Your 2019 Pre-Flight Sales Planning Checklist

Babar Batla


on December 26, 2018
If you’ve been leading a sales team for any amount of time, you know the value of having an action plan to keep your sales organization airborne and on the right course. Especially at the beginning of the new fiscal year. When you have a solid plan from the beginning, you can make adjustments as you go. But when you haven’t taken the time to do your yearly planning, making adjustments every three months at the quarter reset is as disruptive as pulling a bunch of levers mid-flight to see how a plane is going to react. At best you’ll end up with random results. At worst you’ll get pushback from your team — or send your plane wildly off-course. In our experience, most sales leaders end up managing “in the now” rather than thinking about the future. They’re so focused on the sales numbers that are coming in today that they’re not able to course correct for the future. When you take time at the beginning of the fiscal year to truly understand your historic sales metrics, you’ll be able to set up a system to manage in the future, rather than being stuck in the now. Just like every airplane pilot goes through a pre-flight checklist before take-off, so should every sales leader. Before you sit down to do your annual planning, take the time to gather these historic data so you can model your numbers for the future and plan your next year’s goals around solid data. Consider this your 2019 pre-flight sales planning checklist. You can also download the templates for each of the sales planning activities I mention below here: 2019 Sales Planning Toolkit.

1. Calculate how much pipeline you need

Some sales leaders rely on their reps to figure out how many deals they need to chase to make the numbers. But humans tend to mis-remember historical data, and generally do a poor job of modeling in their head. Instead, go through your historicals to figure out last year’s win rate and calculate the pipeline coverage you need to have a safe quarter or year. Keep yourself on course throughout the year by revisiting your calculations as sales reps close new deals, continuing to determine the total pipeline need by figuring out the multiple based on gap to quota.

Your Checklist

Take the total number of deals won by a rep this year and divide it by total number of deals the rep had in a defined early sales stage. Based on that win-rate ratio, figure out how many deals they need to run to win one deal. Multiply that quantity with the total number of deals they need to close to determine how much pipeline they should have at any given time. Tip: If you don’t know how many deals they need to close, take the rep’s quota and divide by average deal size.
Example: Rep closed 10 deals and had 30 opportunities that went through qualifying stage. Average deal size is $25K and quota is $500K. Total approximate deals needed is 20. With a win rate of 33 percent, the rep will need 60 deals to enter the pipeline this year.

2. Determine your leading indicators

If you track progress using lagging indicators (like closed deals and pipeline coverage), it’ll be too late to steer the plane when you notice it’s tracking toward a collision course. Unless you determine your leading indicators ahead of your yearly planning, you’re leaving satisfactory results to chance. Identify which activities are highly predictive of deals going through various stages and build out a scorecard. This lets everyone know the amount of thrust need to get airborne or stay airborne, and is the best way to hold reps accountable. There are two main qualifications for a good indicator.
  • It should be easily measurable
  • You can confidently know the conversion rate from that activity to a won deal

Your Checklist

Examine all the atomic activities your reps do on a daily basis that push opportunities toward a closed deal, and identify 5-6 that are most impactful toward driving sales (such as making outbound calls, qualifying leads, or leading a demo). Then, reverse engineer how many of those activities are needed to close X dollars per month/quarter. Those will be your leading indicator goals.
Example: There are three types of leading indicators that are good candidates for sales organizations: activity-based, relationship-based, and opportunity-based. For example, a software company whose sales process relies on marketing qualified leads, sales qualified leads, intro calls, discovery meetings, demos, and proofs of concepts could use the number of demos completed as a good activity-based indicator. A relationship-based indicator could be the number of net new VPs of HR engaged in a discovery meeting. An opportunity-based indicator could be number of SQLs in the pipeline.

3. Identify — and clear out — plugs in your pipeline

Leading indicator scorecarding without a timeline is dangerous as it can give you false sense of security. That’s because when your pipeline is clogged, large numbers of the opportunities that start at stage one of your pipeline can get stalled along the way due to friction or gaps in your sales process. Look over your historical data to determine at which stage deals are getting stuck. It might be a systematic issue, or it might be an individual seller issue. Regardless, you need to make sure you have good CRM hygiene before coming to conclusion. You don’t want to focus on deal qualification training if your reps aren’t moving their deals forward after qualifying them.

Your Checklist

For each sales rep and for each deal size segment, calculate the median amount of days spent in each sales stage. (You can remove the outliers if you like to ensure you have middle of the pack numbers.) Once you have the timing, calculate the quarterly timing for the leading indicators above, and determine if delays are a sales org problem or a problem with just a few sales reps.
Example: Let’s say your analysis shows that your reps spend 14 days to get a SQL to qualify stage, and the total sales cycle in 90 days. Your leading indicator will need to be X number of deals in qualifying by 76 days prior to the quarter end. This ensures there is enough time for your leading indicator to be predictive of the desired outcome.

Planning for 2019 sales success

Don’t wait to correct the course of your organization until after you’re already in flight for the year. When you take the time now to truly understand your historic sales metrics and set goals for 2019, you’ll be set up for a successful flight.  

Get the latest content delivered to your inbox.