How to form opinions and communicate them after being conditioned to a culture of obeying-without-questioning?

Question

Please help me rephrase the title in case it doesn't properly reflect the content, or isn't professional enough

I am at the same company since I finished education. I was quite enthusiastic about my function from the very beginning and saw some early promotions to senior contributor and then manager. I feel that this was partly also because I was very loyal to the company's goals when the team fell out with senior management strategies (many seniors left or were fired) and as a direct consequence the company saw incredible growth.

Being a strict, "command-and-control" environment though, my own growth (both as a contributor and a manager) was in skills such as implementing and enforcing, always doing whatever the boss asked, finding solutions to functional tasks and solving detailed problems rather than questioning at the grand picture level. Disagreeing with the boss was pretty much prohibited at the company. It was common to shoot the messenger as well, so I made sure I always brought good news only :)

Now that I am working even more closely with the board of directors, I am increasingly asked for my opinion and strategies on a larger scale... and I often react with a blank confused expression on my face - my brain goes blank as if I cannot think/reflect anymore because I am used to be told what to do, or maybe I am just dumb. Actually, the first thing I think is something like "What can I say that will make them happy?" - and I know this is not good/honest.

How can I [re-]gain my ability to think strategically and at the big picture, and then convey my opinion without being shot down?

Answer 1

Whenever I'm put in a position where I must respond with both content and tact, I generally frame my answer according to the following guidelines:

1. Insert decision points: Even if you believe you have developed a clear method to move forward with a given project, construct alternatives even if just to give directors an opportunity to direct. If necessary, you can use this to simplify your decision points as well, as well as practice sycophancy when you always say "well that's what I would recommend" after anyone articulates their viewpoint. Every time their decision differs from your own, you regain a portion of your ability to think critically, and you learn how to do so in a manner that will increase your value to the board.

2. Don't concern yourself with determining objectives: One of the ways to insert decision points is leveraging the following statement "As what we are optimizing in is outside of my personal area of expertise, I would appreciate guidance on this issue." Given such phrasing, oftentimes you can glean rationale for decisions from management and operate under their rationale such as you understand it. Learning their rationales and how they apply them should also aid in learning.

3. Credit team members: If you're in a management position, leverage your team. Bring team members in for presentations and let them field some questions, if you need time to think about something, just say you need to confer with your team (and you don't have to if you don't want, after all, you're part of your team too and can confer with yourself). If you're hiring, consider hiring and training "second" to bring with you who may be a bit more naive and able to think outside the box, as well as fulfill the requirements of an entry level position. Discussion with people fresh from outside the company will likely also be educational, especially if you consider this an objective during hiring.

4. Stretch your brain: You mentioned that you may be just dumb. Frankly it doesn't matter if you're dumb or not, because you should do the same things anyway. One of those things is reading. I've read every article on http://www.joelonsoftware.com/ because I'm in a software field. Spend some time on LinkedIn seeing what industry leaders do. Read The Economist in your down time. Read Brave New World or Hamlet or Heart of Darkness or Frankenstein (maybe Hamlet first, but that's a pretty good order). I promise you'll expand your mind. If someone asks you why you think something and you can start telling them about literature or what Bill Gates does, that can lend weight to your point and value to your position.

Edit:

I feel I should mention: Until you're running the company by yourself, you're still implementing and enforcing. Now you're just implementing objectives and goals instead of projects and products. Figure out what your company wants to do (make money, but perhaps more specific) and figure out ways to do it. In the end it's all implementation details. If you want to be a better leader you may consider softening your stance on enforcement, but that's a personal prerogative.