Why Your Sales Team Won't Update HubSpot (And Why They're Right)

A 20-year veteran's take on why most CRM measurements are pointless

The scene plays out in sales organisations everywhere: Management implements HubSpot with great fanfare, complete with training sessions, workflow diagrams, and stern reminders about "data hygiene." Six months later, the CRM looks like a digital wasteland. Fields are empty, opportunities sit stagnant, and the sales team has developed an impressive ability to ignore every automated reminder email.

Sound familiar?

Here's the uncomfortable truth that most sales leaders refuse to acknowledge: Your sales team won't update HubSpot because they think it's a waste of time. And they're probably right.

The Two Fundamental Problems

After two decades in sales management and CRM implementation, I've seen this story repeat itself countless times. The resistance always comes down to two core issues:

First, it actually is a waste of time. Not HubSpot itself, mind you, but the way most organisations implement it. They layer on complexity like frosting on a wedding cake, creating elaborate tracking systems that would make a NASA mission planner weep with joy. Every click, call, and coffee meeting must be logged, categorised, and analysed six ways from Sunday.

Second, no one bothers to explain why any of this matters. Sales teams get handed a list of required fields and activities with all the enthusiasm of a tax audit. "You must update the deal stage within 24 hours. You must log all touchpoints. You must categorise every interaction." But why? Crickets.

Understanding the Sales Mindset

Good salespeople are like heat-seeking missiles for revenue. They have an almost supernatural ability to identify the exact activities that will move a deal forward and hit their targets. This isn't laziness or stubbornness—it's survival instinct honed by years of commission-based reality.

They're also hypersensitive to anything that feels like administrative overhead. Every minute spent clicking through dropdown menus is a minute not spent on the phone with prospects. Every mandatory field is a speed bump between them and their next deal. They can smell bureaucracy from three departments away, and they will avoid it like a telemarketer during dinner.

This hypersensitivity isn't a character flaw—it's a feature. The best salespeople are ruthlessly efficient with their time because they have to be. They've learned through painful experience that everything that isn't directly contributing to closing deals is, by definition, working against them.

The Beauty of Invisible Measurement

Here's what I love about HubSpot when it's implemented correctly: it can be almost invisible to the people doing the actual work. The system should capture data as a natural byproduct of sales activities, not as an additional burden.

When a salesperson sends an email through HubSpot, it's automatically logged. When they schedule a meeting, it's tracked. When they move a deal through the pipeline, the data flows seamlessly into reports. The CRM becomes a tool that makes their job easier, not harder.

But somewhere along the way, organisations lose sight of this elegant simplicity. They start adding custom fields for tracking competitor mentions, lead source subcategories, and seventeen different ways to classify why a deal was lost. Each addition seems reasonable in isolation, but collectively they transform a streamlined tool into a data entry nightmare.

The Measurement Trap

Just because you can measure something doesn't mean you should. This might be the most important lesson I've learned in 20 years of CRM implementations.

Modern systems like HubSpot offer an intoxicating array of metrics. You can track email open rates, call connection percentages, meeting-to-opportunity conversion rates, and dozens of other fascinating data points. The temptation to measure everything is overwhelming, especially for analytically-minded leaders who genuinely want to optimise their team's performance.

But here's the catch: every measurement you add creates friction. Every required field is a tax on your team's productivity. Every additional step in the process is a barrier between your salespeople and their natural workflow.

The key is ruthless prioritisation. Focus on your leading and lagging indicators—the metrics that actually predict and measure success. Everything else is just expensive noise.

Leading vs. Lagging Indicators: Getting the Balance Right

Leading indicators are the activities that drive future results: calls made, meetings scheduled, proposals sent. Lagging indicators are the outcomes: deals closed, revenue generated, quotas achieved.

Most organisations obsess over lagging indicators because they're easier to measure and more satisfying to report. But lagging indicators tell you what happened, not what's going to happen. By the time you see poor results in your lagging indicators, it's often too late to course-correct.

Leading indicators, on the other hand, give you the power to influence future outcomes. If you know that your team needs to make 50 calls to generate 10 meetings to close 2 deals, you can spot problems early when the call volume drops.

The trick is capturing these leading indicators without burdening your team with additional work. If your CRM requires manual logging of every phone call, you're doing it wrong. If it automatically tracks calls made through the system, you're on the right track.

The Power of Why

Even the most streamlined measurement system will face resistance if people don't understand the purpose behind it. Sales teams are notorious for their skepticism of anything that smells like "management busy work," and for good reason—they've been subjected to plenty of it over the years.

But when you take the time to explain the why behind your measurements, something magical happens. Resistance transforms into buy-in. Compliance becomes commitment.

"We're tracking email response rates because it helps us identify which subject lines and messaging resonate with prospects, making everyone's outreach more effective."

"We're measuring the time deals spend in each stage because it helps us spot bottlenecks and coach more effectively."

"We're recording call outcomes because it helps us understand what's working and replicate successful approaches across the team."

Notice the difference? Each explanation connects the measurement to a tangible benefit for the salespeople themselves. It's not about creating reports for management—it's about making everyone more successful.

When the Experts Push Back

Here's a radical thought: if your sales team consistently resists a particular measurement or process, maybe they're trying to tell you something important.

Sales teams are uniquely positioned to understand what actually matters in the sales process. They live in the trenches every day, dealing with real prospects with real problems. If they're telling you that a particular tracking requirement is pointless, it might be worth listening.

I've seen organisations dig in their heels and force compliance through increasingly punitive measures. Mandatory reports, performance reviews tied to CRM usage, and even commission adjustments based on data entry. This approach might get you compliance, but it will never get you buy-in. And without buy-in, you'll never get accurate data anyway.

The Path Forward

So how do you build a CRM system that actually works? Start with these principles:

Make it invisible. The best measurements happen automatically as people do their jobs. Look for ways to capture data without creating additional work.

Keep it simple. Resist the temptation to measure everything. Focus on the metrics that actually matter for driving results.

Explain the why. Help your team understand how each measurement makes them more successful. If you can't make that connection, question whether the measurement is necessary.

Listen to feedback. Your sales team are the experts on what works in your market. If they're pushing back, investigate why rather than just pushing harder.

Iterate and improve. Your CRM should evolve based on what you learn. If a measurement isn't providing value, eliminate it.

The Bottom Line

After 20 years of watching CRM implementations succeed and fail, I can tell you which measurements actually help and which ones are pointless theatre. Most fall into the latter category.

The organisations that get it right understand that their CRM should be a tool that empowers their sales team, not a digital taskmaster that gets in their way. They focus on capturing meaningful data that drives real insights, and they take the time to help their team understand the connection between measurement and success.

Your sales team's resistance to HubSpot isn't a character flaw—it's valuable feedback. They're telling you that your current approach isn't working. The question is: are you listening?

Because at the end of the day, if your measurements aren't making your team more successful, what's the point? And if your team doesn't buy into the process, even the most sophisticated CRM in the world won't save you.

Maybe it's time to trust the experts who are actually closing the deals.