Here are some of either the most frequent OR the most costly.

1) Not being aware of the age 55 separation exception and/or plan provisions to make installment or adjustable payments not subject to penalty due to the exception.
2) Automatically ordering an IRA transfer when they hold highly appreciated employer shares in the plan eligible for NUA with a proper LSD from the plan; also what constitutes a proper LSD for NUA purposes.
3) Ordering a distribution instead of a direct rollover. This triggers mandatory 20% withholding and they have to front that 20% to complete the rollover and avoid early withdrawal on the withheld portion.
4) Not selecting an IRA custodian that is consistent with their investment style or electing ultra conservative or high cost products in their IRA such as bank CDs, annuities, or day trading thinking they can beat the market.
5) Starting an inflexible 72t plan without knowing enough about their future prospects for another position, healthcare expenses and living expenses over the term of the plan (age 59.5 or 5 years, whichever longer).
6) Not understanding the cost/benefit of keeping their 401k intact for a time.
7) Not understanding that their are differences in the penalty exceptions for 401k vrs IRA early withdrawals.
8) Not understanding the implications of after tax amounts they may have in the plan including pre 1987 after tax amounts and the possiblity of doing a direct Roth conversion with those amounts under the new PPA provision effective this year.
9) The complex options and their impacts if they have a 401k loan outstanding at termination
10) 10 year or cap gain options for those born prior to 1/2/1936, if any

and perhaps the most important:
Making sure they are properly diversified in the plan or in the rollover investments, particularly with respect to too much employer stock.

No doubt there are others as well.

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