The coworker who came in after me did not even land in Japan. He had to do the entire process from the United States. He never had a tourist visa. He was told that he could not wait for the COE inside the country, nor would he receive a change of visa status if he chose to came. So your consecutive visa hypothesis does not pan out in that case.
As for the people that SSJup says managed to do it, I have my doubts that there were not extenuating circumstances of some sort, because the policy is quite clearly that such a change is no longer done. Student visas to work visas are. Work holiday visas to work visas are. Cultural visas to work visas are. But the MOFA has been pretty blunt about tourist visa to work visa.
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Originally Posted by MOFA
If a foreign national who resides in Japan wishes to change the activity that is the purpose of his residence, he must receive permission for change of status of residence for the new activity.
If a foreign resident in Japan intends to engage in an unauthorized activity under his/her current status of residence, and such unauthorized activity falls under other status of residence, then the foreign resident does not have to leave Japan and may apply for changing his/her status of residence in accordance with this procedure.
If a foreign resident intends to change his/her status of residence, he/she must apply to Minister of Justice for changing his/her status of residence in accordance with the applicable procedures as set forth in the Immigration Control Act Enforcement Regulations.
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The issue here is that a Temporary Visitor does not reside in Japan. A change of status would be from say an Instructor visa to an Engineer visa, because the Instructor already resides in Japan.