Coaching Is a Culture, Not a Chore

Ask most SaaS or Managed Service Provider leaders whether their sales managers are coaching, and they’ll tell you yes. You’ll hear, “We do weekly 1:1s,” “We talk through deals,” and “They’re in the pipeline with their team.” Dig a little deeper, though, and you’ll find that more often than not, what’s happening is not actually coaching of any sort. It’s generic feedback to boilerplate reporting. It’s metrics inspection dressed up as development. It’s cookie-cutter meetings where managers run through a rote checklist before moving on to the next rep.

That’s not coaching. It’s pipeline triage. And it’s exactly why performance stalls even when activity is high.

Keith Rogan explains in Coaching Salespeople into Sales Champions that “...coaching isn’t about giving information. It is about responding to the needs of other people. People will resist if information is forced on them.” Watching deals unfold in dashboards is not leadership and it doesn’t make your team better. It’s busy-work that lets management feel informed while neglecting the real job of developing their team’s sales skills.

Your Problem Isn’t Lack of Effort, It’s Misprioritized Time

Between jumping on calls to help save late-stage opportunities, reviewing deals, and back-to-back meetings, many sales managers regularly work 60-hour weeks. But if you look closely at their calendars, you will often see a glaring absence; they aren’t devoting time to  making their people better.

This oversight is everywhere. It is common practice for companies to promote strong sellers into management roles without teaching them how to coach or providing them with the tools to do so. Enablement teams too often focus on onboarding and playbooks, but fail to equip frontline leaders with practical, functional coaching systems, let alone instruct them in their use. And the result is a team that keeps making the same mistakes and running into the same problems while leadership tries to fix things  by pushing harder on pipeline volume or adding another tool to the tech stack.

Even when managers take the initiative to try to coach, absent the training and tools to implement a structured process, their efforts are too scattered to be effective. Mark Roberge points out in The Sales Acceleration Formula that “a common sales management mistake is to overwhelm the salesperson with coaching too many skills simultaneously. Pick one skill and focus.”

Without structure, coaching never rises above one-sided commentary and well-meaning, one-size-fits-most advice that results in no tangible changes to behavior. The team stays busy. The numbers stay flat.

There Is No Such Thing as a Born Leader and You Can’t Coach Based on Vibes

Being an outstanding seller doesn't automatically translate to being a good sales leader; leadership is a skill set in and of itself. Companies that neglect to develop and strengthen these skills among their management are setting themselves up for failure.

Coaching isn’t the occasional pep talk or motivational speech. It’s not a brief “try this” in a 1:1, or a cursory weekly reminder to “stay on top of your deals.” Successful coaching is systematic, purposeful, and intentionally reinforces behaviors that drive deals forward.

Good managers coach to a framework. Be it SPIN, MEDDICC, CustomerCentric Selling, the important thing is that the rep and the manager are speaking the same language. When you employ a system that enables clear communication, coaching becomes specific, actionable, and repeatable.

Without it, feedback devolves into vague advice. Reps are told to “dig deeper,” “show more value,” “build more urgency.” But these are intentions, not instructions, and they don’t help sellers improve.

Here's what it looks like when coaching is grounded in a real framework:

• In SPIN Selling - A rep is demoing too early. Instead of scolding them, the manager asks: “Did you establish enough implied needs before offering the solution? What were the buyer’s explicit pain points?”That’s coaching to Problem and Implication questions which are critical steps before presenting a solution that resonates.

• With MEDDICC - A deal looks good in the forecast, but it’s all based on one contact. The manager doesn’t say, “Keep pushing.” They ask, “Who’s your Economic Buyer? Have they verbally confirmed they control the budget and timeline?”That’s a coaching moment on E (Economic Buyer) and D (Decision Criteria), the difference between real confidence and wishcasting.

• According to CustomerCentric Selling - A rep is pitching features too soon. Instead of asking them to just “do discovery,” the manager says: “Have you helped the buyer define their success criteria in their words? Did you lead with a use-case instead of a product pitch?”That’s coaching based on solution alignment, not product enthusiasm. It’s about enabling the buyer to own the value story.

• In The Challenger Sale model - A rep is playing it safe with a technical evaluator. The manager doesn’t push for a discount strategy. They ask: “What insight did you lead with in the first meeting? What commercial teaching moment have you delivered so far?”Coaching here is about shaping the buyer’s mental model, not being liked.

  
  

Coaching done right doesn’t just fix deals, it teaches sellers how to improve themselves. Strategic coaching is about precision. It’s a question at the right moment that changes how the rep thinks, not just what they do. It’s tied to buyer behavior, not just seller activity.

Managers who coach this way don’t have to guess what’s broken. They are equipped to diagnose and fix problems and to teach their sellers to do the same.

Without this knowledge and discipline, managers have to coach based on gut feelings. The result: sellers repeat the same mistakes. Deals slip. Managers scramble. Forecasts stay fuzzy. And nothing improves.

Information Without Insight Is Useless (more than just the usual, “You Can’t Manage What You Don’t Measure”)

The illusion of control is everywhere in sales. CRMs are full of activity logs and dashboards brimming with a dizzying array of information. But data without perceptive analysis can’t reveal where a process is breaking down. A rep may log 80 calls but still come up short because they’re qualifying poorly, rushing discovery, or reacting passively to objections. And without shrewd and attentive coaching, they’ll never change those losing behaviors.

The crux of the matter is this: time invested in workers’ skill development correlates directly to improved sales outcomes. That means asking not just about what’s closing, but about how the rep is approaching each sale. It means finding out what questions they’re asking, how they’re diagnosing pain, and how they’re responding when prospective buyers go cold. It means taking the time to understand the human elements in a problem before you start applying fixes.

None of that happens when managers are buried in Salesforce reports instead of coaching in the moments that matter (I swear I’m not saying this from experience….)

Coaching Is the System, Not the Fix

Building a coaching culture is not as easy as adding “coaching” to a 1:1 agenda. It requires instituting thoughtfully designed systems where coaching is expected, structured, and has measurable outcomes and where managers know how to run a positive feedback loop that builds more capable sellers, not just busier ones.

The most common mistake companies make when they set out to improve their coaching processes is to try to bolt on coaching without changing the rhythms of the business. They leave the details up to the individual manager’s instincts. And then they wonder why nothing changes.

When your team isn’t improving, there comes a point when you have to stop looking at the sellers and start looking at the system.

Coaching Isn’t Coaching Without a 360° Review

Having your team participate in a 360° review process can help you identify not only your own strengths and weaknesses, but your team’s, as well. It can help you identify future managers and train them in the skills that will enable them to become competent coaches themselves. This allows you to leverage your team's strengths and to know where your coaching energies can be most efficiently spent. It allows you to recognize your own opportunities for growth, and empowers both you and your team to work effectively on your personal and professional development.

Conducting regular 360° reviews with your team creates a container that allows you to celebrate each other’s successes and to help each other grow and improve. It improves team morale and motivation, and consequently enhances performance.

To be an effective manager, it is essential to know where you shine as a coach and leader, and where you have room to grow. Make good use of 360° reviews and your team will literally tell you what they need to succeed. All you have to do is listen and implement!

Final Thought

Good sellers don’t burn out just because they work too hard. They burn out because they are putting a lot of effort into meeting their quotas, generating value for the company, and their managers are not putting commensurate effort into helping them grow.

If you want better win rates, shorter cycles, and higher quota attainment, start by getting serious about coaching, not just as a buzzword, but as a culture.

QuotaCatalyst helps teams build systems where coaching isn’t optional, reactive, or half-hearted; it’s baked into the way your sales org runs. Managers don’t just inspect deals; they help grow outstanding salespeople.

If your managers are reporting more than they’re coaching, let’s talk.