Challenging Conversations

– The Power of Connecting, Transforming and Engaging

You have numerous resources on influencing and effective communication.
Why then is it that you may still avoid ‘the difficult conversations’ that could make the biggest difference to your organisation, teams and key relationships?

Think carefully!
You may be ….
Avoiding conversations you know you ought to have
Desiring to be more assertive and in control
Getting impatient with certain people or personality types
Finding difficult giving negative feedback
Being  anxious before a ‘crucial’ conversation
Thinking of what you “should have” said after the conversation is over
Wishing you had managed a conversation or an individual differently, or
Finding challenging in managing emotional customers, colleagues or employees, team mates.

Many difficult conversations’ are the results of small challenges that become magnified by how you perceive the customer or the co-worker, your boss or team mate.

Your  personal opinions about other people, whether true or false, can stop you from really listening to what they are saying and,
responding in a way that is authentic, honest and can build the foundation of stronger and positive relationships.

You may have observed that many managers and staff have difficulty speaking up when adverse – yet not uncommon – conditions arise.

You may agree that when you have to deliver ‘bad news’ or say ‘no’ to the people in power you could often tempted to placate with a ‘yes.

You may see that avoiding “difficulty issues ‘ won’t make them disappear: years of study have found that in most of the cases they will escalate to conflict if not addressed appropriately and in healthy ways.
Within an organization, these can dampen motivation, affect performance and reduce productivity.

It is the ability to handle controversial discussions that determines how successful you are in your career and personal life

It is by examining the ‘tinted’ views you have of people and situations that you can avoid the inaccurate assumptions that rapidly lead to misunderstandings and friction.

It is by understanding the causes and costs of not speaking up or not being assertive that we can deeply understand the significant impact on our work performance and personal satisfaction.

If your objective is to become more influential as a leader or manager or team leader,
start to build awareness of conversations that you have been procrastinating or avoiding lately. These might be the conversation that can make the biggest difference in your teams and key relationships.

Think for yourself:

What is a “challenging conversation”?
How can I build trust and connection in conversation?
Introducing the InsideOutYou Model for healthy communication
Where does it all start? The power of triggers
Reactions vs. Responses
Thoughts and perceptions
The power of positive communication
Has EQ anything to do with the way we hold challenging conversations?
Choosing blame or responsibility?
Getting to know yourself, getting to know others. Where do I start?
How body language may influence your conversations
Not wanting to talk about it – ever: Why we don’t speak up!
Excuses to avoid conflict or difficult issues and healthy ways to engage and resolve them
Different levels of conversations
Angry, pleaser or…. assertive?
Understanding the ‘sensitive’ and the ‘difficult’ personality
The power of focus
Basic listening skills – hearing is Not listening!
Giving and receiving feedback
Planning your conversation

When ready, we can sit together over a cup of coffee, if you so desire to further explore it.

Why you want to do it – Objectives

Identifying what causes individuals to be ‘difficult’ or demanding and its consequences
Understanding the difference between ‘being reactive’ vs. ‘being responsive’
Discovering different ‘styles’ of reactions in communication
Develop strategies for managing different personalities and motivations
Learning skills to deal with extremely sensitive type of personalities
Learning tools to shift perceptions when we face crucial conversations
Understanding the role of victim and aggressor in conversation
Becoming responsible for building ‘authentic conversations’ and healthy rapports
Planning ahead for better outcomes of your conversations
Applying the power of Awareness , Self- responsibility and Focus when in difficult conversations
Discussing negative feedback constructively
Developing communication skills on empathic listening, defusing anger, managing conflict, speaking assertively
Strengthening relationships at work and in life
Sustaining positive workplace attitudes


Suresh Shah, M.D., Pathfinders Enterprise

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