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Sales execs think their managers need help with deal support. Managers think they need help building the culture, leadership practices, and vision. Join Matt Cameron, Managing Partner at SalesOps Central, as he shares his findings — that managers desperately need help with coaching. Learn how to bridge the divide and increase sales performance through a well-structured coaching program in a culture of vulnerability and transparency. Supporting deals may feel fulfilling, but may not be the best use of a manager's time.

There's very little that goes on around formal coaching training. You might go for a one-day coaching course, but they haven't figured out how to build a coaching motion and coaching culture into the business.”

Matt Cameron | Managing Partner at SalesOps Central

Kevin Micalizzi: This is Kevin Micalizzi, the Executive Producer of the Quotable podcast. I had a chance to sit down with Matt Cameron, Managing Partner at SalesOps Central, to talk through what he’s discovered around what managers want and need versus what executives think they want and need. Let’s jump into it. Matt, welcome to the Quotable podcast.

Matt Cameron: Thanks, Kevin. Good to be here.

Micalizzi: Before we jump into it, let me ask, for those who aren’t familiar with you, would you share a little bit about yourself?

Cameron: Sure. So I arrived here today after about 22 years in sales. I started out by acquiring this accent in New Zealand. For those of you who are not familiar with it, you might know the west island. Some people call it Australia. It’s nearby.

And so, pretty classical technology sales background. So I came up through Hewlett-Packard, for those of you who are old enough to remember, and ultimately ending up in enterprise sales with Electronic Data Systems, Ross Perot’s company.

So that was sort of the first 10 years of my career, and then realized that I really love the process of selling and the science behind it. So I moved to Australia and spent five years doing sales process consulting when I met this little startup that was annoying everybody over there called Salesforce.com. Some of you will be familiar with. And I spent five wonderful years of my career at Salesforce running an enterprise group over there.

And subsequently, I’ve been working with Series A, Series B startups. And my focus very much is on the revenue side of the business and scaling startups. I like to work with companies anywhere between a million and revenue to about 50 million.

Micalizzi: Okay.

Cameron: It’s not a hard and fast rule, but that’s the sort of stage in a company’s growth that I really enjoy. I used to work for Yammer, which many of you will be familiar with. We were acquired by Microsoft and ran their global corporate sales business. So anything under 2,500 employees, really, like, that sort of stuff.

Micalizzi: Right.

Cameron: Building sales engines and then working on big, chunky enterprise deals really gets me excited.

Micalizzi: Excellent. So when you and I had talked about scheduling this, we were talking around something you had discovered in the work you were doing in terms of what sales managers want and need are a little bit different than what the executives are seeing that sales managers want and need.

Cameron: Yes. Yeah, so today I run a boot camp of sales managers. So it’s called FrontLine, and so I’m seeing dozens and dozens of sales managers come through, and in the course of that, it made sense to me to try and understand how these people are being supported and how we can coach executive leadership to provide better context for their people to be successful.

We work with a company called Kimono Metrics, who we did a survey with. And it was very interesting to find a disconnect that wasn’t immediately obvious to me. The disconnect was, if you ask an executive leader how they, what they think their sales managers, their frontline sales managers need, they’ll tell you that they need deal support.

And then if you ask the manager what they think they need, it’s support around building culture, leadership practices, vision, those sorts of things. Because it makes sense intuitively. You’ve been an individual contributor. Now you’ve got responsibility for a team, and you need to create that esprit de corps, right?

And Salesforce, frankly, I think has done a wonderful job of that in terms of aligning their people from top to bottom. But then during the course of our training, what we understand is, whilst they may want that, what they desperately need, based on the performance and what their reps tell us, is help with coaching. Right? How do I effectively build a coaching motion in my business and train?

So we had a think about that and sort of spent some time speaking to the executive and whatnot. And what you find is, it’s not so much they think their managers need help with big deals so much as they just enjoy doing it. You know?

When you’ve been out of the trenches for a while, there’s really temptation to want to be there toward the end of the deal, put the hand of god on it, bless the deal that got through, and —

Micalizzi: Be the superhero who pulls it through. Yep.

Cameron: A hundred percent. Right? Now, I’m not saying you shouldn’t do that. You absolutely should win as a team and lose as a team, and a lot of individual contributors we know have that problem, where they want to be the lone wolf and succeed or fail by themselves. But there’s something that needs to be addressed here.

And that is figuring out to align the needs whilst making it fun. What I’ve discovered — even in very large organizations — is, there’s very little that goes on around formal coaching training. I’ve recently worked with some quite large companies — 100 million plus.

And what we find is, you might go for a one-day coaching course or something like that, but they haven’t figured out how to build a coaching motion and a coaching culture into the business. So I guess, on the back of our findings, what I’m spending time doing is working with sales managers to create a grassroots movement if executives haven’t figured it out yet.

To figure out, well, what is the formal context and cadence for our coaching in our one-on-ones, in our team meetings, in our quarterly reviews, those sorts of things. Aligning that to the sort of overall personal plans we might have — around personal development, annual goals, those sorts of things.

But then making sure that it’s just expected as a cultural item, so that something that’s not necessarily expected or anticipated is, for it to be successful, you need a culture of vulnerability.

Micalizzi: Right.

Cameron: And the ability to be transparent. So if you have people that don’t have the growth mindset — the knowledge that just because I’m not good at something today doesn’t mean I can’t be tomorrow. You’re going to have trouble.

Because people close up. They don’t want to admit to their soft spots or their weaknesses. And therefore the managers can’t figure out how to support them.

Micalizzi: It makes me think of one thing I’ve been hearing, especially recently, is, people talk about managing to pipeline, and managing — they want to understand what the rep’s pipeline is, but they’re really not helping to coach through that pipeline.

So some of them, you have that superhero complex. They feel they need to jump in at the end. Others, I think, look at it as, “Well, as long as I’m asking where your pipe is, then we’re working on this.” So I see this as maybe part of what you’re talking about, where —

Cameron: I agree, and I think you had a guest — Jason Jordan from Vantage — who made a point about forecasting, which I think is closely related to the point you’re making, where — if I might paraphrase him — he basically said that forecasting doesn’t change outcomes.

It’s telling you what’s likely to happen, but it doesn’t influence that. And I’ll nuance it and say I agree almost entirely. I’ll say that if a rep says they’re going to commit a deal, it has a psychological impact that actually does change behavior.

But the essence of what he’s saying I completely agree with. And the issue with talking about pipelines at a numbers level or forecasting is not a coaching exercise. It’s really just, tell me what I need to understand to report up. And I know on work you did with Jason, he talked about managing to the pipeline

Which is absolutely right. You need to have an understanding of the underlying data, the deals themselves that support the number you have on the top line. But if I can take it a little more broadly, when I think about coaching, I think not only about deal coaching, but — just in general — when you’re hiring people, you hire them for skills, experience, and behaviors.

And something that is oft-neglected are the behaviors of success. And they’re very coachable. Right? So IQ we can’t do much about. Although there’s arguments [that seek to prove it over time].

But, as a manager, the thing I can really affect are your behaviors. So for example, for junior reps, explaining to them how they should be preparing for calls. So if you’ve got a rep who’s not getting good outcomes, one of the core issues could be that they’re not preparing adequately.

They don’t walk in knowing the answers, attitudes, and actions they want to get out of this call. It’s a coaching item, and you can set a coaching plan in place, and we can agree to review it.

And in my course, actually, I decided to be a little kitsch about it. I’m sure you’ve heard about the SPIN selling methodology most reps have, and I thought, “How can I leverage this acronym in terms of setting up coaching?”

So what I say to managers is, “Look. Use that to describe the situation and how it needs to be improved.” The key thing is that I make it a double P. I say — so, for managers, you need to ask people for their perspective on the situation. Make sure you really understand that and that you’re aligned. Then provide your perspective.

And you can work through the implications and the need and the solution that you’re going to review together. So what I say to folks is, think about the whole person, and don’t just think about next month’s forecast or the state of the pipeline today. Right? It’s a pretty natural thing for managers to do deal coaching. What I find is, however, is they’re very prescriptive.

They’re very directive. “Do this next. You need to do that.” Whereas you really — if you’re going to build the skills and build the muscle in the individual, you need to be a little bit more contemplative and act more of a mentor and say, “Oh, okay. Have you thought about this outcome? Have you thought about that outcome?”

And, “How might you attack this?” And I’ll give you a specific example. Oftentimes, the problem is, the rep’s single threaded, and in a deal that got one contact — a gatekeeper they can’t seem to get around.

So the coach in a correct thing says, “Right, so let’s think about how we might bring value to a broader audience. How might we draw in stakeholders? How might we connect the dots with our executive and theirs? What do you think?”

Whereas the typical behavior is, “Right. I’ll ring his or her boss, or I’ll do this, or I’ll do that.” And they dive straight in.

Micalizzi: Right. I think that’s a huge challenge in management to begin with. A lot of managers I’ve worked with, and when I’ve managed teams, it’s so easy to drop into the [tell directive] mode. Where you’re just like, “Well, it would be a lot faster if I say, ‘You know what, Matt? Just go do this.’ ” As opposed to asking those right questions to get you thinking about it.

Cameron: Agreed. And also, my observation is, having listened to many, many one-on-ones, the core of running a strong team, frankly, is that — is running a really good weekly one-on-one cadence that is prescriptive in that it has a fixed agenda and a set of data and reports that people are reviewing — but is informed in advance. So that as a manager, I’ve prepared for this one-on-one.

Something I hear all the time is, “It’s the rep’s meeting. I’m here for the rep. I’m here to take away roadblocks; I’m here to be the hero; I’m here to help.” Yes. However, if you ask a 7-year-old what they want for dinner, it’s ice cream.

Micalizzi: [laughs]

Cameron: Right? And an image I like to share is — a typical one-on-one meeting is the rep painting pictures of unicorns and rainbows whilst hiding the skeleton underneath the desk.

Micalizzi: [laughs]

Cameron: So managers need to go into it having looked at the broader picture. So not only just the state of the pipeline, but how is this person prosecuting the territory — having reviewed interactions with the broader team. A great example would be in enterprise sales, when we need strong internal relationships.

So I need legal to want to help me. You know? When I need to do redline reviews, I need sales engineering or presales technical to support me in my deals. And these are core coaching moments, where you can have a rep whose behaviors aren’t supporting success in those areas.

And so rather than just focusing on,what are the deals we need to talk about today? What are we going to work on this quarter that needs changing? Because I can’t just tell you tomorrow, “Kevin, I want you to behave differently when you’re interacting with sales engi —” You know: “You need to get better at that. You need to ask —” You know, blah blah blah.

We need to lay a plan out together and then record observable behaviors that we can assess objectively together. To talk about improving whatever the issue might be.

Micalizzi: Right.

Cameron: And it can be as simple as something like punctuality. Right? Typical coaching item that no one things to talk about. But that can create real problems internally and, of course, externally.

Micalizzi: So I’m curious. To go back to your example for a minute of the rep who isn’t properly prepping for calls. I understand that there’s a coaching moment there. I guess I’m wondering, is there a broader problem with enablement? Because I know, sales is such a fast-growing space.

I mean, if you look at Salesforce, Salesforce grows exponentially. There are always new reps coming on, and we recently had Dan Darcy on the podcast talking about how we enable sales here. And it’s a six-month process to really onboard initially.

Is it an enablement challenge — or is it? I don’t know. I guess I’m wondering if we’re not enabling them right to begin with, or we just have a smaller segment of that population that needs the additional help.

Cameron: Well, I think it comes back to a sort of [bugbear bind]. And that’s around the idea of situational leadership. If you’re an early-stage startup, you’re not going to have sales effectiveness, sales excellence, sales enablement functions [in sync]. It’s going to be the sales leader who does everything.

Now a common mistake is that we might be tight on resources, and therefore we go for more junior reps who we can, quote-unquote, “train up.” But guess what? You can’t train them up fast enough. You don’t have a six-month ramp where you can teach them about hygiene factors like preparing for calls.

Really what you want to train them on is our company, our product, and then the business value of the solution to our ideal persona. So in early-stage companies, you really have to hire people who have all these sales foundation skills there, understand the behaviors, and then you just layer on what I just described.

For later-stage companies that are building an army of people like Salesforce, and then you want to sort of have a farm system where you bring people through the ranks. Then you’re absolutely right.

[Therein] brings up an important point, I think. People often ask me, “Well, who has responsibility for onboarding the rep? Is it the manager, or is it sales enablement, sales effectiveness, productivity — however you term it?” And it’s interesting.

Because I always go back, and I say, “Well, who gets measured on it?” And people — “Well, obviously, it’s sales enablement or sales effectiveness.” I said, “Really? Who really gets measured on it?” Because the ultimate measure is, how quickly do they get to full quota?

And that’s the manager. Because the manager carries the quota. So any manager who says that they aren’t — you know, enablement or effectiveness is doing a terrible job and blah blah — usually is the person who’s not engaged and is just waiting to read the certification reports at the end of the month to see who’s keeping up.

Right? They’re not actively engaging. And my perspective is that the work of the — you know, the demo training, the product knowledge, all that sort of [unintelligible] sure. It sits with effectiveness. But in terms of making sure it’s ingested, absorbed, and can be applied — I believe — sits with the manager.

And back to coaching, I would be setting monthly and quarterly goals around that onboarding practice. And then things like the roleplay and the real-time practice should be done by the manager at some point. In addition to whatever’s happening with effectiveness or whatever else.

You know, my point being that we need to make a distinction between early-stage, under-resourced companies versus —

Micalizzi: Understood. Understood. Most definitely. So we’ve talked about the need to do the roleplaying, to get a better understanding of what the reps need and stop being directive in how you interact with them. What else should managers be doing to try and address this? Especially the gap — you know what I mean? You need that executive support.

Cameron: Yeah. So if I start at the top, what the executives need to do is, they need to provide the guidance to managers on what a coaching culture looks like and provide that ability for people to be vulnerable and transparent. And you have to lead by example.

So recently, people started talking about for early-stage companies the need to invest in mentors and coaches for your VPs. And I think that’s very important. And as you’re mentoring these VPs of sales, the executive leadership, this is a core topic — enabling and developing your people, and providing this environment. So they need to set the tone and provide the framework for managers. And an example of this would be that they say to the managers —

“Okay. Here are the coaching and inspection points that we’re going to set up in this organization. Here’s what is appropriate during a one-on-one. Here’s what a follow-up plan looks like for the individual. Here’s what your quarterly and annual personal development plan looks like, and here’s how we inspect progress quarterly.”

Now that’s the framework. But in between times, I like to borrow from Stephen Covey and talk about sharpening the saw. And my belief is that you should be doing this on an ongoing basis every week.

So for managers that I work with, I encourage them to think about having team meetings that are 30 minutes on the usual course of business — which, by the way, should never be a pipeline inspection.

And so many times it is. We go around the table, and we talk about the deals you’re going to close this week. Which has zero value to the person sitting next to you and wastes a lot of time. I think the place for that’s in the one-on-one meeting.

Sure, we can talk team forecast, headline numbers, absolutely — because everyone’s interested in that. But not to drill into Kevin’s forecast, Kevin’s pipeline. So 30 minutes on the things that matter, and then 30 minutes for sharpening the saw.

And if you’ve got an enablement and effectiveness program, then that’s easy, because they can weave in, and in the end, you’ll have them come in and help about — maybe we’re talking about a specific competitor. And we’re going to practice and roleplay objections or landmines that they’re leaving for us. If, however, you’re just a one-person band, and the sales leader — she’s not got support by sales effectiveness — then it’s very, very simple.

You can do it as simple as, “Okay, give us the 30-second elevator pitch. Stand and deliver. Go.” Or next month’s theme is, you know, you’ve got three people who have just joined the company, and you say, “Okay, look. Talk to me about the argument in terms of total cost of ownership, SaaS versus on-premise. Go.” Those sorts of things.

To create that sort of consistent improvement culture. But you can imagine that if you don’t have this ability for people to be vulnerable, that’s going to be very threatening. So you have to lay the context correctly.

So, the way I think about it is this: It’s a bit like a gymnastics team. Right? The Olympic level, you’re not going for the team gold, you’re going for individual gold. But they all support each other. They all coach each other. They all help each other just fix that little thing that’s niggling, right?

I really like seeing teams — or folks that have done individual sports that are reps, because they’re used to that individual accountability. However, they also have to be collegiate. And it’s up to the managers to create that collegiate environment within the coaching context.

Micalizzi: In that “sharpening the sword” time — because I know earlier you made a distinction between core selling competencies versus product knowledge and understanding the customer, the business — would you use the sharpening the sword for one type of training enablement, or for both?

Cameron: It depends on the level of the team. So for junior teams, I would do both. Right? So, you know, our theme this week might be account plans. And everyone’s going to turn up and just share their account plan at next week’s sales meeting.

We will know that — we’re going to do it, and we’re going to help each other to improve it. And then for more senior teams, it’ll be more about the product, the competition, the industry, that sort of thing. Whereas the hygiene factors we just don’t go into, because we’re not going to worry about it.

Now notwithstanding, I will say it’s appropriate on some cadence, be it biannual or whatever, to just do a little sanity check. Because we forget what we’ve learned, right? And the way to do that, of course, is to take your most senior people and use them as an exemplar.

Kevin, I know you know how to do this, so what I would like you to do, please, is to present first. And you show everyone how it’s done, and that’s how you bring those people in, so they’re not rolling their eyes about having to do something that they’ve been doing for 10 or 15 years.

Micalizzi: Right. Which makes total sense. So if I was a rep in a situation — and I’ll preface this with, I know reps don’t have a very large control of their worlds. But if I’m in a situation where I’m not getting the coaching. I’m not getting that support I need, and it looks like there isn’t that executive investment, what could I be doing individually?

Cameron: Use your networks. So this is something I’m seeing more and more. I’m certainly seeing it at a manager level, where I personally am coaching a bunch of RVP-type folks who don’t have that senior-level support, either because the person doesn’t exist yet in their organization, or because they’re distracted, and it’s not the culture.

But from a rep standpoint, if I’m a mid-market rep, then I would be seeking out people within my network who I can have a monthly get-together on and just talk through these issues and tell them what they’re struggling with. So we all need a coach.

And the great thing about salespeople is that they like problem-solving. Right? And so it shouldn’t be difficult for you to find someone in your network to give you that support.

Micalizzi: So, in your thinking on this, would you say that finding that coach in your network is a different process than my trying to find a career mentor?

Cameron: Yes. So they’re quite different. So mentoring — the way I think about and define it — is about those longer-term goals, which I think you’re articulating, around career, right? So if I’m wanting to position and develop myself for these sorts of things, you know, mentoring conversations typically will happen as infrequently as once a quarter.

Because not a lot changes, right? We’ll do a check-in or whatever, but that sort of carry-on. But from a coaching standpoint, if you’re not getting it internally — a good example would be that I’ve been given 100 accounts, and I just don’t know where to start.

And, you know, that’s a great coaching conversation. How do I prioritize these accounts? How might I research them — figure out where the gold might be? And then moving on from that, once I’ve bitten into a few, I’ve got my hands on AT&T. I’m in this situation. How might you handle it?

Those sorts of conversations I think are perfect. And so then I’m seeking somebody not who did it 20 years ago. I want somebody who’s been doing it very, very recently, if not is still doing it. Right? As opposed to the mentor who might have stepped out of that — you know? Who’s been away from that for quite a while. But can take you through that 10-, 15-year career journey.

Micalizzi: Understood. Yeah, I think sales has changed so significantly that if you’re not actively doing it — or haven’t been in a few years — then you’re somewhat out of touch with the technology and the approaches folks are using.

Cameron: Yeah, agreed. And coming back to the coaching topic for a second, for managers who haven’t had formal training or whatever else, I really would suggest that they seek out the HR support they might have in their organization to figure out how they do that.

Because it’s not a sales-specific discipline, of course. There are coaching frameworks and approaches and whatnot that are applicable across job functions and roles, and if the executive leadership within their functions [is] not providing it, then seek it elsewhere.

Micalizzi: Okay. Excellent. So you talked earlier about how some of these earlier-stage companies don’t have the resources. They don’t already have the established sales enablement teams and things like that. For a company that’s trying to build a coaching culture, what have you been seeing is working?

Cameron: So not only for small, but certainly applicable for small, I’m seeing people creating career frameworks where you can essentially level up within a role that’s outside of just your sales results. Some people are calling them sales academies, for example.

And what I’ve seen and been a part of — which I think was a very interesting approach — is that they use the belt system. You can go from white belt to black belt within roles. And certainly for younger folks who want some sort of recognition for their effort as they’re going through it can be a very effective practice. And it’s very objective.

So, for example, if I’m a sales development person, my quota might be eight opportunities a month, say, and that’s fine. They get some of the recognition.

But in order for me to be eligible for promotion from, say, a mid-market SDR to an enterprise SDR, I might have had to have had the experience of having 100 [optees] qualified and accepted to get to that level. And that gets you to blue-belt level.

And then in conjunction with that, you need a bunch of certifications. So I need to be certified on objection handling and certain product knowledge, competitive understanding — in addition to the hard metrics that I have with my sales role.

And people really like that. Because they can see progress in their career even if the next role’s not available, which is really important for smaller companies. Because oftentimes there will be a ceiling. A real problem is when you’ve got enterprise sales organizations and SDRs. Because you can’t go from SDR straight to enterprise [AE]. You can’t make the jump.

So how do I see progress in 18 months or two years if I’m not moving out of this role? This is a way to solve for that. And something I particularly like about that — in terms of what are the best-practice contexts — is make it collegiate. So if I’m a junior SDR, and I want to get to being an enterprise SDR —

— then for a mid-market rep to get their certification, they need to do the roleplays with the SDR. To help the SDR improve and get ready for their certification. So the word’s “collegiate.” Right?

So within the academy, we’re all here trying to get ahead ourselves, but in order to get ahead, you have to support your teammates. So there’s a very specific recommendation. I think that much larger organization — your Microsofts and your Salesforce and your [SFPs] and whatever else — certainly have career levels.

It’s just a matter of gamifying it a little bit and making it fun.

Micalizzi: Right. Which is fantastic. And I think we’re hearing a lot about that need for recognition. There’s a certain expectation that either you’re leveling up on the gamification side, or you’re anticipating your career progressing more quickly than they normally do.

Cameron: Yeah. And I think — you know, this idea of being a bit more of a meritocracy’s important. So I think I was a millennial ahead of my time in that it sort of frustrated me, when I was 22 or so, that it’s like, “Well, you’ve got to earn your stripes.”

And “You’ve got to be here x many years.” And my thinking was, but if I can sell as much as her, and we’re doing as many deals, why can’t I have her title? You know what I mean? And that’s how people think now.

And I think it’s the right way to think about it as long as you’ve had enough at-bats. So if you’ve seen a hundred optees, you probably know the sales motion. Just because you hit your quota or whatever doesn’t really matter to me. But you have to have had that.

Now, if our assumption is, it takes you two years to do that, but you get it done in 18 months, in my mind, there’s no reason for you not to get that opportunity for progression or promotion.

Micalizzi: Yeah. Don’t create some artificial barrier you have to cross.

Cameron: A hundred percent. Because it’s all about how many stripes have you got on your back? If you’ve seen enough variables that you can interpret new contexts.

Micalizzi: So let me ask you — it’s my lightning-round question — I’m trying to ask every guest. If you can take all of the experience and knowledge you have now, go back to the beginning of your career, and share one thing with yourself, what advice would you give yourself?

Cameron: I would say, “Invest hard in your network early by being generous and paying it forward. Be as helpful as possible to as many people as possible as you can. Never stop.” And secondly, because I got fascinated by enterprise, and that’s really my true calling, I would say, “If you have an opportunity to work inside a large enterprise, regardless of the role, do it.

Do it even if it’s only 18 months or two years, because you get to learn how these things work.

If you’re going to be a great enterprise rep, there’s nothing like having worked inside a company and tried to get a PO approved, right?

Micalizzi: So true.

Cameron: And building political support for whatever you’re doing — that’s such a valuable lesson, right? We talk about the politics of sales and, you know, establishing support with the inner circle and all that sort of carry-on.

But if you’ve worked inside that company — that had a project you’ve tried to [stood up] — then you really understand what your champion is going through.

So if I had to pick one, thought, it would be about being as supportive of your network as you can and investing social capital in people Because it’ll come back and pay back in dividends.

Micalizzi: Excellent. I loved that advice. Having spent years in large organizations, the dynamics are fascinating and frustrating at the same time. You know what I mean? As a sales rep looking in, you’re thinking, “Oh, there are certain hurdles and challenges to getting this deal across.”

And if you’re on the inside, there’s an entire world that doesn’t touch the outside world, but has its own rules. Has its own everything. Fascinating. Awesome. Thank you so much for coming in, Matt. I really appreciate it.

Cameron: It’s a pleasure.

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