Trump's campaign sent an email on Wednesday to supporters, titled "Trump Debate Preparation Survey," that says, "I need your immediate feedback from the first debate in order to win the second one."
Most of the survey questions in the email are on issues brought up during Monday night's debate, but some go as far as addressing the framing of his opponent - a topic often reserved for a campaign's top strategists.
A portion of the questions reflect on his past performance, asking, "On the subject of Hillary's emails, should Trump have brought up the fact that Hillary jeopardized our national security?".
Others are forward-looking, such as, "Should Trump continue to tie Hillary to Obama's failed policies including ObamaCare and the Iran Deal?".
While the use focus groups during campaign cycles is common, sending a mass email soliciting such targeted feedback is not. It's not known how many email subscribers the Trump campaign has, but the mogul's follower count on Facebook and Twitter each exceed 10 million.
"It is a very unusual move," Karthick Ramakrishnan, professor of public policy and political science at the University of California, Riverside, told CNBC. "The campaign will probably say that it indicates that the candidate is eager to listen, but many others will probably see this as a risky, and potentially desperate, move."
The survey questions whether Trump should repeat some of his previous angles of attack on his rival, asking "Should Trump call out Hillary for flip-flopping on NAFTA and TPP in an attempt to gain votes from Bernie's supporters?" and "Should Trump paint Hillary as someone who has betrayed working-class policies in favor of Wall Street?".
Of the 30 questions, 18 of them reference Clinton and give respondents the option the answer with yes, no, no opinion or other, giving space for extended feedback.
"The survey makes no mention of immigration, which was Trump's signature issue from the beginning of his campaign until just two weeks ago," Ramakrishnan said. "Perhaps the campaign sees no additional benefit of raising those issues, and might indeed be worried about the cost of pushing turnout higher among Latino and Asian American Democratic voters."
The survey could even be a sign of disagreement within the Trump campaign, according to one expert.
"This may be a play on the part of his senior campaign staff to gather information to validate their strategic suggestions," Chris Haynes, Assistant Professor of Political Science at University of New Haven, told CNBC.
"It could also be a move on the part of the disgruntled Trump children or Donald Trump himself to seek out support for alternative strategies shot down by Trump's professional campaign strategists," he added.
The email, signed by Trump, appeared to mark a change in tone, after he boasted of winning the first debate.
This was despite the fact the majority of polls deemed Hillary Clinton the winner of Monday night's showdown - the first of three - with pundits praising the Democratic nominee's preparedness for the debate, compared to Trump's free-wheeling style.
Clinton used her prep for the first debate as a weapon, telling the audience at Hofstra University, "I think Donald just criticized me for preparing for this debate. And, yes, I did. And you know what else I prepared for? I prepared to be president. And I think that's a good thing."
This is not the first time Trump's campaign sent out a survey. Leading up to the first debate, the campaign sent out an email with 30 questions, asking, "Do you think Trump should refer to Hillary as 'Crooked Hillary' on stage?," according to the New York Daily News.
Meanwhile, Clinton's campaign also sent out a number of emails to its supporters this week, mainly with the aim of raising campaign funding. One such email came from Philippe Reines, a long-time Clinton aide, who revealed that he had served as Trump's stand-in during debate practice sessions with the Democratic nominee.
The Trump campaign did not respond to immediately to a request for comment.