Setting Annual Plans With Humanity: Beat the Number Every Time

I delivered the closing keynote address at Sales Enablement Collective's Chief Revenue Officer Summit on September 29th, 2021.

 

I shared a framework for building annual plans that actually work by accounting for the messy realities of humanity. Far too many GTM strategies are built on "neat little spreadsheets" that assume robotic perfection—expecting every rep to hit 100% of their quota every month without fail [02:46].

 

This approach is a primary reason the average tenure for a VP of Sales is just 18 months; when unrealistic expectations inevitably clash with reality, leadership is often the first to go [06:08]. In my session, I outlined a six-step process to ground sales planning in historical performance data rather than hopeful gimmicks.

 

We discussed modeling the impacts of ramp time for new hires, planning for both voluntary and involuntary turnover, and placing strategic bets on training and product launches as "cautious gains" rather than critical keystones [13:07].

 

By structuring the calendar to encourage early wins—lowering Q1 expectations to build momentum—we create a culture of winning that satisfies the board while keeping the team motivated [23:01]. This is the intersection of business and humanity: creating a go-forward plan that actual humans can perform against, ensuring we exceed our goals every time while building long-term organizational loyalty [09:27].