Dear Crucial Skills,

Many of us in our personal or professional lives have avoided crucial conversations, not just over weeks and months, but sometimes over years or even decades. How do we even begin to strategize about conversations that have been on the back burner for this long?

Signed,
Finally Speaking Up

Dear Finally,

I am inspired to see someone who has disempowered themselves for years finally own their agency. I think all of us are challenged to examine and improve ourselves when we see someone take such an enormous step. I salute you for taking this step yourself.

There are two fundamental principles you must not violate if you decide to finally step up to a crucial conversation after a long period of silence.

First, given that you have enabled the bad behavior of the other person for so long, you owe them some patience as you announce your intention to discontinue your willing submission of unacceptable circumstances.

Now, in saying this, let me be clear that I am absolutely not suggesting you tolerate abuse, malfeasance, or the ill effects of incompetence one second longer than today. I am simply suggesting that your enduring collusion in shaping the other person’s bad behavior places a responsibility on you to be understanding if they take some time to disentangle from this long practice.

For example, let’s say I’ve had a boss who has frequently been dishonest about expectations. He hypes the possibility of future raises, promotions, or opportunities in order to keep me motivated then appears to do little to make them happen. In the end, he’s always got an excuse and another fair promise for the future.

For years, I have simply grumbled under my breath or gossiped to others about his manipulative ways but never taken responsibility to either require other behavior from him or quit the relationship. As a recent Crucial Conversations grad I’ve decided to candidly express my concerns.

What I’m suggesting here is that while the crucial conversation may go well, you’d be foolish to lay down ultimatums expecting that his deeply entrenched behaviors may change instantly. My goal in the conversation should be to a) agree on ground rules—how he will and won’t treat me in the future; and b) agree on how I’ll respond if he transgresses these agreements. It is part “b” that acknowledges that you’re going to give him some time to adapt to the new reality, but also that you’ll hold him accountable. If your goal in the crucial conversation is to get him to stop immediately and never fall back into old ways, you are failing to give him the same allowance you had in bringing about your own change. You took years to adapt. Giving him a few weeks is only fair.

The second principle helps you Make It Safe while also Mastering Your Story in how you feel toward him. This is a principle of ownership. You must own the fact that the bad situation is not just about him, it’s also about you. As you begin the conversation, make it clear that there is a pattern the two of you have been involved in that you are committed to changing. Don’t blame him exclusively—own up to the fact that you’ve enabled it.

For example, you might begin, “I’d like to discuss something I’m embarrassed to admit I’ve been doing for many years. It’s been wrong of me to not speak up about it in the past but I’ve decided to do so now. I’ve blamed you for many years for it going on, and that has been unfair. I’ve been a part of the problem, and I don’t want to do that anymore. May I discuss this with you?”

Whether or not these are the perfect words, what I’m suggesting is that your “story” needs to be one that stops painting you as a victim and him as the villain. You need to take ownership. This will help you approach him as a reasonable, rational and decent person—someone kind of like you. In addition, you’ll Make It Safe for him because you’re approaching him as a normal, fallible human being, rather than as a reprobate villain. You’re approaching him with the utmost confidence that he, like you, can change. That expression of confidence is an enormous show of respect.

Now with all that said, you should expect him to go through a period of defensiveness. The first conversation may be confusing, upsetting, and provocative to him. If this is the case, don’t go in with the goal of solving it in one sitting but rather to open up the issue. Ask if you could just tee it up and then allow him to reflect on it and get together after a few days when he has collected his thoughts. It’s only fair—you had years to get ready to talk, you should allow him some time to adapt to the new reality as well.

With all that said, let me conclude that by no means am I suggesting that if you are being hurt physically or emotionally, or if others are being damaged by the other person’s actions, you should allow this to continue one day longer. In these instances you have an obligation to take a hard stand on what must happen now, while allowing for patience and adjustment in areas where you owe the person the same season for change that life has allowed you.

Thanks for your inspiring question—and best wishes as you change your world—and hopefully, that of others.

Best wishes,
Joseph