If a prospect is dragging things out, should you close-lost it and kick it back to SDR to re-qualify in a few months, or should you continue to nurture it?

Before diving into the specifics, it’s important to establish the foundational role that Pipeline plays within an organization.

Pipeline serves two primary purposes:

1. Forecasting Revenue: It enables you to accurately project future revenue streams.

2. Evaluating Business Health: It provides insight into the value and stability of your business, helping stakeholders understand how effectively you are converting opportunities into closed revenue.

   • Kick these deals back into the SDR blender and find a way to get them back into the funnel when/if it makes sense.

This may simplify a complex topic, but it is necessary to identify where potential confusion might arise regarding the handling of Pipeline. Let me present two scenarios that illustrate different approaches based on organizational maturity.

Scenario 1: Mature Revenue Organization

For a well-structured revenue team with clearly defined segmentation, sufficient staffing, and the ability to measure revenue performance effectively, the strategy should be to avoid unnecessarily prolonging deals. In this context, the optimal path is to:

• Develop a well-defined sales process that clearly outlines each stage.

• Establish a rigorous process for managing “closed-lost” deals, allowing your team to focus on the deals that have a real probability of closing.

By not dragging out unqualified opportunities, you prevent a misrepresentation of your forecast and ensure clarity in conversion metrics. Your team’s attention should be on driving the Pipeline that is likely to close—this will not only sharpen forecast accuracy but also enhance overall sales productivity.

Scenario 2: Developing Organization

For a growing business still finding its footing, closing out deals that aren’t moving forward may not always be the ideal course of action. Instead, it can be beneficial to:

• Establish specific statuses or tags that allow you to categorize deals that aren't yet ready to be closed out or actively pursued.

• Ensure these deals do not occupy the core focus of your sales team, whose priority should be opportunities likely to close within the established "days to close" window.

However, keeping these deals in the Pipeline enables you to analyze patterns and define potential thresholds for Ideal Customer Profile (ICP) criteria—something critical for a scaling startup. This requires a collaborative effort across Sales, Revenue Operations, Marketing, and the Executive Team to jointly develop and own a process that drives insights from these inactive opportunities and informs future strategies.

When raising, having more pipeline is better than having less. However, if you're still getting your footing on your ICP and feel like your in the "squiggly line" phase of your growth plan, it's not a bad idea to hold onto deals - you just need to be crystal clear in how you communicate managing pipeline expectations so it doesn't artificially inflate your actual forecast.

If a prospect is dragging this out, the most important aspect is getting to understand why...

• Did their priorities change?

• Is the underlying business case not compelling enough?

• Are they not convinced of your solution, so they are buying time to consider competitors?

• Do they intend to move forward but internal circumstances have just pushed out the timeline?

• Have they decided not to move forward, but don't want to hurt your feelings?

• Something else?

Regardless of the situation, you need to find out why because Yes's are great, No's are good, but Maybe's will kill you.

Therefore, I would suggest having a direct conversation with your prospect. You can do that by...

1. Start with the Why: re-summarize the underlying business case narrative by sharing your understanding in their own of words of the Why: 1) why the prospect needs to do anything, 2) why they need to do it now, and 3) why your solution is the best for their situation

2. Objective Observation: share the objective observation that it seems like the deal has stalled, agreed timelines are slipping, or the prospect hasn't met your mutually agreed commitment, etc.

3. Curiosity: explain to the client it is okay if things have not gone according to plan, but in order to be the best partner to them you need to understand why, and then lead with curiosity to understand what may be going on

4. Way Forward: collaborate to align on the best way forward in partnership with your prospect...it needs to be mutual.

Then allow that "Way Forward" to direct what you do next, whether that is marking Close/Lost, circling back when timing is better, or proceeding the sales process with a new found energy.