One of the more important questions to consider before selling a business is why.

"There are many different reasons to sell a business and different goals," says Erik Ginsberg, Slate Capital Group co-founder. "Maybe it's a business you've owned for 30 years and you're done, you want to retire, get the best price you can, hit the beach and enjoy life. Or maybe you want to take a longer run at the business, so maybe you want to sell a piece but retain a significant stake and get a partner that brings some assets to the table."

The size of a business sometimes affects the goal in a sale. For example, a large organization looking to sell a division might be primarily interested in achieving the highest price and certainty of close. Smaller companies, however, often have owners who care very much what happens to the company after the sale. They want to get a good price, but those who intend to stick around also want a good partner. They want to know how the partner can help, the resources they bring, if they're easy to work with, etc. Those who are looking to retire after a sale have another way of thinking. They also want a high price, but they're often thinking about their employee base and making sure they're looked after.

"You need to think about all these goals that you have because it's really going to impact how you approach selling your business, to whom you bring the business to potentially sell it," Ginsberg says. "You always have to begin with what is the seller trying to accomplish."

Jamie Benoit, formerly the CEO of FEDDATA, says he lived those two thought processes in the two sales he experienced with his business. The first time he sold to private equity, a transaction that was all about capital infusion and the acquisition. He took the money from that sale and put it all back into the business.

When he sold the second time, he was in pursuit of a different outcome.

"There were a number of people, roughly two dozen, many of whom were ex-government, who had never had an event like this," Benoit says "Some of my motivation was driven by helping people who were nearing retirement get a liquidity event that they deserved — take care of school loans, mortgages, all that stuff — and then stay on with the business."

Benoit also learned about the difficulties that can come with selling a business. He says the first transaction was painful. But he exited that deal with some good advice that he put to work immediately.

"What I did between that transaction and the second one was I kept a living data room," Benoit says. "And so for the entirety of the time between the first transaction and the second one, I had my team keep probably an 80 percent-done data room at all times. And that did a few things: one, it put us in a really good position if we had an opportunity to do something strategic. But two, it taught everybody a lot about the business that they didn't know, and (about) the way we did business internally."

That living data room, the second time around, meant the work he had to do to transact, even though the second transaction was orders of magnitude bigger, was much easier. That's  because the really hard work was 80 done before he went to market.

"We knew things would come up," he says. "Our buyer would ask questions for documents that maybe weren't in the data room, but we knew where to find them pretty quickly. And the really hard work of on our side on the sell side had been done before we even went out with the company."

Also, the team that was going to be out on the street selling the company were the same people who had been updating this data room. So, when theye went out, the tone was very conversational between them and the world of buyers because everyone was so intimately familiar with the operation of the business that it made for a much easier process — one that only took about five months.

Ginsberg says selling is painful a process for seller who have never been through it.

"You have no idea how time-consuming (it is)," Ginsberg says. "You can't really run a business and sell a business at the same time well, but you have no choice."

That's why it's really important for advisers to prepare sellers for what it is that they're endeavoring to do.

"If you really want to put your company up for sale and do it the right way, it's going to be almost like another full-time job for a few months," he says. "And you're not going to enjoy it. But if you get through it, hopefully you accomplish all your goals and it's worth it. But let's not kid anybody. It's a painful process."

Ginsberg and Benoit, along with BDO's Dan Wahlberg and Saul Ewing Arnstein & Lehr's Andrew Segall, spoke at the Baltimore Smart Business Dealmakers Conference about choosing a buyer for your company. Hit play on the video above to catch the full panel discussion.