This happens a lot with busy founders. You make your first sales hire, maybe your second, and suddenly you’re caught in a cycle of pipeline reviews, target discussions, and metric analysis. And what happens in all this busyness is that founders thinking they’re coaching, but the reality is that they’re just managing. And there’s a massive difference between the two.

What’s the difference?

• Managing is the day-to-day operational stuff. It’s about targets, pipeline reviews, and activity metrics.
• Coaching is about behaviours, not outcomes. It’s about asking the right questions, digging deeper, and sometimes helping your people with things that have nothing to do with your product or your quarterly targets.

Why I changed how I coach

I had an SDR once. Brilliant guy, consistently hitting targets, then suddenly nothing. Performance dropped off a cliff. I could have fired him. Honestly, most founders would have. The metrics were screaming at me to cut him loose.

Instead, I took him for a walk. Not a formal meeting in a conference room, just a walk. And that’s when he told me he was £10,000 in credit card debt. To him, that was a massive black hole following him everywhere, including into the office. It was suffocating his performance.

So, we built a plan together. Ten grand debt meant he needed about £20K in commission after taxes. We mapped out exactly what that would take in terms of the activities, the conversion rates, the timeline. We turned his personal crisis into an achievable target.

Stop confusing coaching with managing

Most early-stage founders get this wrong because they’re used to operating in execution mode. You see a problem, you fix it. Revenue’s down? Push harder. Pipeline’s light? More activity. But people aren’t features you can patch or bugs you can fix with more pressure.

When you just beat someone with a stick by demanding more meetings, more calls, more activity you create one of two outcomes. They either leave or you fire them. Neither helps you build the team you need.

Coaching is different. It’s about creating an environment where people can develop, grow, and ultimately perform at their best. It’s about being in the trenches with them, understanding what’s blocking their success, and helping them work through it.

5 steps to effective sales coaching

1. Start with clarity and aligned outcomes

Before you can coach anyone, you need to be crystal clear about what success looks like. And I don’t just mean revenue targets. I mean the behaviours, the skills, the specific outcomes you’re both working toward.

Build this together. Don’t dictate it. When your sales team has ownership over their development goals, they’re exponentially more likely to hit them.

2. Run consistent one-to-ones

I’ve messed this up myself. You schedule a one-to-one, then a VC meeting pops up, or a customer crisis emerges, and suddenly you’re dragging that calendar invite to next week. Then next week becomes the week after.

Before you know it, you haven’t had a proper one-to-one in a month.

Here’s what you need to understand: when you cancel that meeting, your salesperson has probably already prepared. They’ve thought about what they want to discuss, the challenges they’re facing, the wins they want to share. When you cancel, you’re sending a message about priorities.

Keep these meetings sacred. Weekly, non-negotiable, and completely separate from pipeline reviews.

This is critical: A one-to-one is not a pipeline review. Stop muddying the two together. Pipeline reviews are about the deals, the forecast, the numbers. One-to-ones are about the person—their development, their challenges, their growth.

3. Use technology to shadow and provide feedback

The brilliant thing about sales roles today is that we have conversational intelligence tools, call recordings, and data that previous generations of sales leaders could only dream of.

Use it.

Listen to calls. Watch for patterns. If the data shows your rep is speaking 80% of the time, that’s a coaching opportunity. Great salespeople ask questions and listen. The best conversations aren’t monologues—they’re discovery sessions.

Give critical feedback where it’s relevant, but make it specific and actionable. “You need to listen more” is vague. “I noticed on the call with Acme Corp, you spoke for seven minutes straight about features. Let’s work on asking more discovery questions to understand their pain points first” is coaching.

4. Build a culture of transparent, two-way feedback

Here’s something that might surprise you: your salespeople often have more sales experience than you do. Especially if you’re a technical founder who’s never carried a quota.

Let them teach you. Encourage it. When you create an environment where feedback flows both ways, you build trust and psychological safety. Your team will be more open to coaching when they know it’s not just top-down criticism.

I’ve done 360 reviews with my reps where I ask them: What should I stop doing? What should I do more of? What do you need from me that you’re not getting?

That feedback has been invaluable. It’s made me a better leader and created a genuine coaching culture.

5. Focus on one thing at a time

When you identify areas for improvement, resist the urge to fix everything at once. Pick one thing. One specific behavior or skill to work on over a defined period.

If someone’s struggling with discovery calls, don’t also pile on objection handling, closing techniques, and email cadence optimization. Focus on discovery. Listen to calls together. Role play. Practice. Get that one thing right, then move to the next.

The 3 mistakes i see founders make

1.Confusing High Activity with High Performance

Just because someone is busy doesn’t mean they’re effective. You can turn someone into a busy fool by doing loads of stuff that ultimately doesn’t move the needle.

More isn’t always better. Better is better. Coach for quality, not just quantity.

2.Skipping the One-to-Ones

I’ve covered this, but it’s worth repeating. It’s the easiest meeting to cancel when something that you think is more important comes up. Don’t do it. Your people are your most important asset. Treat them that way.

3. Over-Indexing on Data Instead of People

This is particularly common with technical founders. You love data. You trust data. But sometimes the data is telling you there’s a problem without telling you the root cause.

A dip in conversion rates might not be because your salesperson is suddenly bad at their job. It might be because your messaging is off, your ICP has shifted, or your onboarding process didn’t prepare them properly.

Get in the weeds with your people. Understand the context behind the numbers. Coach the person, not just the metrics.

My go-to coaching framework

People always ask me if I use a specific framework. I don’t, I just ask lots of questions. When someone tells me they had a difficult call, I don’t jump in with solutions. I ask:

• Why was it difficult?
• What happened specifically?
• If you could do that call again, what would you do differently?
• If you’d done it that way, what do you think the outcome would have been?

I basically channel my five-year-old daughter, who once asked me why dogs have four legs… I didn’t have a good answer, but the point is that naturally curious people ask questions until they get to the root cause.

That’s coaching. You’re not there to have all the answers. You’re there to help your people find their own answers through guided discovery.

Once you’ve identified the root cause, focus on solving that one thing together. Listen back to calls. Role play the scenario. Give them space to practice and improve.

The impact of great coaching

When you get coaching right, everything changes. Your team’s confidence grows. New hires come in and immediately sense that this is a place where they can develop.

People want to grow. They want to be better. They’re looking for that sparring partner on the sideline who can see what they can’t see when they’re in the weeds.

Great coaching also encourages ownership. When people feel supported and invested in, they take ownership of their outcomes. They stop making excuses and start finding solutions.

And here’s the commercial reality. Retention improves dramatically. Replacing a sales hire is expensive not just in recruitment costs, but in lost revenue, disrupted customer relationships, and team morale. When you invest in coaching, people stick around. They perform better. And you’ll be able to build something more valuable than hitting quarterly targets, you’ll build a culture that attracts and retains exceptional talent.

That’s the real competitive advantage.

Author: Matthew Codd

I’m Matthew, I have 15 years of commercial leadership experience, helping VC-backed B2B technology companies scale revenue and transition from founder-led sales.  

I use my experience to help early-stage start-ups with GTM expertise, sales best practice, and hiring insights.  

I co-founded Cosmic Partners in 2022. We are SaaS sales recruitment specialists for VC backed B2B tech companies.