Episode 101: Steve Maxwell on Partnering with Frontline Managers for Valuable Sales Coaching

Shawnna Sumaoang: Hi, and welcome to the Sales Enablement PRO podcast. I am Shawnna Sumaoang. Sales enablement is a constantly evolving space and we’re here to help professionals stay up to date on the latest trends and best practices so that they can be more effective in their jobs. Today, I’m excited to have Steve from Cloudera join us. Steve, I would love for you to introduce yourself, your role, and your organization to our audience.

Steve Maxwell: Yeah, thanks Shawnna, I’m glad to be here. I’m Steve Maxwell and I lead the sales enablement function at Cloudera, which, for any of you listening to the podcast who might have come across me before as a rejoining of Cloudera, I was involved with a startup recently called Datrium, and we’ve been recently acquired by VMware, so I had the opportunity to move back to an old organization that I led in the past, which is an exciting opportunity for me today. I’ve been in sales enablement for longer than it’s been called sales enablement, former salesperson, sales leader, and I’ve been in sales enablement for more than 20 years. I’m so happy to be here today.

SS: And Steve, you and I have also known each other for a while now, so I’m really excited to have you on our podcast today. In fact, a few years back, you spoke at one of our Sales Enablement Soirée events, and you had talked about the importance of partnering with frontline managers, right, in order to scale your sales enablement function and its efforts. So how can sales enablement practitioners ensure that sales managers are really well aligned with the goals of sales enablement? Also from your perspective, why is that necessary?

SM: Yeah, it is a critical one and as sales enablement practitioners, we struggle with this all the time. We could have all sorts of research and analysis and discussions and sales leaders say ‘Yes, we need to have our sales team trained and better enabled to be more productive,’ but that last mile of making that actually happen is a lot more difficult. Sales enablement teams are generally small relative to the size of the organizations that they support. So, we could come up with great programs– even in a pre-COVID world, where we were doing workshops in the field and you have events all the time and you’re working with people in the field, et cetera– but there’s only so much the enablement team can do.

Having sales leaders be bought into the programs that we’re running and the outcomes that we’re trying to drive is absolutely critical to the ultimate success. I mean, you might have short term blips in performance improvements or great feedback from you running a session where people say, ‘Oh, that was great’ and rate it on a scale of one to five or one to 10 or however you’d want to do it and people say, ‘Oh, that was fantastic’. But then it oftentimes dies out because there is not that support from frontline managers. So it is really, really critical.
The things that I found– well, the necessary part is easy. I think everybody has come across experiences or have had experiences where everything went great and then it died. And the necessary part is sales leadership aren’t involved or worse, say they’re involved and just don’t– what I call the pocket veto. They look at you and say, ‘Yeah, this is going to be great.

Let’s do that’, and then they just don’t. So, getting leaders and managers aligned with the outcomes of the program, what those outcomes are going to be, communicating what those are, getting the buy-in in advance of running any program I think is always critical to driving the performance improvements that you’re looking for.

SS: Absolutely. Now you mentioned the pocket veto and I loved that analogy, but what are some of the other challenges that you faced in getting buy-in from frontline managers for sales enablement initiatives?

SM: There are some obvious ones, and I’m sure every sales enablement professional listening will know this one, and that is priority. If I’m a frontline manager and my boss, my VP, or RVP, or even CRO says to me, you know, ‘Make a choice between making your number and running this enablement program’. I think that’s an obvious one. So if they’re in the middle of forecast calls, it’s getting close to quarter-end, then it’s QBR time. All of these other competing priorities are difficult ones to overcome. So making it an ingrained part of the culture of the organization is important to make that happen because those challenges are hard to overcome.

That’s not necessarily the challenge of getting buy-in, but that’s getting execution. The challenges of getting buy-in specifically are, do they really believe in it? And having an ongoing dialogue– I’ve always had an enablement council, made up of leaders, frontline salespeople, presales engineers, marketing, et cetera– to constantly communicate and get their feedback on what is needed.

We all do surveys, we’ve just recently at Cloudera done what we call a competency assessment. So really asking the sellers of all role types to assess their own skills in these various competency areas that help drive priorities. Now what we’re doing is going to that council and saying, ‘Okay, this is what the data show. How do you want us to proceed? What things do you want us to make sure that we do first?’ and when you do that, it’s easier to get that buy-in too. If you just go off and create things in a vacuum and then just bring it to the sales organization, a lot of times you’ll get pushback, or you get the pocket veto.

SS: Absolutely. Now, one area where sales enablement will often work very closely with frontline managers is around sales coaching. Now, how can sales enablement better enable frontline managers in order to improve coaching behavior?

SM: Yeah, I think the thing that we’re trying to do with that– and I’ve always tried to do with that– is to get the managers involved in the coaching process. There are lots of tools out there, lots of technology that’s being developed, to better enable and track and understand what good looks like, et cetera. Those kinds of things are important to employ, I think, but even if you don’t want to go down the path of that technology, there are definitely things that enablement teams and leaders can do to help their managers coach reps better.

And that is A.) to understand what you’re trying to coach them to do. I’ve made a shift over the past few years in a more broad enablement discussion of what our enablement leaders need, need to do, what they need to focus on away from what do we need our salespeople to know to what is it that we need our salespeople to be able to do?

And if you do that, then it’s easier to fine-tune what it is that you’re training them on, what programs you need to develop, how you’re going to have those reps demonstrate that they understand how to do those things, whether that’s a sales presentation, whether it’s an elevator pitch, whether it’s the new messaging for this upcoming product release, whatever those things are.

Then even into onboarding, what do they need to be able to do after 30 days, after 60 days, after 90 days, not what they need to know. If you do that, it’s easier to coach that. Now, if I go to my managers and say, ‘Okay, Steve’s a new hire, he’s coming up to his 90 days, here’s what he needs to be able to prove that he can do’. Now I can help that manager coach to that. I can provide an analysis form with the behaviors you’re looking for, what the scale is, what the subjectivity is, what you can do to support that as a way of helping that manager coach that rep to do something because if we just leave it up to them, then they become one-on-ones about deals and they’d never separate the opportunity planning, the opportunity reviews, the territory reviews, et cetera, from actual coaching. I think a lot of things that we can do as enablement practitioners is to provide our leaders with what you want them to be coaching on and how to do it and the forms and the feedback and everything, and then it’s much, much simpler for them to actually do it.

But again, that goes back to the pocket vetoes and all the other kind of stuff. They’ve got to want to do it. They have to see that it’s a critical part of their job, and the more that becomes part of the culture there, the easier it is to do.

SS: Absolutely. Now, for those listeners that may not have had to establish a sales coaching program, yet, from your opinion, what are some of the key components of an effective sales coaching program?

SM: I think there are a few really important ones. As I alluded to a little bit before, one is what do you want them to coach on? Is it purely about professional development? Is it about how to manage a territory? I think the components of a good coaching program are aligned to what the goals of the business are, what the goals of the sales organization are. Do we want to grow our reps? Do we want them to be able to manage large territories, named accounts? Is it small, medium, large? Is it industry-specific? You know, all these kinds of ways that people organize their sales teams.

Then, what does that coaching look like? What are the things that we have to do? And what’s the cadence, the execution steps that you want to be coaching on? And then, how are you going to do it?

What we’ve done always with the coaching form is to provide here’s the three things that we’re coaching on this week, here are the activities that you’re going to be responsible for reporting on how it gets calendared. The more you can provide this as a checklist step-by-step, almost pre-set up for them, those are the components that you need to have to drive the coaching program execution. The things that you want to coach on will always depend on the goals of the organization, where that individual is in their journey. I coach different people differently based on what their strengths are, what their weaknesses are, what projects they’re working on, even.

So maybe I’m talking to leaders about coaching a rep, who’s just moved into a named account role from a territory role and how they set that up is different. Maybe, you’ve promoted a rep to the field from an SDR role, so the coaching on that is maybe a lot just about time management, because now they’re not focused on making a hundred dials a day and setting up meetings, it’s about managing and building a territory. I think the components of the program itself have to be set up in advance. Otherwise, frontline leaders just tend to not do it. They turned those coaching conversations into deal reviews.

SS: Absolutely Steve, I’ve loved this conversation. I have to close on what I think most people find as a very tough question, so I look forward to your answer, but how can you measure the impact of coaching?

SM: Yeah, that’s a tough one, and we struggle with it as well, because, even in enablement, we try to measure everything right. We try to measure, and work with sales ops on the traditional lagging indicators of enablement, which are, are people making their number? Are they generating pipeline? What was the time to their first deal? What was the time to their second deal? What was the time to their first brand new logo? What’s their discounting percentage? Their sales cycle progression, all these things you can measure. but those are lagging indicators.

So now in enablement, we try to say, well, what’s the rate at which they’re consuming enablement assets? What are they doing on the training programs that they roll out? If you’re doing a certification exam, what’s their score? How are they consuming potentially other enablement assets and materials that aren’t assigned to them from your LMS system? And we try to draw correlation from those things to those performance measures.

Coaching is a similar one. It’s almost like how can you measure it? Are you measuring if it’s not happening? Are you measuring if it is happening? How do you tell if the coaching itself delivered an improved result?

I think the things that we try to do is to say, if somebody’s performance was tracking at a certain rate, and you implement a coaching conversation with that rep and you see what that particular person might be coached on. If it’s that this rep is having a really hard time generating a pipeline or just doing the activities that are related to pipeline generation, and you implement a coaching conversation with that rep about those things– ‘Hey, I’m going to coach you on better time management. Maybe you need to do your core PG activity on a specific day, or maybe we want to have you do call blitzes with your partners to generate pipeline’– and as you coach them through how to do that and the progression that they’re making on it, and you see pipeline growing, you can probably draw correlation there.

If it’s more general coaching on just developing a reps professional development, or helping them just be more focused on the tasks that they need to be better at in their day-to-day job, you can observe certain things. It’s hard to get a lot of data on it. So, I think a lot of the coaching becomes a look them in the eye, talk to the leaders, is it getting better? Where are you seeing improvement, where are you not seeing improvement? And then just keep doing it. So, it’s almost like– again, it’s hard to measure the positive impact, but it’s probably easy to see when it’s not happening.

If you can’t draw a direct correlation, but it’s still improving, then I’ve always said to my leaders, ‘Let’s just take credit for that. Let’s just say the coaching is helping’. It can’t hurt, but we know it’s got to be helping if you’re doing it right. If you’re seeing the performance improvements, if you’re seeing attitude changes, if you’re seeing upticks in the right kinds of activities that are driving engagement with their customers and that is part of what that coaching conversation is about, then take credit for it. Then communicate it. Share across the organization that coaching is working, start to build a groundswell of support for others maybe taking a different approach, or maybe they kind of put away the pocket veto and start to change those one-on-ones from territory reviews and account reviews to proper coaching conversations.

SS: I love that. Thank you so much, Steve, for joining us today, I enjoyed our conversation.

SM: Yeah, I did too. Thank you, Shawnna.

SS: To our audience, thanks for listening. For more insights, tips, and expertise from sales enablement leaders, visit salesenablement.pro. If there’s something you’d like to share or a topic you’d like to learn more about, please let us know. We’d love to hear from you.

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