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My Boss Has Impossible Expectations: Communication Coaching for Tough Conversations




We are working with a manager who has a hard-charging boss who isn't open to feedback. When he has tried to tell her that the way they problem solve is unfocused, random, and inefficient, she says, "That's the way it is here." We offered our best communication coaching to work through this tough conversation.


We asked him: "If you trusted her completely, what would you do?"


His answer: "I would be transparent with her and tell her that (1) she needs to help me focus on the priorities, (2) she needs to be more prescriptive in her guidance, (3) she could remove some of the pressure in the system and we would be better for it.


It is only 8 months into the position, and he is ready to leave. He loves the work, but his boss is ruining the experience. We offered 3 possible communication coaching strategies to strengthen trust and deepen the relationship with her.


1. Have a future retrospective conversation. Focus on what you have liked, learned, lacked, and what you long for.


"I have learned so much from you and continue to learn. I really enjoy the work we are doing. I am in awe of your conviction and passion in meetings. One way we could improve our working together is by being more prescriptive in guidance. One thing I am looking forward to is more team members to relieve some of the pressure in the system."



2. Share a third party perspective with some advice. The perspective is also what you experience from the boss, too.


"Did you notice Adam got frustrated in the meeting? You interrupted him at the end of his statement, and he rolled his eyes. I think it is because the priorities changed without his input. You may want to smooth things over when you speak with him again."



3. This is your last resort. It is the final straw conversation. Make sure you can deliver this from a place of peace and even love.


"This isn’t working. I really love the work, and I am growing from the experience. However, it isn’t sustainable, and things need to change. I am working with incomplete information under unreasonable expectations. I am working until 1 am most nights, and I am still not meeting your expectations. The result is that I let you down. I want to stop this cycle. What would you recommend as a path forward?"



Contact Speak by Design to learn how you can develop effective communication skills to navigate your toughest conversations. Delivering articulate messages and active listening are skills that takes practice. Our communication coaching is designed with discussion and role-playing to elevate your professional growth and leadership development.


Explore our private coaching and group training options to understand how we help individuals, groups, and entire organizations improve their leadership communication skills.