The five problems every sales leader inherits (and nobody warns you about)

I got handed a sales team at 20 years old. I had 15 people reporting to me, and I had no real idea what I was doing (not as a leader, anyway). I learned how these organizations break by white knuckling those first few years. Then I spent the next decade-plus watching the exact same failures play out in other people's companies. At first it was dozens, then it was hundreds of them. The role of the sales leader is one of the hardest operational jobs in business, and we set people up to fail at it on day one.

What follows is the map I've built from all of that: five areas where sales leadership consistently gets stuck, regardless of whether you're running a five-person team or a five-hundred-person one.

• Why nobody's actually trained for this job
• Sales and customer execution
• CRM hygiene, and the Excel secret
• Forecasting and prioritization
• Coaching, and the 60-20-20 rule
• Cross-functional collaboration
• What changes when the system works

TL;DR

For the full deep dive, watch the conversation below. If you'd rather have the condensed version, keep reading.

The job nobody trained you for

Most sales leaders got the role by being the best rep on the team. That's the whole selection process at a lot of companies: you sold the most, so now you lead. The trouble is that selling and leading are almost unrelated skills. One is about winning a deal yourself… the other is about building up people who can win without you.

The training gap, however, is staggering. Something like 95% of sales managers have never had a single day of management training. We take our best individual performer, hand them a team of seven, and wish them luck with a role they've never been shown how to do. Then, when the team underperforms, we call it a people problem. It was a preparation problem the entire time. Layer on the fact that average quota attainment sits below 50% globally, and the picture stops looking like a series of unlucky teams and starts looking like a structural issue.

Sales and customer execution

The first area is the actual doing of sales: reps walking into customer conversations sharp and genuinely prepared. When it slips, the leader feels it immediately, because they start diving into deals themselves to save them. That might feel heroic (and natural for talented sales reps who ascended to the big chair), but it doesn't scale. What's worse, it trains the team to depend on you.

The reason reps show up unprepared usually isn't laziness… it's time. A rep's calendar is stacked with demos, and a real opportunity carries weeks or months of context nobody can perfectly recall with maybe 15 minutes of prep.

A decade ago you could win on charm and a little knowledge. Now every buyer has AI and information on tap, and they expect a rep who is specific to their world. Execution problems in this domain are rarely effort problems.

CRM hygiene, and the Excel secret

Everybody hates CRM hygiene, and the reason is structural: CRMs were built for the organization, not the rep. They're slow and joyless, they feel like surveillance, and they don't feel like they're helping you close the deal in front of you. So reps deprioritize it, then paper it over with filler notes to move on with their day. But that leaves a CRM full of junk data.

The tragic/funny part of this story is that almost every VP of sales I've met keeps the real forecast in a private Excel sheet because they don't trust their own CRM. We've collectively built a system none of us believe in.

But, if you put yourselves in the sales leader's shoes… their job is tied to a number. That number comes from the CRM. So if they're flying blind on junk data and miss their imaginary number a couple of quarters in a row, that could be curtains for them. It's an unenviable position to find yourself in.

Forecasting and prioritization

Forecasting flows straight out of hygiene. Bad data in means bad predictions coming out the other end. Bad prediction isn't an abstract sin. I've watched forecast misses blow up fundraising rounds and trigger layoffs.

But there's an art to it beyond the numbers, especially in bigger, multi-stakeholder deals, where you have to read where an opportunity actually sits versus where the CRM claims it is. And forecasting has a twin that gets less attention: prioritization. Good data doesn't just tell you where you'll land, it tells you where to spend your time: which verticals to lean into, where in the funnel you're leaking, and what that says about a skill gap you need to coach.

The prediction and the decision are two different muscles, and both die without trustworthy data underneath them.

Coaching, and the 60-20-20 rule

Almost every team has the same shape. About 20% at the top are crushing it, about 60% in the middle are fine but not all stars, and about 20% at the bottom are hanging on. Most leaders pour their coaching into that bottom 20%.

That's usually a mistake.

The top group is already excellent, so your ceiling isn't very high above their current performance. The bottom group often isn't fixable no matter how many hours you spend coaching them. The whole game is the middle 60%. Move that group up one standard deviation and you've changed the entire business, because that's where the weight is.

The only tool that actually moves people is coaching, and it's the first thing leaders drop when they get busy. It also doesn't have to be a formal production. A 15-minute debrief after a call, built around good questions, does most of the work.

In my last company we wrapped that kind of coaching around every new hire, and the results held up again and again: new reps ramped in half the usual time, and the new-hire failure rate dropped to 2%. One kid we placed as an SDR became a top performer, then a top-performing AE, all inside 24 months.

Coaching doesn't just lift performance, it lifts retention, because people stay where they're growing.

Cross-functional collaboration

The last area is the one that lives in the gaps between teams. A great sales org has to work in concert with customer success, marketing, and product, and those handoffs are where value leaks. I watched a Series B company win pilot after pilot, then toss each one to CS with a shrug, until conversions cratered and reps were getting commissions clawed back on pilots that never converted.

Everybody was working hard, and the outcome still failed, because nobody owned the seam.

There's an upside hiding in the same place, though. Your reps hear everything, every product gap, every reason a deal was lost, every feature a buyer wishes existed. At Grw, Taylor pushes that straight into a customer insight Slack channel the moment a call ends, and it directly shapes what we build next.

The friction between sales and product turns into a feedback loop, if you actually connect the wires.

What changes when the system works

I solved all five of these in my earlier companies, but I solved them with people: coaches, consultants, a lot of manual human effort that was expensive and impossible to scale. The reason to build Grw was that AI finally makes these problems solvable at scale rather than one heroic hire at a time.

The thing I'd leave you with isn't about any product, though. It's that none of these five areas is really separate. Bad hygiene wrecks your forecasting, weak coaching resurfaces as execution problems, and a broken handoff poisons every number that follows. Sales leadership is hard precisely because you can't fix one of these in isolation. You feel the whole machine at once. The leaders who get somewhere are the ones who stop treating five symptoms and start building one system that holds them together.