TL;DR: In an area with a solid mix of disorganized-but-honest and definitely-dishonest businesses, how do I professionally refuse to pay bills when the CEO does not authorize payment? I work as the Executive Assistant to the owner/CEO of a small retail company as of January 2019, and this is my first job where I'm directly responsible for dealing with Accounts Payable (among other things). Despite having 13 locations and making $25 million in sales last year, the "corporate HQ" staff is only eight people, myself and the CEO included. Up until he hired me, the CEO handled all non-merchandise (advertisements, repairs, non-resale supplies, etc.) Accounts Payable themselves. The CEO is extremely hands-on with many other aspects of the business as well, which means he often loses bills or forgets payments. As you can imagine, this means I inherited quite a headache. When he hired me, my biggest task was going through all the accounts and making sure everyone was paid in full and in good standing. I spent over a month reviewing bank statements and calling companies to ensure we were in good standing everywhere. However, because of my inexperience, I failed to get written confirmation that we were in good standing from several of these companies. My issue is two-fold. First, many of the companies we do business are also small, and often disorganized. It's very common for companies to forget to send invoices, or for invoices to not be itemized or to have no invoice number. For example, we recently received a past due bill that is over a year old, and this is the first correspondence I've had with our rep regarding this bill. This happens once or twice a month, and the CEO gets angry when it happens. He usually dismisses these bills as scams to get more money out of us and refuses to pay even if I'm able to prove the bill is legitimate and was missed due to poor organization. He responds that it's not his fault their company is disorganized, and he won't pay them if it's from before I was hired. Second, the CEO is often adamant that he either has paid things already or that the bill is outrageous and he won't pay. He responds this way regardless of how good our relationship with the company in question is. He often tells me to call or visit these companies in person and demand the bill be lowered or dismissed - always after services have been rendered - which is far outside my comfort zone. I have even been told to allow one account to go into collections and lie to people calling to collect because the contract was renewed without the CEO's authorization (whereas I think he should let his lawyer's office handle things like that). Now, let me make this clear. The CEO is not a dishonest person trying to get services without paying for them. He's by far the fairest and hardest-working boss I've ever had. We are located primarily in the rural Midwest, and in our area many small- to medium-sized business are well known for adding extra charges to services without consulting the client first, and only notifying them in the form of a non-itemized bill once some time has passed for you to forget the details and be uncertain. It's also common for companies to resend bills from several months ago, claiming that the bills were never paid. I've had this happen several times since I was hired and keep a diligent record of all bills paid so I can dispute these claims, and my fellow graduates in the area confirm they have the same issues with many of these companies in their current jobs. Despite this, some of the companies sending these bills are legitimate, and either due to their company's poor organization or the CEO being spread thin, the bill was overlooked. All bills from before I was hired are things that I cannot be certain of, due to the number of tasks the CEO was trying to manage on their own and my failure to get written confirmation from many of these companies. How can I professionally handle the CEO's requests to dispute or refuse to pay bills with companies when most of these disputes are issues of "he said, she said" and I have no concrete evidence to back his position, even if I remember calling this company and confirming we were in good standing? And if a bill is proven to be legitimate, how can I convince the CEO that it's not a scam and he does, in fact, own this money to a company, and not have him respond that I've been tricked due to my inexperience? Any and all advice would be greatly appreciated! Edited for spelling and grammar.