Law and Chaos and Proposals

I am by nature a bit of a neat freak.

As a few ex-girlfriends and coworkers have observed (one recently commented on this – a coworker not an ex), my home and office lean toward dust-free and everything in its place. I’ve always been this way because I prefer a clean and therefore touchable environment, and I used to lose things left and right when I was a kid from not cleaning up after myself. Believe me, I’ve had past relationships where they didn’t value neatness like I do, and that alone tested my resolve about whether or not relationships are worth the stress or near-constant nervous eye twitching. Don’t get me started about raising a small child who leaves a room looking like toy-filled bomb exploded in it.

I’m a big believer in a room or home reflecting its occupant. As a writer and observer by nature, I tend to survey someone’s home or office the first time I enter it. It’s amazing what a few pictures, personal items, or general state of their surroundings will tell you about them. For example, I interviewed for a job and when I walked into my potential boss’ office, it was surrounded in artistic or arts-and-crafts style crosses – some hanging on the walls, others as sculptures or tchotchkes of various sizes on her desk and furniture. We had a thoroughly relaxed and stimulating conversation about the position, my background, and government contracting, but not once did she mention or give up any hints about religious beliefs. In fact, I had the distinct impression that she wasn’t very religious at all (because of her somewhat colorful use of language and a few comments about her personal life that are best described as “TMI”). As the interview wrapped up, she asked if I had any other questions, and not really sure if I was still a serious contender for the job, I took a chance and asked about the crosses. It turns out she has collected them since she college, and used them as a litmus test for job candidates – if they asked or made a comment about them, then they were on the potential hire list (i.e., she valued curious and proactive personalities), but if not, then their resume would be relocated to the circular file cabinet.

I’ve found that doing a quick view of any new office space helps clue me in to who I’m working with or how a company is run. An office that’s clean and stylish with little or no clutter tells me that their highly professional and want to make a good impression. A messy or haphazardly equipped/decorated office tells me that they’re too busy getting the work done, operate on a limited budget, and/or couldn’t care less about appearances. I interviewed at company years ago where I was all dressed up, but the “executive” I met dressed in torn jeans and a well-worn concert t-shirt (Allman Brothers Band…I think, and not from a reunion tour). To call the office a “hodge podge” is being generous – the few pictures/wall hangings were probably bought from a roadside flea market, none of the furniture matched, the coffee maker in the conference room sat on a somewhat unceremonious/questionably unstable tower of milk crates, and network cables ran up and down the hallways over carpeting that was not-so-effectively repaired or held down by old and peeling duct tape. On the other hand, I’ve worked at and visited offices where a considerable amount of time, energy, and care was put into interior decorating and cleanliness – uniform office furniture, unique or not-so-commonplace décor, and not a single scrap of paper or other office supplies laying out and about.

By extension, I tend to keep my work laptop in a similar state. As networking and collaboration tools (e.g., SharePoint, Teams) have become the norm, I tend to keep very few files on my laptop. This is because I like my work documents to be accessible anywhere in case my laptop has an issue, and too many files all over my screen drives me crazy. I’ve worked with several executives and coworkers who saved everything on their desktops, and to say my OCD was off the chart trying to comprehend the dozens of files crowding their Microsoft-default backgrounds is a true understatement. One particular executive I worked for used to puzzle me because they were beyond meticulous about certain grammar and/or formatting, but their documents folder had no apparent organization for the hundreds of files in it. And naturally, I’m sure everyone either has been or worked with someone trying to beat the Guiness Book of World Records entry for the highest number of open web browser tabs (I won’t name names, but I’m absolutely certain this applies to at least one of the people I know reading this…and I want to say that I really enjoy working with/for them).

Proposal work can sometimes…no, almost always – feel like the never-ending fight of bringing order to chaos. Any proposal involving multiple writers and/or invested parties trying to complicate (I mean contribute) to submission documents can be a nightmare (I mean full-time job). The advancement of collaboration tools now allowing multiple users to work in one document is simultaneously a blessing (e.g., I cannot stress enough how much I DO NOT MISS consolidating review comments/mark ups by hand) and a curse (e.g., the headaches caused by copying and pasting conflicting/complicated formatting from other documents or changes not saving correctly from too many users).

Proposal managers are the hubs that any proposal effort revolves around, so it’s our job to make sure everything is where it needs to be, and we’re the go-to whenever someone needs to find something. On one particularly elaborate proposal response, a CEO I worked for not-so-jokingly suggested hiring a bodyguard or buying extra insurance in case I was in an accident and couldn’t tell them where things were (this was both comforting and disturbing). Over the years, I’ve come to rely on a fairly static and comprehensive folder structure for keeping proposal resources organized and the process moving along. Of course, the nature of the beast is that every proposal effort has its own “personality” or “vibe” – some are textbook examples of a flawless and by-the-numbers process, others make you wish you could fire a shotgun at the ceiling to get everyone’s attention and bend them to your will.

As a result, a little flexibility is essential since customizing the folder/file structure and process to fit each effort is simply a fact of life. As is having to hand-hold or negotiate with those who are not happy when you adjust what they see as a sacred process on the level of being the eleventh commandment that Moses forgot to mention on top of Mount Sinai. As a private individual, I’ll tell you that nothing drives me up a wall more than discord and chaos, but as a professional, proposal work frequently demands a careful balance of control and nimbleness in what is often a very dynamic process.

I’m a big believer that even a little pre-planning ahead of time can result in a lot of payoff later on. I love efforts where there’s a reliable draft solicitation that offers even a minimal idea of what’s required in a proposal response. Nothing is better for a proposal manager than response documents at a Pink Team level when the final RFP drops. On the flip side, some proposal efforts nearly go off the rails when it’s finally showtime and the response requirements are no where close to what was planned for or expected. For example, a recent proposal required only a few VERY SUCCINCT pages – a far cry from, and a strangely more challenging project than, the massive response effort anticipated by our team. And yes, there are times where planning and preparing too much can lead to near paralysis. I’ve managed pre-RFP efforts that were so deep in the weeds that the effort was locked in an endless, repeating Star Trek time warp of draft/review/revise/repeat.

So, while it may not be fun or easy, a little chaos isn’t to be feared or shunned (emphasis on “little”), but being able to navigate chopping waters during a proposal is a quality expected in any proposal pusher. Now, if their office looks like the poster child for the Third Law of Thermodynamics, then it may be time to bribe the janitorial staff before someone’s head explodes due to their overactive OCD.