4 Ways to Approach Difficult Conversations and Build Trust

[The following is an excerpt from TrustED®: The Bridge to School Improvement]

Do you tense up or lose sleep when you know that you need to face up to a difficult conversation with one of the teachers or employees that you supervise? Entire courses of study are provided on how to participate in difficult conversations. I’ve personally benefited from such courses, as well as from mentoring by those who know how to turn those potentially stressful meetings into opportunities to build a deeper level of trust between myself and those I supervise.

The greatest council I can provide to someone who struggles with entering into difficult conversations, is to prepare. Never go into a difficult conversation cold. Before entering into the conversation, know what your approach will be and know what possible and reasonably expected outcomes may occur as a result of the conversation.  Not all difficult conversations look the same. There are at least four types of conversations that can, and should be, intentionally planned and consistently implemented to turn difficult conversations into moments of trust building:

  1. Reflective Conversations that are non-judgmental and simply provide an opportunity for your faculty or staff member to provide input on whatever the issues may be.
  2. Facilitative Conversations that are data-centered; considering together with the faculty or staff member what we should conclude from the data we have regarding any given issue.
  3. Coaching Conversations where we come along-side the faculty or staff member and help them come to conclusions and discover their own answers to issues. And…
  4. Directive Conversations where we as leaders at times need to set very clear and firm expectations and/or consequences.

Clear communication is a powerful means of developing trust, and this is especially true for the school leader in their relationship to their faculty and staff. Perhaps the most valuable truth in this area that I’ve learned within school administration, and that I encourage other school leaders to embrace, is to not shy away from dealing with difficult conversations.  Rather, embrace difficult conversations as a path to continually improving relationships and the school… [continue reading]



  1. I think in schools we’re really well trained to have difficult conversations with students but not with adults.
    It’s something I specialise in and have trained many school leaders in.
    A good article which I enjoyed reading and can relate to.

    Liked by 1 person

  2. Thanks for your insight – I love how you have mapped out the four different types of conversations. In my experience, some managers tend to shy away from difficult conversations because their ‘leading others’ strategy unconsciously relies on their team members liking them. And there is always the possibility that a difficult conversation will be, well..difficult, and the end result might be a relationship being compromised. When we can support managers and leaders in developing a more resourceful way to lead and inspire others, the cost of a difficult conversation decreases and the rewards for having increase. And so the perception of the conversation changes, thereby changing the way it is approached and thus, usually the outcome.

    Liked by 1 person

  3. The best book I have ever read about having difficult conversations is called “Discipline Without Punishment.” I was very lucky to have read it shortly before I had one of the toughest conversations I have had in my career. The book helps you to prepare–I ended up creating a flowchart of how I wanted the conversation to go, and some potential directions the conversation might take. It turned out to be the most empowering conversation of my career, and for the underperforming teacher as well. Based on that conversation, we were able to develop a wonderful coaching/mentoring relationship, and within 3 months he had gone from nearly being fired to the most popular teacher in the school. This book is never far from my side, and I refer to it often. It is an easy read, and has been most impactful on my way of approaching staff. Hope you will become a “Discipline Without Punishment” convert, too!

    Liked by 1 person

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