When I first started my job, I had NO idea what I was doing. I had no prior experience directing a unit and very little “real world” marketing experience. What I did have was a good measure of luck, for which I am eternally grateful. The position that I stepped into required strong analytical and project management skills, which I had in great supply. So for the first year, I was essentially a “yes” woman in a company filled with “yes” women and sometimes men. But I kept running up against a particular “no” man, and no matter how hard I tried to please him—how much I complimented his work or how sweetly I made my requests—I just couldn’t get him to see my emergencies as his priorities. He was, what we started to call, difficult to work with.
Now this is particularly important because, at my last job, I owned that label. My
experience managing a team of supervisor brats was extremely painful. I resolved that were I ever to get another management job, I would never, never, never be difficult to work with. Never. I would have a reputation of being a solutions-oriented problem solver. I would be tactful, diplomatic—even nice. I would use honey and not vinegar.
I quickly learned that we worked in a culture of fear, constantly putting out fires that were created by a lack of proper planning, analysis or proactivity because of someone’s strategic blunder. Sales and Service Managers would all run around like chickens with their heads cut off, bullying support departments into doing their bidding because “so and so” executive needed it done yesterday. And they would all run into “Mr. No.” He would give them some reason or other why the request couldn’t be completed within the deadline, why there was a systems problem, or why he was severely understaffed. At first, he and I partnered up and helped each other. But as time went on, he started saying “no” to me, too. In an effort to resolve what I saw as his unreasonableness, we had long meetings and after-hours telephone conversations. When that failed, we had down-right battles. But, I preserved my carefully crafted image of “Dolly Do Anything” because people always considered the source.
My second year, I studied him. I started to wonder why his department was the only department that could get away with putting its collective foot down and stopping the buck. We were in the same boat: last minute projects with impossible deadlines flew at both of us from all sides. As I grew in my knowledge of my field and of directing a team, I started to push back gently on unreasonable projects. In the meantime, “Mr. No,” having had enough, left the organization.
Mrs. Impossible.
What happened next surprised everyone, especially me. It may have been my ego—I can admit that—but I started to stop the buck. I was sick and tired of the bullshit. I was sick of saying “yes,” when I really thought “Now that is the stupidest fucking thing I have ever heard.” I wasn’t going to have another person photoshopped into a picture without his permission. I wasn’t going to completely re-do an ad campaign because some tenured employee thought the clipart picture that she had found in MS Office looked better.
No. No. No.
And boy-oh-boy did “no” feel good.
After a scuffle with the recruiting department and the Sales division in the same month (I successfully stopped the buck on both counts, just for the record) a colleague pulled me into her office.
I reveled in the awesomeness of my newfound “no.”
She was talking, but I wasn’t listening. I was running through the defense of my “no’s.” Most certainly, I could say “no.”
No. I can defend my people.
No. I can work to ensure that people are paid fairly, hired fairly and treated fairly.
No. I can say that your fire is not my emergency.
Yes. Yes. Yes. Yes indeed, I could.
After fifteen minutes, she stopped talking and took a breath. Then, she said the most difficult thing I had heard at work in two years.
“People think you’re difficult,” she said. “In fact, several people have come to me and have said that you’re difficult to work with.”
An alarm went off in my head. Images of my colleagues scrolled through my head like the screens on my iPhone. Was it him? No, it must have been her. She had said the dreadful words that I had worked so hard to avoid.
I had become “Mr. No.”
I moped for two days, considering all my efforts to keep people happy at work a failure. I talked to colleagues I trusted about it. I called my husband and my best friend. I bitched and I moaned.
“Oh! The nerve of those back-stabbing, two-faced, so and so’s!”
But they were right. In my usual fashion, I had failed to find any balance between saying “yes” and saying “no.” I had made the changes too abruptly, forgetting that the devil is always in the details. But what I learned is that there is always a way to right the ship, to repair your reputation, and to say “no” gracefully.

Great insights here – thanks for sharing your real world experience. It seems like either extreme – a yes man or a no man – is difficult to pull off. Perhaps we need to find that happy medium where we're not difficult to work with, but we're also not a pushover. Any ideas or advice for knowing when to say no and when to say yes?
Sam – thanks! Yes, I actually wrote a sister post: http://helpyourselfblog.com/2010/01/being-difficu... I think that I actually labeled these posts incorrectly! =) I'll go back and change that! I summed it up in three steps that have worked for me: 1) Say "no" by offering an alternate solution 2) Create a self-service option 3) Build up your currency in the bank of "no." Thanks so much, Sam!
Doesn't "no" actually mean "yes"?!!! hahaha