A Letter to Prudence



lettersDear Prudence,

Admittedly, I’m writing you on impulse. I’ll just come out and say it: I have issues with my direct boss, our company CEO, and I don’t know what to do. The thing is, it’s complicated. He’s also my former husband. For the sake of this letter, I’ll call my ex Cye Tubble.

Cye gave up on us, Prudence. And I don’t mean the family. I mean the office. He just threw his arms in the air and quit today. We never saw it coming. I mean, I suppose there were warning signs we ignored. He was always so optimistic about projects and then suddenly pessimistic. Reflecting back, one could say he was somewhat volatile. I always tried to persuade people this was an intense passion. I tried every which way to get them to see the positive side of demonstrating emotions. But it didn’t help that he would get so easily disappointed when things didn’t go his way.

Since we had such a close interpersonal history, I understood it when those who knew him best at the office described him as temperamental and harsh. And, yes Prudence, I tried to finesse this feedback into several one-on-one conversations with him. I wanted to help him see that he needed to define his beliefs and interests better; that otherwise, even though he seemed cooperative, he could appear lacking in direction. I even attempted to charm him into seeing the light. But in the end, he left.

So, now what do we do? Are we better off without Cye?

Help us Prudence,
Miss Chievous


Dear Miss Chievous,

Trying to manipulate someone into seeing their development opportunities will never work. You need to bring a balance of sympathy and straightforwardness in reflective, behaviorally based coaching questions after you are sure trust has been established. In regards to whether or not you are better off, I would also want to evaluate how Cye tends to react to feedback, or in other words how coachable he really is. This information can also help you understand if and to what extent he learns from his mistakes, and therefore if he will make good judgments and decisions in the future accordingly.

Regarding the behaviors you described in your letter, I would recommend picking up Hogan Assessments’ e-book “Coaching Strategies”. It should be used in conjunction with the Hogan Development Survey (HDS). This user friendly document can help a coach strategically approach delivering feedback around derailing behaviors and cultivate the invaluable strategic self-awareness necessary for sustainable development and change. Performance implications, insightful coaching questions, as well as common specific reasons each derailing behavior emerges, including underlying interpersonal schema are provided.

By the way, I think in situations like these, it’s good for everyone to take pause and reflect. For example, Miss Chievous, it can also be quite risky working with your Ex. I wonder if any impulsive behaviors emerged as a result. But that’s a whole different letter…

Stay on track,
Prudence