How to Unlock Your SDR Team’s Potential with Training & Coaching [Webinar Transcript] 

Not too long ago, we were delighted to welcome the top sales development experts, practitioners, and enthusiasts to our annual online conference — Sales Development Excellence. This single-day virtual event, packed with expert panel discussions, masterclasses, and hands-on workshops, covered the key aspects of sales development mastery. 

The third panel discussion of the conference was dedicated to an integral part of sales leadership — training and coaching SDRs in the modern-day landscape to help them unlock their full potential. They say a team is only as good as their leader, and sales is no exception. 

We had the pleasure of welcoming the following esteemed sales leaders to this panel: 

• Bethany Stachenfeld, Co-founder & CEO, Sendspark
  
• Stuart Moss, Director of Sales Development, Dealfront 
• Jason Bay, Founder & CEO, Outbound Squad

You can watch/listen to this panel discussion as well as the full conference following the link above, but in case you prefer written content — here’s the transcript for you to read through. 

Hope you enjoy it!

How has the sales coaching and training landscape changed over the past couple of years? And has it changed at all, in your opinion? 

Stuart: I certainly think it’s changed. I think the landscape will always keep changing and evolving. I think the difficulty is that not every organization can easily keep up with that pace of change, I think that’s always really difficult for organizations. 

But I think the change is often driven by the recipient of coaching and learning, and their expectations of that material or learning that they’re getting. 

It’s good to be at Sales Development Excellence because SDRs are actually a really easy group to demonstrate that point with because it’s fair to say that a large percentage of SDRs are typically earlier in their career. 

They’re typically, though not always, a younger audience. And how young people consume knowledge is vastly different from how I would have consumed knowledge at their age because things change so quickly. I would have never had YouTube or TikTok or learned from Joe Rogan’s podcast, but now that’s all I learn from. And my SDR team is exactly the same. 

Because of that, the landscape constantly shifts and there’s little value in trying to coach and train people in ways that just don’t resonate with them anymore because that’s not the way the world is. So, yeah, I think it has shifted, and I think it is always going to shift. And one of the challenges that we have as leaders is keeping up with that and making sure that what we do is valuable for our teams.

Bethany: I think that’s a great insight. And I’d also add that just over the last few years, the world has changed a lot. It’s hard to even remember, but before 2020, most of us were working in an office. Now, a lot of teams are remote or hybrid, and so just the way that people are learning is really different. And also the way that people need to sell is very different. 

So we’re talking about this specifically on how are SDRs selling and connecting to people. There’s been just dramatic shifts in the industry over the last few years, and even now we’ve seen a greater drive to efficiency. 

So I think that you’ve always got to think about when you’re training, how are people consuming information and what are they consuming? 

And yeah, the pace of change over the last few years has been just astronomical. 

Jason: I think that the principles of how you train and teach, and how people learn things hasn’t really changed the medium. Stuart and Bethany, I agree with your two points and I think attention span is a really big thing to pay attention to. But I have a bit of a different angle on this. 

The frontline leader is the one delivering most of the training and coaching, and enablement plays in that, I think that that job has gotten much harder because of all of the distractions. To give you an example, working in a virtual environment when you were used to being in the office, I work with teams where frontline leaders are getting bombarded on Slack by their leaders, asking for updates every 20 to 30 minutes. And then they do that to their team. 

And it’s really hard for them to set aside half an hour here, an hour there, to just coach, to do proactive coaching — the thing that every frontline leader should spend a third to a half of their job on, working with their reps.

And I find that, especially in software right now, where there’s so much pressure to get outcomes. They’re getting so much pressure from the top that they’re not able to make that time to actually do the coaching. 

The only other thing that I would add too is that social media plays a big part of it. Just like with our phones, when I ask people, if you got a text right now, would your phone vibrate? And everyone says, yeah, it would. Well, why? 

So if you got a text as this frontline leader, who would you be responding to a text from that’s urgent enough that you need to respond to in the moment. There are so many distractions like that that I think make it harder to do your job now, and protecting your attention is really the biggest challenge.

What role does technology play in SDR training and coaching in your companies? Are there specific tools or platforms that you found improved your training processes and allowed for more effective coaching?

Jason: I think we could do with less technology, actually. When I work with reps and sales teams, when I see them share their screen, there’s usually like five different tools right in their Chrome shortcuts bar. They’ve got to log in and out of all of these different tools, there’s rev intelligence, conversational intelligence, there’s their sales engagement platform, and we’re starting to see some consolidation. But podcasts, YouTube, I mean, that’s the kind of old technology, it’s been around for a long time.

I think the stuff that’s gotten pretty cool is the conversation intelligence has gotten smarter to where you can put trackers and stuff so you can see without having to listen to a call. Is the rep using the new talk track that we talked about? And I’m pretty bullish on AI not really being that great for cold email right now either.

I don’t really see coaching from AI happening very well right now. I think it gets you like, maybe 70, 80% of the way there if you have a lot of the good inputs. But I would say from a technology standpoint, I think we could strip away some of the technology and just get really back to basics.

Like, are you even listening to recordings of reps making calls? Are you using the conversational intelligence tool to look through transcriptions? Are you looking at the emails that they send? I’m just really bullish on getting back to the basics, honestly, with this stuff and stripping away some of the technology and making it easier to do the thing that you really need to spend your time doing.

Bethany: I like your point about focusing on the basics and removing distractions, I definitely agree. But I’m going to say there’s definitely some technology that I found is just a huge time saver, even if not necessarily for our team to use, but for me to use on the analytics side of things.

So one thing that comes to mind immediately, we just got our company set up with June.so for data analysis. And what’s really cool about that is it lets us tie in conversations or outreach strategies or different things. We’re doing top of the funnel to see how that connects to revenue. That lets us optimize campaigns.

So our team’s not really looking at the data, but I am, and so that’s helping me steer people in the right direction. 

And then when it comes to conversational intelligence, I totally agree. We’ve been testing out a few different tools, and the two I like the most at the moment are Update AI and Fathom. With Fathom, it’ll alert you if you talk too much, it’ll be like you’re on a monologue, stop, and let the other person talk. 

So I think things like that where it’s helping people in real-time, or at least afterward, you can go through the transcript, go through the data, kind of figure out some insights that let people continue to improve.

And then, of course, I’ll do my own shameless plug for Sunspark, just being able to record videos and show people like, hey, this is how you update this specific thing in Reply, or this is how you embedded a video here. This is how you fix an account. 

And then having all that information tracked in a reusable way, you’re able to watch the video. Saves me a ton of time, so I only have to say things once and then other people can look it up in the shared video folder. So those are some of the tools I think have been absolute game changers, but always love trying out new things. 

Stuart: I think, Jason, you made an interesting point about AI and email writing. I think some of the challenges, people just lean into the tool, doing the work for them rather than using it to assist. If we were talking about email specifically, I think tools like Lavender are pretty cool for actually helping coach you and understanding how you can improve along the way.

You get kind of those scores and grades so you can see yourself improving and you almost end up competing with yourself. So I think it’s how it’s used alongside coaching and learning that can make the difference rather than expecting the technology to do the job for you.

At Dealfront, we are trying to make much more of a formalized learning for people. So part of what we’re doing at the moment, for example, is building out an SDR university and an outbound academy in a tool called Highspot. So we can kind of have on day one you learn this, on day two you learn this. And within that, we’re being considerate of everyone learning a bit differently.

We’ve got a bunch of videos in there and written content. Some of it is tasks and learning on the job, but it’s trying to mix up different ways that you can learn and absorb because everyone’s different. 

And I think that’s one thing a lot of companies miss is they leverage technology as a one-size-fits-all and they slap learning within it and say, wham, there you go, learn, and then wonder why people aren’t as engaged with that learning along the way. 

So we’re trying to leverage technology to best mix up our learning for our SDRs so that there’s something for everyone and it can be absorbed along the way.

What specific coaching techniques have proven successful specifically for you? Is there any approach that stands out? 

Beth: The first thing that comes to mind is the philosophy that we have which is just really learning by doing. 

I feel like there’s a ton that you could train someone and prepare them for, but the best way you just learn is by being in the same situation again and again and again, and ideally feeling confident that someone else is there to back you up or help if needed and support you.

But we just want people to learn on the job and then get feedback immediately after, and then try again. There’s a study I read forever ago that stuck with me about two art classes where people needed to build clay pots. And in one class they were graded on the quality of the clay pots. And the other one, they were graded on quantity. And the ones who try so hard to make it perfect, their pots were way worse than the ones who just rapid fire were creating pot after pot after pot because you learned by experience. 

So that’s the environment that we try to set is like, it’s okay to make mistakes. Just keep trying and be out there and get feedback and keep iterating and improving.

Jason: So, I think the frontline leader is the most neglected position. Typically in the sales org, they get the least amount of training, it’s usually a top rep that worked up, and they get zero training on how to actually teach stuff. Rain Group has an interesting stat — reps forget that 85% to 90% of the training that they get is no longer effective after a quarter.

The reinforcement of the stuff that you teach is the more important part of the equation. So I have a framework that I teach to frontline leaders called the reinforcement loop. It’s very simple: teach, practice, observe, and coach.

So teaching is different from telling. So I can’t just say, hey, George, instead of sending this email, why don’t you send this one? That’s not really teaching. You’re not giving someone the ability to fish. You’re just telling them what to do. 

Practice is the most neglected piece. A lot of times in sales we practice on prospects. We try something for the first time in a live high-stake situation so that’s everything from role plays, which can be done in team settings, one-on-ones, etc.

The observe piece, so actually taking time to watch the rep in action, and then deliver coaching. And you got to do all of those things. The most neglected pieces that I see are the practice piece and then the coaching piece.

What kind of feedback do we have, what scorecards do we use? Do we create an environment where a rep can self-diagnose their own problem and attempt to help themselves? That would be the framework that I would recommend, looking at those four pieces and kind of grading yourself in each of those areas.

Stuart: I think one of the things that I’ve found works really well is, at Dealfront, when we email people, it’s hyper-personalized. That’s just the model that works for us and gets us really good results. 

And so one thing we implemented during our onboarding process was essentially part of that learning by doing, but in a non-pressurized environment. 

And so our new SDR hires as part of their onboarding will use the Deal front platform to go and find 10 or 20 or 30 prospects in their region in the right markets, the correct ICPs, and then use the model that they’re taught to write outbound emails to those people. 

They then send those emails to the SDR leaders or team leaders like they’re the prospect, who will then provide feedback and critique them, and throughout the onboarding process, the SDRs will iterate those emails and continue to kind of revise them until they’re happy and comfortable with them.

And at the end of the onboarding model, those are the emails that they send out first into the field to their actual prospects. And so it’s that learning by doing, but just using that email part as an example and how we coach that, I absolutely stand behind that as well. I think that’s the right way to do it.

How do you balance training and coaching versus actual work and actual daily responsibilities of SDRs? Ensuring that they have enough time to learn, but also to generate pipeline and everything that we hired them for. How do you find that balance? 

Jason: The general strategy that works pretty well here is less teaching. So, fewer topics going deeper, and then more time coaching and reinforcing those topics. So assuming that a rep is out of onboarding, and they’re ramped, instead of running three sessions this week where we talk about email and then subject lines, and then we talk about objection handling, let’s pick one thing to work with the entire team on.

So where’s the biggest bottleneck in my team? Is it email?  Is it phone? Is it objections? Whatever it might be, in my one-on-ones, I’m going to pick the biggest bottleneck with that rep, and then I’m going to spend the majority of the time reinforcing what we just trained. 

That’s proactive reinforcement –- that’s literally outside of the meetings, listening to reps doing the calls, shadowing the calls live, looking at the emails they’re sending, sending that proactive feedback, asking them to self-assess, etc., and bringing that feedback to them outside of those sessions as well.

I would highly recommend not doing more than two or three group-style team meetings per week. Typically, one of those would be spent reviewing or breaking down a good example of this and providing some feedback on it so reps can see it.

One of those meetings might be pure training and skill development, and then you might use another one of those just for touching base and accountability type of thing, and just really keeping the internal meetings as few as possible. And training should be very narrow in topic and very deep in focus.

Beth: I have a similar mindset where it’s really about the narrow focus. And what I try to keep mine is how relevant is what people are learning to what they’re actually doing. 

Because if you teach something and they’re not actually doing it for two weeks, they’re going to forget it by the time they actually do it.

So it’s really about just going in, maybe this week we’re working on adding video to a sequence or something. And so it’s just going all in and doing that really well before adding different things. 

I don’t like to pre-teach like, oh, here’s a whole lesson, learn everything. Learn all of our systems all at once. It’s just trying to do a very neuroscope, do it well, and only then add more. And that way people feel confident the whole time and are able to practice right away. 

Stuart: Yeah, I think looking at this from a slightly different angle, I think it’s up to the leader to intelligently balance people’s calendars a little bit when it comes to training and coaching, putting time in. Putting training at 10:30 a.m. every day if that’s when your SDRs typically smash the phones and statistically book the most meetings is a bad time to try and book training sessions. 

But I think SDRs are mostly taught cold calling, emailing techniques, social selling, and stuff that revolves around that, and then their day-to-day responsibilities essentially revolve around speaking to prospects.

So there’s the perfect time to try and apply and test those things out that you’ve been taught, hopefully at an intelligent time of the day to do it, because it’s fundamentally your role. So it comes back to that learning by doing.

I think that’s the challenge, though. I think some SDRs struggle with that. I personally know some SDRs that could beautifully articulate the best outbound model in the world, but rely solely on inbound and do very little outbound. And so it’s actually applying what you’re learning and doing it.

And whilst a leader can help coach you and push you, the greatest SDRs absorb knowledge and then just continually test it and augment that with stuff from YouTube, podcasts, and books that they read to then just outpace other people because they can apply that additional knowledge.

So I think some of this lies on the SDR themselves being motivated to take that learning, test it, make it their own, and then deliver against it. But the leader absolutely has the onus of making sure they’re balancing an SDR time and not being disruptive and doing it at a good time. That means the SDRs can take that, use it, and apply it to be successful.

How do you measure the ROI of coaching and training efforts? Do you only look at obvious things like meetings booked and revenue generated by those reps, or is there anything else? What are your best ways to measure whether the coaching efforts are efficient? 

Stuart: Yeah, I think one thing I always do with my SDRs is get them to zoom out a little bit. And I always use the terrible analogy of if you’re trading stocks, right? Unless you’re a perfect day trader, which I certainly am not, if you’re constantly looking at the chart, you will have a heart attack 15 times a day at the ups and downs.

But actually, if you zoom out and you leave your investment there for a while, you can see where you started and where you got to. And usually, that journey is quite inspiring and you become proud of it. And I think SDR training and coaching are exactly the same. 

If you zoom out a little bit with SDRs and think about: Where were we? What did three months ago look like? How were we working then? And what does today look like in terms of the quality of your meeting, the velocity of those meetings, the outcomes that we’re getting, dispositions and sentiments of calling, the response rate you’re getting to your emails, and positive responses. 

Actually, I think taking a moment to step back and having a look at it can be and really understanding where you were and you’re from and you’re to essentially is one of the most sobering things, and SDRs are typically really proud of that journey that they’ve gone on in a really short amount of time as well. 

I think SDRs also forget how quickly they learn stuff and deliver against it and the value that they’re delivering for an organization. So I think with SDRs, one thing I really like to do is just take a step back with them from time to time and assess those things with them.

Bethany: Of course you’re looking at how well they are performing on the job — meetings booked,  leads, things like that. But I would say when I think of coaching, I’m really looking at how the employee should be progressing through the organization.

And I’d say, especially Sendspark — we’re a startup, we’re a small team. A lot of people have a lot of responsibilities, and there’s a lot of different ways for upward mobility that depend on that specific person and what they want. Do they want to be a manager or do they want to go to be doing enterprise sales or do they want to be doing webinars and public appearances? It’s like, what do you really want?

And so before I hire people, that’s an important part of the interview process — I try to figure out where they will be moving in the organization if everything goes well, what do they want for themselves? 

And so then when I’m looking at how the coaching, the onboarding, all this integration is going, I focus on whether they are on track to hit the goals that they want for themselves and that I envision them doing in the organization? So I’d say that’s the secondary thing that’s important and important for employee retention and satisfaction.

Jason: Effort, efficiency, and effectiveness. I think what’s really important when you are training and coaching as an enablement team is just to think about what are the key behaviors that we are looking to drive, what would make our efforts a success? I know it sounds very simple, but a lot of times we just do training for the sake of training.

Effort is one of the leading indicators. That’s a great way to see if behavior change is happening because behavior creates the outcomes. 

Efficiency is if we’re getting reps to send more emails or make more calls, are they getting through, are people picking up, are they getting replies, are they getting opens? 

Then, ultimately the effectiveness, what are the outcomes of that? You can apply that same framework across sales development or the work that you’re doing with AEs as well.

I think the big thing is to know what you’re actually trying to make an impact on and what those key behaviors are that drive the outcomes, and to focus on the behavior. And measure it, which you can do with all the technology that we talked about today. You can measure the behavior.

Watch the panel discussion (+ more) on-demand

Check out more Reply events with industry experts:

• Cold Email Deep Dive

• Sales AI Summit

• Sales Development Excellence 2022

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