Tough Conversations That Lead to Growth | Extraordinary Business

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Leadership can be a wonderful experience…. until it isn’t.  Having tough conversations is part of job description, and unfortunately most leaders don’t get the training they need to prepare for and have those conversations vertically and horizontally in an organization.  One of the toughest conversations you can have as a leader is when your boss is out of line or going down a path riddled with problems, and it’s your job to talk to your boss to resolve the situation or to protect your team from the fall out.

Andrea Williams wrote an article titled, “3 Leaders Reveal Their Hardest Conversations” focused on the following areas: 1) Calling out a trusted team member, 2) Giving the boss an ultimatum, and 3) Owning up to your own mistakes. The lessons learned in each story are invaluable and a must read for anyone aspiring to grow into a leadership role.  You can read her article here.

A tough conversation I had as a leader was when I hired as a contractor working for another contracted vendor to help a business achieve their next level of success.  For eight months I managed my area, monitoring the project on a regular basis to make sure everything was on track. It came as a total surprise to receive an email from the lead contractor questioning my work and my overall commitment to the client because of several challenges that were occurring on the project.

I had been working for this contractor off and on for many years. We had a great deal of respect for each other, and he knew me better than that.  I also knew I needed to process through my anger and manage my own emotions first before addressing his email.  I purposely worked on other projects for the rest of the day to clear my head. The next day I called him up and was very honest about my surprise and frustration with the content in his email – especially because of our previous work history.  I then went through his email line by line and responded to every area of concern he indicated.

By the time I was done, the lead contractor realized he had been unfairly projecting his own frustration about the challenges in the project onto me and apologized for doing so.  The moment he took responsibility for how he reacted, I calmed down as well, allowing both of us to work together to find solutions to those challenges.  If I had not been confident enough to have that conversation, it would’ve affected our working relationship and the project from that point forward…which would’ve been bad for everyone – especially the client.


Are you avoiding a tough conversation with someone at your organization?  If so, we can help. Our Aepiphanni Ascend Leadership Development program is designed to customize leadership development opportunities to take you to a higher level of performance.  Fill out the form below and we’ll be happy to schedule a Coffee & Consult to chat in more detail about how we can help.

Kris Cavanaugh Castro is the People Development Coach at Aepiphanni, the trusted advisor for business leaders who are seeking forward-thinking solutions to help them plan for and navigate through the challenges of business growth.  Kris has over 25 years of coaching, training and mentoring leaders to greater success; and she periodically writes about leadership development and facilitates change management conversations.

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Need the tenacity to have tough conversations? Start here.

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