Leadership
Obama has been an attorney in Sidley and Austin, a law firm where, reportedly, he was one of the best attorneys. On the other hand Trump’s chain for hotels and other countless brands which have gained huge success not only in the US but all over the world, which reflects his good leadership and managerial skills.
Education
Obama has been graduated from Harvard and he also got his degree in law from the University of Columbia. Where Trump says he enrolled in Fordham University from 1964 to 1966 which was clearly denied by the students of that batch. But Trumps has done his BS Economics Wharton School of Finance, University of Pennsylvania, which was verified.
Career
Trump took over his family business from his grandfather and father and with his own addition and success which made it worth more than $10-15 Billion, where his own net worth is $4.5 billion. But here is another thing Trump did not started his own he took his family business. But Obama is more above then the average. His career was full of ups and down and similarly, during his rule country also sometimes suffered from economic failures.
Conclusion
These are some facts about both of the president for making a comparison but it is o early to say anything about them. For making a good conclusion need to analyze more about them.