Sales Coaching: Balancing Accountability & Encouragement w/ Chris O’Connor

#60: Listen as Chris O’Connor, Head of Sales Development at Ambition, discusses sales coaching and the balance between accountability and encouragement. He offers insight into coaching sales reps and raising the bar to help your reps get the most out of their careers.

Listen to the episode by clicking play below OR search “the sales lift” wherever you get podcasts.

Sales Coaching: Balancing Accountability & Encouragement w/ Chris O’Connor

Episode #60 of The Sales Lift Podcast w/ Tyler Lindley


[00:00:00] Tyler: Hey Sales Lift nation, it's your host. Tyler Lindley. Today I have Chris O'Connor on the podcast. Hey Chris, how's that great,

[00:00:10] Chris: Tyler. Thanks for having me.

[00:00:11] Tyler: Yeah. Happy to have you here. So by the way, just to remind everybody, the show notes for this episode will be on the sales So if you want to check those.

Feel free to go there. After the episode, Chris O'Connor is the Head of Sales Development at Ambition he's located in Chattanooga, Tennessee, just up the road from me here in Atlanta, just drove through there, beautiful area for anybody who has never checked out, chatting. And today we're going to talk a little bit about sales coaching, which I know is a topic near and dear to both of our hearts, Chris, specifically around the balance between accountability and encouragement.

Where do you as a sales leader, as a sales coach, you do have to fall. Are you more accountable? Are you more of an encouraging. Or maybe it's a balance of the two. What is your thoughts on that, Chris? What does good look like from a sales coaching perspective on that side?

[00:00:58] Chris: The perfect recipe is a balance in between both accountability and encouragement, in my opinion.

And I think most sales leaders are going to fall closer to one of those two ends on the spectrum. So they may be very hard driving and tough and really lean into that accountability. Or they might be encourager are cheerleading their team, but are setting a lower bar on the accountability side of things.

And so I think being somewhere in the middle is really where you want to be. And for myself personally, I would say that I tend to sometimes fall closer to the encouragement side of things. So I have to hold myself accountable to making sure that I'm setting a high standard for the team, holding them accountable.

And really like showing some of that tough love. You

[00:01:48] Tyler: mentioned that you fall a little bit more towards the encouragement side. Do you think that's just your nature, your background was that influenced by other coaches you had throughout your life?

[00:01:57] Chris: That's a good question. I think it is part of my nature.

I think about the best coaches that I've ever had. They are that right balance. It's easy for us to gravitate towards people that we like and are our natural encourager. But in the long run that the people that end up being the best coaches, the best bosses are the ones that still hold us to that high standard.

But we know that they do care about us, right. So they are encouragers. They've found that right back.

[00:02:29] Tyler: I agree with the line, the people that we, I think we are naturally gravitated towards those almost like the people that we like, but the people that we know that we can get away with things, because if we're not holding ourselves accountable and if they're yeah.

Halfway holding us accountable. Then we might slack off a little bit. We know we might take off early on Fridays and we might mail it in at the beginning of the month. So which in sales is hard, right? If you take days off and if you're not holding yourself accountable or your manager or coach isn't, you may not hit quota consistently because as we both know, quotas are high, right.

And it requires a lot of daily dedication. And I think that if you do have a coach that leans more towards that accountability side, it might be harder. But it might make it a little bit easier to hit quota.

[00:03:12] Chris: That's right. We all know that sales is a tough profession. There's a lot of ups and downs. And so naturally as a leader, it may feel more natural to be that encourage or to make sure, Hey, keep your head in the game.

This is a tough job. And naturally you want to encourage your reps. That's supernatural. And I think we want to continue that. That's an important piece of being a good coach. Is that cheerleading aspect. I think again, in the long run, if you aren't setting that hard line setting high expectations for what performance should look like.

And as a coach, you really understand what is the ceiling for each rep. They may think that their ceiling is eight meeting set per month or a certain closed one number per quarter. It's your job as the leader. Raise that ceiling for them and say, I know you think that this is your bar, but I see more out of you and I'm going to hold you to that until you get there.

So I think that's a really important piece. As we think about raising the ceiling, raising the bar for


[00:04:20] Tyler: reps. I love that. I love what you said too about what's natural. What comes natural. You probably naturally fall more on that accountability or encouragement side of the spectrum, but then there's, what's natural versus what's needed for the business and then the ceiling.

Wow, that's great. I love that's really our job as sales managers, as coaches, as trainers. Like we want to raise that ceiling for everyone, because if we can do that across the board, we likely can hit our numbers more easily as a team, given that you've naturally fell more on the encouragement side of the space.

How have you built that accountability muscle for yourself? For

[00:04:54] Chris: me, it's all about visibility, visibility into performance and painting the full picture for what performance is, and just being very open and transparent with your reps about what those expectations are and where they fall. And so that for me makes accountability easy because the numbers do and the talking and while a lot of reps are coming, pitting against one another.

At the end of the day, it's really about competing with themselves. And again, raising that bar for themselves, beating what they did last quarter last month. So I think visibility into, into metrics, not only the outcomes, so the quota type metrics, but the activities, what are the leading metrics that are going to get them to those quota metrics.

And so I think once you have the right visibility into that, it makes it a lot easier to hold them accountable there. And we're on the same page, right? I certainly want all of my reps to hit quota. And so we put the numbers in front of them and say, let's figure out what's the right path. What are the activity mix that we need to get there?

And so it feels a little bit more, yeah, I'm holding you accountable to these numbers, but we're in this together. It's not me bringing the hammer down on you. It's, that's the standard that we have to get to. So let's figure out how we get there.

[00:06:22] Tyler: I love talking about that visibility into performance. You have to build that into your culture.

I think from day one of that employee joining, you have to know that there's going to be. That level of accountability. And we're going to be looking at these numbers on a consistent basis. So I want you to keep an eye on them. I'm going to be keeping an eye on them. You have to set that standard from the beginning versus being a little bit more wishy-washy on what activities lead to the outcomes that we're looking for.

Because if you're wishy-washy at the beginning, they may think, oh, they care that I hit $50 a day. They don't. So maybe I'll just do 40 today and then take a lot, unless I'm really struggling. So that, I think that that's an interesting thing. You bring up, how do you set that standard from the beginning?

How do you build that culture of, we are going to look at the data. We are going to have those numbers visible. I'm going to use that throughout my management of you as a seller.

[00:07:13] Chris: It's a lot about consistency. So it's easy for someone to sit down in their one-on-one coaching session with a rep and shoot the breeze and talk about really high level topics and then never really get into what are some of the areas we needed to improve on.

And again, giving that visibility in the metrics. And so I think consistency in your one-on-one. Documenting things in ambitions product. We have a really cool thing called a productivity quadrant. And if you don't use ambition, you can easily create this, but it's essentially a skill versus will chart. So it's going to look at all of their inputs, so their activities and calls, emails, things like that.

And then the outputs. So how many meetings are they setting? How many qualified opportunities, things like that. And when we plotted on a chart and it shows that. One, is it an issue of they're not doing enough activity or is it an issue of the doing the activity, but there's not enough quality there to get the outcomes that we're looking for.

And so it easily paints the picture for us. Do we need to focus on you just putting more effort in doing more activity or do we need to focus on maybe some call coaching, maybe some like more quality in your emails to get the right mix there to hit your numbers. And so I think highlighting that for the rep, showing them the exact areas where they may have some weaknesses is important.

And then I go take it to the next level there too, and show that same chart to the rep. And plot their peers on that same quadrant and say, okay, this is where you fall amongst your peers. And for some people that may feel very uncomfortable, but at the end of the day, again, it comes back to the visibility and the transparency and those metrics and raise it, raising the seal.


[00:09:09] Tyler: is there? Because I liked that activity. Plotting the reps against the showing them where their peers stand on that skill versus will chart. How does that typically go? What does that conversation look like? Cause I imagine that they see things in that data that shows they're clearly, probably maybe above average in some areas and probably below average in other areas.

How do you, how does that conversation typically go when you show them that, that specific.

[00:09:37] Chris: Yeah, it's normally just a, it goes over really well, because I think it's so easy to, as for the rep to just look at the outcome metrics and say, I know I'm hitting quota, or I know I'm getting close, so I must be doing great or I'm not getting close to quota.

So I must be doing terrible at this. And so it really informs them. Where do I personally need to improve? And from a mindset standpoint, that really helps them because a lot of the equation of successful sales is, you know, what you're putting into it yourself. And some of the things you could tweak. So it.

The conversation is normally easy and what I tend to see following that conversation, it's just open eyes to their own performance and what they can improve on, which gets to the heart of what we're trying to accomplish. We want them to see where they need to improve and be able to take action.

[00:10:37] Tyler: And is this kind of a thing that you can show this to them once, and then they can just self-manage after you, after they know that that exists, is this something you arm them with and they can see how that changes on their own?

Or is this something that you revisit every single week? Um, and they kind of see the changes then when they don't have visibility into it on a day to day.

[00:10:58] Chris: Yeah, it's a big, w what I like to do is show them the charts, show them the metrics that are involved in creating that chart, and then put it back to them and say, given this level of knowledge that you have about your performance now, what do you think that you need to change or do in this upcoming week and this upcoming month to improve personally?

And so when I put it back on. Allows them to really think, okay, like what, what do I need to change? What do I need to do? And then I'll obviously like make corrections there if needed. And then the, again, the purpose of the one-on-one is to. Hold them accountable to that as well. So document whatever findings came out of that conversation and then make sure we're re you know, touching on that every single

[00:11:45] Tyler: week.

Yep. That makes sense. Yeah. I love what you said there about you asking the questions, ask them, what do you think about this data? What do you think might need to change? Because obviously you could just tell them like, Hey, this data says this and you need to do this. It's sometimes more effective to have people solve the puzzle themselves, or think about it themselves.

Think more critically, because then I think they're taking a more active approach to getting better versus passive. Just I'm looking for you to give me the answers. I think that can help develop a lot of skills that they can take far in their sales career or anything else that they do versus just giving your reps.

The answer is that you find yourself asking more questions than telling, asking versus telling as you're managing your.

[00:12:27] Chris: For sure. I definitely want to build that muscle of self-awareness within our reps so that they can begin self-diagnosing some of these things as they move on in their careers and yeah, I think that's really important.

And to take it to the next step. One of the things that I'll often do is if a rep is struggling in a certain area for right now, let's call it. Objection, handling. I will empower that rep to actually I'll say, Hey, you're actually going to lead a training for the entire team. On objection handling. And for them they're like, oh no, like I'm terrible at this.

I don't want to lead a training on it. But what it forces them to do is really dig into what are the areas I need to improve here? What can I do to make some significant changes here? And if I have to lead a train. No, I need to be the expert on it. And so it empowers them to, to really improve in that area and then teach it to the rest of the team.

And I've found that to be a really powerful tactic for getting Rex to improve.

[00:13:37] Tyler: Yeah. Yeah. I love that. I love that because they probably initially do have that. Oh, oh no moment of, oh, I'm going to be put on the spot. However, if you can teach somebody something. You cannot, you obviously know it yourself and that forces forces them to get up to speed quickly so they can at least get ready for the presentation and likely some of that rubs off on them too.

So I love that. I love that as an area of focus. What else Chris, do you think is important as we're thinking about managing reps and coaching them, what else haven't we discussed yet that you think is key for managers to consider as they become better coaches for their

[00:14:12] Chris: team? Yeah, it's a good question. I think we touched on a little bit around the one-on-one experience, but I think this is the most important interaction that you're going to have with your reps on a weekly basis.

And you really want your reps to be excited and looking forward to this 30 minutes, 45 minutes, whatever it is with the manager and the rep, and a couple tips that I would have there is to really. Empower the rep to lead that conversation. So we're there really to benefit them and coach them. And so I want them to take control of that 30 minutes and say, all right, Chris, this is what I want to cover.

I want to get your perspective on this is what I want to improve in. And so when they lead that conversation, it tends to be. A little bit more valuable, a lot more valuable for them. And certainly my perspective coming into that conversation could be very different from theirs. And so that's another thing that I always suggest is empower them to lead that discussion.

And then certainly I may have some questions of my own, but that's an important point that often gets

[00:15:29] Tyler: overlooked. Do you think you have to give them some kind of guidance on best practices there? What they should be thinking about? Are they, do they naturally pick up if you're empowering them to lead the one-on-one?

Do they naturally pick up what we should be talking about? Or do you find that maybe initially they're way in left field here and they're scattered and like you have to coach them to how to do that? Or do you find that most of them just pick that up right off?

[00:15:54] Chris: Yeah, it's a good question. Early on. It can be intimidating.

They don't necessarily know what we should be talking about. What I like to do is give a really high level agenda. And again, it's not set in stone, but it's a high level agenda so that they know, okay, these are some of the big topics that I'd like to cover in this conversation, but I want you leading within that category.

What do you need help with? Where do you want to steer this conversation? And so, yeah, that's

[00:16:21] Tyler: how I typically do. For you at ambition, you're leading sales development there. So as you talk to your STRs, what are some of those key buckets that you typically have? If you're setting that agenda, what are some of those overarching themes that give them at the beginning and then they can fill in the gap on each theme?

What are you talking about?

[00:16:38] Chris: So this is another like important suggestion that I have, especially if you are managing a reps that are remote, you're not right. Yeah. You're not face-to-face with them. You can't really, truly get a pulse for how they're just how they're doing. So I think the very first question that I always ask in one wants is.

Work or otherwise, how are you doing Tyler? How are you doing? And some reps will give me the short. Yeah, I'm doing great. Things are good. But I also find that some reps use that to say, Hey, I am struggling with this one area. Or there's some things going on outside of work that. Have kind of been bothering me like, and so it just creates that forum for us to, before we jump into numbers and tactical things, just to get a pulse check on how are you doing?

And so that's the number one question that I always ask when we sit down in a one-on-one, the second thing that we always cover would be, what are your goals for this week? I typically have my one-on-one on a Monday or Tuesday, so early on in the week. So that we can have some goals, have some plans and get that taken care of early on in the week.

So that's the second question. What are our goals for the week? The third is what is our path to quota this month? And this is a really big area where they, I want them to take control of the conversation. So. Okay. Based on my conversion percentages, here's the math. I need to make this many calls. I need to have this many call connects so on and so forth.

And then the next question that's really important for me is what do you need from me to win this week? And so, again, that, that kind of opens it up to do. We need additional training, Tanny me to just run a report for you out of Salesforce, whatever it may be. Yeah. Figured it out. What I can do to help him.


[00:18:35] Tyler: Yeah. I liked those buckets to recap. Like initially you just ask, like, you get a pulse check on how they're doing. You just ask worker otherwise, how are you doing? May they may give you something. They may give you nothing, but at least just start there. And then second is goals. Third is what is our goals for this week?

Specifically three what's our path to quota for the month and then four, how can I help you win this week? So I like, you're trying to remove the blockers there. So I like that. That you bucket those things. And I like put the onus on them. Tell me what your goals are. Tell me what your path Dakota is. I could obviously figure that out for you, but you need to figure it out for yourself.

So I like, I liked the way that you framed that up. Anything else you think our listeners might find interesting, Chris, from a sales coaching perspective, anything we haven't touched on before we wrap up?

[00:19:21] Chris: I think the last thing that I would say is, is really dig in, get to know your reps and understand what motivates them, because now I've got a, I've got a team of 10 and it seems like almost every rep has a different driving factor.

Some are just. Competitive and want to be at the top of the leaderboard. Some have a keen focus on money and their finances, and really want to grow that in some have family, motivating factors, things like that outside of work. And so I think what's important is to really dig in with each rep, understand what motivates them and then use that in those conversations, use that throughout them to help get the most out of them.


[00:20:02] Tyler: Yep. Raise that ceiling. Like we talked about earlier. Perfect. Chris and my listeners want to find you online. How can they.

[00:20:08] Chris: Yeah, we'd love to connect with anyone on LinkedIn. So you can find me there I would love you to just check out some of the sales, coaching and gamification features we've got there.

[00:20:18] Tyler: Perfect. Yeah. Awesome. Ambition is a really cool platform. So if anybody's looking for a way to do some sales, coaching, or gamification in their sales org, definitely give Chris and his team a call. Chris, thanks so much for hopping on and really appreciate it. Thanks, Alex. Appreciate it.

[00:20:31] Chris: Awesome.

Thank you so

[00:20:35] Tyler: much for listening to today's show. You

[00:20:37] Chris: can find all the links discussed and the show

[00:20:42] Tyler: That's the T H E sales, S a L E S. Lift L I F T. Dot

[00:20:49] Chris: com have questions for

[00:20:51] Tyler: me, email We look forward to seeing you back here next week, and we hope today's show brings you the sales lift.

Your business needs. Remember ideas

[00:21:04] Chris: plus action equals

[00:21:06] Tyler: results.

[00:21:07] Chris: You've gotten new ideas. Now it's time to take action and the results will follow. See you next time. .

Chris’s Bio:

Chris is the Head of Sales Development at Ambition – the leading sales coaching and gamification platform for metric-driven teams. He is lucky to oversee some of the best SDRs in the game and loves to coach and scale revenue-generating teams. Chris lives in Chattanooga, TN with his wife Maggie and golden retriever, Barry.

Important Links:

Chris O’Connor’s LinkedIn Profile

Ambition’s Website

Don’t feel like listening? Read the Episode Cliff Notes instead below:

Encouragement and Raising the Bar (0:42)

The perfect recipe is a balance between accountability and encouragement, and most sales leaders will fall closer to one of those two ends on the spectrum.

An important aspect is to know where your rep’s ceiling is and raise it for them. For example, say, “I know you think that this is your bar, but I see more out of you, and I’m going to hold you to that until you get there.”

We want to raise that ceiling for everyone because if we can do that across the board, we likely can hit our numbers more easily as a team.

Building Accountability (4:40)

It’s important to be very open and transparent with your reps about expectations and where they fall. That makes accountability easy because the numbers do the talking. 

While a lot of reps are pitted against one another, it’s really about competing with themselves at the end of the day.

Once you have the right visibility, it makes it a lot easier to hold them accountable and stay on the same page. Put the numbers in front of them and figure out together what’s the right path to get there.

Look at those numbers consistently and set that standard from the beginning versus being a little more wishy-washy on what activities lead to the outcomes we’re looking for.

Chris uses a productivity quadrant, and if you don’t use Ambition you can easily create it. It’s essentially a skill-versus-will chart.

Highlighting opportunities for the rep and showing them exact areas where they may have some weaknesses is important.

Coaching to Empower (12:21)

We want to build a muscle of self-awareness within our reps to begin self-diagnosing as they move on in their careers. It’s important to empower them. 

That one-on-one interaction is the most important interaction you’re going to have with your reps every week. So, you want your reps to look forward to that 30-minute slot.

When they lead that conversation, it tends to be more valuable for them, which is why Chris always suggests empowering them to lead that discussion.

It can be intimidating for them because they don’t necessarily know what we should be talking about. So what Chris likes to do is give a really high-level agenda of what he’d like to talk about, but not set it in stone.

Setting The Agenda (16:23)

Working remotely poses other challenges since you’re not face-to-face. 

A simple “how are you doing” is a great way to open up that discussion. Some reps will give a generic answer, but others will use it as an opportunity to let you know what they’ve been struggling with. 

The second thing Chris always covers in his one-on-ones is what goals the rep has for the week. Again, it’s helpful to have the meeting early on in the week to set goals and make a plan.

The third is what the path to quota this month is. That’s a really big area where you want the rep to take control of the conversation and make a plan for themselves. 

This leads to asking what the rep will need to win that week so you can help them get the tools they need to succeed.