Ditching ‘Just Checking In’: Sheriff Shahen on Contextual Sales Outreach

In a recent LinkedIn post, Sheriff Shahen challenges the efficacy of traditional sales follow-up tactics, particularly the ubiquitous “just checking in” email. Shahen argues that this approach, born out of uncertainty, signals nervousness and guesswork to potential buyers and is often sent at precisely the wrong moment.

The post highlights the common sales scenario where a proposal is sent, followed by an unnerving silence. This period of unknown, Shahen notes, leads to internal second-guessing about pricing, competitive pressures, or internal roadblocks on the buyer’s side. This lack of information compels salespeople into the often-ineffective “just checking in” follow-up.

“We have no idea what’s happening on the buyer’s side. You send the proposal. You feel good about it. Then the silence starts. 24 hours. Nothing. 48 hours. Nothing.”

The Problem with Blind Follow-Ups

Sheriff Shahen asserts that the “just checking in” email is a symptom of a lack of visibility into the buyer’s journey. As Shahen points out, this type of communication inadvertently reveals the sender’s anxiety and lack of concrete information. The timing of such emails, according to Shahen, is particularly detrimental because the sender is operating without any insight into the buyer’s current engagement or internal processes.

The Shift Towards Informed Outreach

The turning point for Sheriff Shahen, as detailed in the post, came with the implementation of DealHub.ai. This technology provided the crucial visibility needed to move beyond speculative follow-ups. Shahen explains that with this tool, sales professionals can now monitor when a stakeholder accesses a deal room, observe their interactions with specific sections like pricing or security terms, and ascertain if key decision-makers, such as the CFO, have reviewed the proposal.

“I stopped sending those emails when Deel implemented DealHub.ai. Now I know the moment a stakeholder opens the deal room. I can see what they’re spending time on.”

This enhanced visibility transforms the nature of sales outreach. Instead of sending a generic check-in, Shahen advocates for a more strategic approach. When activity is detected in the deal room, the sales representative can engage their champion with a contextually relevant conversation.

Context is King in Sales Conversations

Sheriff Shahen contrasts the outdated “checking in” method with a more effective, context-driven engagement. The goal shifts from merely seeking an update to offering timely assistance based on observed buyer behavior. As Shahen suggests, a proactive call informed by data is far more valuable than multiple emails sent into the void.

“So instead of ‘just checking in’ I can call my champion the moment I see the buying committee is active. Not to check in. But to say: ‘I wanted to jump on quickly in case there are any questions being discussed right now.'”

This refined approach, according to Sheriff Shahen, fosters a more productive dialogue. It positions the salesperson as a knowledgeable partner rather than an anxious vendor. The core message is that informed timing, enabled by visibility into the buyer’s process, allows for more impactful and effective sales interactions.

“That’s a different conversation entirely. One call with context beats ten emails in the dark. Timing is a choice if you have the visibility to make it one.”

Ultimately, Sheriff Shahen’s insights underscore the importance of leveraging technology to gain visibility into the buyer’s journey, thereby enabling more strategic, contextual, and effective sales communication.