“By failing to prepare, you are preparing to fail.” – Benjamin Franklin

So often the anticipation of having a “difficult conversation” is worse than the reality of actually having the conversation. We build it up in our heads, avoid it and imagine the worst case scenario for it. We may feel too emotional about a topic to hold a productive conversation or we may anticipate the subject may be too emotional for the other person so we may avoid it for too long.

I recently had the opportunity to teach a few half-day classes for a financial services client; this particular client is going through a major transformation in how they provide technology services internally.   As a self-described “nice” culture, the organization’s leadership wanted to enhance technology leaders capacity to confront business leaders productively and transparently, and help business partners to own the change implementation process alongside the technology function; thus, they needed to build managers confidence and competence in leading delicate conversations with the internal client groups they serve.

So often, what makes the difference between a difficult and productive conversation is our level of care and planning in advance of the conversation. What I increasingly appreciate in reflecting on this topic intensely over the last several weeks is that our tolerance and savvy for difficult conversations grows exponentially the more we do it.

Here are some questions you can ask yourself and also practice answering with a thought partner when you are thinking about broaching a difficult conversation with someone else at work or in your life:

1/How could having this conversation positively advance the cause?

2/What could be the worst case scenario of having this conversation?

3/What would be ideal outcome of having this conversation?

4/Do you care enough about this person, this work and the beneficial outcomes to broach this topic?

5/What is the most constructive, positive next step(s) you can take to prepare for the conversation?

In teaching this topic, I have had to ask myself whether I am fully seizing every opportunity I have to be a positive change agent as a coach and consultant, a parent, a friend and colleague, and as a concerned citizen. I realize that with lots of practice, it has become much easier and even seamless for me to regularly confront difficult topics, and also to make those “difficult” conversations natural, respectful and even enjoyable.

Especially in today’s climate, where political outcomes and decisions in Washington, DC may have thrown us for a loop, it’s grounding and affirming to be able to speak up and impact change in our sphere of influence.   It seems there is no better time to be able to navigate and confront meaningful topics, in face of an increasingly volatile national and international climate.

Want more? You might also enjoy reading our entry the road from ‘no’ to ‘yes’.