Sales Leaders: Stop Sending Lifeless Sales Reports (and Do This Instead)

Recently, the team at OpenView Venture Partners was fortunate enough to host former ExactTarget CEO Scott Dorsey for a day at our Boston offices. Scott — whose friendship with OpenView founder Scott Maxwell goes back more than 10 years — was incredibly generous with his time. And the highlight for most of us was an hour-long “Lunch and Learn,” during which Scott shared ExactTarget’s incredible founding story (you can see a full interview with Scott and OpenView Principal Blake Bartlett here).
Scott recounted a lot of great stories over the course of that hour, but the one that struck me the most revolved around what he called “My Friday Notes” — a weekly email report that he sent to ExactTarget’s entire team recapping his week and the company’s highlights.
As Scott told our team (and our founder, Scott Maxwell, wrote about in a recent post), those emails weren’t just about keeping employees informed about key goals or objectives. They also delivered much-needed color, personality, and transparency. As the business scaled to several hundred (and then several thousand) employees, the emails made Scott seem more human and personable, and strengthened his leadership.

In the Era of Automation, Personalization Can Be Priceless

There’s something to be said about that level of transparency and personalization in an era of auto-generated reports — and not just for founders or CEOs.
Most sales leaders send weekly (and, in some cases, daily) updates to key stakeholders that recap key performance and activity metrics, and those updates are very often automated through Salesforce (or some other CRM system). But while that data is important, it doesn’t always paint a complete picture of your customers, competitors, or market.
That’s where I think sales leaders can learn a lot from Scott Dorsey. Yes, you should be sending daily or weekly reports that reflect on what you’ve accomplished and where you stand against key goals. But it wouldn’t hurt to infuse those reports with a little bit of context and color, too.
For instance:

• What are buyers saying about your company or product?
• How are they responding to messaging?
• What are their most common objections?
• What kinds of content are they asking for?

That kind of qualitative information may not seem like a big deal, but it can be incredibly helpful for the entire organization. For example, knowing how messaging is resonating with prospects can help marketers fine-tune the content they create, while feedback from a product demo may help the development team optimize its workflow.

If Scott Dorsey Has Time for Detailed Weekly Updates, Why Don’t You?

Maybe the most impressive thing about Scott Dorsey’s “My Friday Notes” is that, over the course of five years, he never missed sending one. That includes the Fridays he was on vacation, out of the country, or home sick.
Think about that for a second. This is the CEO of a company that was acquired by Salesforce for $2.7 billion. His schedule was perpetually full of management, board, and investor meetings. Yet, he always found time to send a colorful, personalized weekly update to his team.
So, what’s your excuse?
When we work with our portfolio companies’ sales teams, we actually encourage business development reps (i.e., the most junior team members) to send daily updates to the CEO that include key insights from their conversations with buyers. That might sound crazy, but we’ve found that CEOs actually want to receive this information.
So, keep that in mind the next time you prepare to send another bland, automated sales report to your senior managers or executives. Yes, activity and performance metrics are important, but there’s also room for color and context. The more you’re able to combine the two, the better informed the rest of your organization will be and the more you’ll build your reputation as a leader.
For more tips on how you can create visibility, take initiative, and catapult your sales career, check out my guest post for SalesHacker on how to become a better sales leader. 
Photo by: Summer Skyes 11