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Deals have lots of moving parts, no matter the size of the business or the size of the deal. Lots of issues move simultaneously. Losing track of an issue can hurt. You might lose money or increase risk. (I wrote a book about how complex even small business deals can be.)
Most deal attorneys I know keep track of the deal by using a checklist. Sometimes they call it a "closing checklist." My checklists are brief - usually 1 or 2 pages long. I identify pertinent information at the top - information I may need frequently, such as the parties' legal names, lender information, the purchase price, and the opposing attorney's information. This gives me a quick reference. Then I create a two-column table. The left column contains the names of all the documents that need to be drafted to close the deal, with each document populating a cell in the table. I leave the cells in the right column blank. I hand-write brief notes in the right column about the status of each document. I print a new checklist every few days so I can update my notes as progress is made. Other deal attorneys I know have more elaborate checklist formats and type all their notes into one master document. There's no right or wrong way to format and keep the checklist. It's a tool that is customized by the person using it. The point is that the deal usually goes better if someone is using a checklist to manage the deal.
Checklists keep us on track. They also can help set and manage expectations about the deal because you can see all the moving parts and what's going on with each one. I also use my checklists as agendas for meetings and phone calls with my client and opposing counsel. The time spent creating and updating the checklist is a significant investment in the success of the deal. It helps things run smoothly.
If you are working on a business or real estate deal with an attorney, ask for a copy of his or her checklist at the beginning of the deal and periodically as the deal approaches closing. It will help you understand the deal and its progress. It also will help you see what still needs to be done to get to closing. You might sleep better with all that information.