5 Effective Sales Coaching Tips

Great sales coaching isn’t about having all the answers. 

It’s about asking the right questions, listening well, and knowing when to step back. 

But almost every sales leader learns that the hard way.

Sian Taylor, Sales Manager at Klaviyo, shared a story on the ‘Why Did It Fail?’ podcast that many sales leaders will recognise.

One where the best sales coaching intentions didn’t land as expected.

A conversation with an underperforming sales rep, centred on performance sales coaching, started with data.

But it ended in a total breakdown of trust and a need to rethink her sales skills when it came to coaching.

Sian said:

“I went into that conversation armed with my list of, like, ‘hello, what are you doing here?’ metrics. All it did was drive a wedge between me and this rep.”

What followed was a months-long sales coaching journey to rebuild the relationship, regain trust, and completely rethink her leadership style.

The lessons Sian learnt along the way are pure gold for any sales manager who’s ever walked into a 1:1 with the best intentions and numbers in hand, and walked out wondering why it didn’t hit the mark.

1. Focus on the person, not on the metrics

When a rep is underperforming, numbers are often the first thing a manager looks at when sales coaching in sales teams, and for good reason. 

Activity, pipeline, conversion: these can be early indicators of where a rep needs support. But as Sian learned, sales metrics without context can lead to misjudgement.

Looking back on one of her earliest leadership experiences, Sian went into a performance conversation with what she thought was everything she needed: the KPIs, the gaps, the coaching history, the urgency.

“I was all about the numbers. I was like, hang on a second, this rep, there’s no activity, the account penetration isn’t there. What is this rep doing?”

The problem wasn’t the data. It was what she didn’t consider: the person behind it. What was going on for the rep that week? 

What was their communication style? How did they respond to pressure? None of that factored in. This is a huge question sales managers need to ask themselves.

Sian said:

“I didn’t check what was going on with that rep… what was going on outside of work. I didn’t think about how that rep would respond based on personality or communication style.”

In that moment, the numbers, win rates, etc., spoke louder than empathy, and the sales coaching conversation fell flat.

What could have been a collaborative discussion turned into a breakdown in connection and trust, and became a bigger issue in the sales process than this rep’s actual sales performance.

2. Always show empathy

The problem with getting a sales coaching conversation wrong isn’t just that it doesn’t work; it can actively damage your relationship with a sales rep. And that’s exactly what happened.

By leading with data instead of empathy, Sian unintentionally undermined the rep’s confidence and her own credibility as a sales coaching leader.

Sian said:

“I could see how from their side of things it would be like, ‘She’s not in my corner… doesn’t know how hard I’m trying…’”

That loss of trust didn’t disappear after one or two follow-ups. It stuck, and it took time, humility, and consistency to start rebuilding the relationship. 

Sales teams and sales professionals need to take this into account when discussing sensitive topics within the sales process and sales cycle.

She added:

“It probably took about three months to rebuild my relationship with that rep and have them trust me again as a leader, as someone who was in their corner.”

The irony? The rep had a history of high performance. They were competitive, driven, and had achieved a lot in their previous role. 

But Sian’s delivery of the sales coaching conversation made the feedback feel personal, not professional. This can be a huge point of learning for many sales professionals, not just Sian.

For sales managers, it’s a critical reminder: if the sales coaching feels like criticism, you risk losing not just performance, but the person. This is why you have to really think about how to start the sales conversation.

3. Admit when you’ve made a mistake

Faced with a disengaged rep and a broken relationship, Sian could have doubled down.

Instead, she took a step back and asked herself the harder question: “What did I miss?”

That reflection led to a fundamental shift in how she approached sales coaching conversations within sales teams, one rooted not in performance management, but in empathy.

Sian said:

“Seek to understand before you’re understood. That was told to me by a fantastic VP of Sales, and it really shaped the way I went on to manage.”

It started with a tough, honest conversation. Sian acknowledged that she’d made a mistake in how she handled the situation, and opened the door for a different kind of dialogue.

“I said, ‘Hey, I don’t think I went about that the right way. I didn’t try to see things, or at least try to get your side of the story, before I went through my side.’”

That simple admission didn’t fix everything overnight, but it marked a turning point.

Because sales coaching isn’t just about giving direction; it’s about building trust. And trust starts with vulnerability within sales teams.

4. Adapt coaching styles to each rep

Once the trust began to rebuild, Sian didn’t stop at an apology. 

She changed the way she coached altogether.

Every leader has their own sales methodology, but Sian was now learning how to implement the right coaching techniques to reach the right sales goals, whatever she was going to be talking to her reps about:

Customer engagement, sales cycles, sales targets, sales pipeline, sales funnel... Anything!

Rather than relying on generic advice, AI tools, or one-size-fits-all frameworks, she adapted her approach and coaching techniques/feedback to suit the rep’s learning style, communication preferences, and personality.

“They were a very visual learner, so we stopped doing spoken coaching and moved into shadow sales coaching instead.”

That meant more time spent walking through cold calls together, writing things out, and building context through collaboration, not instruction.

She also made an effort to connect on a human level, not just a performance one.

“I checked back in on this rep a lot more often… I made sure that we had more rapport at the start of our one-on-ones.”

The result? Not just performance recovery, but a stronger, more productive working relationship than before.

By investing the time to coach the person, not just the rep, Sian unlocked results that sales data alone couldn’t deliver.

5. Discover what motivates your reps

Sian’s experience is a reminder that great sales coaching and performance evaluation are more than KPIs and dashboards; they’re personal. 

And getting it wrong can cost more than just a missed target.

So, what should leaders take away?

First, don’t abandon the numbers, but don’t let them drive the whole performance evaluation conversation either.

“You always need to know your numbers as a leader. I wasn’t wrong to surface them; it was the way I delivered them that caused the challenge.”

Second, make understanding your reps a priority from day one. One way Sian does this now is with a “Working With Me” doc, a simple exercise that helps uncover how someone works, what motivates them, and how they respond to stress.

“Everybody responds differently to pressure and stress. I always ask: What motivates you? What’s the best way to get you out of a slump?”

Coaching is most effective when it’s contextual. And that context can only come from getting to know the individual, not just the inputs.

Final thought: Sales coaching is a game of chess

For Sian, the biggest shift wasn’t just tactical, it was mindset. She now sees sales coaching as a strategic, long game. Not about quick wins or rigid scripts, but about learning the board, piece by piece.

“My sales team are probably sick of me talking about sales like a game of chess, but it is.”

“The more you understand where the pieces are on the board, even when a prospect, or a rep, puts their piece somewhere you didn’t want them to, the more you can adapt and keep moving forward.”

Coaching isn’t about being perfect. It’s about being present. The best sales leaders know when to challenge, when to listen, and when to own their own mistakes. That’s what builds trust, and ultimately, performance.