Replacing a technical leadership position seems to me to be particularly difficult for a small company for two reasons: a) The new person needs to have a match

Replacing a technical leadership position seems to me to be particularly difficult for a small company for two reasons: a) The new person needs to have a matching skillset, but for the transition period, duplicating the skill set is not very economically or would mean a large increase in IT investment. b) When the new person turns out to be a bad match or quits early, the overall impact on a small company is greater than on a large company. A single position can determine much of the fate of a small company. Any suggestions how best to cope with this problem?