MANAGERIAL/ LEADERSHIP DILEMMAS

Situation 1
A leader in a staff position was required to initiate a significant change and had scheduled a
meeting with key stakeholders from line functions for this purpose. She put together an
elaborate and detailed presentation. But soon she started to worry about the negative attitude
and the likely resistance of the individuals in line functions to whom she had to make that
presentation. She realized that her unproductive self-talk and negative internal chatter were
making her anxious and defensive. Once she became aware of her anxiety, she approached a
trusted colleague and shared her concern.
Let us say that you were this trusted colleague. How will you respond? Please consider the
following two scenarios:
1. Since most of us tend to listen with a view to respond (NOT with a view to understand), they
quickly give their advice and insights. In such a mode, what will you tell her? When does this
approach work, and when does it not work?
2. Let us say that you control your “advice-giving” instinct and play a more facilitative/
catalytic role in your attempt to help her. What will be your response in this scenario? When
does this approach work, and when does it not work?
3. More generally, when an individual shares an emotional situation/ challenge with you,
a. What are a few things that are supportive of the person?
b. What are a few things that are best avoided (what NOT to say)?

Situation 2
In his book “Search Inside Yourself”, author Chade-Meng Tan describes a workplace dilemma he
faced at Google. His friend and co-worker Joe built systems used internally in the company.
Meng was one of Joe’s delighted internal customers. In a fairly routine operation, Joe’s old boss
moved out, and a new manager Sam joined the company as the boss of Joe’s team.
Within a few weeks, unexpectedly Sam called Joe to state that Joe’s performance was
unsatisfactory, and his dismissal procedure would soon be initiated. Not surprisingly, Joe was
heartbroken. As his friend and well-wisher, Meng was not only unhappy, but also angry. He
wanted to help Joe. He decided to speak to Sam about this matter. He realized that he was just
a colleague from another department, and so Sam was not obliged to listen to him or be
influenced by him. He reflected on his approach.
1. Please put yourself in the shoes of Meng. What are your reflections on how Sam may THINK
about your desire to talk to him about Joe. In other words, get into Sam’s “HEAD” space.
Next, how might Sam FEEL about your request to talk to him. In other words, use your

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 ‘heart’ to reflect on what Sam’s “HEART” may feel. Then, putting together your thoughts on
how the other person thinks and feels, how will you ACT? How will you approach the
conversation with Sam?

Situation 3
An eager and hardworking technical professional took up a leadership position in a start-up
company. Soon she faced seemingly endless stream of operating problems, inexperience across
the board, lack of clear procedures, disputes among her people, and a senior management that
provided little or no support. She did not create these problems, but now it was her job to
resolve them. She decided to work hard as usual. She shut herself up in her office; she worked
long hours on a narrow set of familiar problems. She neither sought nor received timely and
helpful feedback. As she ran into one crisis after another, she found it more and more difficult
to sustain her motivation. After some time, she was fired from her job. She was dazed and
wondered how it all had happened to her.
1. What course of action should this professional have taken in her leadership role? What
explains a bright, hard-working professional getting derailed in career? For new leaders,
what shifts are required to attain success? What are important insights for you from this
short illustration?