Why Your Sales Team Is Underperforming (And It’s Not Their Fault)

By Nathan Jamail  |  Sales Leadership Speaker

Here’s what most executives don’t want to hear: when a sales team isn’t hitting its numbers, the first instinct is to look at the salespeople. Maybe they’re not motivated enough. Maybe they’re not working hard enough. Maybe you hired the wrong people.
 
But more often than not, that instinct points in the wrong direction.
 
As a sales leadership speaker for corporate events, I’ve walked into hundreds of organizations where underperforming sales teams had the talent to win. They just didn’t have the leadership to get there. That’s not an accusation – it’s a pattern. And until you recognize the pattern, nothing changes.
 
The Real Culprit: A Leadership Gap Disguised as a Performance Gap
 
When sales numbers are down, companies tend to respond with training programs, new CRM tools, revised comp plans, or territory changes. Sometimes those things help. But they rarely solve the core problem.
 
The core problem is almost always this: salespeople aren’t being coached. They’re being managed.
 
There’s a massive difference. Managing means checking in on activity – call counts, pipeline updates, deal stages. Coaching means developing the person – helping them get sharper, stronger, and more confident in every sales conversation.
 
If your leaders are running pipeline reviews instead of coaching sessions, you have a management culture, not a coaching culture. And in a management culture, your salespeople hit a ceiling – and stay there.
 
Three Signs Your Leadership Is the Problem
 
You don’t have to guess. These three signs show up in virtually every underperforming sales team I’ve worked with:
 
1. Leaders react instead of prepare.
When a deal is going sideways, the leader jumps in to help close it. That’s reactive. A coach prepares their people before the call – running through objections, sharpening the pitch, doing the work in advance so the rep walks in ready. If your leaders are constantly firefighting instead of pre-gaming, your team is winging it.
 
2. Accountability is tied only to activity, not outcomes.
‘Did you make your calls?’ is not accountability. Real accountability means holding people to the standards and skills they need to win – and having direct, honest conversations when they’re not meeting them. Leaders who are uncomfortable with those conversations tend to default to activity metrics because they feel less personal. But soft accountability produces soft results.
 
3. The expectations aren’t clear.
Ask ten salespeople on the same team what ‘great’ looks like, and you’ll get ten different answers. If the standard is fuzzy, performance will be too. Leaders who don’t define and repeat expectations constantly leave their people guessing – and guessing doesn’t close deals.
 
Coaching Is Not Micromanaging – Get That Straight
I hear this pushback a lot: ‘We don’t want to micromanage our people. We want to trust them.’
 
I get it. Nobody wants to be the boss who hovers. But here’s the thing – consistent coaching is not micromanaging. It’s the opposite.
 
Micromanaging is when a leader can’t trust people to do their jobs, so they monitor every move and make decisions for them. Coaching is when a leader is deeply invested in their people’s growth – running regular skill development sessions, giving honest feedback, preparing reps before high-stakes conversations, and holding them accountable to excellence.
 
The teams that get left alone the most are not the most empowered. They’re the most neglected. Consistent, skilled coaching is how you build people who are actually capable of operating independently – because they’ve been developed, not just deployed.
 
What Great Sales Leadership Actually Looks Like
 
When I work with companies as a sales leadership speaker for corporate events, this is the model I come back to every time:
  • Regular one-on-ones built around skill development, not status updates.
  • Pre-call coaching – running through the plan, the likely objections, the goal for the meeting – so reps go in prepared.
  • Post-call debriefs that are honest, not just encouraging.
  • Clear performance standards that are communicated early and reinforced constantly.
  • Leaders who model the behaviors they expect – energy, accountability, commitment to growth.
 
This isn’t complicated. But it requires leaders who are willing to be present, consistent, and direct. That’s harder than it sounds in a world where everyone is busy and uncomfortable conversations are easy to avoid.
 
The CEO’s Role in All of This
 
If you’re in the C-suite, here’s your part: the culture of your sales organization starts at the top.
 
If you’re tolerating leaders who manage by spreadsheet and avoid real coaching conversations, that becomes the standard. If you’re not asking your VP of Sales how they’re developing their people – not just what numbers they’re hitting – you’re missing the most important part of the job.
 
A great sales keynote can shift perspective. A great workshop can build skills. But the real work happens back on the floor, every week, when leaders decide whether to run a real coaching session or just check the boxes.
 
That’s the decision that determines whether your team wins or keeps wondering why they can’t break through.
 
The Bottom Line
 
Your salespeople are not the problem. Your leadership system is.
 
When you invest in developing leaders who coach consistently, set clear expectations, hold people accountable to outcomes, and prepare their teams to win – the numbers follow. Every time.
 
If you’re ready to change the culture of your sales organization, start by changing what you expect from your leaders. Not less involvement – better involvement. Not less presence – more purposeful presence.
 
That’s the shift that actually moves the needle.
 

 

Nathan Jamail is a keynote speaker on winning teams, leadership author, and coach who has trained hundreds of thousands of leaders worldwide.Nathan Jamail is a keynote speaker on winning teams, leadership author, and coach who has trained hundreds of thousands of leaders worldwide. His straight-talk approach to leadership development helps organizations build high-performance cultures that produce consistent results.