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How to make my sales team feel safe under pressure.


Man in business attire with his hands up trying to stop a stone ball rolling towards him


When sales teams are under pressure to hit their numbers without a healthy coaching culture, an interesting phenomenon happens: sellers get creative. But unfortunately it’s not the kind of creativity that sales leaders would want to see. Instead, the team’s attention is focused on self-preservation. 


Essentially their question becomes: “what do I need to do to avoid drawing negative attention to myself?”


Here are some examples of what this looks like:


  • Waiting to enter opportunities in the CRM until they’re later stage (so their win rates look higher than they really are)


  • Advancing opportunities to the next stage in the CRM even though critical information is missing about why the buyer should buy


  • Logging a high number of activities such as calls, emails, etc without any focus on the quality of those opportunities


The result? Opportunity quality suffers. In other words, each opportunity is less likely to close, or will have a lower average deal size. That's because attention has not been given to that specific buyer’s world and exactly how your solution would help them.


Without a healthy coaching culture, the sales team has a handicap when it comes to qualitative information. Instead, quantitative information is used as a shield for self-preservation.


Psychological safety and what happens when it’s missing


Psychological safety is defined in Harvard Business Review as “a shared belief held by members of a team that it’s OK to take risks, to express their ideas and concerns, to speak up with questions, and to admit mistakes — all without fear of negative consequences.”


In the sales world, if a health coaching culture exists, there will be a regular cadence of coaching between frontline manager and sales rep. The rep is asked questions to prompt his or her critical thinking about the opportunity, and what information still needs to be gathered in discovery.


Coaching creates a safe space for reflection and identifies the seller’s blind spots – not to play the blame game but to increase the seller’s awareness and ability to improve the quality of the opportunity itself.


Coaching is not just asking questions like “when will that one close?” or “how many new opportunities did you enter this week?” Instead, true coaching is asking the seller questions such as: “what will happen to this prospect if they don’t fix this problem?” or “what is prompting the prospect to address this now rather than waiting another year?” or "what other information do you need to quantify the Cost of Inaction?"


If you’re a frontline manager, are your hackles going up because you don’t have time to coach your team members? Consider this: just 10 to 15 minutes of quality deal review coaching per week per new opportunity can significantly improve the outcome of that deal.


How to create psychological safety through coaching - what makes your sales team feel safe under pressure.


I want to be clear that shifting to a healthy coaching culture does not mean you give up on your targets. It actually means you increase the likelihood of reaching those targets by focusing on what matters most: quality and quantity.


So how do you start?


  • Demonstrate open communication. Regardless of whether you’re a frontline sales manager, VP, or C-Suite leader, you can set the example: ask questions that prompt dialogue. Make it clear that you’re not looking for perfect answers – instead, you’re looking for critical thinking.


  • Model humility. Admit when you don’t have an answer or are unsure. Talk about a mistake you made and what your learned. This is vital for creating psychological safety.


  • Create a regular coaching cadence. Again, just 10-15 minutes of deal reviews per week for each new opportunity can make a world of difference. Ideally this should be 1:1 time with each rep.


The result? Over time you can expect to see better quality deals in your pipeline with a higher likelihood of them closing. When you have better information on that opportunity from the start, you have a deeper understanding of that customer which means you’re more likely to retain and grow that customer over time.


Stay tuned for next week when I’ll share exactly what is the quality information that should be gathered on each opportunity.


PS Know someone who could benefit from this newsletter? Forward it to them now!



"How to make my sales team feel safe under pressure."

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