39. The Art of Debrief: Building a Winning Sales Culture

[00:00:05] Welcome to B2B Sales Trends, the podcast dedicated to sales leaders in the B2B space, where we share conversations about innovative and successful sales transformations to keep you up to date on the latest trends. This podcast is brought to you by Global Performance Group.

[00:00:22] Welcome yet to another fabulous episode to the B2B Sales Trends podcast, the show that brings you hacks, tips, thought leadership for sales, marketing, and customer success.

[00:00:35] My dear people, it's brought to you by Global Performance Group. We are a revenue improvement boutique that implements behavior change for salespeople to sell with confidence and competence and courage to negotiate and position based on customer and prospect outcomes.

[00:00:55] We solve three problems for our clients, which is increasing the win rates, reducing their sales cycles, and protecting their margins.

[00:01:05] My name is Harry Kandelbacher, and today I have with me Stephanie Wilkinson.

[00:01:10] And Stephanie is the CRO of the Simpro Group. Welcome to the B2B Sales Trends podcast, Steph.

[00:01:19] Thanks, Terry. I'm super excited to be here.

[00:01:21] As a form of introduction, Stephanie, if you could share a little bit about yourself, where are you at and what Simpro Group does, that will be fabulous.

[00:01:31] Yeah, so I joined Simpro Group about a year ago.

[00:01:36] Simpro Group is in the field service management space, and we are a company that started out of Australia but expanded into the UK, expanded into the US, and we're continuing to expand in revenue, expand around the world, expand kind of in functionality.

[00:01:51] And when I joined Simpro, I took over sales, implementation, support, and customer success with a goal of aligning the field and making sure that we had that customer-centric viewpoint.

[00:02:02] So, exciting. I come from a varied background of startups and big companies, and so it's been a fun journey to kind of apply that into the growth of Simpro.

[00:02:11] And through our initial call that we had a couple of weeks ago to prepare for this podcast, one of your sort of expertise is the optimization of sales ops and specifically the techniques for refining sales processes to improve customer acquisition and the strategies associated with it.

[00:02:40] Share a little bit, if you would, with our audience some thoughts on that topic.

[00:02:46] Yeah, it's all about getting the new sales in the door so that we can then expand them downstream.

[00:02:51] So, I totally agree.

[00:02:52] And I think there's, you know, three things that come to mind right away.

[00:02:56] And, you know, one of them is how you create that learning mindset in an organization where they're continually improving their craft.

[00:03:05] I think it's really easy for sellers that have been enrolled for a year or two, much less five or ten years, to just feel like they know what they're doing and get in that auto-repeat mode and make a lot of assumptions about what the customer is going to say or what they've seen in the past.

[00:03:20] So, creating that natural curiosity, learning mindset is such a key part in building the culture of a sales team and kind of recreating that culture.

[00:03:29] I think the second thing I'll mention is, you know, on the revenue operation side.

[00:03:35] So, I think it's really key to be able, when you're talking about processes and just running efficiently, you know, our world's changing all the time.

[00:03:42] And when you think about B2B SaaS, like, it's evolving.

[00:03:46] So, we can't get stuck in what worked two years ago or three years ago.

[00:03:49] And technology is changing.

[00:03:52] Buyer mindset is changing.

[00:03:53] Oh, my gosh.

[00:03:54] Even, you know, after the whole COVID, like, everything's changed.

[00:03:57] So, we want to make sure that we're putting in place, like, eyes on not just what we're doing the day-to-day, but also the long-term success and redefining what that looks like.

[00:04:07] And the RevOps team that we created at Simpro Group has been incredible and kind of being that outside view eyes.

[00:04:13] And, you know, they work as a data, applying the data that they're consolidating across my different sales teams into insights for me to be able to come and take action and then roll out improvement and process.

[00:04:24] And I think that goes to the third thing is, if you're in a continually changing organization, because you've got a learning mindset, you've got a great RevOps team, you have to create the art of the debrief.

[00:04:34] Because I think if you just roll out a process and then just let it run, the risk is it's hard at the CRO.

[00:04:42] At the C-suite level, it's very hard to get it right first round.

[00:04:46] So, you've got to be listening to the people in the field about what's working, what's not, what skills are they applying, what's not, what process is working, what's not.

[00:04:55] So, we can take that information back and kind of make those micro-adjustments on a regular basis.

[00:05:01] It's so funny because I think a lot of, I think a lot of sales leaders get in and they're like, here's my playbook, here's what's worked in the past.

[00:05:09] And they put that exact playbook in and want it to work in the future.

[00:05:12] But I do think it's all about that micro-adjustments as you go, just because we're in such a high, fast pace area.

[00:05:19] But that's what makes it fun, right?

[00:05:20] Like, that's probably what a lot of us like about high tech.

[00:05:23] You shared something that intrigued me and we're on a little bit off track here.

[00:05:27] Share with me, you mentioned the art of debrief.

[00:05:30] What are your thoughts on that?

[00:05:32] How would you like your people to behave there in terms of the managers, in terms of the salespeople, the art of debrief?

[00:05:43] So, I'm a big believer that leadership sets the tone.

[00:05:46] But I do think as an individual seller, you can set tones as well.

[00:05:49] Like, you can take that influencer role.

[00:05:51] So, it's not just leadership.

[00:05:52] But I do think leadership sets the tone here.

[00:05:56] And I think there's – I'll give you the negative side first and then what I mean by the art of debrief.

[00:06:00] I think it's easy to – when I first started setting up deal reviews for people to get in and they think they're being audited or questioned or they can't do their job, right?

[00:06:09] And that's such a mindset of, you know, I work independently.

[00:06:13] I do my job.

[00:06:14] I don't – like, I hide my flaws or I hide the things that don't go well.

[00:06:18] I celebrate things that do go well.

[00:06:20] But nobody learns from that.

[00:06:22] And there's no way to kind of expand.

[00:06:23] So, when I first set up deal reviews, like, people were super nervous to come in.

[00:06:27] And what I found is after I get in teams and start doing them for a while, we create a change in culture where people just expect it.

[00:06:34] So, then every time they run into a bump in the road, they're like, I need a deal review.

[00:06:38] And all of a sudden, people are competing to get the time in deal reviews.

[00:06:41] Because what they're seeing it is, is more people gathering around them for success and more people trying to make them successful in what they're doing.

[00:06:50] But one of the things that I love about it as a leader is that also creates the art of debrief.

[00:06:56] Because now people are like, oh, they're very open because they're not threatened in any way or worried about, like, you know, what the ramifications will be to admit fault and admit successes.

[00:07:07] And so, the more people do that, you have a sales team that starts to perpetuate on each other.

[00:07:11] So, it's almost like you have a team that is starting to share information back and forth of what's working, what's not working in a very authentic way where they can learn from each other.

[00:07:22] Not a spinning way that everybody, you know, is trying to compete with the impossible.

[00:07:26] And that's where real goodness comes out.

[00:07:29] And so, whether it's a win, whether it's a loss, whether it's a deal review in the middle of a prospect, it doesn't matter.

[00:07:34] If you're debriefing on those steps, it almost just becomes natural and nobody, like, the defenses drop and everybody creates that learning mindset going in.

[00:07:43] It's great.

[00:07:44] It's a cool thing from a leader because I think early, I wish somebody gave me that advice early in my career.

[00:07:48] Because I felt like I had to be part of every single one and, like, I had to coach it or I had to do it.

[00:07:55] But once you get that machine going, you can scale organizations because they start relying on themselves.

[00:08:00] So, all of a sudden, what I could do in a call just expands out and the teams start helping each other.

[00:08:06] I like the thought, scale through the art of debrief.

[00:08:10] And I want to come back to that culture element that you've mentioned now a couple of times in a second.

[00:08:16] How often do you do these deal reviews?

[00:08:20] Are they mandatory?

[00:08:21] Are they from a certain size of deals?

[00:08:23] How have you implemented that with your organization?

[00:08:27] Yeah.

[00:08:28] I've got my academic answer, my book answer.

[00:08:31] Like, I'd like to do them over a certain amount on a really regular basis.

[00:08:34] But I think when we get into the field, it never quite works in the academic form.

[00:08:39] You know, I'm a big fan of deal reviews on deals that need extra thought.

[00:08:46] So, my end goal to get to is that people voluntarily want to do deal reviews.

[00:08:51] And we open it up for areas that it's something they haven't seen.

[00:08:56] They have risk.

[00:08:57] They want extra ideas on it.

[00:08:58] And people are very proactive.

[00:09:00] So, the end state of what I try to work toward is setting them up on a regular basis, almost like an office hours.

[00:09:08] Like, you have a block on, you know, a Friday for one of your sales teams.

[00:09:12] And then a few days before, they sign up for which three.

[00:09:15] Like, the leader chooses, okay, these are the three we're going to do.

[00:09:17] But they do it from ones that are volunteered.

[00:09:20] That's the end goal where I want to get to.

[00:09:22] It never works that way in the beginning.

[00:09:24] When I first take over a team or as I joined Simpro, they hadn't really had that notion.

[00:09:28] And people thought I was respecting them.

[00:09:30] So, there was a little bit of, okay, I'm nominating these deals over a certain amount.

[00:09:35] And then I had to come in a little bit with Kid Gloves because I want to make sure that everybody feels right and, like, sharing ideas.

[00:09:42] And we're just giving the perspective.

[00:09:44] And I'm leaving that control with AE.

[00:09:45] Like, we're not telling AE what to do.

[00:09:47] We're brainstorming together.

[00:09:48] So, I had to be really careful, you know, not to use my experience and be like, we're doing this, this, and this.

[00:09:53] Because then more people would be hesitant.

[00:09:55] So, in the beginning, I do try to do them weekly per team.

[00:09:59] And then I have, when I start to get bigger teams, like, I expect my leaders in the regions to do them.

[00:10:05] And then I do nominate accounts.

[00:10:08] But my goal is to get to the point that everybody is volunteering them.

[00:10:11] And if I don't get volunteers, then I do pick big accounts and pipeline.

[00:10:15] Like, I kind of go through my pipeline and pick the ones that I think might be at risk or have questions around or seem stalled.

[00:10:21] Maybe there's no activity for a while.

[00:10:23] You mentioned earlier the culture of a sales team.

[00:10:28] Now, if you'd have to frame that up in a couple of sentences, I'm curious what your definition would be, the ideal culture of a sales team.

[00:10:37] Yeah, I love it.

[00:10:39] And I think it ties a lot back to the theme of the podcast, right?

[00:10:43] Like, even where you talk about your company and what you're doing.

[00:10:47] And it's really about, I want people that are confident in what they're doing, but they rely on each other to win.

[00:10:56] And we're laser focused against our competition.

[00:10:59] And I do think it's easier sometimes for sellers to get focused more internally, especially the bigger the company or the faster growing company.

[00:11:09] It's easier to get focused internally a little bit where their competition is products not building enough or, you know, so-and-so.

[00:11:16] I'm competing against another seller or I'm competing for territory.

[00:11:19] Like, it gets interesting to see the dynamics of the focus.

[00:11:22] That's all got to stop.

[00:11:23] Like, I need a team who is working collaboratively.

[00:11:26] They're sharing their best figures.

[00:11:27] They're trying to elevate their game because they see that they win as a team.

[00:11:31] And the reason I talk about it a lot, because I actually think it's really hard.

[00:11:34] I think it's something people miss a lot.

[00:11:36] Like, sellers by nature are very independent thinkers, right?

[00:11:40] Like, we all kind of, we're all kind of lone wolves in the sales side.

[00:11:43] So, kind of breaking that and having them function as a path and, like, building our strengths, I think is so important to be able to, again, laser focus on competition.

[00:11:52] Because at the end of the day, what we want to win is market share.

[00:11:54] And if they see that as their goal and what their puzzle piece is in there, we start to really get better and better at our game.

[00:12:04] Right.

[00:12:04] Which is what I want.

[00:12:06] Now, you've had a great track record with a variety of companies.

[00:12:13] I'm looking at my notes here.

[00:12:14] IBM, again, to Adobe and so forth.

[00:12:18] How have those experiences impacted sort of what you implemented, implementing now at Simple?

[00:12:26] Yeah.

[00:12:26] I think, you know, I worked for a big company.

[00:12:29] Went to a startup company, Crossroads.

[00:12:31] Got bought by IBM.

[00:12:33] Did well at IBM.

[00:12:34] Decided I wanted to go back to a small company with Magento.

[00:12:36] Got bought by Adobe.

[00:12:37] Stated Adobe.

[00:12:38] Really liked it.

[00:12:39] And then came back to a kind of smaller company to grow.

[00:12:41] And what I really am thankful for my experiences is that it's taught me to function in a small company way, which is this, you know, fast growth, fast moving, fast decision.

[00:12:55] Very agile type company environment.

[00:12:58] But it's also taught me working for the big companies.

[00:13:02] And I stayed at the big companies for years and years.

[00:13:05] And so because of that, I learned how to operate in that highly matrix, highly operational.

[00:13:11] You know, you're coordinating with a lot of different groups and you're reporting up in a very formal way.

[00:13:16] And so I think the combination of those things, my sweet spot now is how I can take companies or divisions within some of the bigger companies and really expand them and grow them.

[00:13:27] And operate maybe a little bit more like a high growth startup or a high growth, you know, growing from 15 million up and get them over the hundreds of million line with whether it's a startup or whether it's in that company.

[00:13:40] I've gotten really good at that.

[00:13:41] But I think it's the experiences of both.

[00:13:44] And I think people sometimes will come in because acquisitions happen all the time and say, well, I'm really good at this.

[00:13:50] I'm really good at that.

[00:13:51] But I actually think, again, going back to the learning mindset, we all can learn.

[00:13:54] And I think if you can build that experience to be able to do both, that's what helps you be able to scale and grow.

[00:14:00] Love it.

[00:14:02] Absolutely love it.

[00:14:03] I think that winning mindset is really key.

[00:14:06] Is that something that when you hire new people, let's say, is that something that people can learn?

[00:14:13] Is that something people are born with?

[00:14:15] What would be your comments on that?

[00:14:18] Yeah, I just had a debrief with some of my sales leaders the other day.

[00:14:23] I think we need to be careful hiring sellers because I do think we can teach skills.

[00:14:29] It's hard to teach mindset.

[00:14:32] So I'm sure this is probably a little controversial.

[00:14:37] I actually think it's hard to teach a learning mindset with a really closed-minded person.

[00:14:42] I think we can spend a lot of time and make a little progress.

[00:14:46] Sometimes you can crack it open if it's maybe in there inside, but I think that's difficult.

[00:14:52] So one of the key things I look for when I hire is that learning mindset and how are they adjusting?

[00:14:57] How are they learning from others?

[00:14:58] Because that's the piece I can't teach.

[00:15:00] I can teach field service management.

[00:15:02] I can teach the technology.

[00:15:03] I can teach the demo.

[00:15:04] I can teach sales skills on mutual sales plans and all the other pieces, mutual success plans and closing and negotiation.

[00:15:11] But I think the aptitude, like some of the core things that people bring to the table and learning mindset is the very top of the list.

[00:15:19] I think that is hard to teach.

[00:15:22] But I think individuals can decide to do it.

[00:15:25] I think we all change over our career and we change our skill sets and personalities.

[00:15:29] I think if an individual realizes that they need a learning mindset to be successful and happy and continue growing in career, they can make the decision to do it.

[00:15:39] And then they're a great hire and we can feed off it.

[00:15:41] And how do you hire for that?

[00:15:43] How do you assess that through a series of interviews?

[00:15:45] I have never figured that out.

[00:15:48] I'm hiring people all the time.

[00:15:52] But how do you assess that in the interview?

[00:15:55] Yeah.

[00:15:55] You have a seat.

[00:15:56] It's hard.

[00:15:58] You have to get really disciplined in how you interview.

[00:16:01] So I force myself.

[00:16:04] I very much prepare.

[00:16:07] And I go in with what are the skills, not experiences.

[00:16:11] So I do not focus on the experience of the person.

[00:16:14] I can screen resumes ahead of time.

[00:16:16] I don't need them to tell me about their experience.

[00:16:18] Experience can be taught.

[00:16:19] But I want to know what the attributes are that I need in that person to have.

[00:16:24] And learning mindset is always one of mine, like right at the top, no matter what role I'm hiring for.

[00:16:29] And I ask a lot of questions relative to experiences that drive to that.

[00:16:34] So I'll ask for the learning mindset one.

[00:16:36] And I'll ask a lot of questions around, you know, give me a time when you are successful.

[00:16:42] And they love to talk about that, right?

[00:16:44] And that kind of warms them up a little bit.

[00:16:46] And then I'll say, what did you learn from that?

[00:16:48] And it will be interesting to hear some people come in and they're like, no, I did everything perfect.

[00:16:52] I was great.

[00:16:53] And there's other people that will be like, yeah, you know, if I just did this one thing different, I could have, you know, had a little bit more.

[00:16:58] Or, you know, in hindsight, like I could get a little better.

[00:17:01] Or this next time around, I'm going to roll these pieces in.

[00:17:03] So they'll feed off that question.

[00:17:06] And then the second one I'll ask them after that to maybe keep going is, tell me about a case when it didn't go the way you expected.

[00:17:13] And then what did you do about it?

[00:17:15] And, you know, what was your next step on it?

[00:17:18] And a lot of times you can hear right away either people getting defensive or people learning from it.

[00:17:24] And what I look for in there is I want people that admit to mistakes.

[00:17:28] And I want people that own up to it and are confident in, like, the next path.

[00:17:32] And so if somebody kind of can laugh and say, yeah, it didn't go the way I wanted, but I tried.

[00:17:37] And I learned this from it.

[00:17:38] Like, that's a perfect interview in that learning mindset.

[00:17:41] And I kind of move on to my next attribute I'm looking for.

[00:17:44] And if I can't get that, I'll ask a third.

[00:17:47] And if I can't get it out of the three, I literally do, like, three sets of questions.

[00:17:51] If I can't get it by the third, then I determine they don't have a learning mindset.

[00:17:54] I've just learned something.

[00:17:56] So thank you.

[00:17:57] That's good.

[00:17:59] Final question, Stephanie.

[00:18:03] You've dealt with a lot of salespeople.

[00:18:05] You've dealt with good ones, with not-so-good ones.

[00:18:08] What would you say are the top three skills and behaviors that top salespeople have mastered to be elite salespeople?

[00:18:20] Well, funny.

[00:18:21] I would have said, as my number one, is being that guide and, you know, being able to help coach a person through the sales cycle.

[00:18:31] So, you know, a lot of times I think sellers come in and they just assume the buyer knows what they want.

[00:18:35] And they just start asking the buyer, like, what are you looking for?

[00:18:38] What are you interested in doing?

[00:18:39] When are you interested in buying?

[00:18:40] Like, all those traditional questions a seller will ask.

[00:18:42] But at the end of the day, like, your job is to be the guide in the sales cycle and help guide them.

[00:18:47] You have more experience in B2B SaaS software and with your specific software piece than what your customer has as a purchaser.

[00:18:55] And so your goal is to guide them and listen to them.

[00:18:57] So that's number one.

[00:18:59] I would have said listening number two.

[00:19:01] No surprise because we talked about that a little bit.

[00:19:03] But I think, again, it's easy to get preemptive in, like, what people want and just get a little bit into demo jockey mode or let me just tell you what you need.

[00:19:11] But really listening to the customer because you don't know what their little tidbit is that's going to tip them over the line of wanting to purchase.

[00:19:19] And it could be something really different.

[00:19:23] You know, we bought a new surfboard.

[00:19:25] We bought a new foil surfboard.

[00:19:26] And my selling point, which I bet the buyer had no idea, was that my 16-year-old and I do that together.

[00:19:32] My husband, right?

[00:19:32] So it's like a family.

[00:19:33] It's hard to get 16-year-olds to participate with parents.

[00:19:35] So that was my selling point.

[00:19:37] But I guarantee that is not what the sales rep thought he was selling to.

[00:19:41] And so it's so important to listen and kind of hear what their individual motivation is.

[00:19:46] And then the third one, which I'm going to tweak a little bit based on this conversation, I would have said, you know, expert in the field.

[00:19:52] So I think everybody can get better at their game.

[00:19:56] Even professional athletes have coaches.

[00:19:58] But you said it in the beginning.

[00:20:00] It's more around that confidence and kind of what sellers have.

[00:20:03] And I do think it's probably more what you said in the beginning.

[00:20:06] It's that confidence to be an expert.

[00:20:08] Because if you don't know it, it's okay.

[00:20:10] You just go get the information.

[00:20:11] You don't feel like you have to guess your way through it.

[00:20:14] I think there's a lot of value in that.

[00:20:16] But it's really being that trusted source of, you know, giving them the information for them to make educated decisions on the buying cycle.

[00:20:25] So guide, listening, confidence, expert, and field.

[00:20:29] Love it.

[00:20:30] Thank you so much, Stephanie.

[00:20:32] I know our listeners very much will appreciate your insights and thought leadership on that.

[00:20:38] Thank you for your time today.

[00:20:40] Yeah.

[00:20:40] Thanks for having me.

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[00:21:16] Happy selling.

[00:21:16] Bye-bye.