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I'd also be curious about to what extent this is a skills issue Vs. one of orientation (what you like to do) and/or one tied to some form of blocks. The books will be useful if it's mostly about skills. To the extent you don't look at the forest because it's hard to let go of the trees, you'll probably need someone to help you.
Is there anyone else in the company who's good at big picture who you trust with your vulnerability in this area?
A good way to differentiate the "forest" from the "trees" is to think in terms of the precedence or implications of a decision or recommendation.
"Trees" (more tactical decisions/recommendations) are typically one-and-done -- good for the particular circumstance/situation, but not much more. "Forests" (more strategic decisions/recommendations) are more "one-and-some," meaning they address both the current circumstance/situation AND future choices relevant to it or that may arise as a result of it.
To get a better feel for the difference, look at a decision one of your more strategic coworkers recently made. Consider its depth and breadth. Why THAT decision? What sort of precedence does it establish or work within? Buy them a cup of coffee and ask them about it, how they approached the matter, identified possible options, vetted those options, and ultimately came to a conclusion. Ask them to explain their thinking in as much detail as is helpful to you.
Now look at one of your more tree-like decisions and ask yourself the same questions. Compare and contrast the two and notice the differences in approach and methodology.
Now ask another coworker. And another -- until you start to recognize some patterns behind big-picture skills and how you can incorporate them into your own decision-making. Share what you've learned with your boss and get his/her input and insights, as well. Make better "big-picture" thinking a routine part of your 1-on-1 meetings.
Lot's of great ideas have been shared, if I were to answer the question of what is the most important and immediate step I could take, the answer would be to define the big picture. My experience has shown that a request to be big picture implies that one has not included the company and/or departmental objectives in their thinking. The frustration of the boss is a result from the fact that tactical implementation almost always leads to unintended consequences or missed objectives in other areas.
Project manager: The tactical approach is to look at the job from a couple of elements - job complete, on time and the customer is happy. The big picture approach is the customer receives what was contracted, on time, profitability, billed properly, absent organizational disruption, etc.
Sales Manager: The tactical approach is to meet the revenue objectives of the company. The big picture approach is to meet the revenue objectives, from the desired target market, in the assigned territory, at the desired price, within budgeted costs, etc.
A starting point is to identify all of the elements of success. How is your boss's performance judged? What are the objectives of the company?
Initiate an open an honest discussion to define the bigger picture. Manage your efforts to support the big picture.
Mark and Barry give some excellent advice. Let me add something in a different direction.
You're trying to develop a skill, a way of thinking and seeing.
The most effective way to do that seems to be, to do it for a focused period of time -- every few days. Like learning a foreign language or a musical instrument, you're trying to build new brain circuits. For that you need attention and repetition.
Here's my suggestion:
Before each (say) weekly staff meeting, take a big sheet of paper and create a grid of rows and columns. Along one axis, put departments or interest groups around the firm (plus maybe customers and vendors). And, add one for "the whole firm." Along the other axis, put the topics being brought up at the meeting.
In the intersections you've created, try to make some educated guesses -- and write a few words that will capture the spirit of how that particular department VIEWS or IS IMPACTED BY that topic.
Now, during the meeting, see if those stakeholders do in fact have the views, or face the impacts, that you guessed. Mark down their actual responses next to your guesses.
This technique provides you with three things:
1. Regularity -- it's weekly, so you get regular practice.
2. Self-testing -- a proven study technique, you're guessing and then checking.
3. Artifacts -- you can look back at earlier attempts and see if you're getting better over time.
Bonus fourth value: Other people will notice you as you see things from their perspective. They'll be impressed.
Nice advice from others and I would add this - Ask Questions.
Much of the time people are attempting to "see the big picture" without the curiosity necessary for it to come into view. The analogy of forest/trees is a nice image, so the question is prompted, "What is the forest in this scenario...we're all looking at the trees but what is the forest?"
Having the orientation towards asking larger questions helps. It's also more engaging since asking the question of others has them participate much more than simply telling them what the big picture is.
On the simple level of practice, you can use some real world examples like the forest/trees. i.e. take a look at what the neighborhood is from up above via google, then pull back to see the city, then region. After a while, the practice of looking for the bigger picture in nature will translate into the bigger picture muscle being strengthened. In the same way a tree is a bigger picture of branches and leaves, an organization is a bigger picture of departments. And by practicing 'obliquely' like looking in nature, one has the tendency to bypass the normal barriers one has about it, and draws out an already existing ability.
While coaching, we assume the person already has the ability and something is obscuring it, or interfering with it's natural organic presence. It would be helpful to inquire either via a coach or via self-reflection as to what it is that's blocking your natural ability.
Seeing the big picture in business is an important skill that is often only attained with a lot of career experiences.
I recently wrote the lead article for the QHSE magazine titled "Identifying Cascade Effect Risks in Organizations". My 12 page article uses gamification and a unique deck of cards I created to teach professionals about the big picture cascade effect risks potentially present in organizations. Here is a link to the article: http://leansixsigmaandbeyond.com/my-lead-article-in-the-september-issue-of-qhse-focus-magazine/ . It's a good primer in the big picture of business and why things go wrong. I hope it helps a little in your learning quest.
I agree with Paul. The greatest asset any of us has is personal awareness, including identifying our style of thinking, communicating, strengths, There is nothing inherently bad about not being a big picture thinker, just like it's ok to have brown eyes. However, if you are in a job where it is important to be a big picture thinker, you are in a bad spot. Personally, if I had to deal with a lot of numbers in my work, I'd be in big trouble!
The suggestion of some type of assessment is one I would encourage you to consider. I have had great results with my clients using the Winslow Personality Assessment, and there are other good ones out there as well. And of course, a coach never hurts.
Developing your talent to be more strategic is a process that involves a set of interconnected leadership competencies. This development process can take couple of decades of progressively more demanding assignments along side of coaching and career development.
I do not know what your career path has been, but the best place to go is your HR. Learn about talent development and career path opportunities and have them guide you through it.
From a hiker's perspective, the only way to understand the forest is to get in the forest. It might be that you spend so much time doing your specific job that you don't get "out and about" in the company, which will help you gain a fuller understanding of the organizational vision and mission(s).
During my Navy Career, I spent a lot of time seeking knowledge from those outside my personal work area and profession. While I didn't have to, I learned how to drive ships, learned war-fighting techniques, the operation of boilers and steam engines, navigating skills, and other areas way beyond my particular level of expertise and knowledge. I would do some jobs for others to hone skills and learn new techniques.
The same is true today. When I teach a specific program in a high school environment, I interact with other departments to learn all they are about, I talk with other teachers about particular skills and experiences.
Life is about having the "Broad View" and being a systems thinker. Managers are homed into their particular management field, leaders are about the broader-view, looking at the big picture and learning well beyond their own micro-focused job.
Although an old principle, MBWA - Manage By Walking About - still applies today. I took it a step further with LBWA - Lead By Walking About.
Maybe you are asking the wrong question. Knowing whether you are a systematic thinker or a conceptual thinker or a combination of both is a critical piece for answering the question. If you are a systematic thinker (work systematically from start to finish - tactical) and not a strategic thinker (big picture) chances are you won't change that.
If you're a big picture, strategic thinker security oriented type person chances are we are talking about low self esteem issues. Understanding whether self-limiting belief's or your personal natural style of interacting with your environment or low esteem could be determined quickly by taking an Optimist Profile and a DISC Profile Assessment.
The truth is the best use of your gifts and talents may not be in the executive suite. Time to gain more self awareness and begin exploring the paths that match your personal desires, than to stay locked in a career expectation (illusions).
The real question is, is your present job/career or career environment providing you the energy, inspiration, challenge and excitement that is encouraging you to expand, grow and transform into a leadership position. What do you want? Getting your own clarity about what you want maybe the first step in clearing up your vision issues. A coach can provide that result! All the best!