Sales Management Is Hard. But Are YOU Making It Harder?

An uncomfortable conversation about sales leadership, accountability, and why your salespeople might not be the problem.

You know what? I'm just going to say it.

Sales management is hard!

It's like herding cats that are chasing mice that don't particularly want to be caught. And somehow, you're responsible for making sure everyone arrives at the same destination, on time, and with the correct paperwork.

Yeah, that's what goes on inside my brain. Now you understand why my wife deserves sainthood.

But I digress.

Before we get started, a quick disclaimer: Yes, I'm a sales consultant. Yes, I would love to do business with you. But I also hope you get something valuable out of this article whether we ever work together or not.

Now, let's discuss something that might make a few people uncomfortable.

What if your salespeople aren't actually your biggest problem?

What if the problem is you?

Ouch.

Here's something I've learned over the years: Sales management is difficult enough without us making it unnecessarily complicated.

Yet that's exactly what we do.

We hire salespeople, give them a territory, a quota, a CRM login, perhaps a few product presentations, and send them into the world to make magic happen.

Then we're surprised when the magic doesn't happen.

We expect them to know what to do, how to do it, when to do it, and what success looks like.

And when they don't deliver?

Well, obviously, it's their fault.

It is then time for a Performance Improvement Plan (PIP). Or perhaps we should just replace them with someone who knows how to sell.

But here's a question I think every sales leader should ask before reaching for the PIP paperwork:

Have I actually given this person everything they need to succeed, or have I simply given them a number and wished them luck?

Those are two very different things.

I've said this many times, and I believe it wholeheartedly.

A sales plan tells you what you want to accomplish.

A sales process defines how you're going to accomplish it.

You need both.

Sounds pretty obvious, doesn't it?

Then why do so many organizations have one, the other, or some Frankenstein version of both that nobody actually follows?

Let's start with leadership.

Who makes the final decisions regarding your sales organization?

And I don't mean who has the fanciest title or the largest office.

I mean who actually has the final word?

Think about how you qualify a prospect. You want to know who the decision-maker is, right? The person who can authorize the purchase.

Well, who is that person inside your own sales organization?

If your sales manager says one thing, your CEO says another, and your operations leader has a third opinion, congratulations! You've created a sales organization where everyone is in charge and nobody is accountable.

That should work beautifully.

Now, what about your sales process?

What are the specific stages? What activities must happen between those stages? What evidence demonstrates that an opportunity is ready to move forward?

Let's take something simple.

What exactly is a qualified opportunity?

Ask five salespeople that question, and you might get seven answers.

Does the prospect have a budget? Have you identified the decision-maker? Is there a legitimate business need? Has the prospect agreed to a next step?

Whatever your definition is, does everyone understand it?

More importantly, does everyone follow it?

Because if your salespeople are operating under five different definitions of qualified, you don't have a sales process.

You have five individual interpretations of what selling should look like.

Good luck forecasting that.

Ah, the CRM.

That wonderful system everyone agreed was going to transform the sales organization.

Until somebody actually had to enter information into it.

Let me ask you a few questions.

Is your CRM the single source of truth? Does everyone know what information is required? Are your opportunity stages clearly defined? Can you look at your pipeline and reasonably believe what you're seeing?

Or is your pipeline filled with opportunities that haven't moved in six months, prospects who stopped returning calls, and deals that are apparently going to close "next month" for the fourth consecutive month?

I've seen sales managers who are absolutely terrified to remove opportunities from the pipeline.

Why?

Because removing them makes the pipeline smaller.

Here's a thought: Removing a dead opportunity doesn't make your pipeline worse. It makes your forecast more accurate.

A prospect who isn't qualified, isn't engaged, or has no realistic path to closing shouldn't be sitting in your active pipeline pretending to be revenue.

You can continue nurturing that prospect.

You can absolutely revisit the opportunity later.

But stop pretending it's something it isn't.

Your CRM is supposed to help you manage reality, not create an alternate version of it.

Let's talk about sales meetings.

You know the ones.

The manager starts at the top of the pipeline and asks each salesperson for an update.

"What's happening with ABC Company?"

"Still working on it."

"Think it'll close this month?"

"Yep."

"Great. Next opportunity."

Outstanding leadership. Truly inspirational stuff.

If your CRM is accurate and current, why are you spending an hour having people read information you should already have?

That's not a sales meeting.

That's a very expensive data-entry verification exercise.

Instead, use that time to examine the opportunities that matter.

Ask questions such as:

• What does the customer believe the next step is?
• Has that next meeting actually been scheduled and accepted?
• Who are the decision makers and influencers? Are they all onboard?
• What could prevent this opportunity from closing? Don’t say NOTHING, there is ALWAYS something.
• What concerns haven't been addressed?
• What evidence supports the proposed closing date?

And here's one of my favorites:

What happens if the purchase order doesn't arrive next week like your salesperson promised?

Because we all know how that conversation usually goes.

"The PO should be here Friday."

Friday comes.

No PO.

Monday comes.

No PO.

And suddenly everyone is chasing someone who apparently disappeared into the witness protection program.

A good sales manager identifies these risks before they become emergencies.

This is one of my favorite comparisons.

Superman saves people.

Nick Saban built championship teams by developing people, establishing systems, demanding accountability, and preparing them to succeed.

Now, which one sounds more like an effective sales manager?

We've all been there.

It's the end of the quarter. There's a large opportunity on the table. The salesperson is struggling, the deal is slipping, and you desperately need the revenue.

So what do you do?

You put on your cape, fly into the opportunity, take control, and get the deal closed.

Quota achieved!

Crisis avoided!

Everyone celebrates!

Wonderful.

Now, what did your salesperson learn?

Absolutely nothing.

You saved the deal, but you didn't develop the salesperson.

And guess what happens next quarter?

Yep. Get the cape dry-cleaned. You're going to need it again.

Now, I'm not suggesting that a sales manager should stand around watching a major opportunity collapse just to teach someone a lesson.

That would be ridiculous.

What I am suggesting is that you should coach the salesperson through the situation instead of simply taking over.

Help them identify the problem. Work through the options. Let them participate in the solution. Teach them how to recognize and handle the same situation next time.

Because if you're always the person who saves the day, your organization can only grow as fast as you can personally rescue deals.

That's not scalable.

Great sales managers don't stop managing people. They manage people through effective systems, coaching, and accountability.

People create results.

Systems create consistency.

And great leaders develop people who can eventually lead others.

That's how you build something that grows beyond your personal ability to swoop in and save everyone.

Here's where things might get a little uncomfortable.

Your sales team isn't hitting quota.

Management is unhappy.

Pressure is building.

Someone has to be held accountable.

So naturally, we start looking at the lowest-performing salespeople.

Maybe they need additional coaching.

Maybe they're in the wrong role.

Maybe they genuinely aren't capable of doing the job.

Those are all possibilities.

But what if most of your team is missing quota?

If only a small percentage of your salespeople are consistently achieving their targets, are you really going to tell me that you just happened to hire an entire organization of underperformers?

Possible?

Sure.

Likely? Hmmmm...

I'd be asking some serious questions before accepting that explanation.

I've always believed that a healthy sales organization should strive to have the overwhelming majority of its properly ramped salespeople achieving quota. My personal benchmark is around 90%.

That's an aspiration, not some universal law of sales management.

But if your organization is nowhere near that level, shouldn't we at least consider the possibility that the problem goes beyond the salespeople?

Maybe the quotas aren't realistic.

Maybe the territories don't contain enough qualified prospects.

Maybe the pricing isn't competitive.

Maybe your services no longer align with what the market wants.

Maybe the messaging isn't resonating.

Maybe you're expecting every dollar of growth to come from new customers while ignoring expansion opportunities within existing accounts.

Or maybe the process you created simply isn't working.

Here's the question I've always asked myself:

If I were a salesperson working for me right now, with the same territory, pricing, resources, and expectations, could I consistently achieve 100% of quota?

And I mean an honest answer.

Not the answer your ego would like to give.

If the answer is no, why on earth would you expect everyone else to do it?

I've worked with plenty of leaders who respond to missed sales targets with some version of:

"We need more activity!"

"Make more calls!"

"Create more opportunities!"

"Close more deals!"

Brilliant.

Why didn't anyone think of that?

Here's the problem.

Telling someone to do more of something that isn't working doesn't automatically make it work.

Sometimes more activity is absolutely the answer.

But sometimes it's not.

What if your salespeople are contacting the wrong prospects?

What if your ideal customer profile is outdated?

What if your messaging is ineffective?

What if your sales cycle is longer than your forecasting assumptions?

What if you're measuring calls made instead of meaningful conversations generated?

You need to diagnose the problem before prescribing the solution.

Think of it this way.

I've gone to a chiropractor because my shoulder hurt, only to discover the underlying issue was somewhere else.

The pain was in my shoulder.

The problem wasn't necessarily originating there.

Sales organizations work much the same way.

Your symptom might be missed revenue targets.

But the underlying problem could be pricing, positioning, leadership, process, territory design, or a dozen other things.

Putting a salesperson on a PIP won't fix an uncompetitive service offering.

Although I'm sure it makes somebody feel like they're doing something.

Here's another uncomfortable truth.

Sometimes the very processes we worked so hard to build are the things holding us back.

Markets change.

Customers change.

Technology changes.

Competitors change.

And yet, some sales organizations are still operating under processes designed for a completely different business environment.

Why?

Because that's the way we've always done it.

Fantastic. I'm sure your competitors appreciate your consistency.

I believe sales leaders should review the effectiveness of their sales plans, processes, and systems at least quarterly.

That doesn't mean you need to completely rebuild everything every 90 days.

It means you need to be willing to question what you've built.

What's working?

What's not?

Where are opportunities getting stuck?

Are our assumptions still valid?

And most importantly, what needs to change?

Sometimes the answer is a minor adjustment.

Sometimes you need to tear something down to the studs and rebuild it.

Neither is a failure.

Recognizing that something isn't working and correcting it is intelligent growth.

Refusing to change because you're emotionally attached to your own brilliant idea?

Well, that's a different problem.

This may be one of the most important principles of sales leadership.

Your team learns what matters by watching what you actually do.

Not what you say.

What you do.

If salespeople consistently arrive late to meetings and you ignore it, you've established that punctuality doesn't matter.

If your top producer refuses to update the CRM and you allow it because they're making quota, you've established that your rules are optional.

If you constantly talk about revenue but never gross profit, don't be surprised when salespeople discount their way into deals that barely make the company money.

If you reward activity without evaluating its effectiveness, expect lots of activity.

And if you keep rescuing the same salesperson every month without coaching them, expect to keep rescuing them.

Congratulations.

You've built exactly the organization your behavior encourages.

The solution?

Define the outcomes you actually want.

Communicate them clearly.

Measure the activities and results that contribute to those outcomes.

Reward the right behaviors.

And hold everyone accountable.

Yes, everyone.

Including the superstar salesperson who thinks the rules don't apply to them.

And, perhaps most importantly, including yourself.

Maybe.

Some salespeople simply aren't right for the role.

Some lack the necessary skills.

Some don't put in the effort.

And some genuinely need to find another profession.

But before deciding that your salespeople are the problem, ask yourself whether you've built an organization that gives good salespeople a realistic opportunity to succeed.

Do they have a clear plan?

A documented and consistently followed process?

Aligned leadership?

Effective systems?

Meaningful coaching?

Realistic expectations?

And an organization willing to change when something isn't working?

If the answer to those questions is no, perhaps it's time to stop looking exclusively at the salespeople.

The problem might not be who's selling. It might be how you're leading.

And the good news?

Glad you asked.

You can fix that.

Although, technically, I asked myself. Occupational hazard.

Over the years, I've developed a methodology designed to help organizations address exactly these issues.

It's called P².U.L.S.E.

Not because the world desperately needed another acronym, but because effective sales management requires several interconnected disciplines working together.

P² — Planning and Process

What are we trying to accomplish, and exactly how are we going to accomplish it?

U — Unity

Are sales, marketing, operations, service delivery, and leadership actually working toward the same goals? Or are they operating like separate companies that occasionally share a conference room?

L — Leadership

Who is responsible for what? Who makes the final decisions? And who is accountable for making sure the plan actually happens?

S — Systems

The CRM, meetings, handoffs, rules of engagement, documentation, and operational disciplines that turn your plan into a repeatable business process.

E — Execution

Because a beautifully documented sales plan that nobody follows is just an expensive paperweight.

Execute, measure, coach, adjust, and repeat.

That's how you build a sales organization that doesn't require Superman to show up at the end of every quarter.

Why talk to me?

If you're an MSP owner or sales leader who's wondering why your sales organization isn't performing the way you expected, I'd be happy to have a conversation.

I offer a complimentary one-hour consultation to discuss your sales organization, identify potential issues, and explore ways to improve performance.

If we solve your problem during that hour, fantastic.

If you need additional help, we can discuss that too.

No pressure. No elaborate sales presentation. Just a conversation about what might be holding your business back.

Finally, WHAT MAKES ME DIFFERENT THAN ALL THE OTHER CONSULTANTS OUT THERE?

1) You get me and not a team that you do not know and trust. I meet with you, I help design the plan, I help you get it in place.

2) I am NOT looking to put in place a system where you need to pay me a monthly retainer and give you a workbook to implement on your own. I want to be the HINGE of consultants, “made to be deleted”.

3) If you do not know about Hinge and their marketing, it is brilliant and you should look it up. HOWEVER, it is a dating app, so make sure your significant other knows what your doing so I do not get yelled at for your breakup!

If you would like you one hour, no charge consultation, reach me at mkkoenig@whitetigercc.com to schedule some time or use the scheduling link on the website.

Let's get your sales organization hunting like a tiger.

And perhaps retire that Superman cape once and for all.