The Most Challenging Leadership Job

If I had to single out the leadership job that's hardest to do, I'd say head of sales. And not just because sales brings in the revenue and tends to feel the friction from the external environment first, though both are certainly true. But because in addition, sales organizations are unique in ways that create singular challenges.

First of all, in most cases, its members are spread out physically all over the place, since sellers tend to stay close to customers, not to headquarters. Not being all together makes substantive interactions among members and between staff and leader difficult.

Second, there's no standard educational path, or shared body of knowledge, for sales professionals. Accounting leaders can look to the Generally Accepted Accounting Principles. Manufacturing leaders can look to Six Sigma and other well-defined processes. Human Resource practice is bound by regulations and case law stipulating what is acceptable and what is not. But sales professionals have, well, the experience of other sales professionals and a lot of books to choose from in the marketplace. Few of them have university degrees in sales, since so few institutions of higher learning even offer one. They come to the job with backgrounds in everything from philosophy to physics, each with its own outlook and ways of thinking. That makes training part art, part science, and all on the job.

Finally sales professionals tend to be prima donnas. I'm not saying that's bad, particularly (I've spent a large part of my career leading sales organizations), but if you've worked with sales professionals, you'll recognize the pattern of their typical strengths. They have a tendency to challenge authority. They're very driven toward results, and they have strong preferences for how those results are achieved. And of course more often than not, they have extravert personalities.

I've had the luxury during the last decade to work with many great sales leaders, and the best of them tend to share a common set of traits and practices. In no particular order, this is what marks them out:

• They lead with metrics. Everyone knows that the ultimate measures of success in sales are revenue and profit. But while critical, they are lagging indicators. The best sales leaders focus on leading indicators, as well — metrics like "key milestones in a long sales process" and "increases in the value of a pipeline," which are predictive of success or failure while there's still time to adjust. When your interactions with your staff are limited, few things are more powerful than having the right balance of both of these kinds of metrics.
• They coach and develop talent. Coaching has been in vogue for a number of years, but it's particularly critical for people learning most of their job on the job. That means that sales leaders need to put a premium on developing the capabilities of their staff. Gallup research indicates that having the right manager can improve a seller's performance by 20%. Too many sales leaders are promoted because they were great at selling but then fail to devote enough attention to teaching their staffs to do what they (used to) do. But the best sales leaders make coaching a priority. After all, even prima donnas want to improve their craft, be more successful, and earn more.
• They provide strategic guidance. I have rarely seen a competitive strategy that did not look terrific in a PowerPoint presentation in a boardroom or conference center. But I've also rarely seen such strategies translated into specific actions for the members of a sales team. It is up to the sales leader to make it clear how their teams are expected to implement those plans so that the strategy is carried out effectively.
• They keep the focus on value creation. I'm not talking about the value of the company's offerings; I'm talking about the value created by sellers in the selling process. Sales leaders must continually draw the focus of their teams away from simply discussing features and functions and toward the value they can create by helping clients define their needs, establish success measures, and meet their objectives with the company's products and services. When a sales staff guides customers to see needs they hadn't considered, helps them understand the impact of those needs, and introduces them to solutions or configurations they were unaware of, the chances for differentiation are far greater. And so is the likelihood that your company will earn the clients' business.

I don't want to imply, of course, that just because leading sales is hard other leadership jobs are easy. I doubt there's an easy leadership job anywhere. But if there are few schools that teach sales, there are even fewer (are there any?) that teach sales leadership — it's entirely learned as you go along, while the top line of the company is resting on your organization. But, no pressure....