Nope, I’m not talking about brewing a pot of coffee and plotting out the future of your organization in the wee hours of the morning. When “Late Show” host David Letterman announced he was retiring after more than 32 years on the air, network executives moved quickly to announce his replacement, reportedly spurred by concerns over meetings with advertisers next month.

In the post-Conan era of late-night host selection, I imagine CBS executives put more than a few days of thought into who would fill Letterman’s shoes. However, the network’s choice, Comedy Central’s Stephen Colbert, brings up a familiar problem in succession planning: whether it is better to promote from within or introduce a fresh face.

The arguments for Colbert are pretty clear: His show, “The Colbert Report”, which airs at 11:30 p.m., could bring with him tremendous viewership in key 18-49 demographics, which CBS badly needs to compete with NBC’s new late-night juggernaut, Jimmy Fallon. And, the argument has been made that in order to ultimately beat “The Tonight Show”,  CBS will have to completely overhaul its late-night format. Finally, Craig Ferguson, Letterman’s one-time protégé, has consistently low ratings in the 12:30 a.m. testing ground (CBS is reportedly replacing Ferguson with E! talk show host Chelsea Handler).

On the other hand, as one writer put it, the Colbert with which people are familiar is the ‘Colbert’ in quotation marks – a faux-conservative talk show host. Trying to transition his send-up of Bill O’Reilly to an hour-long network show would be disastrous, but abandoning it all together could mean alienating a significant portion of his current audience.

Although we can’t claim expertise in late-night host selection, in the corporate world, outside hires face tremendous challenges, and studies show that more than half fail, many within the first 18 months on the job.

For more on succession planning, check out our free ebook, From Potential to Performance.