Oh my gosh, folks, for some reason I thought I had finished the series; life has been crazy over the past several months! But I definitely would like to finish this series as I truly believe that this is a timely and important post for me and for others.
So, let’s recap. Months ago I saw this post from Jay Vallotton (an awesome guy that you definitely want to follow, FYI) that talked about preparing ourselves and growing ourselves because who you are in 5 years isn’t accidental, it is intentional. I definitely took some liberty and decided to go deeper into these 5 actions. We covered each and now are on the last one – “the conversations you engage in.”
“What the hell are you doing to your family.” I was asked by someone that I looked up to. We (my wife and I) were sitting at a table and being completely vulnerable to mentors, to family members, to leaders in our lives about a direction that we felt we needed to take. This was the response, and it was neither helpful nor vision-setting. We had started researching our next steps nearly 6 months previous after not experiencing the most success during that period of our lives. And let me clarify – we had met wonderful contacts and learned so much, but we knew that the current way we were living and working HAD to change. As we engaged in this difficult conversation it was remarkably different from another conversation we had had just weeks or days previous. Another couple of trusted advisors listened quietly and intently, questioned our motives positively, pushed us to consider multiple options, and ultimately encouraged us toward a definitive decision without driving us.
What a difference between the two conversations. Both were difficult to be vulnerable in, but one was difficult and yet helpful, directional, and vision-casting. At that moment, I learned a valuable lesson – that the conversations we were engaging in could encourage or could destroy.
Difficult conversations are necessary
You may read the above paragraphs and think that we did and continue to avoid difficult conversations, but the inverse is actually true. Difficult conversations are a necessary part of life and when you know how and when to engage in them, they not only help you reveal issues but also can create points of success.
If you go back to the third blog in this series – “The People You Spend Your Time With” – I talked about the different layers of people that you have in your life. Of course, sometimes you think that people are in one layer, but you find out (through trial) that they aren’t. This adds complexity to what I’m about to say. Regardless, I am going to lay out a few “guardrails” for difficult conversations. I call these “guardrails” because they don’t always occur and sometimes things just happen, but if you can follow these, it is extremely helpful:
- Plan to have the conversation. Like I said above, sometimes you can’t avoid it, but there is nothing wrong with saying, “It seems like we need to have a difficult conversation. Can we reconvene or meet in 30 or 60 minutes?” This allows you to get your mind in the right place for the conversation and gives everybody a chance to get focused.
- Take your time. I can’t overstate this. Many hard conversations go bad when everyone is in a rush to talk or to “be heard.”
- Identify the goal. Sometimes hard conversations are about helping see each side, sometimes it is about making a decision, and sometimes it is about venting (true). Be explicit about what you are trying to accomplish.
- Set boundaries and stick to them. If the conversation isn’t with someone you are building with or that you trust with your vision, then this becomes a higher priority. Do not allow boundaries to be broken and do not break boundaries set.
- Know when to end the conversation. This sounds like a “duh” moment, but there are so many times when I ended a conversation early because I was uncomfortable and times I extended a conversation that shouldn’t have been because I was trying to get to resolution. Sometimes the conversation is just over.
Conversations that empower
What made the example above so difficult was that, unlike its counterpart, it didn’t empower. Both conversations were difficult, both had the same goal, and both had similar attendees, but only one helped us in achieving our goal. Before we move on, let’s define “empower” – to give official authority or legal power to; to promote the self-actualization or influence of; to give someone the freedom to do something. When we have conversations, sometimes we are looking for permission to accomplish a goal. While the person or persons we are talking to may not hold the authority, we sometimes are looking for someone to grant this to us because we are in a place of uncertainty. One of my favorite books is by Brene Brown called Dare to Lead. Brene doesn’t hold any office to grant me the authority to lead, but something in the book “empowers” me to take on difficult tasks and venture into unknown territory.
Good conversations, even though they can be difficult, always bring empowerment to the people in them.
Where to Start
I truly would like to say that you can walk away from this blog and say, “Let me do hard conversations that empower only!” but we all know that it doesn’t happen that way. We make choices daily around who we surround ourselves with and the conversations we engage in but with each step, we can grow ourselves to a point where conversations are meaningful.
At the least, I hope this blog and this series of blogs have encouraged you to think differently, to start looking more intently and focused on your next 5 years, and take steps to get to that point. Let me know what you think. What else do you think will help people grow? What did I miss? Anything you want to go even deeper into?

