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How to start a tough conversation



Most leaders confront people ineffectively because they are either too aggressive and seen as conflict seekers or too indirect and seen as conflict avoiders. Effective leaders don’t confront – they ‘carefront.’ 


Why it matters: ‘Carefrontation’ enables you to address issues directly without sugarcoating, downplaying, or smoothing things.


The big picture: ‘Carefrontation’ is a 2.0 capacity of Transformer Potential leaders in which 1.0 Centric Potential leaders are incapable because they have a limited capacity to hold opposites simultaneously. 



The problem: We’re walking on a fine line when starting tough conversations.


  • If we start too directly, our conversation partners get defensive and block any channel to effective communication. Since 85% of the leaders use operating system 1.0, they will reject, dismiss, defend, fight back, or avoid conflict.

  • If we start too softly, our message might be lost in the packaging. A common practice is to sandwich problematic issues between two slices of niceties. People will eat the bread and throw the “rotten cheese” between the slices.

The solution: There are two requirements for effective tough conversations.


  1. The skill aspect: How to effectively start a tough conversation - the 'carefrontation' framework

  2. The capacity (potential) aspect: How to evolve our capacity to lead a tough conversation.

You need both these interdependent aspects. You will be effective even without the framework if you have the capacity. If you master the framework without the capacity, you'll still struggle.


However, the more you use the ‘carefrontation’ framework to start tough conversations, the more you grow your 2.0 capacity. 


The 'carefrontation' framework


The ‘carefrontation’ framework has seven sequential steps. I perfected this framework over hundreds of practices with executives who constantly needed to start tough conversations with board members, investors, executives, and business partners.


Every step is necessary; you have only up to 60 seconds to complete the opening and then step back. Straight to the point. Zero rambling.


To illustrate the framework, let’s look at a tough conversation a CEO at a B2B enterprise software company has with the CRO about business results falling short of the quarter target.


Step 1 – The issue and impact


This step is the most critical and the toughest. The issue on the surface is usually not the real issue, but it’s just the symptom. There is a deeper issue, which is the problem.

Since you’re initiating the ‘carefrontation,’ you have time in advance to reflect on ‘what the real issue is.’


You have to peel the onion to get to the core of the issue so that you tackle the problem rather than the symptom. 


In our example, not meeting the numbers is too general and may lead to a conversation about external factors.


You have many avenues to explore. What are you noticing? What’s your hypothesis? 

Is it resources? Is it the sales management performance? Is it the people in the sales organization? Is it the sales organization culture? Is it the collaboration with marketing?

Thus, you ‘carefront’ with a hypothesis that is just the starting point. You’ll uncover more throughout the conversation.


Let’s assume you decided to ‘carefront’ the transactional nature of customer relationships. 

If this is the issue, what’s the impact?


Effective communication combines contribution (issue) and impact (effect). It’s like binding features and benefits. One without the other doesn’t make the cut.


In our case, the impact is a decline in partnership with customers that affects long-term sales.


So, the opening sentence may sound like:

“Hey Bill, I want to talk with you about the impact transactional relationships with our customers have on our ability to develop long-term partnerships with them.”


Step 2: Example


A common mistake is to confront the example rather than the real issue. In this framework, the example always comes second and is always in service of the real issue, not a stand-alone one. 


The CEO may say something like: 

“I read the summary of the meetings your team had with customer XYZ that ended without sales and noticed that most of the time was spent on the contract terms, with little conversation on the future value for their customers.”

If the example becomes the real issue, you will derail into the minutia of meeting minutes, and Bill will perceive you as attempting to micro-manage. 


Step 3: Feeling


Most people interchange ‘feeling’ with ’thinking,’ like “I feel you should have…” That’s not feeling. It's a cognitive judgment. Feelings are emotions. To express your emotions, you must be aware of human beings' seven emotional states.

Unless you graduated from the FBI Academy at Quantico, I recommend you Google "Feeling Wheel” and identify three emotions that resonate most with you in each of the seven emotional dimensions. Equipped with these 21 words, you will always express your emotions effectively.

“I'm very disappointed that our relationship value wasn’t embodied in these negotiations.”


Step 4: Why


Why is the real issue important?  What’s at stake?

“Relational rather than transactional is the DNA of our company culture.  Transactional conversations deviate from this culture.”


Step 5: Apologize


What? Yes! Apologize even if you have nothing to apologize for. By apologizing, you show that there are two sides to relationships. Apology removes the defensiveness that naturally occurs in confrontation.

“I apologize for not discussing it with you before the quarter's end.”


Step 6: Resolve the issue


When leaders close their ‘carefrontation’ pitch, they derail from the real issue. The three common mistakes are:

  1. Closing with the impact

  2. Closing with the example

  3. Closing with the why

We should always close with the real issue you started with in step 01.

“I want to resolve the issue of the transactional relationships with our customers.” 

Not revenue. Not future growth. Not the culture. Not your disappointment.


Step 7: Inquiry


Starting a tough conversation is like setting the stage for a deeper conversation in which you put an initial hypothesis but hold it loosely with an open mind to explore new avenues.

That's why we are in an inquiry mode. The tough conversation may end with a different issue.

“I’m curious. What's your point of view?” 


Put it all together 


Seven steps in 60 seconds or less of a well-thought, highly strategic real issue. Here is how it looks in one flow in less than 60 seconds:


"Hey Bill, I want to talk with you about the impact transactional relationships with our customers have on our ability to develop long-term partnerships with them.


I read the summary of the meetings your team had with customer XYZ that ended without sales and noticed that most of the time was spent on the contract terms, with little conversation on the future value for their customers.


I'm very disappointed that our relationship value wasn’t embodied in these negotiations.

Relational rather than transactional is the DNA of our company culture.  Transactional conversations deviate from this culture.


I apologize for not discussing it with you before the quarter's end.


I want to resolve the issue of the transactional relationships with our customers.


I’m curious. What's your point of view?"


Less than 60 seconds. Right?


Have you noticed how this opening is:

  • Powerful AND respectful

  • Direct AND empathetic

  • Bold AND sensitive

  • Confronting AND caring

The next post will explore how to continue a tough conversation and create deep trust amid a conflict.


That closes the technical aspect of starting a tough conversation. 


If you'd like to learn more about the different Leadership Potential capacities, I'd like you to take the Leadership Potential Discovery questionnaire.


It takes 15 minutes, it's free, and you get the report immediately. (It’s not an assessment but an educational tool.)

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