This document discusses techniques for managing upward and leading leaders. It provides a 5-part toolkit for managing upward, including understanding leaders and their goals, communicating persuasively, negotiating management style, knowing when to challenge, and building skills for difficult situations. The document also profiles Cyndi Mitchell and Jo Miller, who provide coaching on leadership skills.

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LEADING YOUR LEADERS: HOW TO MANAGE UPWARD
Cyndi Mitchell, Managing Director, ThoughtWorks Studios
Jo Miller, CEO, Women’s Leadership Coaching Inc

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Corporate Subscribers

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Jo Miller
CEO, Women’s Leadership Coaching Inc
•Over 12 years providing leadership coaching and seminars
• Coached hundreds of women worldwide
• Seminars for women’s networks at Intel, Oracle,
Alcatel-Lucent, Nortel, Rockwell Collins, UBS, and more
•Silicon Valley’s “Women of Influence”, 2008

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Cyndi Mitchell
Managing Director
ThoughtWorks Studios
•Joined ThoughtWorks in November 2002, and has served in a variety of roles
including development, consulting and general management.
•Prior role was as Managing Director of ThoughtWorks UK.
•Over the past sixteen years of her career, Cyndi has been helping businesses
use software to innovate and create value.
•Has provided hands-on software development, consultancy and advisory to a
number of Global 1000 IT organizations.
•Prior to joining ThoughtWorks, Cyndi was a Senior Architect with Sun
Microsystems in New York, Chicago, and London.
•Started her career with Andersen Consulting in Chicago.

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Cyndi Mitchell
Managing Director
ThoughtWorks Studios
•Cyndi has a Bachelor of Science degree in Chemical Engineering from
Northwestern University.
•Is married and lives in London.
•Enjoys yoga, and theatre.

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What are some things you
did early on in your career,
that helped you to be
recognized as an up-and-
coming leader?

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Leading Your Leaders
A Tool-Kit for Managing Upward
1. Understand your leaders and their goals
2. Communicate in a style they find persuasive
3. Negotiate a management style that works for you
4. Know when to challenge your leaders
5. Build skills for dealing with difficult situations

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Have you had employees
who ‘managed upward’
well with you?
What did they do that you
appreciated?

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Leading Your Leaders
A Tool-Kit for Managing Upward
1. Understand your leaders and their goals

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1. Understand your leaders and their
goals
• Success in any role begins with understanding your
leaders and their goals.
• Check in with them frequently to ask about their most
important goals and greatest challenges.
• Find out what business goals they are responsible for.
• Aim to understand what motivates them, and to discern
their personality type and communication style.

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What steps do you take, to
understand your leaders
and their goals?

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Leading Your Leaders
A Tool-Kit for Managing Upward
1. Understand your leaders and their goals
2. Communicate in a style they find persuasive

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2. Communicate in a style they find
persuasive
• Do they prefer to communicate via email or in person?
• Is it more effective to schedule time, or catch them in the hallway?
• Do they like high-level overview, or deep dive into the data?
• Do they like to hear the entire story or just the bottom-line?
• Do they want to be informed of the entire plan or the end result?
• Do they prefer to make decisions quickly or think it through?
• Who are they influenced by: Are they a lone decision-maker or do
the crowd-source decisions?
• Is it best to share bad news Monday morning or Friday afternoon?

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What advice can you share,
on communicating
persuasively with leaders?

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Leading Your Leaders
A Tool-Kit for Managing Upward
1. Understand your leaders and their goals
2. Communicate in a style they find persuasive
3. Negotiate a management style that works for you

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3. Negotiate a management style that
works for you
• Know thyself!
Communicate with your leaders:
• What is the best way to manage you? For example:
• Do you prefer management that is hands-on or hands-off?
• Do you like specific directions or the overall picture?
• Do you prefer frequent check-ins, or being left alone?

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How should a person
approach their manager to
negotiate a management
style that works for them?

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Leading Your Leaders
A Tool-Kit for Managing Upward
1. Understand your leaders and their goals
2. Communicate in a style they find persuasive
3. Negotiate a management style that works for you
4. Know when to challenge your leaders

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4. Know when to challenge your leaders
• Build trust and respect first!
• Always ask permission.

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Can you tell us about a
time when you had to
challenge a leader or
disagree with them?
How did you handle that
situation?

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Have you ever have to give
your manager feedback on
their performance?
How did you communicate
the feedback?

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Leading Your Leaders
A Tool-Kit for Managing Upward
1. Understand your leaders and their goals
2. Communicate in a style they find persuasive
3. Negotiate a management style that works for you
4. Know when to challenge your leaders
5. Build skills for dealing with difficult situations

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5. Build skills for dealing with difficult
situations
Become resilientresilient…
and know how to stand up for yourselfstand up for yourself…
while remaining diplomaticdiplomatic.

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What advice do you have,
for dealing with a difficult
situation involving a
leader?

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EXERCISE:
1) Review the 5 skills in today’s Tool-Kit for
Managing Upward
2) Identify which of the 5 skills you plan to work on.

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Leading Your Leaders
A Tool-Kit for Managing Upward
1. Understand your leaders and their goals
2. Communicate in a style they find persuasive
3. Negotiate a management style that works for you
4. Know when to challenge your leaders
5. Build skills for dealing with difficult situations

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Q&A

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Cyndi’s Keys to Success
1) Have a vision for yourself and what
you are trying to achieve
2) Surround yourself with people who
inspire you
3) Have fun!

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Discussion Questions
1) In your company, what are the best ways to get to
understand your leaders and their goals
2) Share an example of communicating in a style that
a leader finds persuasive
3) What management style works best for you?
4) When is it OK to challenge your leaders?
5) Share an example of skills to use when dealing
with difficult situations with leaders.