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The Art of Feedback in Sales: 4 Steps to Effective Coaching

Explore the ins and outs of giving meaningful feedback in leadership. Learn from real-life situations and discover practical tips to enhance your coaching skills. Let's make coaching conversations genuine and effective.

If you’ve read a sales leadership book, been soothed by the sounds of a business podcast, or been harassed by a customer support survey, you’ve likely picked up on this axiom: giving feedback is critical! Especially giving it… quickly.

The great Kim Scott makes a strong case for immediacy in her widely adopted leadership bible, Radical Candor. Feedback has a shelf life, so if you don’t strike while the iron’s hot, you risk giving it with little context or having it ignored.

This only scratches the surface — the list of potential downfalls of sitting on feedback is long.

But what does “immediate” actually mean?

If you’re new to leadership, correcting something as soon as you see it is actually useful, and often untaken, advice. Finding a few minutes right away to pull your rep aside and address an area of concern, be it tactical or behavioral, is the best way to nip problems in the bud in most situations.

If you want to graduate to the next level of “situational leadership,” it’s also important to understand the context of the moment. Sometimes, pausing can provide a chance to make sure your feedback lands in a way that will resonate. After all, your end-goal is never to give feedback; it’s to change behaviors.

Rational voices have to meet rational ears, but that opportunity doesn’t always present itself right away. How do we reconcile the importance of correcting something promptly with the common reality that people aren’t always ready to accept immediate feedback?

Let’s look at a real-life example

A frontline sales leader, Teddy (not his real name) was working on an important deal with a rep, Bill (also fake), at the end of the quarter. Bill made an impactful mistake during the negotiation process. It didn’t kill the deal by any means, but it definitely put a damper on the momentum of the buying process.

Teddy pulled Bill aside and immediately delivered feedback on what he should have done differently. Teddy delivered the feedback “tactfully” (more on that below), and his assessment of what went wrong and what should have gone differently was 100% accurate.

Unexpectedly, Bill shut down in a way Teddy had never seen before. He even stopped responding to Teddy’s Slacks and emails.

When Teddy confronted Bill, he diplomatically shared that Teddy wasn’t being helpful and wasn’t providing the support he needed to get the deal done, so he reasoned he would be better off going at it alone.  

After a lot of deep examination, Teddy reached an important conclusion.

When Bill made the error, they still had a primary goal: getting the deal done! To do that, Bill had to be focused and confident… and needed Teddy to collaborate on the best next steps to get to the finish line.

Teddy reasoned that even though addressing the mistake was important, he could have waited until they landed the plane on the deal by having a post-mortem in the books whether they won, lost, or pushed the deal.

This would have brought out the best in Bill as they were closing the deal while holding himself and Bill accountable to improve in a more receptive moment.

P.S. One of the most fascinating aspects to this true story is that both Teddy and Bill were some of the highest-performing individuals in the entire business unit and had been working together for over four years. These weren’t rookies; they had a very long, trusting, and successful working relationship where direct feedback was common.

How do you deliver feedback “well?”

Like most aspects of sales and leadership, giving feedback effectively is both an art and a science.

A lot of the practice ties into how a rep might prefer to receive feedback (you should always ask them this, by the way) as well as a leader's relationship with the rep.

Here are some feedback basics to use as a checklist the next time you need to course-correct with one of your reps:

  1. Ask for permission

Why do you need to ask for permission? Isn’t giving feedback part of the job? Yes, yes, it is. But asking for permission to coach or give feedback is one of the most effective ways to disarm the rep and align on why you’re giving them feedback in the first place – to make them better and successful.

Most of the time, we aren’t that receptive to unsolicited feedback in our regular lives, and our natural inclination is often to question the intent and motives of the person giving it to us. Our defenses go up, and our ears shut off.

Here’s an example of how to ask for permission: “What I want for you is to feel like you have more control over the negotiating process because I’ve seen this correlate to much higher deal sizes for other reps. Are you open to some suggestions?”

Some coaching methodologies try to formalize this.

The best one I’ve seen is Keith Rosen’s process of enrollment, who’s often quoted saying, “When intentions aren’t clear, people default to fear.”

Set the stage: share the topic or observation of interest, what you want the rep to achieve or gain as a result of the conversation, and confirm the rep is open to having the conversation and that now is a good time for them. This significantly improves outcomes.

  1. Be specific and concise

It may seem evident that citing a specific example and its impact would be important, but many managers shape feedback around feelings, generalities, or abstractions. In fact, they often conflate the example with the feedback itself:

“You need to be more confident.”

“Your questions need to be more open-ended.”

“You need to do more discovery.”

“You spoke 50-60% of the time, but you should only be speaking 30%” (yuck)

All of these could be good advice but without a clear connection of the dots, it’s vague, unhelpful, and essentially unusable. Here’s what a good example looks like:

“In the beginning of the call, you asked a good question about their current contracting process. But after they answered, you jumped right into the flash demo, and by the end of the call, you didn’t come away with a clear understanding of their pain to differentiate our solution with what they are currently doing. Next time, it’s more effective to resist the urge to dive into the product and ask deeper questions about that pain point or a different one. Here’s an example …”

  1. Champion a culture of consistent feedback

Some more tenured coaches reading this might say, “I like to ask the rep what they think went well and what they think can be improved.”

This approach is an awesome coaching technique, especially after a call, key selling moment, or event.

But it speaks to having a more extensive culture around coaching and feedback. When feedback is the norm on your team and at your company, it becomes a lot easier to give and receive it.  

Make it business as usual to give and listen to your team’s feedback. As a leader, demonstrate you can receive and apply it from your manager, peers, and reps. Your reps will quickly learn this is how you operate instead of racing to the worst possible conclusion as to why they are getting pulled aside.

  1. Manufacture a more comfortable, rational environment (if needed)

As we saw in the scenario, sensing when emotions run high can make all the difference.

Setting a few minutes aside on the calendar in the near future to discuss after you ‘enroll’ your rep is a great way to ensure that you both know what to expect and can prepare to be more receptive to the conversation.

Asking for permission can help you catalyze this moment so you can give feedback sooner rather than later.

In my experience, practicing and applying all of the tips, rather than one or two, is what moves the needle in creating a genuine feedback and coaching culture for your team.

Remember, in the scenario, Teddy employed some of these tips but not all, which was the difference between a good coaching conversation and an ineffective one.

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