#250 - Lead Playbook: Armand and Mark Teach You How to Train Your Team
1 Feb 2024 · 29 min
In this episode of the 30 Minutes to President's Club Playbook, hosts Armand Farrokh and Mark Costaglo dive deep into practical sales enablement, focusing on how sales leaders can design, deliver, and sustain effective training programs. They begin by differentiating training (information transfer) from coaching (behavior change), then outline a six‑week onboarding framework that blends an intensive in‑person boot camp with five weeks of virtual deep‑dive sessions. The conversation moves to the progression of new reps—from role‑plays to low‑risk supervised calls to independent selling—and discusses how to identify and cut mis‑fits early. They share a nuanced view of certifications, advocating internal mastery before external proof. A central tool is Mark’s 3×3 change‑management matrix that maps cognitive load (low‑medium‑high) against capability levels (aware‑competent‑mastery) to prioritize quarterly training initiatives. The hosts argue that training alone does little without a supporting program and culture, and they explore when to bring in external trainers versus leveraging internal expertise. Finally, they stress the importance of simple, searchable documentation—using existing tools enhanced with AI—to keep knowledge accessible. The episode ends with actionable takeaways on onboarding structure, matrix‑guided prioritization, and the need for a holistic training program.
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Everybody. And welcome to this playbook episode of 30 Minutes to President's Club. My name is Armand Farouk and I'm here with my wonderful leadership co host, Mark Costaglo. And today we're not talking about deal reviews, we're not talking about how to run a board meeting. We're talking about how to get your team actually trained to do the job. It's how to, how to train your team as a sales leader. Mark, why should people listen?
Arman, do you know that over the last 10 years, almost every single survey that I've read about salespeople has listed something consistently in the top three that high performing salespeople want, need and require from their employers? The answer is training. People want to grow, they want to be up leveled, they want new skills, they want coaching. And it's one of the most difficult things for sales leaders to figure out how to do when the rest of the business needs to be run. The reason that you should listen is because today we're going to give you some ideas of how to think about training in a way that helps you do it inside your org without being disruptive and helps you really get the results that you want to get.
That's right. Specifically, we're going to go through three or four buckets of training. Bucket number one is onboarding. Someone walks in the door, what do you teach them? Bucket number two is your team is ramped. How often are you reinforcing up, leveling the game and how do you even decide what to do every single quarter in terms of ongoing development. And then bucket number three is sort of everything else. So we're going to talk about external trainers, we'll talk about some systems and best practices for documentation and other things that you can do to make sure that you are successfully training, training your team. And three, two, one, let's ride. All righty, Mark. So let's start with just some basic definitions on training versus coaching. So when you think about training, how do you see training being different from day to day, hands on coaching with your reps?
I would say the difference is like if you play basketball and you watch a video about how to do your jump shot and it's just you and you just watch a video about it and then you go about the rest of your day doing whatever you do that's training. It's the transfer of information. Coaching is I watch the video and then I go out and I do 100 jump shots and I maybe get a buddy that watched the video and he's watching me do the jump shots. And it's an interactive thing where I'm acquiring a skill or making a change based on information that I've been given. So training is just relaying the information. Coaching is the ability to change behavior because of the information you've been given.
Bingo. That's totally spot on. You've always got these great analogies, Mark. And so the way that I would think about this folks is to put it in sales terms, if you want to train your team on Med Pick, for example, there are really two parts of that. You need to train them and explain what is Med Pick. And then inside of your deal reviews, you need to have ongoing coaching that, that constantly reinforces and applies that training, AKA builds the behavior. For the sake of today, we're not going to be talking about the coaching element. We're going to be talking about the training element. So, Mark, let's start with onboarding. I've tried a million different onboarding programs. I've done a onboarding, sdr, onboarding, leadership onboarding, all kinds of onboarding. If you think of the ideal onboarding program, what does that usually look like? How long is it? What are the sessions like? How do you balance doing versus learning, things like that.
The best onboarding training that I've ever been a part of is I had a enablement leader at outreach named Jerry Farr. And Jerry put together a list. I think it was a six week long program that included the first week in person at a boot camp, eight to ten hours a day, go eat breakfast, lunch and dinner with the crew. Find your way culturally like get into the company, but you're going to get basically dumped on from the fire hose. A ton of information and the idea is to get you aware of what's going on. Then the following five weeks after that we're all done virtually. And those were group sessions that were scheduled on the calendar. It was usually an hour or two a day where we did ongoing training, where we went in deeper and we tried to solidify those concepts and get them really burned into how someone thinks and how they're operating inside the company. So I think the perfect onboarding thing is about half a quarter, six weeks. It involves an in person boot camp where you learn and you make friends and you can have those peer connections and then you go through the entire area of what people need to know to get a general awareness of it. And then you have a program afterwards that is consistent for, for the remaining five weeks where you dig in deep into each of those areas and really up Level someone's understanding of it.
So, Mark, I'm curious from your standpoint. One thing I always struggled with is you talk about this first six weeks, and I used to always be like, all right, we got to get them to learn everything in the first three weeks. Let's put them in a classroom. We got to show them all the demos, we got to teach them about the Personas, we got to do all this stuff. And I usually found that it was actually somewhat destructive to have them in a room not actually doing the job for a month straight because one, they won't retain much, and then two, that's also time that they could be using to get started on their territory, shadowing some calls, things like that. And so how do you think about not having them in the action, or are you slowly onboarding them into live action during those first six weeks?
Yeah, so I think training can just be learned by watching. It can be learned by listening, or it can be learned by doing. And so I think that what you need to do is you need to find out. Generally, most people learn by doing. And so a lot of the training that we did in onboarding was, all right, we're going to show you it now. Go do it now. We're going to show you it now. Go do it. You might not get it quite through all the way and you might not get a mastery, but you're aware you're getting oriented to how things work. You're starting to see, oh, when I look at an account, I'm doing this research and I need to keep in mind that I'm going to go look at contacts and this research for here can help me over here so I don't have to do it twice. Right. And so you're starting to see how to connect things. So I think learn by doing is definitely the way to do it.
So if we take those six weeks and we dive in a little bit more, you said it's really building a lot of the awareness. It's the big information dump and all of that stuff. Could you give me a sense of, let's say we're doing an AE onboarding, what would those six weeks look like? Week one, product, week two, demo, week three, discovery, things like that.
I don't know if I have, like, exactly what it would look like. I just know first week is everything firehose, take it all the way through sales methodology, watching demo, setting up your email account, all of that kind of stuff. And then each week afterwards has a theme. So maybe if you're an ae, maybe the first theme is how we do our sales methodology and forecasting. The second theme, which is the third week now of your onboarding, that's where we go deep on product knowledge. And then we go into, all right, how do we actually run the meetings? And then like, what does our pricing and packaging look like? And so the idea is you need to just bucket it up into these understandable areas of information and you need to have all of those present in the first week and then pick a bucket each of the following fifth week and like really hone in on that bucket. But I'll tell you, Armand, you want somebody to have something that they can lean on that makes them be like, I feel confident about this, like, I'm off to a good start. Because, you know, sales is like 90% confidence. If you are feeling good about your product, your sales skills, the person you're talking to, you're going to be successful. If you don't, good luck. So Armand, like, there's this seminal moment where like, all right, we're going to put this new person in front of actual live customers that we can't just screw up with. So how'd you get to the point where you're like, okay, time to give them customers?
So there are a couple different pieces of this and this starts to go into certifications. But let's say that I'm training a mid market ae. The progressions that I will bring someone through are, number one, you need to be able to just demonstrate throughout the first two weeks that you're retaining some of these concepts. Number two, then you need to actually show in practice that you are capable of at least getting through a call. And this is through role plays, mock discoveries, et cetera. I'm a big fan of mocks and I will give you a ringer of seven AES that you should go do mocks with over the next X number of weeks. Right? So this is all pre live customer. Then from there, depending on what segment you're in, what your company looks like, I see a lot of companies that have really small deals or SMB deals or whatever it is. And sometimes these deals can be false signals. But I would oftentimes have my reps train on smaller companies that would be coming inbound or leads that we might normally dq. So I would have them be in lower risk environments and I would have them train on those types of deals with heavy manager and AE supervision. And then the final piece would be, okay, you're taking calls with manager, AE supervision within your segment until finally you're comfortable enough to be taking them alone. So it goes from roleplay to low stakes customer conversation supervised, to normal customer conversations supervised, to unsupervised conversations. So, Mark, let's say that a month in, someone might be on a three or a six month ramp schedule, but you see, it's not quite working. And I know this might not be a comfortable topic for everyone to come to talk about, but a lot of times I've gone through one or two months of onboarding and I've seen a rep that I just know early on something's not quite the right fit here or they're not quite getting it. What do you do if at the end of month one you're like, like, I don't know if this was the right hire or something's not quite stuck stick in here.
I think when it comes to, is it time to move on? There's more error that happens by waiting too long than not waiting long enough. So I can tell you a couple stories of reps that same way. Like, Jerry was doing an onboarding session on day two. Armand, he called me and he's like, this person can't work here. We need to let him go. I went to my HR team and said, hey, I'm getting some real signals. They wouldn't let me. That person stayed at outreach for almost eight months and never closed. $3,000. Like that's almost impossible to do with how we were operating, what we're doing. That's how bad the person was. We should have got rid of them. Day two. So I would tell you like, one, identify people that aren't a fit as fast and as early as you can be aggressive with it a little bit more than maybe you naturally want to be. And then make sure you have HR partnership that allows you to move on from people before they really start hurting the business. That person hurt our business. You know, if you're a month in and your gut's telling you they're not going to work, I would suggest that more times than not, that's right. Just go with the gut and the mistakes you make, you make right. You just live with that later. But I would rather somebody bat 20% on getting it wrong. Meaning, like, okay, 80% of the time we get it right and the person shouldn't be here. And 20% of the time they should have stayed here if we just gave them a little bit more time. I'd rather see somebody do that than to hold on to people way too long. And that 80% stays here for three or four quarters versus getting cut right away 100%.
And I know there are going to be some people on this who are like, oh my God, you're going to let them go during training or maybe they've been let go early before and it's a personal experience and I totally get it folks. It's not easy. But the reality is like number one, in this kind of market you can't be burning a high qualified inbound lead with someone who's just not going to get it. But, but then number two, it's actually a disservice to that person if you know they're going to be six months in, out the door, it's going to look worse for them. And I've made the mistake of sometimes keeping those folks around. Mark, earlier on in my career where I hadn't seen this as much and what ends up happening is it's not just this person doesn't make money. Number two, usually other reps are getting frustrated because they're like, what's going on? Number three, the worst thing is this person oftentimes has irreparable confidence damage because they go for six months just eating crap in a job that they're not the right fit for. So you have to keep in mind for the sake of your reps, for your team and for that rep, it is the right decision to not string someone along if you see early on that it's not the right thing for that person and that's okay. Mark, the only last thing we didn't really talk about is before you exit onboarding, how do you think about certifications or anything like that?
I have like a love hate relationship with certifications and I think that there's a way to do a certification that doesn't allow you to actually be good at what you're trying to do. And it creates a robotic, non responsive way of doing something that can hurt. And however you set the role play up, it's never going to be quite right. So if you're going to do certification, you should do internally. Once they're good enough internally, then they should provide external proof that they can do the thing that you're asking them to do at the level of mastery, which I consider to be 80% the way that we show people how to do things. So that's how I would think about certifications, is they're not certified until they can do it in the wild and make sure that they're not practicing on customers.
That's right. And so you want to have these Gates of you want someone to be minimally, viably good with your reps internally, but the reality is they're not truly certified until they're able to do this stuff with customers. So on this note, Mark, let's get off of onboarding upfront training and you have this really interesting way of diagnosing. Here's where my team stands, here's what they're good at, not good at, and here's what I should be training them on for this quarter. Where do you start when you're doing that initial diagnostic of your team's ability to.
So I have a matrix that I use and the purpose of the matrix is to understand how much change management capacity you have and then how much you're feeling that capacity. And so think about this like a xy axis and a 3 by 3 grid. The y axis is cognitive load. That's like how hard is something to do? You can have low cognitive load, which means I'm going to just click a different button and it's going to be green instead of blue in Salesforce to generate my quote. But I pretty much understand how CPQ software works and like that's a low lift, right? A high cognitive load would be. We're going to ask you to change how you demo this large feature that is an area of differentiation for us. And you actually have to change up your demo flow, change up some of your discovery questions, change up some of the screens you're going to. All right, so we got the Y axis is cognitive load, low, medium, high. The X axis is capability. How aware do we want them to be? So there's all the way on the left hand side there's aware, which means they know about it. Then there's competence, which we talked about earlier. That's my ability to demonstrate how well I can do this skill internally with a role play or my manager or my VP or somebody. And then there's mastery, which is. I'm now providing evidence that I've done this skill way that you've asked me to at least 80% in the wild in a real world situation. So if you look at that 3x3 grid, we start to create nine boxes and each of those boxes has a point value. So the leftmost bottom most box is one point. Inside the rest of those nine boxes there's different point values. We'll provide that image so that everybody can see how to score it. At outreach, I found out my Reps could handle 16 points of change a quarter. So that could mean we could do one nine point change and maybe a seven point change and that's it. Or we could do a nine point change and I could do seven one point changes. And so what that did is it allowed me and my enablement person to do two things. One is we're like, all right, these are the things you're asking us to do so we can make sure that we're not doing too many things. And the second thing that it allowed us to do is to say to the people that wanted the training, like our CEO or CRO, we would go to them and be like, listen, we, we're training people to be aware. They're not going to demo it the way you want to, but they're going to mention it and show you that they're aware of it. If you want to go to competency, which means, hey, they'll probably demo it but not quite good. They'll talk about it, but it won't be quite what you want because they're only going to have to show us internally how well they're good at it, then that's where we can go. But that's more points than just doing aware. So if you want that level of capability with the reps, then we're going to have to not do some other stuff because I can't build a month long program to get somebody to that competency and build a bunch of other programs because there's just been up being doing training all the time and most people can't digest that much information anyway. So we need to treat adults with an adult learning philosophy which says that we understand they have a capacity for change. We're going to measure that and we're going to fill that capacity up as much as we want to. And here's my hypothesis, if you go up to that level of capacity, Armand, then you can pretty much guarantee someone can digest it, do it and you can get to the level of comp capability that you want to get to. If you go a little bit over, the only thing that you risk is the extra project or two are not going to be nearly as good as the rest of what you've done. That is inside the capability boundaries. If you go way over, then everything is done like there's nothing that's going to be digested. Everybody's going to just spit out everything you throw into their mouth and it's just not going to work. That's what I see happen in tons and tons of company is they just treat sales reps like they're a computer. If I just input the information, they now have it, learn it, can use it and do everything with it. And that's just not how people operate.
This is totally making sense. So folks, just to recap, there are two axes that you should think about in terms of how important something is to train your team on or how much mastery it requires, AKA the capability and then the cognitive load of that thing. In other words, like how challenging is that concept to grasp? And as a sales leader, you're going to get all kinds of crap thrown on your plate. And the reason for that is you're the gatekeeper to those customers. You're going to get marketers who are like, hey, we want to try this new crazy MQL workflow, let's try calling these leads this fast kind of thing. But meanwhile, if you know the most important thing for your team to do is to get really, really good at getting access to power. That is an enterprise level skill set, a mid market level skill set. That's not an easy skill to train. That's high cognitive load. To teach your team how to get into the back door to power, use three or four different ways to get access to the top. And what you're going to want to do is you're going to want to surround your team with as many different ways to reinforce, enforce those principles as possible. You're going to want to have that every single place a rep lives. And so it's your job to let certain things burn that are less important for the quarter and not wrap your team around the axle and change fatigue. Because if you get them up to 24 points total and you're trying to teach them everything, they will remember nothing and your team will just be exhausted with the 17th training that you threw on their calendar.
I would argue that training does next to nothing. What makes someone change is a program. A training would be, hey, you know what, y' all like, let's do some shout outs from reps on some big deals. And you know what? We're gonna have LJ talk about a couple things he did in this deal that really helped them. That's like a training. And it's good, it's interesting, but it's not going to do anything for the whole team. And what you want to do is you want to build a program that supports the training and makes sure that it works. And if you can't build a program, then you shouldn't do the training. The program is forcing adult learners to do the stuff that they did in high school to get good grades. They won't do at their job when the reward of doing it good on your job is more money for salespeople, it's kind of crazy that they won't take it seriously. So you build a program to help them have the discipline to take it seriously. And that's how you get people to actually progress and get the benefit. And then you have to build a culture of people that want to get better. I would say at outreach, you know, I had 150 or so some odd AES. There wasn't one AE that wasn't like, I'm getting better today. And everybody was dedicated to getting better. And so if one person was killing it and negotiating call, everybody wanted to see how they were doing it. So that's what training can do for you if you build a program and a culture around it. But if you're just doing training cause your CEO or your founder is like, we need to train people on this competitor and you do a training and you spend all this time putting a deck together and you expect people to get out of it. It's just like you sitting in your favorite math teacher's high school class and do an email while they're teaching advanced calculus. You're effed.
Look, I love my enablement people, but it's gotta be freaking tactical. That's why you listen to this podcast and all of the fluffy trainings, they freaking suck. So the best thing that you can do as a manager or as a leader is you can create a structure for a training. For example, for this call or for this playbook episode, we broke it into onboarding, training, external training, etc. But then you need to get your top reps filling in the gaps and actually helping you bring out the secrets from the field. Because that's going to show one, the real stuff, but then two, it's going to show that the elite reps can get involved in the training and make it fun. And the other thing that I would recommend to Mark's point is don't just do a bunch of stupid classroom style trainings. Do one training a month, that's the video on the jump shot. And then for the next four weeks, pick one place that you're going to reinforce that jump shot. So you want to make sure this isn't this boring academic exercise where people are slacking around because they don't want to listen to your stupid product marketing leader. Do something. You want this to be something that actually works in the game and you want people to get in the game as soon as humanly possible. All Right. So on that note, there are a lot of people who are die hard med pick command of the message, force management people. What is your overall take on bringing in external trainers? AKA should you bring them on and if so, when or what situation would you bring them in?
So I brought in external trainers a lot in my career. I've also resisted suggestions to bring in external trainers. And for me the way that I do it is, is one is do we internally know how to do this? We just need to operationalize or codify it and then train people on how to do it. And is there somebody in our own organizations that's already a master at it or is this a skill or a concept that we just don't even have in our DNA that we need to inject in? So when it's we don't have it, you got to bring it in. When it's you have it, you should just develop what you have and do it. The other reason that I bring in external traders is to validate things that we're already doing. And so for example, Skip Miller's concepts are a big part of how I explain how to do deal bait or stage based deal management. And so I bring Skip into my orgs as a third party validation to reinforce the things I'm talking about as an external voice. So it's just not me and my leaders and reps talking. So yeah, I think that if you don't have it in your DNA, you gotta do it artificially. So you bring somebody in and if you already have stuff that's working really well, but people need that extra legitimacy, then I would bring in somebody external to reinforce something that you already have. But I think usually if you have a great skill and someone that does it great, the best option is to sew into and invest into that skill and codify it, operationalize it and train on it internally.
Yeah, I think oftentimes people will be like, I'm going to bring an external trainer and they're going to solve all my problems. I think every sales leader should be able to get on a call. In Tango. I used to love cold calling with my reps and showing them that I was still in the game. But one thing is for sure, you cannot have external training without having internal training and internal coaching. So whatever you get from these external trainings, you need to turn it into your internal version for your company. And you need to make sure that if you're going to bring in medpic, it's up in your salesforce stages, it's in Your deal reviews. If you're going to do Sandler, you need to be reviewing upfront contracts and all of your deal reviews and in all of your sales calls. Because if you just bring in one of these external trainers and that's it, you are literally just going to burn $50,000 for no reason whatsoever every time. All righty mark. So the last thing, everyone's favorite topic, documentation. Where do you keep track of all this stuff?
So I have a saying, process makes you great, documentation makes you legendary. I think that you have to have some kind of system where you're documenting things. I don't know if it matters. It could be Google Docs notion. It could be an LMS like seismic or high spot or something like that. It just depends on how fancy you want to get with it and what all you want it to do. I will say though that wherever you start to capture it, it needs to have an AI component that doesn't make someone have to like know how to navigate to the right thing or search for the exact thing. Like oh, I'm searching for qualification and I just got 93 seismic articles. And that's a really strong application of AI is to have, hey, this is where we put everything. You just ask the AI the question and the AI will sort all the stuff out and figure out what you need to do to deliver an answer. But let's just get it documented and then have AI help us organize it the right way.
Yeah, I totally agree that a lot of people will lead with the system. They'll be like, we're investing in training and enablement, let's get an lms. And I actually think that's the biggest mistake in the world to introduce another tool. I think you should start with your existing tools that could be a Google Doc. KD on another episode literally talked about, anytime you're doing some sales process, write a five bullet checklist of when you're setting an agenda. Say these five things. You don't need an enablement person even if you don't have one yet. But it helps if you have one. But it's as simple as just documenting the steps to any given process. The other thing that I would recommend is organize all of your materials in chronological order and just paginate things in a way where a rep can be like, okay, first thing I want to do is open a deal. I should probably start at step one. I would literally keep them on a notion wiki and then have pages and checklists underneath each of those categories. So it was easy to toggle through. Alrighty folks, no need to go crazy on documentation here. Hopefully you got a couple things around how to structure your onboarding program and your training program. Here are a couple key takeaways. Number one, your onboarding program, those initial six weeks are really that heavy immersion that awareness. Then from there it oftentimes transitions to more of the both doing while learning on the job. From there, Mark went through his assessment matrix which you can find in the show notes where you'll understand one what is the cognitive load required for what you want to train your team on? Low, medium high this quarter and then two how good do you want them to be at that thing? Aware, competent or masters of that? The more high cognitive load things you have and high mastery things you have, the fewer things you can train your team on. Versus if you have a lot of really easy to understand things that they just sort of need to know in a multiple choice QA test, then you can train them on a lot of those things. And then lastly, don't let your external training be a substitute for your internal process as well. All righty Mark, Anything else before we wrap here?
Training is identified as reps in growth, as one of the top things that young reps require want and desire inside of a company. If you don't have a great strategy about how to continually uplevel coach train your reps, you're missing a key component that really great talent expects and wants. And then secondly is our job as a leader can be boiled down to one word efficacy. The ability to effect change. Can you get someone to change their mindset, change their behaviors, change how they think, change their results? Training and having a great program for that is a catalyst for change. It's how you create changes, how you follow through with change. And so I would really encourage you if you want to be an effective leader, come up with your strategy for how you do training, coaching enablement. Because that will help increase what your teams are able to get done and increase your results, but it'll also increase your value as a leader.
Boom. Well, there it is folks. One thing you can do to change your behavior is go check out that matrix that Mark put together in the show notes and stick around for the next playbook episode of 30 NPC Leadership Edition. Cheers folks.
Bye.
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