Why Sales Leaders Fail

My job is to help CEOs and leadership teams scale companies profitably. And one of the things you see as a business coach is that heads of sales fail at a disproportionately high level compared to other roles. Heads of marketing do too. Right now, we're going to focus on heads of sales.

And the reason they typically fail are two things. One's probably pretty obvious. One might not be as obvious. So number one, we usually promote our best salesperson to be our head of sales.

Those are two completely different behaviors, unfortunately. Meaning the ability of one person to be able to build a relationship with a prospective client and be able to surface pain in the sales process and ultimately help them purchase our product or solution is way different than someone who's able to look at that as a system or sales process and use data to be able to help others to grow in that role. So the real simple test where most heads of sales who struggle, they all struggle or fail at this, which is if they have a pipeline of where each of their salespeople is succeeding, they are not able to look at the number one, like let's say it's a basic pipeline where you have leads, Number of proposals, number of sales. They're not able to look at that and say, okay, across the board, what's the average conversion rate from lead to proposal out?

What's the average conversion rate from proposal to sale? They can't look at those. Number one, establish where the average is. Two, find people who are above and below that average.

Three, be able to help people come up with exactly where they are struggling in the sales process in those areas to be able to systematically improve those percentages both for the salesperson and for the company over time. And that's literally what it will be. A lot of cases, we literally, if someone's struggling, we'll literally put a spreadsheet in front of them and say, where does this person need help? What are the three things this person has to work on if they're struggling in this part of the process or this part of the process?

And what you see consistently is they cannot say, they usually say, I don't know. I don't know where they're struggling. It's not because they're a bad person. It's not because they aren't smart.

Aren't skilled or aren't capable. It usually is just in how people are built. Sometimes our ability to be really, really super task oriented and focused on data is not the same as being able to build a relationship. Those are two very different skill sets.

Those are two very different behaviors, excuse me, and skill sets to some degree, because these are very, very high level when it comes down to salespeople. But that simple test is, can I look at a pipeline? Can I help identify with the salesperson that's struggling through either listening to their calls or you know, being on their Zoom meetings or seeing the, you know, going reviewing the AI summary of the Zoom sales meeting they had or going with them in person, can I observe where they're struggling and be able to help them improve? So, for instance, let's say someone is struggling from getting someone from the lead stage to a proposal stage.

They're probably struggling at their discovery process. And there's probably a couple of things that they need to do differently to be able to surface enough pain for that person to be interested in a proposal. So what they would come back with is one that, you know, if you're, if you're head of sales that's good at coaching, you ask them where do they think they're struggling? And hopefully Hopefully they can come up with those answers and sometimes you may have to coach them along and say, well, I noticed this, I noticed this, I noticed this.

What could you work on to be able to get you better at this particular part of the process? And that is exactly where they struggle. They just cannot get that deep using data as a backbone to be able to make people successful. Most heads of sales think their job is to go sit with someone and then give them feedback after the fact about how effective the sales process was.

That is mildly helpful, but it is nowhere near as helpful as being able to back up that discussion with data There's literally a ten x difference in performance if you have data to be able to help someone know where they're struggling relative to everyone else and be able to know what are the two or three things they have to work on specifically. And maybe it's not all the process at once, but in part A of the sales process this month or this quarter to be able to consistently become successful. So that's really it with heads of sales. It's a hard role to hire for hard role to find the behaviors are just it's not it's not something you find commonly.

You don't find it in nature. You have to find people that that are comfortable not taking commission, but they find a ton of satisfaction out of helping other people succeed. So if you're a CEO and you struggle with this problem, a lot have. And by the way, one slot left for coaching into 2026.

And if you're interested, there's a link in my bio where you can fill out a growth assessment and I'll schedule a follow-up call with you. So thank you. Leave your comments below.