal workshops

at company for practice

DAY 19
Hold yourself
accountable
With concrete objectives, a strategy in place to confront
weaknesses head on, and a date for measuring results,
you’re well on your way to holding yourself accountable.
Since most people find it difficult to audit their own
performance, enlist trusted colleagues, mentors and your
own team to provide feedback.
Accountability as a manager can be tricky, especially when

it comes to gauging your performance in the eyes of your
team. Team members might feel uncomfortable giving
direct feedback, especially if it’s critical, which is entirely
understandable. While it’s recommended to promote
transparency within the team, allowing for anonymous
feedback is the best way to get unfiltered thoughts from
your team. It’s the critical feedback, after all, that will help
you develop and grow as a leader. Whether you choose to
administer a short, anonymous survey or use technology to
anonymously pulse-check your employees, be sure to close
the loop on critical feedback in a transparent manner.

Some tips for showing your team that
you’re accountable:
If you’re collecting feedback anonymously, compile the

data that comes in and address the findings as a team.
Acknowledge weaknesses and propose ways to improve.
Then, ask the team to discuss these solutions with you,
together, so they are part of the improvement cycle.
Make a habit of candidly asking team members,

“What do you need from me?” This simple question shows
that you are there for them, and opens the door for feedback.
If a suggestion comes in from the team, and you decide to

implement it, make sure you close the loop. Reinforcing the
power of feedback is the single best way to promote more
feedback down the line. Actions speak louder than words.

DAY 20
Let’s audit the key lessons of this chapter

to see how we’re stacking up:
Are you acting in accordance with how you want to be

viewed as a leader?
Are you finding small ways to demonstrate empathy

to your team?
Have you set the appropriate boundaries?
Are you effectively balancing confidence with authenticity?

Have you identified your personal management style?
Have you written your personal mission statement

as a leader?
Have you identified your weaknesses, either through

self-assessment or through feedback?
Have you put pen to paper when it comes to your personal

leadership goals?
Are you holding yourself accountable to your goals?

PRO-TIP
“Just because you are CEO, don’t

think you have landed. You must
continually increase your learning,
the way you think, and the way you
approach the organization.”
Indra Nooyi
Chairman & CEO of PepsiCo
Chapter 3
Focusing
on talent
development
When companies successfully scale, it’s rarely due to sheer
luck. Growing a business is closely linked to developing
and retaining talent amid rapid change. One of the most
common missteps new managers take is to assume their role
as a manager is 90 percent delegation and 10 percent talent
development. We would flip that ratio around.
Great managers know how to make themselves replaceable.

This does not mean shifting all of your duties to your direct
reports so you can kick back and await a swift and early
retirement. Rather, this means that effective managers know
how to align team members’ strong suits and passions with
the needs of the business. They also know how to properly
train team members up into greater responsibilities over time.
As one manager we spoke with put it, “If your team members
aren’t getting promoted, you’re not doing your job.”

DAY 21
Step into the role

of player-coach
As we previously wrote about, being a player-coach is
hard work. You’re responsible for your own tasks as well
as those of your team.
A common mistake early managers make is to put too

much emphasis on their duties as a player (that is, an
individual contributor) while letting the develop of their
team members slip through the cracks.
Your new role as a player-coach might be one of the

most surprising aspects of becoming a manager.
Suddenly, the very strength that got you promoted—individual

performance—must now take a back seat to the entirely new
skillset of a coach. As the Harvard Business Review points out,
“You can’t be a good manager if you’re not a good coach.”

You’ve already proved yourself as a
player. Here’s how to improve as a coach:
Take an interest in people development: Work with

each employee to develop custom career development
plans for which you can help hold them accountable.
Set clear and realistic expectations: Let your team

know what’s expected of them and, more importantly,
why by providing adequate context.
Ask instead of command: Bosses might boss their team

members around, but managers know how to ask their team
to step up without sacrificing professionalism.
Be a pillar of support: Even when you can’t jump on

the proverbial field next to them, ask what you can do
to help them achieve their goals and make a genuine
effort to get them there.

DAY 22
Up your
communication game
As an individual contributor, you might have skated by with
mediocre communication skills. As manager, you’ll soon find
that your ability to effectively communicate will directly
influence the performance of your team.
For instances of proactive communication (i.e. a conversation

initiated by you), begin by considering the desired outcome. For
example, “I would like Sarah to feel empowered and motivated
to take on this project” or, “I want Simon to know how critical
it is for a task to be completed a specific way.” In each of these
cases, the desired outcome will dictate the communication.
In the first case, you might choose words designed to pump

Sarah up for the challenge ahead (“I know your skills are the
right match for this assignment”). In the second example, you
might clearly outline steps and even repeat yourself to drive a
point home (“To be clear, Simon, we need to send the file through
by end of day this Wednesday, or else we’ll miss the deadline”).

Beyond how you communicate delegated tasks, giving and
receiving feedback is a separate skill entirely. It involves
creating a culture of transparency and being open as a
manager to asking for and actively listening to feedback
from the team. Conversely, employees can also benefit from
receiving ongoing feedback from their manager, as well.
Here are some best practices for

communicating as a leader:
Exude confidence, but leave your arrogance at the door.

Command respect with your knowledge and preparedness
to lead—avoid talking down to others.
Be cognizant of timing. The way in which you communicate

something can be just as important as the message itself.
Listen! The best communicators are the best listeners.

They understand their audiences, empathize with them and
tailor their communication style to unique motivations.

DAY 23
Know how to negotiate

Being a skilled negotiator is as much of a skill in the
workplace as it is in life. What most people get wrong about
motivation is that they think it’s a game, and that the aim
of a negotiation is to “win.” This approach tends to harm,
not help, a negotiation. The correct approach to negotiation
is to see it as a conversation in which both parties can
potentially win, with some compromise in most cases.
As a manager, you might find yourself in the midst of

negotiations big and small, ranging from agreeing to a
team member’s vacation schedule to fighting for someone’s
promotion or bonus.
In all cases, knowing how to effectively navigate a negotiation

will strengthen you as a leader.

Follow these steps to navigate your
way through a negotiation:
Come prepared: Do your homework before entering

a conversation. Get the facts and understand the context
prior to diving in.
Identify your starting point: What is the ideal outcome

you hope to achieve?
Identify your bottom line: What is the least favorable

outcome you’d accept?
Exercise empathy: Take stock of what’s motivating

the person at the other side of the table. Factor these
nuances into your offer.

DAY 24
Practice collaborative
goal-setting
Studies show that when employees help set their own
goals, they are more likely to achieve them than those
who are instructed to following a series of goals mandated
by their manager. In fact, in this latter scenario, employees
tend to demonstrate an adverse reaction known as
psychological reactance.
Across decades of research, psychologist Edwin Locke found

that people are most likely to reach their goals when they
1) understand their importance and 2) are convinced they’re
capable of achieving them. Working with your team members
to establish their performance and career related goals, and
providing feedback and support along the way are the keys
to motivating people in their own development.

Here are some ways to foster more
collaborative goal-setting:
Ahead of performance reviews, ask employees to submit

a first draft of how they’d like to set their goals. Implement
their goals alongside your own.
Limit goals between 3 to 5 priority items so that they are

easily remembered and measured.
Formalize feedback windows in order to discuss progress,

challenges and next steps.

PRO-TIP
“Even your most talented employees

have room for growth in some area,
and you’re doing your employee a
disservice if the sum of your review is:
‘You’re great!’ No matter how talented
the employee, think of ways he could
grow towards the position he might
want to hold two, five, or 10 years
down the line.”
Kathryn Minshew
Founder, The Muse
DAY 25
Line up
personal passions
with team goals
Collaborative goal-setting and active listening will help
reveal to you the personal passions of your team members.
For example, perhaps your star analytics associate, Matthew,
is an avid writer on the side, and is curious to explore
opportunities to develop those talents at work.
Matthew’s best fit on the team is likely in his current role, but
that doesn’t mean his writing talents can’t be utilized in a way
that benefits both the he and the company. After all, being a
leader means finding opportunities to let your team members
shine and empowering them to take on new challenges.
Armed with the knowledge that Matthew enjoys writing,

you might offer him the opportunity to contribute to the
company blog, for which the marketing team desperately
needs fresh content.

PRO-TIP
“One of the most important things

you can do is to be a support system
for your team. I make it clear that I’m
investing you. I want to have a personal
relationship and understand where
you’re trying to go.”
Sara Correa
Global Head of Marketing, TE Connectivity
DAY 26
Track progress
to goals
Helping hold team members accountable to their goals is
one of the biggest jobs you’ll have as a manager. In many
cases, goals are not concretely measured. In those qualitative
instances, it might make sense to work with your employees on
a system for measuring progress and eventual achievement.
Here’s how to do it: After setting a series of goals (remember

to prioritize three to five at most), ask, “What does success
look like?” for each. Just as you collaborated with employees
to set the goal, you can also work with them to establish
success metrics.
For example, if Sasha wants to improve her presentation

skills, indicators of success could mean leading an internal
training session, or participating in a new business pitch.
Once you paint a picture of what success looks like, it will be
much easier to establish trackable milestones along the way.

PRO-TIP
“Managers need to do two things.

First, they need to understand that their
job is about helping others succeed;
in fact, not just succeed, but to make
their employees more successful than
they are! Second, managers need to
encourage their employees to speak
up so that they can help shape the
experiences they want to have at work.”
Jacob Morgan
3x best-selling author, most recently of The Employee
Experience Advantage, Speaker, & Futurist
Learn more at: https://thefutureorganization.com

DAY 27
Allow for flexibility

Kaizen is a Japanese method of goal-setting that focuses on
tiny micro-improvements that lead to tangible progress over
time. It’s the system employed by engineers at Toyota, for
example, who operate within a culture in which continual
small improvements push the company forward over time.
Kaizen is a powerful means for achieving goals because
it inherently allows for flexibility.
As we all know, workplaces and teams are not static

entities—they are complex and dynamic systems that are
in a constant state of flux.
While establishing goals and milestones (i.e. “drawing lines

in the sand”) is necessary to holding ourselves and our team
members accountable, it’s also important to be flexible
should conditions change along the way.

Some best practices of flexible
goal-setting include:
Ensuring that the three to five priority goals are, for

the most part, immovable. These are mission critical
objectives that should only change in extreme circumstances.
Revisiting sub-goals over time to ensure that they

remain the best way to achieve the bigger picture goal.
If there’s a more efficient means to reach a goal, amend
the sub-goals as needed.
Contextualizing feedback with the big picture goal in

mind. If team members are off track, explain how their lack
of progress toward sub-goals affects their bigger goals.
From there, provide support to overcome challenges or
work together on more effective sub-goals.

DAY 28
Ask, “What do
you need?”
Your approach to management says a great deal about you
as a leader. The best managers view themselves as servants
to the long-term development of their teams. To that end,
while your team will be delegated tasks based on your
strategic directives, you should be constantly asking how
you can better “serve” them as a manager.
The simple question, “What do you need from me?”

demonstrates to your employees that you are invested in
their ability to succeed in your role. Asking, “What do you
need?” has a secondary benefit, too, as it empowers your team
members to think more proactively about what they need to
complete a task or progress in their role.
It takes the bonus off of you as the manager and makes

them more accountable for their own success.

Here’s how to put it into action:
When you assign a task to an employee, provide the

context needed, such as the project’s relationship to
larger, more strategic goals. Give them a clear deadline,
and set expectations for what success looks like.
Now, step back and listen. Does the employee understand

the mission? Are they missing any key pieces of information?
Finally, ask, “What do you need from me?” Encourage

them to view you not only as a manager, but as a resource
and coach, guiding them to eventual success.

DAY 29
Be an advocate for
your team members
When you become a manager, you assume a unique position
in that you are a key stakeholder when it comes to the future
career trajectory of others within the organization, and within
their careers as well. As an individual’s day-to-day manager,
you will amass a wealth of knowledge about a person’s
strengths, weaknesses, aspirations and setbacks. With this
insight comes the responsibility of stepping up to be an
advocate for their growth. Being an advocate can take many
forms, beginning with an ideal scenario in which an employee
is consistently exceeding expectations and maturing out
of a role they’ve been placed in.
This is a dream scenario as a manager, because it likely

means you are providing the support they need to grow.

Communicating successes in this regard, especially to
HR when it comes time for performance reviews, is an
important role. It’s on you to make a case, so approach
employee evaluation with the thoughtfulness and
thoroughness that your team deserves. Use anecdotes
and data to demonstrate to the organization why this
person deserves to take the next step.
Advocating for your team doesn’t only occur with the

superstars of the group. Undoubtedly, people will face
challenges, or perhaps decide that the current career
path ahead of them is not a fit. As a manager, you must
also support individuals in these scenarios, helping to
identify ways to improve or support should they decide
to move on from the team.

PRO-TIP
“Asking people to expose their logic

can be enormously helpful to both
of you. Often, something feels much
clearer in someone’s head than it is in
reality. By having someone explain ‘why’
he is thinking a certain way, you can
help him sharpen his ideas.”
Russ Laraway
Co-Host, Radical Candor Podcast
DAY 30
Let’s audit the key lessons of this chapter

to see how we’re stacking up:
Have you shifted out of the “player” mindset to that of a “coach?”
Are you actively working to improve your communication skills?
Are you using negotiation best practices to your advantage?
Are you working with your team members to

collaboratively set goals?

Have you gotten to know your team members so
you can match up their personal passions with team
and company needs?
Are you tracking progress to goals and providing

ongoing feedback?
Are you allowing for flexibility as conditions and

dynamics change?
Are you asking, “What do you need?”
Are you advocating for your team members in good

times and in bad?

PRO-TIP
“Talent is the multiplier. The more

energy and attention you invest in it,
the greater the yield. The time you
spend with your best is, quite simply,
your most productive time.”
Marcus Buckingham
Leadership Expert & Author
Chapter 4
Establishing
a healthy &
productive culture
Research shows that 70 percent of U.S. workers are “not
engaged” at work. It’s unfortunate that most of us are unhappy
in our careers, seeing as we spend the majority of our waking
days surrounded by our colleagues. In fact, managers have a
lot of pull when it comes to employee happiness. As leadership
expert Victor Lipman puts it: People leave their managers,
not their companies. Are you feeling the pressure yet?
The environment you create as a manager is critical

to supporting a healthy, engaged and productive team.
As a new manager, it’s important to establish the type
of culture you aspire to lead early on. The first few weeks
can set the tone for your entire career.

DAY 31
Communicate
the big picture
A common mistake many beginner managers make is to
delegate tasks to their teams without filling them in on the
broader context of the assignments. For example, a senior
marketing manager might delegate to his or her coordinator
the tedious task of updating a CRM database to ensure
customer information is accurate and up-to-date. Without
context, this might feel like a menial project; but in reality,
keeping the database fresh is critical to your team’s customer
engagement strategy. In other words, let your employees
know why their work matters!
Communicating the big picture can be as easy as a one-

sentence add on to an email or Slack asking someone to tackle
a task. Take a minute and put yourself in your employees
shoes. Explain the importance of the project to the team and
company. This will have the dual benefit of increasing their
investment in the task, and it will also help educate them on
the more strategic goals of the team. Remember: As a manager,
you’re doing your job if you are getting your people promoted.

Here are some tips for providing the
big picture context:
When you delegate a task, make a habit of providing

one sentence as to why the project matters in the context
of the team’s mission.
If an employee is laying the groundwork for a bigger

project (e.g. research statistics for a whitepaper), providing
the end product so they can see how their efforts
contributed to the final product.
Give credit where it’s due. On a team, all contributions should

be recognized and celebrated. Call out where employees
have contributed, even if those contributions seem minor.

DAY 32
Make your
weekly “all hands”
meetings count
One of the first things you’ll do as a new manager is set up
weekly team meetings. These provide a platform for aligning
goals and keeping each other up to speed on priorities. That
said, having meetings for the sake of meetings can drain
productivity, so it’s important to approach “all hands”
meetings strategically. You might approach your weekly
team meetings by defining a set agenda for each, with
templates that employees can fit their own updates into.
Perhaps you use the first few minutes to articulate the top
priorities for the week, and then ask each employee to provide
a brief update on what they’re working on. For example,
Brian Wong, founder & CEO of Kiip, asks his employees to
share their PPFs for the week: Priorities, Progress and Fires.
Round out the meeting by giving employees an open forum to
share feedback, and practice active listening to demonstrate
that their opinion matters.

Here’s a sample 30-minute “all hands”
agenda for you to customize:
Set the tone: Communicate the top team-wide priorities

for the week and provide context around their importance
to the company overall.
(5 minutes)
Individual updates: Allow each team member to provide

their updates in a brief, formatted fashion. Three-minutes
per employee is usually more than enough time.
(15 minutes for a team of five)
Feedback: Close the loop on any actionable feedback

received from the week prior, and open the floor to
next feedback.
(10 minutes)

DAY 33
Get out of the office

Consider occasionally moving your one-on-one meetings to
someplace that’s not your office. Is your office building nearby
a new coffee shop, or convenient cafe lunch spot? Grab a
team member to join you for a quick coffee or meal. You’d be
surprised at how much more people open up when they’re
out of the corporate confines of the offices. Even for more lax
and informal work settings, physically meeting outside of the
office will help you get to know your team members on a more
personal level and allow you to gauge their overall happiness.
This approach is especially beneficial for team-wide outings.

Set up a standing breakfast meeting to get team members
interacting outside of the office, or plan a quarterly social
outing to boost team dynamics. These events need not be
overly elaborate or expensive. The idea is to simply get
people interacting outside of their desks.

Some ideas for team activities include:
Wine tastings, cooking classes or other educational activities
Group tours at a local museum
Group fitness classes (beginner level so as not to intimidate

or alienate anyone)
Volunteering opportunities at local nonprofits or charities
Supporting a team member for one of their outside passions

(e.g watching a colleague run the local marathon)

DAY 34
Recognize wins
The perception of the “manager” or “boss” in pop culture is
often that of a domineering individual whose sole mission
is to reprimand his or her employees. While giving negative
feedback is part of the gig, of equal, if not greater, importance
is knowing how and when to recognize a job well done.
Reinforcing good behavior will promote future good behavior,
just as providing feedback on mistakes will help ensure
that those missteps do not occur in the future.
With tools like Slack and Skype, it’s never been easier to
give props to your team members. If someone hits a task
out of the park, let them know.
Avoid being gratuitous with your flattery, but don’t be afraid

to vocalize and celebrate exceptional work. Calling out a job
well done publicly is another motivational tool, as it plants
a seed for others who might want to be the subject of formal
recognition for their own work.

Here are some simple ways to
recognize wins:
Honor a performer of the month and celebrate the

winners publically.
Use real-time collaboration tools as a means for informally

giving positive feedback to your team members. Something
as simple as, “You’re a [firework emoji]!” shows your people
you care and that their efforts are appreciated.
Keep note of major wins in a log, so that when review

time comes around, you’ll have anecdotes and stats to
back up your case for rewarding a bonus or promotion.

PRO-TIP
“I used to think the best way to show

appreciation was through monetary means:
bonuses, salary increases. I’ve learned that
employees respond to different rewards.
One of my employees favors free time.
I would try to entice him to work weekends
by offering him money, but what he really
wanted was free time to spend with his
family. Another one of my team members
likes having a sense of purpose and getting
recognition for his talent. I empower him
by giving him projects that line up with his
passions and allow them to flourish.”
William Bauer
Managing Director, Royce, Forbes columnis
DAY 35
Employ technology
to track happiness
With 70 percent of the U.S. workforce “disengaged” in their
jobs, keeping people happy will be one of your biggest hurdles
as a beginner manager. Reinforcing happiness begins and ends
with knowing where your team stands, and having a constant
pulse on their mood relative to their roles on your team.
Fortunately for you, it has never been easier to keep tabs

on how your team is feeling. Tools like Butterfly make it
seamless to gauge employee happiness over time.
And, as you’ve learned earlier in this book, data is only as

powerful as what you do with it. Monitoring engagement
trends over time can help guide the decisions you make as
a manager, as well as how you communicate those decisions.
Want to see Butterfly in action?

Contact hello@butterfly.ai for a free demo.

Here are some ways you can put employee
intelligence to work:
Notice work/life balance is becoming a challenge? Perhaps

your team is heads down on a major deliverable. Reinforce
the importance of the project, and let employees know there’s
an end in sight. Offer a free personal day to people who are
consistently putting in extra hours toward a mission.
Perhaps employee mood around the office environment has

dipped as of late. Consider what has changed in the office to
cause this. Did you move to an open office setting? Open the
topic up for a team-wide discussion at the next standup.
Is one employee consistently providing negative feedback

on team dynamics? With Butterfly, you can enter an
anonymous one-on-one chat with them to get to the source
of the problem. This safe environment will foster more candid
feedback from your employees and allow you to remedy
difficult situations or escalate them to HR as needed.

PRO-TIP
“The smart use of technology can help
managers supercharge their listening skills.
Getting a regular ‘pulse’ reading of how people
are feeling can help address issues before
it is too late. Annual review meetings just
don’t cut it—and are often counterproductive.
Moreover, the importance of being able to
also interact anonymously with your team
members through the use of technology
allows managers to get an honest sense
for how things are going. Without getting a
good sense for what lives among your team,
there is little prospect for generating a highly
engaged and effective organisation.”
Jan-Emmanuel De Neve
Associate Professor of Economics and Strategy
University of Oxford
DAY 36
Turn insight
into action
Using real-time feedback to improve work conditions for
your team shows your ability to listen and lead. Use playback
to communicate when changes that have taken place are a
direct result of someone speaking up. This will prove to your
employees that their opinion is not only heard, but that it
can affect change in the real world, too.
Simple language adjustments can drive home the importance

of team feedback. For example, perhaps your team members
give you feedback that the addition of a new hire has made
them feel unsure of their current roles and responsibilities.
You might say, “A number of you expressed a desire to review
the revised org chart together, so we’re going to take a few
minutes to do so today.”

DAY 37
Reverse troubling
morale trends
When you have a constant pulse on your team’s
engagement and happiness, you’ll quickly detect when the
vibe is good, and when things are rocky. Several factors can
contribute to employee happiness (that’s why Butterfly’s
tool tracks five key metrics and allows for custom drivers).
If you spot dips in morale, it’s time to act as a leader and
remedy what’s ailing the team.
Proactively addressing negative sentiment across the team

is one of the most critical functions you’ll have as a leader.
After all, bad vibes have a tendency to spread much faster
than those “feel-good” moods. When you identify this trend,
your first course of action is to solicit feedback and listen.
Then, act on the feedback accordingly.

Some things to keep in mind by way
of employee morale:
Determine if the morale issue is isolated within an

individual or group, or if it’s team wide. Deal with
individuals on a one-to-one basis. If the morale issue
is bigger than that, consider more sweeping steps that
will benefit the entire team.
Consider enlisting the expertise of HR if you fear that

morale is affecting productivity. HR is your ally in situations
like this. Lean on their experience.
Always look to the root cause of the issue before coming

up with a solution. Throwing perks like team dinners and
“free” days off might sound great, but if the issue is about
growth opportunities or company leadership, these types
of perks will not remedy the situation.

DAY 38
Support
constant learning
and education
Developing your employees doesn’t begin and end with the
specific job functions of their roles. As a leader, you should
strive to support their well-rounded education in your
industry and in the professional world overall. As a manager,
you can support this by making room for an education stipend
in your team budget, and encouraging employees to enroll
in courses or attend conferences where they make sense.
Informally, you can also encourage employees to share

their wisdom among the team during regular meetings.
Is your analytics manager a rockstar at pivot tables? Ask
them to prepare a 5-minute 101 tutorial so they can share
their expertise with the team. These moments elevate the
talents of individual contributors, and by the way, do so
to the benefit of the broader team.

Some ways to promote ongoing learning:
Set an educational budget for the team for conferences

and paid courses
Share paid subscription logins for magazines and other

online resources
Invite team members to lead 5-minute mini tutorials on

focused topics that everyone can benefit from
Consider investing in a team wide Lynda or Coursera account

(if those are not offered at the company level)
Supporting a team member for one of their outside passions

(e.g watching a colleague run the local marathon)
Educate your team members around company learning and

development programs

PRO-TIP
“The job of the leader is to grow

more leaders.”
Robin Sharma
Bestselling Author & Leadership Expert
DAY 39
Manage
expectations around
work/life balance
Work/life balance is a tricky concept during a time when
smartphones give employees (and managers) constant contact
to email and collaboration platforms like Slack. How can
people create boundaries between work and life when our
smartphones blur the lines between them?
How rigid a line you draw between work and life will depend
on a variety of factors: company culture, your team’s function
and your personal leadership style. Important to note is that
there is no one way to approach work/life balance; however,
for all managers and all teams, managing expectations is the
No. 1 way to ensure work/life balance does not deter employee
engagement or happiness. It’s all about communication and
how you set the stage for your team.

Here are some best practices for
communicating your approach toward
work/life balance:
From Day 1, set clear ground rules with your team members
regarding expected hours, your “work from home” policy and
expectations around scheduling time off and vacations.
Set ground rules and expectations for smartphone-

connected platforms like email and Slack. A simple
statement like, “I might email you outside of work hours,
but I don’t expect you to reply then,” let’s your team know
what’s expected of them.
We all face times when the workload is heavier than average.

In these instances, make sure you are clear with employees
on why that’s the case. “Team, as you know, the quarterly
report’s deadline is fast-approaching. I want to thank you in
advance for the extra effort that’s going into this over the next
five days, and I know it will pay off when we deliver it to the
Board come Friday.”

PRO-TIP
“For me, business is life. My sense of

being is work. I’ve realize that it’s not
the same for everyone else. I hope my
employees look forward to work, but not
everyone is the same. For some people,
work is just a paycheck. It pays their
car bills and helps send their kids to
school. As a first-time manager, I failed
to see how the strain of long hours and
working weekends affected my team.”
William Bauer
MD, Royce
DAY 40

In this section, you learned how to promote a healthy
and productive team culture.
Check your progress by asking the

questions below:
Are you actively communicating the big picture and

providing context?
Have you set an agenda for your “all hands” meetings?

Does that agenda include time for soliciting live feedback?
Are you getting the team out of the office?

Have you recognized and celebrated wins within the team?
Are you actively monitoring the team’s happiness

and engagement?
Are you using the feedback you receive to

improve conditions?
Are you using the feedback you receive to address morale

issues head-on?
Have you demonstrated your support for learning

and development?
Have you clearly set expectations around work/life balance?

Chapter 5
Growing
as a leader
What, you think just because you read this book that you’re
ready to become the next Dale Carnegie? Au contraire!
Leadership is a journey. You must remain open to ongoing
learning and development to hone your craft over time.
With all the resources available to you, we know this can be

a bit daunting, so we’ve summarized some of our favorite
resources, tools and methodologies that will help you grow
as a manager, even as you reach the final pages of this book.

DAY 41
Bookmark
these awesome
leadership blogs
Harvard Business Review
HBR’s leadership section is the crème de la crème of
management insights.
https://hbr.org/topic/leadership
Radical Candor
Career and management straight talk.
https://www.radicalcandor.com/blog
The Pinkcast by Daniel Pink

Short videos with snackable leadership content.
http://www.danpink.com/pinkcast

Management Matter
Management expert Victor Lipman, who provided insights
for this book, shares leadership tips in Forbes.
https://www.forbes.com/sites/victorlipman
Lead Without a Title

We had the pleasure of meeting Robin Sharma and hearing
him speak at the World Government Summit.
http://www.robinsharma.com/blog
Leadership Freak
Quick reads that drop leadership knowledge in 300 words
or less.
https://leadershipfreak.blog
Lolly Daskal
To-the-point tips from a top executive leadership coach.
https://www.lollydaskal.com/blog

PRO-TIP
“Leadership is about empathy. It is

about having the ability to relate and to
connect with people for the purpose of
inspiring and empowering their lives.”
Daniel H. Pink
A Whole New Mind: Why Right-Brainers
Will Rule the Future
DAY 42
Browse some of these

leading management
podcasts
Podcasting is a great way to hone your skills while you’re
on your commute. Here are some of our favorites.
Radical Candor
A leadership podcast that focuses on one specific management
topic each episode. Radical Candor is interesting in that it
addresses questions that managers might have regarding their
teams, as well as questions an employee might have regarding
their own manager.
www.radicalcandor.com
Leadership and Loyalty

Though aimed at Fortune 500 leaders, there is something
for everyone in this podcast, which focuses on emotional

intelligence in particular.
dovbaron.podomatic.com
Stanford eCorner
For aspiring leaders and entrepreneurs, Stanford’s eCorner
podcast is one to bookmark. The free weekly podcast taps into
the influence and reach of Stanford’s network to bring you
insights from some of the most inspiring entrepreneurs
in the game.
www.ecorner.stanford.edu/podcasts
Coaching for Leaders

The Coaching for Leaders for podcast emphasizes the fact
that leaders can be shaped over time, and that everyone has
the potential to be a strong leader. More than 100,000 monthly
listeners make this a Top 10 Career podcast on iTunes.
www.coachingforleaders.com
Engaging Leader
The Engaging Leader podcast teaches managers how to instill
core cultural values into each of their employees, emphasizing
the importance of employee engagement when it comes
to effective leadership and strong company cultures.
www.engagingleader.com/category/podcast

DAY 43
Bookmark
these top-ranked
leadership books
How to Win First Break

Friends & All the Rules
Influence Marcus
People Buckingham
Dale Carnegie
Start With The Personal

Why MBA
Simon Sinek Josh Kaufman

Built to Last
James Collins
The Five Dysfunctions of a Team:

A Leadership Fable
Patrick M. Lencioni
Drive: The Surprising Truth

About What Motivates Us
Daniel Pink
The 21 Irrefutable Laws of Leadership

John C. Maxwell
The Effective Executive

Peter Druckner
The New One-Minute Manager

Kenneth Blanchard, PhD

PRO-TIP
“A leader’s job is not to do the work

for others, it’s to help others figure out
how to do it themselves, to get things
done and to succeed beyond what
they thought possible.”
Simon Sinek
Rule the Future
DAY 44
Use this tool to

develop your team
over time
Great leaders have a constant pulse on their teams,
actively listening to employee feedback to improve team
dynamics and develop talent over time. In an era of real-time
communications, managers can use workplace collaboration
tools to draw out ongoing insights into team culture.
Butterfly is one such tool.
By integrating Butterfly within existing tools (like

Google Suite, Facebook Workplace or Slack), managers
can field anonymous pulse surveys on a regular basis,
unearthing trends in real-time and creating more candid
pathways for communication with their teams.
Intrigued?
Send us a note at hello@butterfly.ai to schedule a demo.

Empower your team to
share candid feedback
Respond in
real-time and track
emerging trends
Get personalized
coaching based on
team inputs
Drive engagement
through active
listening and action

DAY 45
Lobby for
educational
opportunities at
your company
While many resources (like this book) exist to provide
you with the fundamental tools needed to lead a team, as a
manager your learning should never stop. Some companies
offer an array of trainings and tools to help managers grow
over time; however, the reality is that most organizations
do not invest in these places. Talent teams balance many
functions, and have limited budgets, which means that it’s on
managers to make a case for resources where they make sense.
In fairness to talent teams, it’s difficult to understand

what exactly employees need by way of educational tools
without individuals raising their hands and providing
actionable feedback.

If you could benefit to a paid subscription,
learning tool or workshop, bring this idea
to your HR teams and explain how this
will help you develop as a leader.
Identify ways that the tool or publication can function

as a shared resource across many managers or perhaps
the entire organization. Cost-effectiveness is always
a powerful selling point.
Explain to your talent leadership the tangible benefits

you expect to reap from the investment. Draw parallels
between your knowledge gaps and the needs of your team
instead of simply passing along a flashy brochure.
If technology is involved, offer to vet and lead scheduling

for a necessary demo or overview, thus taking some of the
burden off of HR. Invite others across the organization to join
so you can discuss pros and cons as a collaborative group.

DAY 46
Seize opportunities
to teach others
One of the simplest ways to concurrently build your leadership
skills as well as promote yourself as a leader is to offer to share
your knowledge with other managers at the organization. Did you
approach a team challenge in a particularly unique way? Is your
method for running weekly meetings proving to be value when
it comes to setting priorities? Find ways to share what’s working
with your peers, so they can replicate on their own teams.
Once the communication channels have opened, you’ll find that
other managers will be happy to contribute their best practices
as well, creating a well of insights across the organization.
These moments of cross-pollination can be as simple as a short

email note or voiceover at a management meeting. In other
cases, you might find it helpful to set up an internal workshop
to walk peers through the approach and process. In either
case, be sure that your communication is benefit-led, meaning
that you are emphasizing the approach and the result in a
replicable way. To keep the conversation flowing, ask peers
how they would approach a similar situation.

PRO-TIP
“Being a leader doesn’t mean you

know everything there is to know
about leadership. In fact, the best
leaders are the ones who pursue
their own education.”
Forbes, 2016
DAY 47
Lean on your
team to help you
grow as a leader
At Butterfly, we believe that collecting and acting on team
feedback is key to becoming a manager. This doesn’t just mean
checking in here or there or administering a once-per-year
survey; rather, it’s a about building a transparent team culture
where feedback flows freely. No matter how you capture this
feedback, be it team meetings, one-on-ones, or anonymous
surveys, it’s important to view this data as fuel to your
continued education as a manager.
Remember that chapter on kaizen, the Japanese art of micro-

adjustments? That applies here, too. By listening to your team
over time, you can optimize your style based on that which is
resonating, as well as proving ineffective.

Some easy ways to get started:
When you implement a new process or approach, open

a conversation instead of mandating an announcement.
Ask team members what they think, and field their
questions and concerns.
Use one-on-ones as opportunities to gut-check how team

members feel about your management style. Are you
checking in too frequently? Not enough? What types of
support are they seeking that you’re not currently providing?
What’s working well?
If you use employee engagement tools or anonymous

surveys, take the time to parse the data and share a summary
with the team in a format to which they can easily react. Have
an open and candid discussion about the data in aggregate.

PRO-TIP
“I’m a big fan of in the moment

feedback. Feedback—whether positive
or constructive—is most actionable
when it’s tied to a specific occurrence.”
Matthew Field
Co-Founder, MakerSights
DAY 48
Make management
progress part of your
performance review
At many companies, managers assume the hybrid role of
player-coach. This means that your performance review as
a manager might be more about hard performance metrics
(e.g. did your team hit their target sales numbers?) and less
about employee engagement and development. If honing your
leadership skills is important to you, we suggest proactivity
offering this up as a personal objective in your reviews with
your own manager.
Some forward-thinking companies make this easy on

employees by allowing individuals to present their own goals
to their manager as a starting point (this is that “collaborative
goal-setting” we were discussing before). If this is true of your
organization, now’s your chance to make it known to your
manager that people development is a top priority for you.

Here are some ways to measure
the KPIs (key performance indicators)
of solid leadership:
Team engagement scores via pulse surveys or informal

feedback. How engaged and motivated are your team
members about the company mission and their role within it?
If you leverage a software, sourcing these statistics can
be done instantly.
Team promotions or anecdotal evidence that points to

employees progressing with regard to their own career goals.
Low turnover numbers, which can also point to an

engaged and motivated team.

DAY 49
Be patient
Developing your leadership skills is an ongoing journey,
and great leaders aren’t born overnight. During your first
few weeks as a manager, you’ll likely hit roadblocks and
setbacks. You’ll encounter challenges to which you do not
have an immediate solution. You will get frustrated. You will
question yourself. All these things are common and you’re
not alone. In these instances, the best course of action is to
be proactive and open to help from others. Remember our
advice about getting to know HR?
Your talent leadership are expert in people management

and should be used as a resource as you grow into your
role. Utilizing time spent with your mentor is another way
to bounce ideas or capture insight. Beyond your immediate
network, there’s a wealth of information out there to guide
the decisions you make as a manager.

Here are some quick tips for if and when
you get stuck:
If you’re unsure about a course of action, tell the

employee or the team that you will regroup with them
at a later time. It’s far better to schedule a follow-up
conversation than it is to go back on your word.
Consult peer managers if they’ve encountered a

similar situation. If so, ask them to walk you through
how they handled it, calling out what worked, what
didn’t and what they’d do differently.
View HR as a resource in these situations.

Finding a few minutes to gut-check a decision or run
ideas by someone from your talent team will allow you
to access their experience in working with many
managers across many teams.

DAY 50
Join the conversation

This guide is designed to start a broader conversation
about modern-day managers and the future of leadership.
We’d love to get your feedback and stories!
Email us at hello@butterfly.ai, or send us a tweet

@bttrflapp to tell us about your personal leadership journey,
and we just might include it in the next version of our book.

Conclusion
Evolving from a manager to a leader is
one of the most important steps you can
take in your career.
On a personal level, growing into a leader means you

have honed your soft skills to a point in which you can be
held accountable for motivating and managing the wide array
of personalities on a team. At the company level, building
strong leaders into every layer of the organization isn’t just
a nice-to-have; it is a requirement for building a healthy
and productive work culture.
We hope this book has provided you with a solid foundation

to build on as you grow into your new role. We’d love to
keep the conversation going, so please send us a note at
hello@butterfly.ai or on Twitter @buttrflapp.

About Butterfly
Butterfly is an employee intelligence and management

coaching software designed to transform managers at
all levels into exceptional leaders. Butterfly helps modern
organizations gather regular employee feedback that
drives actionable insights and builds stronger, more
transparent cultures.
A pioneer in AI-powered management coaching, Butterfly’s

self-learning technology uses real-time team feedback
to deliver customized leadership training and content to
managers on an ongoing basis.
Companies like GE, Citibank, Ticketmaster and Ogilvy rely

on Butterfly to grow leaders and build stronger, happier
teams. In 2017, the Webby Awards, the internet’s highest honor,
named Butterfly as one of the top 5 platforms in its category.

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Your First

Written and edited by Butterfly.ai

Butterfly: Your First 50 Days 3

When we first became managers, we were a bit lost. There was

So, here we are. Congratulations! You’ve just been promoted.

“Your First 50 Days” is the book we wished we had when

Butterfly: Your First 50 Days 4

It’s something you should be proud of, and also something

Nobody knows everything there is to know, and if they

Let’s get started!

Butterfly: Your First 50 Days 5

Did you update your LinkedIn headline? Great.

We know it’s only Day 1, but believe us, being a manager is

Butterfly: Your First 50 Days 7

Assess the situation

Take an audit of what tools and resources you have available,

Butterfly: Your First 50 Days 8

What does your company’s HR team look like?

When are performance reviews?

How are bonuses paid out?

What is the process for when an employee is failing to

Butterfly: Your First 50 Days 9

Audit your team

What motivates them, what frustrates them and where do

Butterfly: Your First 50 Days 10

Career journey: How did you get to this job?

What is your favorite thing about your job now?

What do you wish there were more of?

How do you feel about senior leadership?

How do you feel about the team’s overall dynamics?

How do you feel about the office environment?

Butterfly: Your First 50 Days 11

Tiffany Pham, CEO & Founder of

When setting up these meetings, avoid vague phrasing such

Butterfly: Your First 50 Days 13

What do you wish you knew when you first became

What is your advice for giving tough feedback?

How should I celebrate wins within my team?

What’s the best way to motivate the range of personality

How can I better collect feedback on my management

How can I lead by example when it comes to

Butterfly: Your First 50 Days 14

Effective management is as much about about scaling

Effective delegation involves pairing the right individual with

Butterfly: Your First 50 Days 15

How you communicate the tasks you delegate will set

Providing support and micromanaging are two very

Give feedback. After a task or project has been completed,

Butterfly: Your First 50 Days 16

With more on your plate, efficiency will become exceedingly

A ten-second Google search will yield hundreds, if not

Butterfly: Your First 50 Days 17

Block your calendar: Instead of creating to-do lists,

Stop multitasking: Interruptions are the enemy of

Prioritize and say, “No.” Savvy managers know how to

Butterfly: Your First 50 Days 18

Whether you rely on technology to collect and give team

Butterfly: Your First 50 Days 19

At the end of weekly team meetings, make it habit to ask

Always acknowledge feedback. If an idea isn’t actionable,

Use technologies like Butterfly to automate team feedback

Butterfly: Your First 50 Days 20

Holding regular Butterfly meetings will