Stop Making the Donuts: What Organizations Need Before Hiring Sales Enablement

When companies miss revenue targets, leadership often reaches for the same solution: another sales methodology, another round of training, or another push for sellers to work harder.

But after more than two decades working inside healthcare tech organizations, I’ve seen a pattern repeat itself:

Most sales problems aren’t skill problems. They’re system problems.

There’s an old Dunkin’ Donuts commercial where a tired baker wakes up every morning muttering the same phrase: “Time to make the donuts.” In many organizations, sales enablement can feel a bit like that. Another quarter missed. Another training program rolls out. Another attempt to make better donuts.

We keep teaching reps to make better donuts, faster donuts, and more donuts without ever pausing to ask whether the machine is broken, the recipe is wrong, or if customers even want donuts anymore.

Salespeople rarely fail in isolation. They struggle inside systems that make success unnecessarily difficult.

That’s why sales enablement can sometimes be placed in a tough position. Organizations hire enablement expecting quick results, but the underlying engine hasn’t been aligned yet.

Before enablement can truly move the needle, there are issues organizations need to address.

Many are probably familiar with the Skill / Will / Hill framework - it’s a helpful way to diagnose why sellers might be underperforming. While the Go-To-Market environment can be considered part of the “Hill,” in many modern organizations the revenue engine has become so central to performance that it deserves its own focus.

The Engine 

The Go-To-Market (GTM) engine is the system that surrounds the seller. It includes strategy, processes, technology, and cross-functional alignment. When the engine works well, sellers can focus on customers. When it doesn’t, even great sellers struggle.

Before organizations expect sales enablement to transform performance, they need to examine whether the engine itself is functioning.

Here are a few areas worth looking at first.

1. Diagnose the Real Problem: Skill, Will, Hill… or Engine?

When sales teams struggle, the default assumption is often that the problem is Skill or Will. Leaders assume sellers need more training or more motivation.

But sometimes the real issue isn’t the seller at all.

It’s the Hill they’re climbing or the Engine they’re operating within.

If the strategy is unclear, internal processes are chaotic, and systems are misaligned, even highly capable and motivated sellers will struggle to produce consistent results.

Training can improve performance at the margins. Fixing the system can improve performance at scale.

2. Establish a Clear Go-To-Market Strategy

A surprising number of organizations attempt to operationalize sales execution without first establishing a clear GTM strategy.

When there is confusion around the Ideal Customer Profile (ICP), market positioning, or how the company wins in the market, that ambiguity flows directly into the field. Sellers receive mixed signals, messaging becomes inconsistent, and enablement teams struggle to build effective plays.

When the strategic direction is unclear, enablement compensates for gaps that originate much earlier in the system. Enablement works best when it is reinforcing a clearly defined strategy.

3. Repair Internal Processes That Slow Deals Down

Another common friction point appears in internal workflows.

Many deals slow down or stall not because of the seller or the customer, but because of internal friction. Pricing approvals, contract reviews, and cross-team handoffs can derail momentum.

I’ve seen organizations invest heavily in training programs while deals continue to get stuck in approval queues or delayed by internal processes.

Before asking sellers to close more deals, organizations should ask a simple question: is the internal process helping or hurting?

4. Simplify the Technology Stack

Sales technology was designed to make selling easier, yet many organizations have unintentionally created the opposite outcome.

With multiple platforms, overlapping tools, and disconnected systems, sellers often spend significant time updating systems rather than engaging with customers.

As more AI-powered tools enter the market, the temptation to add another platform grows even stronger. But without alignment across systems and workflows, new technology can add complexity rather than leverage.

Enablement is most effective when tools are streamlined and align with sellers' workflows.

When the Engine Works, Enablement Works

Sales enablement should not be viewed solely as a training function. At its best, enablement helps reinforce the systems that allow sellers to succeed consistently.

Skills training and coaching become far more powerful when the engine is functioning well, strategy is clear, processes support the journey, and tools are aligned with daily workflows.

But if the engine itself is misaligned, even the best enablement programs will struggle to deliver lasting impact.

Sometimes the most important step isn’t teaching people to make better donuts.

It’s fixing the machine.

Let’s Compare Notes

One of the things I appreciate about The Enablement Squad community is the collective experience here. Many of us are seeing similar patterns across different organizations and industries.

I’d love to hear what others in the community are seeing.

CTA: Share your thoughts in this quick survey here:Time to Make the Donuts Survey

In the next post in this series, I’ll compile the responses and explore what the community is seeing and what it might mean for the future of sales enablement.