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50 Days
Your First
50 Days
Actionable Tips for Evolving
from Manager to Leader
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
So, what do you say, are you ready to hatch out of your shell
and become the leader you always knew you could be?
Shifting
your mindset
Butterfly: Your First 50 Days 6
You did it! You’re a manager.
Now that we got that out of the way, it’s time to roll up your
sleeves and get to work.
What are the key processes you should be familiar with when
it comes to management training and team development?
What are your personal career goals and how can I help
create a plan to get there?
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.
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.
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.
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.
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.
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.
Joe Burton
Founder & CEO, Whil Concepts
Chapter 2
Leading
from within
Butterfly: Your First 50 Days 32
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.
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.
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.
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.
Set boundaries
It’s natural to want to be liked. New managers in
particular struggle with navigating the tricky balance
between likeability and respect.
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.
Warren Bennis
Organizational Consultant
DAY 15
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.
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.
Storytelling, improvisation
& off-script presenting
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.
Indra Nooyi
Chairman & CEO of PepsiCo
Chapter 3
Focusing
on talent
development
Butterfly: Your First 50 Days 56
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.
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.
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.
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.
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.
Jacob Morgan
3x best-selling author, most recently of The Employee
Experience Advantage, Speaker, & Futurist
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.
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.
Russ Laraway
Co-Host, Radical Candor Podcast
DAY 30
Marcus Buckingham
Leadership Expert & Author
Chapter 4
Establishing
a healthy &
productive culture
Butterfly: Your First 50 Days 81
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?
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!
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.
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.
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.
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.
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.
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.
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.
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.
William Bauer
MD, Royce
DAY 40
Growing
as a leader
Butterfly: Your First 50 Days 106
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.
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
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
Daniel H. Pink
A Whole New Mind: Why Right-Brainers
Will Rule the Future
DAY 42
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
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
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
Bookmark
these top-ranked
leadership books
Dale Carnegie
Simon Sinek
Rule the Future
DAY 44
Intrigued?
Send us a note at hello@butterfly.ai to schedule a demo.
Respond in
real-time and track
emerging trends
Get personalized
coaching based on
team inputs
Drive engagement
through active
listening and action
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.
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.
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.
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.
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?