This isn't the first time, and it might not be the last. Dominant social network Facebook (NASDAQ:FB) is reportedly looking to challenge LinkedIn (NYSE:LNKD) in the enterprise segment, among others. The Financial Times reported that the social kingpin is developing a new "Facebook at Work" site geared toward corporate settings.

The service is said to feature ways to communicate with colleagues, connect with other professionals, and collaborate on documents. Personal profiles and professional profiles would be segregated for the sake of privacy, and would be free initially. Beyond LinkedIn, this service means Facebook would compete with other large enterprise software makers like Google (NASDAQ:GOOG)(NASDAQ:GOOGL) and Microsoft (NASDAQ:MSFT), as well as start-ups such as Slack.

Does Facebook have a chance? Let's look at all of these areas where Facebook wants to make a dent.

Connecting people
Helping people make professional connections is LinkedIn's claim to fame, and the company has established an incredibly strong business in connecting recruiters with job candidates. Before even considering monetization methods, Facebook is a much larger overall network, which means it has a shot at growing its position here.

At last count, Facebook boasted 1.35 billion monthly active users, or MAUs, worldwide. That's over four times LinkedIn's count of 331 million registered members. Of that total, 89.7 million members log in on a monthly basis. LinkedIn reports these as unique visiting members, but in practice they are the same as MAUs for the sake of comparison.

"Facebook at Work" is unlikely to tap into Facebook's entire network, since its rollout is still speculative and would likely be on a small scale. Still, there's definitely some long-term potential here if Facebook builds out the rumored service, and eventually integrates it with its broader network.

Communicating with colleagues
Microsoft Exchange is the dominant player in enterprise email, but a slew of popular chat applications are also used in the workplace. Slack has been skyrocketing in popularity recently, and is now one of the fastest-growing enterprise software applications ever.

The key to Slack's success is the ability to integrate with a plethora of third-party services that are already popular within the enterprise segment, creating a platform out of the enterprise messaging service. Slack also has powerful search features to help workers find what they're looking for. The start-up's blistering growth has already attracted the attention of high-profile venture capitalists. Slack recently raised $120 million at a $1.1 billion valuation.

In general, messaging is becoming an increasingly competitive arena. Facebook has both Messenger and WhatsApp under its blue belt, so the company undoubtedly has plenty of experience with developing messaging products and services. Facebook might have some strength in consumer-oriented messaging, but it seemingly lacks the deep integrations that rival services like Slack can offer.

Playing well with others
On the collaboration front, Microsoft acquired Yammer in 2012 for $1.2 billion. Yammer is a private social network that integrates with collaboration software and business applications, and is now part of Office 365. Yammer is a big part of Microsoft's strategy with collaboration software as it transitions away from SharePoint.

Microsoft also recently partnered with Dropbox. By integrating the other's services, Microsoft and Dropbox will bolster the collaborative features that are critical to each company's enterprise customers. Google Apps for Business has also been winning customers from Microsoft for years, becoming a notable player in the collaboration space in the process.

This is easily the most important area of enterprise software, since employee collaboration is so critical to productivity. This is also where Facebook likely brings the least to the table. Current providers of collaborative tools offer comprehensive feature sets and have become very entrenched in the enterprise. Facebook will face a steep uphill battle in this area.

We don't know what we don't know
To be fair, not much is known about "Facebook at Work." The company reportedly uses the product internally, and only began testing it at other companies within the past year or so.

Facebook's current portfolio of consumer offerings might not be representative of what it hopes to offer the enterprise space. However, it's hard to imagine the company could develop a full-featured offering that spans all of these areas in under a year when incumbents have spent many more years specializing and catering to these precise needs.

On top of that, Facebook is predominantly associated with personal social networking. The ability to separate personal and professional activity might be an attempt to blur the line, but consumer connotations aren't easily shifted. Besides, aren't Facebook's privacy settings cumbersome enough already?

Shares of LinkedIn fell 5% of the news that Facebook could be developing a competing service, so it seems there is indeed some investor concern. However, history doesn't inspire much confidence in Facebook's professional abilities, which should downplay these fears.

Facebook acqui-hired job-search site Pursuit in 2011, but hasn't done much in the job listing space that LinkedIn is disrupting. Third-party professional networking service BranchOut attempted to carve out a niche within Facebook as a free application (casually known as the "LinkedIn within Facebook"), but failed spectacularly and is now trying to sell itself.

The risk is that Facebook could become distracted by its pursuit of the enterprise segment, rather than focus on key business developments, notably building out the infrastructure for video ads or determining some type of monetization strategy for WhatsApp.

As an investor, I do like when Facebook takes calculated risks, such as Paper or Home, even if they fail. But those were inherently low risks with high potential rewards. Enterprise software is indeed a very lucrative space, but the time, energy, and development resources that it would require for Facebook to meaningfully challenge are simply too high.

Evan Niu, CFA owns shares of Facebook and LinkedIn. Evan Niu, CFA has the following options: long January 2016 $150 calls on LinkedIn, short January 2016 $200 calls on LinkedIn, long January 2016 $125 puts on LinkedIn, and short January 2016 $140 puts on LinkedIn. The Motley Fool recommends Facebook, Google (A shares), Google (C shares), and LinkedIn. The Motley Fool owns shares of Facebook, Google (A shares), Google (C shares), LinkedIn, and Microsoft. 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.