Selling your largest position can be a tough mental hurdle to clear but being on the lookout for red-flags can help you make the right decision. In the following video, Motley Fool analsyts David Hanson and Matt Koppenheffer tell viewers when they would sell their top holdings: Markel and AIG, respectively.

David points to poor insurance underwriting, the exit of CIO Tom Gayner, and a lofty multiple as reasons he would dump shares, while Matt highlights to importance of a smooth executive transition atop AIG.

David Hanson owns shares of American International Group and Markel. Matt Koppenheffer owns shares of American International Group and Markel. The Motley Fool recommends American International Group and Markel. The Motley Fool owns shares of American International Group and Markel and has the following options: long January 2016 $30 calls on American International Group. Try any of our Foolish newsletter services free for 30 days. We Fools may not all hold the same opinions, but we all believe that considering a diverse range of insights makes us better investors. The Motley Fool has a disclosure policy.