Coaching Salespeople into Sales Champions: 3 Times To Step In (& How)

Sales coaching typically looks one of two ways…

  1. Micromanaging the rep’s every step
  2. Letting them learn through trial by fire

But coaching salespeople into sales champions doesn’t happen in the extremes. And lucky for you, too much and never aren’t your only options when it comes to sales coaching.

Because extremes — personally and professionally — can end in disaster.

I’ll never forget taking my boys canoeing for their first time one summer. August was almost over and the leaves were beginning to change colors. I was excited because I knew this was going to be a great bonding experience for my two boys, ages 9 and 5, and me.

Now if you’ve never been on a river in southern Missouri with 2 boys under the age of 10, I highly recommend it. Not because it’s fun, but because most of us need to work on building more patience.

The day started well. The sun was peeking over the hills as we gently glided our canoe into the river. I sat in the back as the Captain, with my two young shipmates holding down the middle and front responsibilities.

As we pushed off, the boys were laughing and full of excitement. And I was too. I imagined how we would grow closer in our relationship and make a wonderful memory we could look back on for many years to come.

canoeing with kids is like sales coaching


Within the hour, we were angry and wet, canoe upside down, with our lunches floating down the river.

What was meant to be a special bonding time between a father and his sons quickly went from gentle suggestions for Canoe Navigation 101, to more firm recommendations based on my own limited river experience. It ended with drill-sergeant levels of yelling, a submerged canoe, and praying everyone had their lifejackets tightly secured.

And this is a lot like coaching our teams.

There will be times when performance is good and the water is calm. Everyone is happy and looking forward to the immediate future. “Hopes are high for this quarter. This team has tons of potential…!”

However, faster waters often lie ahead, and they will require direction and instruction from us as leaders. Caution is encouraged. The worst can be just around the bend. Sales coaching that is not received and applied can produce very undesirable results during some of the most critical times of the business, leaving people yelling, screaming, and soaking wet in failure.

If we believe that coaching is part of a sales leader’s everyday duties (and we should), then it makes sense to break down the different times to coach and how they’re different — from crystal clear and calm to white water rapids!

These are the 3 times we should coach. When we see…

  1. Good Performance
  2. Poor Performance
  3. Problem Performance

Now, let’s look at the guidelines and tips for each of these instances.

Good Performance: Coaching Wins

While coaching good performance is the easiest time to coach, it is (surprisingly) the least common amongst sales leaders.

The truth is, while we would all agree we should, we rarely take the time.

RELATED: How To Manage A Sales Team: 12 Expert Tips For Success

Every day, we hear someone on the phone ask great questions, close, or handle an objection, and yet we often fail to stop whatever we’re doing, call out what they’re doing right, and point out their tiny, little win.

Shame on us.

It can be fun, and it’s one of the best parts of our job. So why don’t we do it more?

As leaders, we have a tendency to think we are working hardest when we are solving problems. Hence, we walk the floor looking for issues to solve. What unique, super complex deal can we find today that only someone with our vast amount of experience can navigate?!

We neglect coaching good performance at our own peril because, as the great management author Ken Blanchard says, “Good performance that gets noticed, gets repeated.”

It’s safe to say that if we want to see our teams do more good work, then we need to point it out when we observe it. Coaching good performance isn’t complicated and can be done in less than 60 seconds.

Guidelines for coaching good performance:

  • Be on the constant lookout for people doing the right things. Catch people doing things right.
  • Be specific about the action and call it out
  • Explain how it gets them/us where we want to go
  • Do it now. Don’t wait. Don’t email. Say it. Say it loud enough for everyone to hear.

Imagine you’re observing a rep on a call with a customer. She’s asking great questions that are going to lead to a solid deal. As soon as she hangs up…

“Hey Kristi, I really liked the way you asked that customer why finding a software with XYZ security feature was important to them. That helps us better understand why they would move forward and gets you closer to your goal this month. Nice work.”

Boom. You’re done.

Coaching good performance is incredibly easy to do and makes everyone feel great. It also adds another layer of trust to the coaching relationship (bonus manager points for you).

After we dumped our canoe a few times, it would’ve been very easy for me to focus on what had gone wrong and solely be on the look-out for what could happen next. And this is exactly what I did.

After a couple of hours I realized my boys weren’t having the time of their life and neither was I. Instead of creating a great memory, I was creating a very long day by shouting out commands like, “Paddle left. No, no, no, the other left!” and constantly giving unsolicited feedback.

After a much needed (and a little soggy) lunch, I changed my strategy and started trying to catch my boys doing something right.

Anything right.

When I saw them paddling on the correct side or in the proper way, I immediately praised them with a “Perfect! That’s the way you paddle like a pro!”

It seemed obvious to me, but this little effort changed the whole mood. We started having fun again and, surprisingly, the boys listened more and their canoe skills improved. All because I was looking for what they were doing right and taking time to coach their good performance.

Poor Performance: Coaching Mistakes

Now I know what you’re thinking. “Great story, Shawn, but let’s get back to the part where you were struggling! We can’t just smile and ignore it when performance is less than what we need! I’ve got numbers to hit this month!”

You’re right.

Sales coaching is letting people know that how well they do their job matters.

RELATED: How to Turn Your Sales Managers into Effective Coaches

In sales, we have the distinct advantage of a constant scorecard letting all of us know just how our teams are stacking up. Coaching in the real world is about boosting sales performance.

Now, we know a foundation of trust has to be present in order for us to begin building the sales coaching relationship — but that’s just the beginning of what it takes to help people achieve new levels of performance.

When performance is low, our job is to intervene and help people get good at their job.

But it’s important to understand why people underperform. We’re not curing a disease here. Nobody is sending a man to the moon.

What’s the problem? We are top performers, so why isn’t our team performing at their highest levels?

Here are some reasons for poor performance:

  1. People don’t know what’s expected
  2. People aren’t held accountable to expectations
  3. People don’t have the right tools
  4. People don’t have the right training
  5. People don’t have the right skills
  6. People don’t have the right support

Let’s ask ourselves, “What do these all have in common?”

If you answered, “These are all our responsibility as leaders and coaches!” then you would be correct.

As soon as we observe poor performance, we must carefully look in the mirror and become accountable for the proficiency of our rep.

Have we done everything they need to be successful? Was there a specific onboarding program to get them up to speed? Are we scheduling weekly 1:1s to coach them to proficiency? What is the ramp up time? Are we holding them accountable to a standard?

We should never coach a rep without asking ourselves these questions first. Only then should we begin using these tips for coaching to the next level.

Guidelines for coaching poor performance:

  • Keep it positive. Remind them this is about helping them get better. It’s not to punish them.
  • Keep it focused on the actions and the job – not about who they are. We’re not psychologists.
  • Ask them how they think they’re doing, how the last call went, etc. Many times, they’ll be much harder on themselves than you ever would be. You can still be the good guy! Yea!
  • What ideas do they have to do it better next time? As mentioned earlier, sales is not complicated. Many times, they know what they should have done but didn’t do it because it’s not second nature yet. That means they need to role play and practice more.
  • Role play the scenario with them. If they are unsure what they should’ve said or done, model the skill first, then have them try it.
  • Follow up. Make that skill their focus for the next couple of days, weeks, whatever. Have them shadow a peer who is really good at that particular skill. Listen in on their calls and discuss that skill in the next 1:1. Show them that how they do their job matters. Performance matters.

A problem performance conversation might sound something like this…

Manager: Becky how do feel last quarter went? What went well?

Becky: I tried really hard and I think I have some good deals in the pipe that just haven’t closed yet.

Manager: I agree. You were counting on those deals for this last quarter, so that’s a shame. I noticed your pipeline is a little light though… Why do you think that is?

Becky: I’m really having trouble prospecting and getting ahold of people. When I do reach them, I’m having difficulty scheduling a demo of our software with the decision-makers. It’s very frustrating.

Manager: That’s one of the toughest things you have to do in sales. What do you feel is working right now? What isn’t? What do you think you should do?

(Dive deeper in the discussion here and give Becky the opportunity to come up with her own answers. Then role play. If she misses key points, nudge her in the right direction with more questions or further exploration.)

Manager: Ok, it sounds like you know what you need to work on to build your pipeline, prospect more effectively, and schedule those demos. In addition, I think it would be good for you to shadow Susan this afternoon for a couple of hours. She’s really efficient with her prospecting and her demo to call ratio is one of the highest. See what you can pick up from her, and let’s talk about it in our next 1:1 on Friday. Cool?

Becky: Sounds like a plan.

Manager: In the meantime what additional support can I give you?

Becky: I think this role play was a real eye-opener today. I’ll let you know how it goes.

Manager: Excellent…as always I’m listening to calls, so I’ll be sure to let you know if I hear anything on your calls this week.

Of course, sales coaching isn’t always this clean. Becky has a good attitude right now and seems to want to get better, so that’s a big help. But what if we’ve had this conversation and the rep STILL isn’t performing?? Even worse, what if we’ve had this conversation several times?

First of all, remember that getting good at a job takes time. Poor performance is usually not an indicator of poor attitude.

I still believe that most people want to do good at their jobs. As the leader and expert coach, we should have an accurate idea of how much time it takes to get proficient in our team’s roles. After they’ve been coached for a reasonable amount of time but still show little progress, the accountability spotlight turns to them.

Problem Performance: Coaching Attitude

Poor performance unresolved is problem performance.

When observing problem performance with your rep, ask yourself one simple question: “Do I believe they want to get better?”

This is where the proof is in the pudding. If asked, almost everyone will say, “Of course I want to do well!”

The question for top-performing leaders is, “Do their actions show it?”

RELATED: A Sales Coach’s Tactical Guide on Setting the Right Goals for Sales Reps

There are many parts of a sales job you can observe to measure “want to.” Activities like dials, Salesforce hygiene, and attitude are all easily observable and require zero skill – only “want to.”

If someone consistently has 25 dials, isn’t picking up the phone, and they know they’re supposed to make 50 dials a day — that might be a “want to” issue.

It’s not always a matter of skill. Everyone knows how to pick up the phone.

However, if they’re not making calls because they don’t know how to engage the customer, get past the gatekeeper, or schedule a demo — they’re probably uncomfortable or fearful, and they need to learn those skills before they’ll pick up the phone 50 times a day.

These are skills you can teach, and you can quickly see an increase in performance with focus.

Be aware, some people hate doing things they’re not good at. With them, you have to help them get good before they’ll “want to.”

All of this is determined in the coaching poor performance process. You’ll discover very quickly if you are working with an absence of skill or a lack of “want to.”

My boys genuinely wanted to do a good job on the river that day. They were listening (although distracted by the occasional snapping turtle). They were trying their best, but the fact of the matter was they were developing new skills.

While they both later proved to have the ability, it would take time for them to get to “acceptable” in their performance. Getting “good” and at a level of river proficiency was still a couple of summers away.

When I started really being a good coach was when I began to hold myself accountable for their performance. I had to stop and make sure I was giving them the right information.

RELATED: 5 Avoidable Sales Coaching Mistakes Even The Best Leaders Make

I had to check if their equipment was working properly. Did they have everything they needed from me to succeed? Was I delivering the coaching with care and building trust, or was I destroying trust and actually slowing the learning process with harsh words and unrealistic expectations?

Only after I took a hard look at my reflection in the water could I evaluate their level of “want to.”

While leaders can put out the fire of self-motivation through micromanagement, poor communication, and more — we can’t create the drive people need to produce lasting and meaningful results. They have to supply that.

After you observe activities and attitude and conclude the answer is “YES! They want to get better!” then we have someone we can get to the next level. Give them time.

The skills may come slower for them, or they may need a different approach. While we can teach sales to anyone (I’ve done it thousands of times) it comes more naturally to some people than others.

However, after several coaching attempts where the data and attitude point to a serious and consistent lack of “want to,” we have a whole other problem. Now we have to take action on the problem performance.

A top CEO mentor of mine once told me, “The problem with problem performance is most leaders don’t want to have the difficult conversations.” He was right.

Most of us are leaders because we like people and want to help them succeed. We enjoy coaching people to their next level of performance. We love to win — and even better — to win as a team.

That’s why coaching problem performance is such a drag. Nobody wants to have difficult conversations with people after spending thousands of hours building a relationship with them.

At best it’s an uncomfortable 30 minutes with a team member, and at worst, we could be firing someone and impacting their whole life.

This is exactly why many sales leaders avoid the problem-performance conversation.

Remember, problem performance is simply poor performance that’s gone unresolved. It rarely gets better and, most likely, will get worse. As the sales leader, you have to take action.

On the surface, it seems harmless (and even kind) to give people more and more time to correct their problem performance. However, the delay in reinforcing your standards hurts the person, hurts you, and kills sales morale.

Taking action with problem performance means we are drawing a line in the sand and saying…

“Your level of performance matters. This is your last chance to improve. If you can’t bring your performance up to this level then you can’t be part of this team anymore.”

Ouch. That’s tough.

But necessary.

Sales is unique in that it’s almost entirely based on what you can DO. Can you execute? Did you get the deal? Did they close? Nice! Time to get paid. If not, we’ll get them next time. However, too many deals lost — and we’ve got a problem.

That’s why problem performance isn’t the kind of conversation we want to avoid. It’s the exact one we need to face head-on.

Guidelines for dealing with problem performance:

  • Schedule a dedicated time to meet with the rep. This way you can come prepared with data, final expectations, and consequences. This is NOT real-time sales coaching. This is often the final conversation before you let someone go, so it needs to be scheduled and approached with great consideration and care.
  • Keep it factual. Emotions can run high in these final conversations, and your rep could get defensive or even angry. They may blame other people — including you — for their problem performance, so expect it to become emotional. Keep your emotions in check. State (and restate if necessary) the facts of their performance vs what the job requires.
  • Reinforce that you want them to succeed. If you’re putting someone on a performance/success plan, then share your desire for them to win. “Nobody wants you to succeed more than I do! I believe you can meet these numbers and even excel beyond this.” Reinforce you’re there to support them. They need to know this is not you trying to get them fired.
  • Ask if there’s anything they need from you. Most likely they’ll say no, but it’s good to ask. Remember, at this stage, you’ll have been coaching them in poor performance for a while, so you’ve already checked yourself to make sure you’re giving them the tools they need. Just to be sure, it’s always good to ask again.
  • Hold them accountable. Don’t draw a line in the sand you’re not willing to hold people to. If you say they have to meet 100 dials/$50,000 this month or they’re terminated, then you have to follow through when they only reach 72 dials/$32,700. The rest of your team is watching and these critical times, demonstrate what kind of culture you’re really trying to build.

A problem performance conversation might sound something like this…

Manager: Becky I scheduled this special meeting to speak to you about your performance this last quarter.

Manager: As we’ve discussed in our weekly 1:1s, you have to hit $150,000 a quarter. In order to do this, you agreed to make XXXX calls, set XXXX meetings, and close XXXX amount of customers. At end-of-quarter last Friday, you were well below those numbers.

Becky: “But I tried. I couldn’t because XXXX.”

(Note: Reps will give you all kinds of excuses. Some are even valid. Remember, at this stage, we’ve talked with Becky many times and worked with her to eliminate these obstacles. Her performance has not improved. Go back to the expectations of the role and what she agreed to last time you coached her.)

Manager: I hear what you’re saying, but we agreed that you would make XXXX calls, set XXXX meetings, and close XXXX amount of customers. You said you could do this.

Becky: “But… (excuse — blame someone else — excuse).”

Manager: The reasons why aren’t why we’re meeting today. We’ve talked about those many times. We’re meeting today because you either weren’t able or chose not to follow through on what you said you would do. Unfortunately, neither scenario works for our team.

Manager: Becky, I believe you can do this if you want to. So I’d like to give you one more opportunity. In the next 2 weeks, you need to make XXXX calls, set XXXX meetings, and close XXXX amount of customers. If you are unable, or choose not, to do this, then you’ll no longer be part of the team. Do you understand the expectation?

Becky: So you’re going to fire me if I can’t close XXXX deals in 2 weeks?!

Manager: No, I’ll be firing you for not following through on what you’ve committed to do several times. If I can’t count on you to do what you’ve committed to, then I don’t know how we can continue to have a working relationship.

Manager: Like I’ve told you before, nobody wants you to succeed more than I do. We’ve spent a lot of time working together and I want to help you get past this, but the position requires XXXX calls, to set XXXX meetings, and to close XXXX amount of customers. So that’s what we need to see. Do you have any questions?

Becky: No…

Manager: Is there anything you need from me to meet this goal in the next 2 weeks?

Becky: No…

Manager: Ok great, then let’s get back to work and let me know if you need help from me.

Not very pleasant, but essential to creating a high performing team.

Of course, terminations are a little different for everyone, depending on your HR policies, so you’ll want to work with an HR partner if you have one.

However, the principle remains the same. As a leader, you will get the culture and the performance you accept. There is nothing mean or cold about holding your people to a high standard of performance. It’s your job as the sales leader.

RELATED: The One Proven Strategy to Move Your Sales Team Performance Bell Curve

Coaching problem performance is some of the hardest sales coaching you’ll do. When so much is on the line, emotions can run high, so we must use emotional intelligence to respond properly as our reps make excuses for their shortcomings, become defensive, or even blame us!

In the end, we have to see the big picture and look past this small snapshot in time.

We are trying to coach salespeople into sales champions. This is about turning a negative into a valuable experience they can grow from — even if that means having difficult conversations, working harder to stay afloat, or getting off the river and trying mountain biking instead.

Great Sales Coaching Doesn’t Happen on Accident

Ultimately, we all want the best for our teams, so we push them to levels they may never achieve on their own.

It may be uncomfortable, but remember that sales coaching is an investment.

That day on the river, I wasn’t just trying to make some fun memories; what I really wanted was to teach my boys a new hobby they could enjoy the rest of their lives. But because of my poor coaching, what I got was a morning of frustration and an afternoon trying to rebuild trust.

Luckily I was able to turn the tide with my boys and finish the day with smiles all around.

Few professions require results as much as the wonderful role of sales leader. If we believe great coaching leads to teams performing at higher levels, then we have to assume these kind of results don’t happen on accident.

The key to consistent performance is sales coaching on purpose.

By focusing on these 3 times to coach, you’ll begin to make coaching a more frequent and familiar part of your team culture. People will know that how well they do their job matters, and that, as the leader, you care about achieving greatness together.

You’ll be building the coaching relationship, crushing numbers, and taking people somewhere they could never get on their own — and that’s leadership.

Shawn Buxton is a professional speaker, author, and performance coach. Shawn’s worked with top performing leaders all over the world including the US, UK, Canada, Central America, Ireland, and India. He currently leads the International Sales Leadership program for LogMeIn. For questions, keynotes, or speaking engagements please reach out to

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