There are probably lots of places to lay the blame for the lack of good sales leadership.
First, many organizations incorrectly assume that they need sales managers instead of sales leaders. Exceptional sales people can easily be destroyed by micromangement.
If you have hired managers, you need them to master true leadership as quickly as possible. If they can do that, much of the management stuff takes care of itself.
The next problem is that there is a general lack of understanding of the whole sales process at the executive level. That inability to understand what sales is all about is often the fundamental reason that sales organizations don't reach their potential.
The problem is compounded by management's laser focus on quarterly results, and the inability to appreciate the effort required to keep an account buying at high level much less a higher and higher level each year.
The truth is how can you possibly manage a process that you don't even understand? Yet the world is filled with ad hoc sales managers who often do more harm than good to their organizations.
Managers who don't trust their sales people are often obsessed with tracking deals, especially "big deals." Most of these managers have likely never even sold a box of donuts.
There is an inverse ratio between a manager's understanding of sales and their need to track what they perceive to be every step of the sales process. The less that they understand about sales, the more detailed explanation they will want of your what you are doing which in the sales world is often termed "your pipeline."
Many traditional managers views sales as some sort of voodoo magic where you trick the customer into saying they will buy a product. There are plenty of sales training courses built around this whole concept.
The reality is that if you are doing a large enterprise sale, it is a little like throwing pebbles in a puddle and trying to get the ripple of water to go in a particular direction.
Sometimes it takes a lot of pebbles and effort. At the end it is hard to say which exact pebble was the one that made you successful. A good sales person has lots of pebbles in their pocket.
Often you have to start small and build gradually into a large success. Unfortunately management often thinks no small sale is worthwhile. Sometimes that first sale to an account is a huge victory.
It is not unusual to hear that the "cloud" or the web is the solution to managing your sales people.
I don't buy into that. Tools like Salesforce.com or other CRM packages can be useful, but they should not be used as a substitute for management time in the field. I believe that more often than not sales management tools have become a square peg that lazy sales managers try to force into round hole.
There is nothing wrong with tracking some sales activity. However, assuming that the knowledge of the exact timing an initial small order is the measure of a good sales person is absolutely false.
A good sales person usually knows an order is coming and is already working on follow-up business instead of tracking what is already done.
You should track sales activity to know if your products, pricing, and positioning are correct. However, any decent sales system can tell that from monthly billings instead of forcing sales people to recreate a wheel that is already in motion.
If products, pricing, and positioning don't line up competively with the competition, it doesn't matter how good your sales people are, long term success will elude you.
A good sales leader spends enough time in the field with the sales people to know what is happening and to trust what they are doing. It there is no trust, the whole thing will create more stress than humans can take.
Even with the right products at the right price, the lives of good sales people are not easy. On top of the daily challenge of rejection, there are even companies like Apple who believe that the best sales people are ones that fight others in their own company for their business.
In day's hyper-competitive sales environment, there is nothing more demoralizing than to lose a sale to someone in your own company. In a more enlighened company that person who took your sale would be on your team instead of competing with you for business.
Having your own organization or channels compete over business is a good way to convince the customer that your company's left hand doesn't know what the right hand is doing.
Good sales leadership takes time and practice, and it starts with an open door and a willingness to listen.
I can't count the number of successful sales that have resulted from sales people walking into my office and "bouncing" something off of me. Usually my participation is limited asking a couple of questions that perhaps offer a different perspective.
You should also ride shotgun with your sales people every opportunity that you can.
Listening and some account call reinforcements are often the only help really great sales people need. New sales people are of course a totally different story and perhaps another post someday.
In the end much of successful high level enterprise sales cannot put into a data entry screen on a computer. However, it can be learned in the real world with the right leaders in charge.
The real value of great sales people and sales leadership is best seen when trying to get large customers to make a leap of faith which is often required with new technology.
While the Internet has made much of technology for individuals almost viral, there is still a big world out there where businesses carefully consider their options. That's where sales leadership and the teams they bring to bear on the challenges are often underappreciated.