Disappointing Conversation With Your Boss?

​Have you ever experienced a disappointing conversation with your boss?

I recently had a coaching conversation with a manager who had just been through a tough performance review. He came away from the discussion knowing for sure that he isn’t meeting his bosses’ expectations. The problem is, he has no idea what he needs to do differently in the future.

I learned a few more key facts during our discussion.

1. He loves his job and his company and wants, desperately, to be seen as a star performer.
2. Before reporting to this individual they had been work buddies, even socializing outside of work occasionally.
3. He feels he was set up to fail in a variety of ways – that even though he pointed out the likelihood of failure on each occasion, he wasn’t given additional resources, and then was blamed for the inevitable failure.

Ouch.

I know he’s not alone, because I coached many workers through nearly identical situations in the course of my HR career.

Maybe you’ve been there too? (If not, do me a favor – no, do someone else a favor – and pass this along to a person who needs it!)

My very first recommendation was that he absolutely must go back to his manager for further discussion, and keep going back until he gets clarity about what it would look like for him to be seen as a star performer.

That social relationship could be getting in the way. Even if he doesn’t feel awkward about it, his manager may. I encouraged him to ask his manager to set aside their personal relationship and be as straightforward as possible. To give his manager permission, in a way. Because, to quote Brené Brown, “clear is kind.”

Then I turned my attention to that third bullet.

Obviously he’s the kind of person who hears a new plan and immediately sees all the possible points of failure. And then feels compelled to point them out. He reacts this way because he cares deeply about this organization and its success. The problem is, that’s not the message others receive when he responds negatively to their ideas.

Don’t get me wrong; the world needs people who think that way. Your organization needs people who think that way. Poking holes in the plan is an important way to make it better. But it doesn’t win friends and influence people. Until and unless he figures out how to finesse his approach a bit, he won’t be effective.

We spent the rest of our time together talking about ways he can come across as a more positive team player. With practice, I know he can get better at sharing what he likes about the plan before he jumps into all the problems with it. He can also make sure he’s explicit about his purpose – that above all, he wants the organization to succeed.

Even when he falls back into his old patterns, as he becomes more self-aware, he’ll be able to follow up with the important stakeholders and say something like, “I’m afraid I may have come across as negative in the meeting this morning. I just want to be absolutely clear that I’m on board; my deepest interest is in making sure this plan succeeds.”

I don’t know if this manager will be able to turn things around. Often people who “don’t get it” realize they need help only when it’s already too late.

My hope is that my words will lead him to insights that will have some impact in his life or career anyway.

My hope is there’s some nugget here that you (or the person you pass this along to) will be able to use today.