Episode 237: Dianne Kleber on The Value of Coaching

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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 Dianne Kleber from Paradox join us. Dianne, I would love for you to introduce yourself, and your role in your organization to our audience.

Dianne Kleber: Thank you for having me here today. As you said, I’m Dianne Kleber and I am the VP of sales enablement at Paradox. If you’re not familiar with Paradox, we help companies with their talent acquisition. We do this through our text and conversational ai chat tool and we have so much fun doing this. I’m having so much fun in this role in sales enablement. It’s actually my first official sales enablement role, but I say it all the time, and this is part of my background. I have been a seller, a sales leader, and passionate about sales enablement for my entire career. I started in high school selling shoes at a shoe store and from the moment I sold that first pair of shoes, I’m like oh I’m sold. This is what I want to be doing and have really throughout my entire career been focused on helping sellers be the best they can be through training, coaching, and leadership.

SS: I’m excited to have you here. Based on your experience surrounding enablement and as you mentioned, your experience as a sales leader as well, what is the value of enablement for sales leaders?

DK: It’s so interesting because sales leaders, prior to sales enablement being its own thing, sales leaders had to do it all. They had to absolutely lead teams through all efforts and help them to be the best that they can be. They were even doing training and whatnot. Now, what’s super exciting is this is a team effort. I love the fact that I get to work with the other sales leaders at Paradox and we put our heads together and really try to figure out exactly what our team needs quarter over the quarter so that we can achieve our goals. The value of enablement for sales leaders is, I think number one, that they’re not doing it alone. I know that when I was leading sales teams, even though I was one of many leaders within the company, I felt like I was alone many times. The enablement teams that are now out there, we’re partnering up with those sales leaders and really making a difference. The value of those sales leaders is that they can focus on exactly what they need to do related to deals, deals strategy, and those types of things, and allow folks like myself who can really work on elevating the sales team to the next level.

SS: I think that’s absolutely true that there is a ton of value delivered to sales leaders from enablement. One area where I often see enablement partner really closely with sales leaders is around coaching. I noticed that LinkedIn coaching is one of your areas of expertise. How has your background as a sales leader influenced how you create coaching programs?

DK: Coaching is my passion in both sales leadership and the enablement side. I think the time that I spent as a sales leader has greatly influenced how I’m developing programs now because I was in the weeds and I had the experience of sellers of different levels. There were folks that this was their first job and then there were some that had been doing it for years and years and each of those reps had different needs and skills. The thing that’s beautiful about coaching is that it meets those folks where they are. That’s the goal. Training, on one hand, says, okay, we have this track and we know these folks need this knowledge, whereas coaching is like I want to meet you where you are and help you get to the next place you want to be. By being that sales leader and understanding like I would at one point I was managing 17 individual contributors, which is way too many, everybody knows that, but 17 individual contributors are direct managers. That’s 17, 1 on 1 meeting in a week and every single one was different.

Now, as I work on coaching programs, it’s focused on how we allow each of the reps to be their individual selves to meet them where they are, and the other side of it too is I feel very strongly that everybody shows up really trying to do their best every day. We don’t want to make anybody wrong, we want to help them find the best way for them to be right on that given day. Really, a lot of thought goes into how we create a coaching program that allows that to happen, but at the same time has a container or a space that really allows you to measure the growth and the change of a rep. There are a number of components that absolutely go into that.

SS: As you mentioned there, there are a lot of different types of coaching, You’ve mentioned one on one coaching. Can you share with our audience the difference between one on one and group coaching and your perspective on either the value of both, but in particular one-on-one coaching?

DK: I think they both really have great value. Group coaching, I find, is generally centered around a topic or an event and it relies on peer involvement and sharing of wisdom. I think those are fantastic coaching sessions and an example of that would be, I’ve had some coaching programs where we asked reps to bring a call recording to a session, and maybe it’s around a given topic or it might be a snippet of that recording, and they play that recording and then we all put our heads together on what we heard and how that rep could make it better and just offering suggestions. We do that too with a deal strategy session. Group coaching is really great for that pure brainstorming and shared wisdom.

On the other hand, one thing that I particularly love about the one-on-one coaching is it allows that rep to be the unique seller, a unique person that they are. It also allows them to be vulnerable and authentic. When I’m coaching, I establish this is a safe space and everything that we talk about remains confidential. In a really great one-on-one coaching session that rep can get to the place where they’re like, okay, I do want to get better, these are the challenges I have and they can be honest with themselves, honest with me if they’re coaching with their manager just having that really open conversation. That allows a level of accountability with that.

In one-on-one coaching, I just want to call out two different areas. Number one is skill coaching, that’s things like, hey, I’m struggling with X and I need to know how to do it better. There are things like call reviews, we can evaluate calls and meetings with a rubric and we can have specific skills that we’re seeking. Skill coaching is fantastic and that tends to be a little bit more of a conversation around what I should do is the timing and the pace, you know, those types of conversations. Number two, there’s another layer of coaching that is around growth and this is where a rep is saying, I think I’m doing an okay job, but I know I want to be better, get better, but it’s not a specific skill, it’s more around, well, I’ll be honest, it’s really up to that particular individual, what’s important to them, where they want to go, what they want to work on. For example, I’ve been in coaching sessions where someone just wants to work on just attitude and showing up day after day because sales are hard. We all know this and it takes a lot out of you and you have to really have an amazing attitude day after day how do you do that? Sometimes that’s what we’re talking about is how we bring the right energy to a day, whereas another rep can come in and say I’m absolutely struggling with getting my workouts in and that’s so important to me in my professional life as well as my personal life and so sometimes a coaching session is around how they are going to find a way to get their workout in. Growth coaching is really fun stuff, but skills coaching, at the same time, those little tactical things help make that person better day after day. I love the one-on-one.

SS: I love that as well. How would you say mindset plays a role in the effectiveness of one on one coaching and what mindset would you recommend leaders have when they go into a one-on-one session with a rep?

DK: Mindset is huge on both sides. Let me start with the rep themselves. I think everybody could probably relate to this. You can’t be coached if you don’t want to be coached. The rep needs to show up saying yes I’m here, I’m going to do the work, and I’m going to allow myself to be coached. The flip side of that is the leader. One of the things I know, when I prepare myself for a coaching session, is it’s almost like a little mantra that I say before I even get on a call, I have to give myself the space to let go of everything I was doing prior to that session, providing focus, turn the phone off, step away from everything, but then actually saying to myself, my role here is to help this rep discover all the possibilities for themselves.

It’s funny that coaching is a lot like doing a really great discovery in the sales process and that you don’t have to know the answers to the questions, you just have to know the right questions to ask. The mindset of curiosity I think is the most important thing a sales leader needs to have. I know that there have been times where there’s maybe a day where I’m just not 100% focused and we’ve all done this thing to where it’s like, oh I think I know what they’re going to say next, and make that assumption. If you can have the mindset of curiosity, and openness and I am here to ask the right questions so this person really figures out on their own where they need to go, those are the best coaching sessions. Mindset is huge in this and there’s actually, I would say, for anyone who is listening and thinking about starting a coaching program or bringing more coaching into your leadership role, I would even suggest if you have a day where you’re like, I just don’t feel like I’m ready or I don’t know that I’m in the right mindset, I would say don’t do the session. It’s actually better to say that and say, I think we need to come back to this another day, another time when I’m in the right space to work with you. My mindset is huge.

SS: That’s absolutely fantastic. Do you have some recommendations or advice for the next steps post-coaching call? Is there a process that you use for ensuring that the behaviors that were discussed in the coaching were actually implemented?

DK: I think there are a couple of ways to do this and I’ve done it a few different ways. My favorite is having the rep hold themselves accountable, so creating an accountability plan that we co-create. I could certainly set up a number of accountability structures, but really if the rep wants to have change and really grow, they are the ones that need to create the accountability plan. I like the method of let’s co-create, what’s the plan that you need to or want to follow, and then even going as far as seeking an accountability partner. It’s one thing to say to your sales leader or coach if you’re working separately with either a leader or a coach or both, something to say to them, but then it’s another thing to say it to appear as a friend. An accountability plan can look a lot of different ways and a lot of times requires some visual triggers or cues. Some folks like post-its, some like notepads, and some like images that they have to put up, like what is the cue that you need to put in place to remember the habit that you’re trying to create here.

The flip side of this is that in an actual structured coaching program, there could be an actual document. Just like I’m a huge fan of sales one on one meetings which are different from sales, one on one coaching sessions but having some kind of a document where everybody’s keeping track of what we talked about and it’s a shared document that both the sales leader and the rep can access and reference. Same with the coaching, having that accountability plan but also having a document where you’re keeping track of what are the behaviors, specifically when we’re talking about skills coaching because skills coaching, as I mentioned before, I’m a fan of a rubric, especially if we’re evaluating calls or a manager sitting in on an actual meeting, let’s have that rubric, let’s document that and actually document what that rep wants to work on so that you can go back the next time and say, okay, how’s it going and really see if there are other tactics and other things that we need to talk through.

SS: I love that. Last question for you Dianne, how can coaching impact sales productivity?

DK: It’s funny that you ask this because I just had this conversation with our CRO last week. I have certainly in my career seen a lot of different methods for increasing or impacting sales productivity. Training is obviously huge. There are certain things that everybody needs to know to become more productive. Tools and technology are such a huge part of sales productivity and making sure that every team member knows how to use those tools is so important. I think, especially with newer reps, and what I mean by newer, it could be someone early in their career or someone new to the organization, which we’ve had this huge growth at Paradox, so we have a lot of folks who’ve joined the team in the last 6-9 months, and one on one coaching, I think actually has the greatest impact on those newer sellers. Really working with them on both the skills as well as the growth and taking the time to meet with them is important. It’s like the 1% rule. If you can get 1% better every day then by the end of the year you’re going to be an amazing space.

Coaching can impact not just productivity but actually can impact the end results and revenue. I think any organization if you have those new sellers or reps who are going along in their career and get a little stagnant, coaching can take them to the next level where they learn some new tricks. You can teach old-selling dogs new tricks and become more productive. I really think it has a huge impact and if I could say what would be the best thing you can do for your sales team, it would be to work in a coaching program if you don’t already have one.

SS: I love that. Dianne, thank you so much for joining us today and sharing your insights on coaching. It’s been a fantastic conversation.

DK: Thank you. It has been such a pleasure as you can probably tell, I love it, I’m passionate about it and it makes me want to go and coach someone.

SS: To our audience, thanks for listening. For more insights, tips, and expertise from sales enablement leaders, visit salesenablement.pro. If there is 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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