Sales Leadership Mediocrity: It’s Your Mostly Fault, and Here’s Why - Plus How to Course-Correct

Seven ish years ago, someone told me, "You bring out the worst in me."

Backstory, this was in fact a Senior Leader who was vehemently opposed to my promotion due to my RBF. After we worked on a few projects and she got to know me, she realized, I'm just a straightshooter and she grossly underestimated what I was capable of.

As we sat having a drink and she uttered the words, "You bring out the worst in me". It stung

At first, I wondered if I was really that bad. But after some reflection, I realized the truth: I’m just good at discovery. Really good at a problem-centric discovery (in fact - it's a superpower).

I wasn’t being mean. I was digging deep into problems, challenging the status quo, and pushing for change. It wasn’t comfortable for her, and frankly, that’s the point. Change never is.

Looking back now, I laugh. I was ahead of my time.

But fast forward to today, and I’m concerned. No, scratch that—I’m VERY concerned.

Why? Because mediocrity is everywhere. I see it in sales leadership. I hear it in the conversations with managers who are stuck in reactive cycles. I get it in my dms when reps reach out and spill the tea about what's going on in the company.

And I watch it unfold in real-time as these leaders chase the next quick fix or shiny object, thinking it will solve their problems. (if you are saying phrases such as: oh, we will get to that when x, we are waiting for y, it's just, I need more headcount, we need this new tech tool, we have to wait until we are cash flow positive - and worse one I've heard yet this year- "we are just going to to raise more money" (vs. investing $20k with a direct line of site this year to make revenues.....they are only a couple hundo thousand off).

Here’s the brutal truth: the next quick fix isn't going to solve the glacier that is under the water.

The Problem with Mediocrity

Win rates of 4%, 8%, or 10% are not sustainable. I'm not making these up - these are numbers clients share with me. The best I've seen is a 35% win rate, but deeper digging has uncovered, this is at proposal stage - so late stage. I'm talking qualified opportunity creation to close - sub 10%.

That means, losing 90%!!!!

And yet, many of you are watching your teams barely scrape by while you preach “more activity” and “do better.” But are you inspecting what you expect? Because a CRM full of useless info, burned-out sellers, and unreliable forecasts aren’t exactly signs of crushing it.

Let’s break this down:

• Your CRM is a data graveyard: Reps are inputting fluff because they don’t know what meaningful information to collect. And guess what? You don’t either. Because it's about the buyer, not the seller and most sellers don't know enough about their buyers to have more than surface level convos. "Because they don't have our solution" - is not a compelling reason for them to buy. Shallow buyer input data is one of the main reasons you have a pipeline full of fluff!
• Deals keep falling through: Reps aren’t making a compelling case for change because they don’t know how. And if they don’t know, whose job is it to teach them? A case for change is when reps are able to demonstrate why the cost of change is greater than the cost of same. Meaning, that the impacts in the current state (or future state for risk based) are so BIG that implementing your product or tool to fix becomes a no brainer.
• Your forecast is a joke: Reps are “gut feeling” their way through projections. There’s no real buyer input data, and you wonder why your forecast accuracy is in the toilet. Just this past week I heard the phrase "we do shallow deal reviews". Me - "what is shallow" - "we go over all the MEDDIC fields to ensure they are in there to be able to forecast the deal". I of course ask what BUYER data they have - what's the motivation for change, how big the problem is and how are those problems showing up. DEAD EYES.

So, let’s stop pretending these issues are minor or will fix themselves. All the AI and new tools in the world will most likely just band aid what's going on and guess what sales leader? It’s entirely your fault.

Time for a Reality Check

When was the last time you looked in the mirror and asked, "Is it me?" Have you done everything in your power to change the trajectory of your team?

Or are you being penny-wise, ignoring the real investment that will make an actual difference? Are you chasing the next band-aid solution instead of addressing the real root causes?

Here’s the deal: If you haven’t called in the experts for a diagnosis, you can’t be mad when the board holds you accountable for your team’s performance. You can’t point fingers when your ship is sinking and all you did was slap on another coat of paint.

The Cost of Ignoring the Problem

Let me be clear: If you’re not actively fixing the core issues, you’re setting your team—and yourself—up for failure. The shiny object syndrome isn’t going to get you out of this mess. More “sales activity” isn’t going to magically increase your win rate.

You’ve got to get serious about real change. That means inspecting every layer of your process and what the broken parts are stemming from and making hard decisions. It means investing the right training and reinforcement - which means you have to be in it for the long haul as no training that is 1-2 days will change behavior or metrics unless your team is actively being coached, reinforced and you, the leader, builds in enablement long term.

So ask yourself: Are you willing to do what it takes? Or will you continue to coast on mediocrity until it’s too late?

Because, make no mistake: If you’re leading a sales team and they’re underperforming, it’s a little bit on them, but it's mostly on you.

For a deeper dive into tools vs. behavior from a management lens, check out the behavior vs. results matrix.

A little tough lough from Celeste - a Certified Gap Sales Trainer who has so many calls with teams on the cusp of greatness who instead of wanting to dive in and fix it, turn to the easy button.

There is no easy button, but there is line of site to hitting goals if you start today!