Sneak Peeks

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Sneak Peeks

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If you've ever thought, "Hmm.. I'd love to 10x my Ops career," Jeff is your guy. Literally.

With his OpsScale newsletter with a "10x your Ops career" tagline, Jeff regularly shares advice that he has picked up along the 15+ years in Marketing and RevOps roles. Over the years, he's built operations teams that utilize tech and process in innovative ways at companies like Workfront, Whistic, Hopin, and now, Coalition, Inc.

In the latest episode of Change Enablers, Jeff and Ken cover:
• the six phases of Jeff's Ops career maturity model and how they span across a tactical vs. strategic spectrum
• ways ICs can start thinking about enablement impact well before they’re in the next phase of their career
• being a strategic partner and change agent in Operations
• measuring success when you shift from order-taker mode to highly strategic and high-value work
• prioritizing real-time enablement for your end users

Where to find Jeff Cullimore:
• LinkedIn:
• Newsletter:

Where to find your host, Ken:
• LinkedIn:
• Twitter/X:
• Change Enablers, a community by Tango:

Like what you heard? Subscribe, leave us a review, and let us know who in Operations and Enablement should be our next guest.

Ken Babcock (00:00.942)

All right, everyone, welcome to the Change Enablers podcast. I'm super pumped to have Jeff Cullimore here with us today. Jeff is the founder of 10X, your ops career, which is a newsletter, and he's built that newsletter through direct experience in operations. You know, he's a marketing operations senior manager at Coalition today, has held operations roles at Hopin, Wistick.

work front, um, and ops guru that we're pumped to have on the podcast. So Jeff, welcome.

Jeff Cullimore (00:34.498)

Thanks, Ken, it's great to be here.

Ken Babcock (00:36.946)

And I'm just going to jump right in because there's so many great things that we want to cover today. Um, you know, your view of sort of the career maturity model as well as, you know, why teams need to embrace real time enablement, which is something we feel passionately about at Tango. Um, but I like to start with, you know, just a simple icebreaker and, you know, that one today is what's the most underrated ops function and why.

Jeff Cullimore (01:03.854)

Yeah, I think that's a great question. And as I was kind of pondering my answer, there were a lot of different directions that I thought I could go, depending on the size of the company, the size of the team. But I'm gonna go with data, actually, I think, today. My background's in technology, and I'm a big believer. We've talked about enablement. We've talked about all of the ops things that can be included in that. But...

If you don't understand the data, then you can't really provide any direction. You can't really kind of point the way and say, this is what we need to do. This is what needs to change. And so despite that being kind of a well-known ops role and probably pretty well staffed on most teams, I do think that it's still underrated and probably doesn't get its due when it comes to the overall ops function at this point.

Ken Babcock (01:53.694)

I, yeah, I mean, you're, you're speaking my language as a former analytics person. You know, I think we had, we had someone on the podcast actually recently, uh, one of my former coworkers from, from Uber. And she talked a lot about the principles of measure what matters, which I'm sure a lot of folks have heard about, but the, the layer that she added on top of it was like, your teams also have to know what you're measuring. You can't just say measure what matters. Here's the metric we care about. If nobody knows how to move it.

and how specifically it's measured. It's, you know, you're basically telling people to chase after something that they don't know how to do that. So I totally agree with you there. Let's maybe shift into some of the stuff that, you know, you've been sharing in your newsletter and, you know, that you've learned over the course of your career. I wanna talk about the career maturity model, which I think is really interesting.

you sort of built that and shared that. Can you talk the audience through the six phases of that model, this tactical versus strategic spectrum and kind of how they can think about their own career maturity?

Jeff Cullimore (03:01.452)


So a lot of this was born out of kind of my own questions and struggles as I looked at my ops career and I thought, how can I progress? How can I grow, you know, whether that's a promotion, whether that's increased responsibility or improving my skillset. And I mentioned in a LinkedIn post that I shared about this, that I'm not actually a huge fan of maturity models. I think they're pretty squishy. It's pretty easy to say, well, we're, we're at a four in this area, we're only a two here. So we'll average it out and we'll call it a three.

Jeff Cullimore (03:31.824)

fall on that, but the model that I've kind of started to play around with, like you mentioned, it falls into six different categories. And the first one is where you're really concerned with how things get done. You're in a tool and you're learning how to push through the different buttons and the order that things need to get done and the functionality of the tool. And

The payoff comes when you actually are able to complete a task or complete a project or something like that. The next phase comes with efficiency. So a spreadsheet is a great example of this. You know some formulas, you know, to do some sorting, but maybe you don't understand pivot tables. And then once you learn about pivot tables, you go, wow, this is great. Now instead of counting row by row or using all of these sorts or groups or different things, I can throw it in a pivot table and have an answer, you know, in three, three or four minutes.

or the next phase is are you working on the right things? Are you working on the things that are going to provide an impact? Are you working on things that are important to your stakeholders? Because any ops person could stay busy all day long doing all sorts of different things But that doesn't help move you or the teams that you support to the next level the fourth phase is communicating what you're working on and I think ironically, especially for a lot of marketing operations pros and

folks that I work with, this one is one of the more difficult ones because you feel like you're almost tooting your own horn. You feel like you're walking around saying, Hey, we've completed this integration or we've got this data cleaned up or something. And it can feel a little self like you're promoting yourself and, and trying to make yourself look good. But the truth is, I think in most cases.

Teams want to know what's going on. So much of what happens on an ops team is it seems like it's in a black box. And so by publicizing what you're doing and telling why it's important, that really helps illustrate the value that you're providing to the organization. The fifth one is...

Jeff Cullimore (05:29.794)

Considering how what you're doing enables others to be efficient and effective in what they're doing So you've you know how to do things you're working on the right things you are communicating what's going on But is your work freeing up others is allowing them to do their best work Whether that's providing data that they need whether it's helping them learn how to use a tool better You know really focusing on that I think is almost peak performance when it comes to

operations role. And then the last one is if you are really focused on the impact, and this overlaps a little bit with are you working on the right things, but are you really determining what those things are based on the overall impact to the organization? Are you focused on

tasks that are aligned to team level or organization level goals. And are you doing the things that are actually going to move the needle on those goals? So it's a, it's a process. I think people go back and forth on this, depending on where they are, uh, in terms of, you know, their role in a specific organization or the team or the resources around them. And I'm sure there's other ways to look at it, but that's kind of the approach that I've taken to helping me, you know, what's the next best.

thing I could be doing right now. Am I doing the right thing? Okay, great. Well, now I need to start communicating that.

Ken Babcock (06:53.99)

Yeah, I really like it because it's straightforward. It's not super nebulous. I tend to agree with you on maturity models. It's like, all right, that sounds good, but like, what does that actually mean? Whereas this, fairly simple, do the thing, do the thing faster, do the right things, share the thing that you're doing, enable others, and then drive impact. I mean, to me, that makes a lot of sense. You mentioned that people kind of shift back and forth.

You know, I was going to kind of ask you, Hey, how do you know where someone falls on that scale? But is that even the way that we should be thinking about it? Or should we be looking at this like on a project by project basis? Um, rather than like maybe assessing where we are personally.

Jeff Cullimore (07:39.486)

Yeah, that's a great question. I, I honestly may not have really considered it on a per project basis, but I think, I think that definitely helps gauge where you are on a specific project or where, where you may be on a, on a given day, honestly, you probably move back and forth between these, depending on who you're working with and, and which stakeholders you're, you're reporting to and all of those different things. And, um, I, I do think at a.

at a very high level, you know, if you look at generally how you spend your time. And I think the things that you focus on, that was actually kind of one of the, the things that started me down this path was I was, I was at

level one, basically I was in a tool, I was learning a new tool, and I was able to do something that took me a couple of days to figure out. I had some help from the CSM, and I had some help from some online tutorials, and I got really excited when I was able to do this relatively simple thing. And I kind of realized as I was reflecting back on that, that

I was so focused on wanting to get that thing done that a lot of these other levels, whether or not it was the right thing or what impact it had, they kind of fell by the wayside to a certain degree. But as I look back now, that was probably six or eight weeks ago, my use of that tool and my ability to make an impact with that tool have changed significantly. So I would say I'm probably more at the five or six level, if you term it that, on the

Jeff Cullimore (09:12.976)

to drive results and create an impact. So I do think it's situational. I don't think people are stuck. I hope, you know, if somebody considers using this to perhaps measure their own progress, it's very much, it's a tool. It's not a reflection of someone's ability to provide value or their worth as an employee at a given organization.

Ken Babcock (09:38.75)

Yeah, you know, but I'm sure you probably get the question of like, how do I rise to the next level? And I remember, you know, when we'd be in promotion discussions at Uber, you know, a question we'd, you know, we'd have to ask was always, are they performing at the next level? Which was a little counterintuitive. Cause it's like, well, do they have to do that before we promote them or, which is always kind of funny, but I'm not going to get into corporate bureaucracy now.

Jeff Cullimore (10:02.659)


Ken Babcock (10:07.766)

But I'm sure a lot of people are asking that. If you find yourself firmly in the like, all right, I'm finding efficiency, how do I raise to the next level? Or I'm sharing my work, but I'm not quite ready with enablement. How would you push people to think about kind of rising to the challenge of that next level?

Jeff Cullimore (10:30.21)

Yeah, that's a great question. I think it has to do with, I guess I look at it a little analytically and I think how are you spending the bulk of your time? Maybe the bulk of your time you are just at the level of kind of communicating what you're working on and you're still kind of trying to figure that out and maybe you've gotten some feedback from a boss or something like that and they're saying, hey, you know, I appreciate that you shared this update, but.

I don't really know what I'm supposed to do with that. Maybe you could customize the information for me a little bit more and so you're fine tuning that. So if the bulk of your time is spent there, maybe look for a percentage of your time that you can carve out, whether it's daily or weekly or monthly to focus on that next level. Okay, I'm communicating consistently. What can I do to find an area where I can go back and do some...

Can I rework something to enable more people to be successful? Or can I spend some time with somebody as they go through this process to see where the roadblocks are? So I think being intentional about how you spend your time is a way to not only quantify what you're doing currently, but then look for ways to kind of bridge up to that next gap. And that does end up becoming, like you said,

an indicator to people who the powers that be essentially that, oh, maybe, you know, maybe at this case, Ken's ready for a promotion because he's starting to perform at that, that next level. And it's not necessarily a guarantee by any means, this isn't a widely adopted maturity model or anything like that, but, uh, I think just, uh, even having a rough idea, it's not like you need to put it in a spreadsheet or anything, but having a rough idea of how you spend your time is helpful.

Ken Babcock (12:09.738)

Yeah. And, you know, I'm curious, maybe stepping away from the framework and, and reflecting on your own experience, you know, that, that example of like enablement that you started talking about, you know, I think that's kind of a way where you can, you can also, you can show that impact.

you can share more effectively. And so this can be sort of woven into a couple of these levels. And so in your experience, how have you identified opportunities to enable others? And what have you seen as the most effective ways to do that?

Jeff Cullimore (12:46.122)

Yeah, that's a good question. A lot of my background is in marketing technology. So evaluating tools, matching them up against use cases, going through the entire process of implementation and setup and then onboarding. And one of the things that I'm a firm believer of is that the real work starts after the tool is implemented. Just because you spend a bunch of money and a couple of weeks getting a tool up and running doesn't mean that it...

you're going to realize all of the benefits immediately. It doesn't mean that you're gonna be super successful and that everybody you bought the tool for is just gonna have this light bulb turn on and think like, oh yeah, great, Salesforce, sure, I get it. I'll log in and I'll use it to the full extent of its capabilities. So I believe that, yeah, the work really starts and a lot of that work is enablement work. A lot of that is the ongoing support. It's great to have a big.

launch and excitement and training and videos and documentation and everything.

Most of the time, my experience has been that when somebody gets stuck, they're going to choose one of two paths. They're either going to go back to how they did it before, or they're going to reach out to you and they're going to say, Hey, I've got a question. I don't know how to do this or this is broken and you know, I'm stuck. Help me. So, uh, that's kind of the critical moment. You need to have a lot of SaaS companies will talk about an aha moment where a user of their tool will realize, Oh, this is the value that it creates for me. This is why I'm going to use this tool.

And you kind of almost by proxy are trying to create that same moment for your users. You have invested time and energy and money in this tool and having enablement available not only at the beginning, but as users go through the entire process is definitely I think key to any successful, in this case, software implementation.

Ken Babcock (14:42.662)

Yeah, because that shoulder tap can be expensive. And we think about that a lot where, hey, look, we all want to be human. We all want to help each other. We're not going to turn that down, but the frequency of that happening when you're trying to figure out Salesforce, that's not something repeatable that the next user that encounters it.

Jeff Cullimore (14:47.246)

Mm-hmm. That's it.

Ken Babcock (15:10.838)

is going to be able to solve on their own, right? It's like, oh, that lives in a DM somewhere. And so when you're in that position of getting a lot of those questions, how do you think about, okay, how do I enable someone in the future to basically answer this for themselves?

Jeff Cullimore (15:28.566)

Yeah, I think there's a couple pieces there that I've seen be successful. One is,

I always try and find a champion. I always try and find someone on the team, one of the users who's there with their peers in the trenches who can find some early success and then you can kind of point to them and say, hey, this is Jeff. Jeff's been really successful. You know, his, whatever it is, his conversion rate has increased or his number of opportunities has gone up. And so replicating what that person has done, usually kind of in bite size, real time, real life.

examples is really, really key. I think whether it's a quick loom video recording or it's a walkthrough in a slide deck with screenshots or something, being able to make it really applicable to the...

the person or the people that you're working with to empathize with them and say, I get it. I get that updating an opportunity in Salesforce is a pain in the neck, but let me show you how to do it quickly and efficiently. And let me show you the value that will come if you're able to do that on a consistent basis. I think highlighting those things makes it really relevant and you start to see increased adoption at that point.

Ken Babcock (16:35.978)

Yeah, totally. I mean, that's that aha moment, right? Is that value. Because like you said, in the first level of the maturity model, you're clicking buttons, you're moving through a tool, you're not even maybe necessarily understanding the value of what you're doing, you're just trying to do it. Whereas I think as you move up and when you're thinking about enablement, it's not only here's how you do it, but it's also...

Here's the value back to you, to the organization. I think that matters a ton. Now, the way you've articulated this model is like, you know, you kind of have to get through these steps, right? You can't get more efficient if you don't know how to use the tool. And you're probably not sharing until you know it's the right thing to share. And so my question there is like,

Is there other points where it breaks? Are there points where you're like, actually I should have been thinking more strategic there, even though I was maybe in the third or fourth level. Like, are there opportunities that pull you sort of more to that strategic end?

Jeff Cullimore (17:47.886)

Sorry, hang on just one sec. Might have to have you repeat that question.

Ken Babcock (17:52.659)

Yeah, no worries.

Jeff Cullimore (18:06.142)

Sorry. Let's retake it from that question. Okay.

Ken Babcock (18:07.198)

All good. All good. Yeah, no, it's honestly, it gives me an opportunity to re say it too, because it was kind of complicated the way I said it. But let me start again. So the way you've articulated this maturity model is that

Jeff Cullimore (18:13.759)


Ken Babcock (18:22.33)

You kind of have to go through each of the steps, right? You can't become more efficient if you don't know how to do the thing. And you can't necessarily be sharing and be effective in sharing it through the team if you're not doing the right things. And so, you know, it seems to be like there's a progression. But are there projects or ways that breaks down where?

Maybe you personally had wished, I wish I was a little bit more strategic there, even though I was in level two or level three.

Jeff Cullimore (18:56.95)

Yeah, yeah, absolutely. I think at some point, depending on workload and other priorities and things that are going on, sometimes you just resort to the, maybe the lowest common denominator and you just try and get something across the finish line. Somebody's asked for maybe a really tactical ask, like an email getting it sent or something like that, and you just have to be okay with.

getting it done and maybe not being as strategic or tactical as, or sorry, as strategic as you would have liked to be with that. So yeah, I definitely think it breaks down. I think the overall value to your career kind of comes with that consistency. I think a little bit about...

I think a little bit about it like compounding interest. If you're able to be at level five most of the time, then typically I think that's how you're gonna be perceived in your organization. If you're typically at level two, then that's probably how people are gonna going to look at you. So.

I'm also a big believer in not adding more stress where stress isn't needed. Marketing ops and rev ops pros and operators in general typically deal with a fair amount of stress and so it's intended to be I think more motivational rather than more the carrot than the stick at this point.

Ken Babcock (20:15.298)

Sure, yeah, that's always a helpful reminder. In all these fast moving, high-paced organizations, you're constantly thinking about, all right, how do I do this better? And that's actually a good segue to kind of my next set of questions, which is really around how to be a strategic partner. You talked a little bit about working on things that will last, as opposed to...

you know, addressing things in the moment. You know, I think it's obviously long-term solutions versus kind of short-term band-aids, but how do you sort of reconcile that approach with how...

you know, a lot of operations folks view themselves, which is being change agents and taking yourself from V1 to V2 to V3 to V4 where inherently, some of those things aren't gonna last because you have a new version of your company, you have a new version of thinking about things. And so how can you help reconcile that for the audience where you do want people to work on things that last, but also acknowledging that the shelf life might not be as long as you had hoped.

Jeff Cullimore (21:24.278)

Yeah, yeah, I think a lot about paradoxes when it comes to operations. And I think this is one of the fun ones to think about and noodle on and maybe one of the more tricky ones to figure out for sure, because yeah, I just had a conversation this morning about something that has been a project that my team and I have spent probably the better part of the last two quarters on and.

The conversation was forward thinking, looking ahead maybe a year, year and a half, and I realized, wow, everything that we just went the last three and a half months on.

is probably not going to be needed at that point. So in the moment right now, I feel great about it. I feel like, yeah, this is meaningful. It's impactful. I can draw a direct line to things that are objectives for the marketing team, but knowing that that'll, will move away in the future. I think you have to be, you have to be kind of comfortable and okay with that. And you kind of also have to have the combination, I guess, of, you know, the IQ and the EQ to say,

I realized that this is what's important in the moment and I'm going to work on it. And if we get to the point in six months or a year or two years where it's not important anymore, then we'll move on from it. And if you learn from it and if you can take lessons away from it, then I think there's some lasting value there. I think the biggest.

Jeff Cullimore (22:47.73)

scenario where that things that last idea comes into play, maybe even more in the day to day. It's so easy to default, okay, it's the end of the day, my brain's frazzled, I'm tired, but I need to keep doing stuff, I just need to get something done, and so you may kind of default down to something that's super easy to get out the door, but maybe in the end, that wasn't super critical or very important, but you could have spent that hour on.

something that is going to maybe have more staying power than an email that gets sent once a month or something like that. So it's a fun thing to think about at the long-term high level for sure because it's almost inevitable that things that you think are going to be around forever now are going to go away.

at some point in the future. But if you can think about it in the moment, like, okay, yeah, I could choose this thing that I know isn't really impactful, or this thing that I know at least for the next six months is gonna drive some positive impact and results, then maybe that's a helpful tool to use at that point.

Ken Babcock (23:34.349)


Ken Babcock (23:49.55)

Yeah. And I'm curious your take on this because, you know, I thought about this a lot is, you know, do you think organizations almost like change too fast for, you know, for, for working on things that will last to be a reality?

Jeff Cullimore (24:08.286)

Yeah, that's a great question. I think that, um, I, I do think there is something to be said for. Consistency and for showing up and for tackling a problem and, and organizations may, they may bail out from a process that's working because they want something that works faster. When in reality, that original process would probably be the, the thing most likely to get them to where they want to go.

But it's tough. We live in a world where there's, I mean, AI is literally taking everything over and you've got VCs and boards and IPOs and all sorts of fun economic considerations. And so I get that there's a lot of external considerations when it comes to that, but yeah, I do think that there are organizations out there that commit to something and just keep hammering away at it and then get there and maybe it's not fast and maybe it's not super exciting, but ultimately they are very successful.

Ken Babcock (25:05.079)


Now, and you bring up AI, I was just listening to a report earlier today. It was a study where they looked at GitHub Copilot specifically, and they looked at a team of engineers that was using, or at least had the opportunity to use Copilot in a group of engineers that didn't. And they gave them the same task, the same prompt, and the engineers with Copilot actually were able to complete the task in 55%

less time and The magnitude of that, you know economists get excited about 2% productivity growth on an annual basis, you know 55 is crazy and so, you know if you think your organization is changing fast now Just wait just wait a couple months That's yeah, no a really helpful way to think about it

I want to shift a little bit. You know, we talked a little bit about this maturity model. Now we're talking a little bit more about being a strategic partner. How do you as a leader and you've been a leader at these various organizations, how do you set the right guideposts for?

people on your team to understand what is the strategic high value work. So, you know, we've been talking a lot from the lens of like individual contributors, but as a leader, how do you give people the right frameworks to understand, okay, this is the right thing to do. This is the most strategic thing I can be working on.

Jeff Cullimore (26:47.99)

Yeah, I think a lot of it really boils down to having really clear and open communication. I think sometimes leaders assume that because someone is competent at a certain task or using a certain tool that they're going to have all of the inputs that they need to make a decision. And

as team leaders, we're inherently just involved in more meetings and more conversations and have more context than a lot of people on our team. And so it's a learned skill and ability, I think, to be able to synthesize that down and say, you know, for the different tasks and responsibilities that are going to come your way, then here are the additional things you need to know for prioritization. You know, there's a concept called

the initial term, give me a second here while I think of it. It's a.

Jeff Cullimore (27:45.321)

I think. Let me Google this really quick.

Jeff Cullimore (27:54.41)

Yeah, that's what it is. Okay, so I'll pick up that answer again.

Jeff Cullimore (28:01.698)

Yeah, I think it's really incumbent on leaders to take all of the additional information they have from conversations and meetings and emails that they're included on and to really boil that down and to help their team members have the correct inputs to be able to make those decisions on their own. There's a concept which I believe is derived from, from the military called commander's intent, where you essentially set the, the finish line. You set the destination and some.

parameters, some guideposts around what needs to be done in order to get there. And, and then you enable your teammates and the people that work with you and your stakeholders to then make decisions autonomously towards getting closer to that goal. So it's a, it's definitely a balancing act. I think that's one of the more difficult things for new leaders as well as to understand.

There's maybe a little bit of excitement, like, oh, I'm included in these strategic conversations now and you're kind of just soaking it all in, but you have to realize that you have a responsibility then to turn back around and get the important information to your team to make sure that gets all the way to the end of the row so that they aren't wasting their time on projects that ultimately aren't going to have, uh, you know, an impact on getting to where that final goal is.

Ken Babcock (29:15.338)

And that truthfully is a form of enablement. I think we tend to think about enablement, especially in the way that we've talked about it through the lens of tools, but context is also a huge knowledge gap that a lot of team members have. So I appreciate you bringing that up. Reflecting on enablement, how do you sort of bring in

Jeff Cullimore (29:20.767)


Ken Babcock (29:44.758)

metrics for your teams to help them understand whether they're being successful, whether they've been enabled or they're providing the right enablement to the rest of the team.

Jeff Cullimore (29:56.938)

Yeah, yeah. Measuring the, the concept of measuring process adherence or how many times that something get done correctly. I know there are tools, I think Gong and chorus and some of the sales call recording tools claim to have the ability to, you know, you put in your framework, your med pick or your spice or whatever your framework is, and they can go through and kind of determine whether that's being followed, but.

Yeah, I think for more of your day-to-day enablement, understanding what the positive outcome looks like, sometimes you can measure that with, sometimes you can measure that in a quantitative manner with data and metrics. You can go and look at the percentage of Salesforce fields on an opportunity that have been completed, or you can look at the overall number of...

tickets that were created using a certain process or something like that. That helps you understand quantitatively whether or not the process is being followed. But I think it's also helpful to still get in the trenches, get down in the weeds with the teams that you're enabling and just do an over the shoulder kind of situation where you're walking through things with them and you're just observing and you're saying.

how things actually work. Are they doing what you train them to do or what you think you train them to do? I think it's important as enablers to take responsibility for at least some of the success of the process. You can't just train a team and then expect them to all execute on it perfectly because we're human, we miss things, there are questions or edge cases or scenarios that come up that aren't necessarily accounted for. So the metrics piece is interesting because

It's, I think it tells a lot of the story, but it definitely doesn't tell the entire story. You may see metrics that indicate that the, the process is being followed correctly, but maybe the process doesn't actually have the eventual outcome that you thought it did when you started developing it.

Ken Babcock (31:56.23)

Yeah, I loved what you brought up about how, you know, we, we can't just assume that because we did the training that everyone's going to be successful. Um, we are human. We're not AI yet. Um, but, you know, I think that also sort of makes the case for more real time enablement, knowing that, you know, in the moment people are going to encounter situations.

and be provided context that they need to make a decision on. And it's not always gonna line up with like a training module. And so I'm curious how you prioritize more of that real time enablement for your end users versus traditional training modules, classes, upfront work that's maybe done by like a customer success team on the other side, but why is that real time enablement piece so critical?

Jeff Cullimore (32:53.218)

Yeah, I think it goes back a little bit to what we were talking about with, with the aha moment and how that's really the, the point of the point of no return, somebody's either going to see that the process is working and how it can benefit them and they're going to muddle through it until they figure it out and they're going to continue to adopt it, or they're going to go back to however they were doing it previously. And then you almost have even more work on your hands because you've got to go back and say, Hey.

We rolled out this process, you're not following it. You know, there's a little bit of a, an admonishment there where maybe they feel a little embarrassed because they're not following it or they don't understand it. So I think, you know, the actual implementation or the actual execution of that, I think differs depending on the scenario and the team and, you know, is it a tool or a process or what they need to do, but providing that visibility into.

Where people might get stuck getting that consistent feedback, which I think is also a huge part of real time enablement. If you're iterative and you're adopting and, uh, excuse me, if you're adjusting and making sure that you're making changes as you get feedback, I think. That willingness to be responsive and to see the people receiving the training is, uh, you know, as, as humans, as people who are working through this and have, um, feedback and opinions and thoughts as well, and making them an equal

partner in it, I think you'll get better adoption and better buy-in. So there's a lot of tools and tactics out there and different ways to do it. But I think if you fail to consider that you're going to need to be ready to do real-time enablement, then you're definitely going to get stuck.

Ken Babcock (34:31.818)

Yeah, and I think like there's a concept that we talk about a lot, the ambivalent adopter, which kind of comes back to that high stakes aha moment where you decide, all right, this is either helping me or it's not, and defaulting maybe back to the old way of doing things.

And I want to be clear when I say ambivalent adopter, that's not like a derogatory term. I mean, it's not meant to be associated with people being lazy. It's just that like for a lot of highly efficient folks, if they can't see the value or a new process or tool feels too cumbersome relative to what they're familiar with, they're probably not going to adopt it. And so.

How do you mitigate that if you definitively know, hey, this new process is gonna be better for you? How do you get ahead of some of those ambivalent adopters?

Jeff Cullimore (35:29.462)

Yeah, I think acknowledging the fact that a change is hard, that something new is going to take some time and take some getting used to, typically helps. And I think soliciting feedback and having an open feedback loop and displaying a willingness to make change, make changes to a process is a great foundation and a place to start. I also think that there is a certain level of

empathy and research that's involved there as well. I think if you involve individuals who are going to be impacted by the process change in the development of the process, then that typically helps you get a little bit more buy-in as well. I know when I was at Wistick, a small startup, you know, there were probably...

25, 30 people at the time. And, and as it was a startup, we were rolling out new tools and processes all the time. We were figuring things out on the fly. We purchased different tools just because nobody had ever needed them before. And our sales team was growing and it was time to start rolling things out. And we had

individuals who we knew were going to be a little hesitant, a little reluctant to change, individuals who had been there for a while and been able to thrive, honestly, without a lot of those processes in place. But they were things that a growing organization needed. And so making sure that those individuals were involved or at least aware of those changes beforehand helped us to mitigate a lot of the.

pushback or what's even more damaging possibly than the pushback, which is this ambivalent adopter where you feel like things are going well and you're not getting any feedback so you're assuming everything is good but at the end of the day nothing is really changing because the process isn't being followed.

Ken Babcock (37:13.174)

Yeah, yeah, that's a that's a dangerous one. Because again, it's like some people might resort back to that thing that they're familiar with and you talked earlier in the podcast about.

the champion, you know, I think Jeff was the example you used, the champion of the tool or the champion of the process. Bringing people in upstream is also the way to create that, you know, I think that's just a good lesson for, you know, not just tools and enablement, but in life in general, like if you want people to be bought in.

you know, bring them upstream, you know, make them feel like they're a part of the process. They're part of creating the ideas that, that fuel what eventually you're going to do. So I totally agree with you on that. And, you know, do you feel like there's almost an increased importance on real time enablement?

in a remote work environment? I mean, I'm coming to you from my basement. So, we're a remote company. I've seen how real-time enablement has impacted us. I've seen how it's impacted our customers. Do you think there's a heightened importance with remote work?

Jeff Cullimore (38:26.75)

I do. Yeah, absolutely. There's

There's so much positive about remote work in terms of what it enables and who it allows to, to join the workforce or be a contributing part of the workforce. But it, it does add some additional barriers when it comes to that spontaneous spur of the moment communication. Whereas four or five years ago, we'd all be sitting in an office. If you had a problem or a question with the process, then you could come over. You could knock on my door, tap me on the shoulder, and we could sit down at your computer and hammer it out in 15 minutes. But now you've got to ping someone on Slack.

available for a call and then you've got to figure out the whole screen sharing. And we're used to a lot of that now, but it's, it's more steps or at least different steps than it would be if we were in person and, uh, yeah, there's, there's so much, so much rides on that adoption process going smoothly, or at least questions getting answered that I would say it's certainly increased in, in importance. And I don't know if the.

The consideration of or the creation of that real time training and enablement has been considered as strongly as it probably should have been in remote environments. I think in a lot of times.

individuals or teams that are designing the training enablement are probably still falling back to a lot of things that they're comfortable with. A lot of things that they've seen that have worked in the past, maybe not factoring in that they're not going to be there two feet away or just down the hall to answer a question if need be.

Ken Babcock (39:56.91)

Yeah, totally. What are you doing? You hinted at some of these, but when you don't have that synchronous time, which can feel harder in a remote world too, because it's like, well, I don't want to disrupt. I can't see that person. I don't know where they are. When you don't have that synchronous time, what methods are you using to create materials for real-time enablement? Is it mostly looms? What does it look like for you and your team?

Jeff Cullimore (40:10.583)


Jeff Cullimore (40:23.05)

Yeah, a lot of videos and I've found that even though it is a little time consuming to do it and it feels a little silly to click through it sometimes, actually putting a step-by-step walkthrough, whether it's in a dock or a slide deck with screenshots, I try to be overly simplistic and obvious and that way you just don't leave any room for questions or the questions that you get are things that are way out of left field that you do need to address.

I put a video together earlier this week for a couple members of my team for a tool that we're using for sending emails. And...

I tried to be very thorough and before I realized it was a 20 minute long video, which is not necessarily great for real time enablement. People don't usually have 20 minutes to sit down and watch a video, but it was the right thing for the scenario. We need a team of people to be comfortable with this tool. We're sending emails. There's a fair amount of QA and setup that's involved. So I wanted to make sure that...

we were all on the same page. So I think being conscious of the fact that, you know, if you use that 20 minute video as an example, it was great for getting a couple of team members up to speed on a brand new tool, but it would not be great if it was a team of 55 sellers who were trying to get certain number of emails out or a certain number of prospects reached in the day. And, you know, you would need to have a much more bite-sized direct concise communication at that point. So yeah, video in a remote world for sure. I think video,

if you can put your face there too. Loom does a great job of that. It kind of personalizes it a little bit, makes it seem a little less like you're just sitting there going through an endless training session. But yeah, video, audio, you know, everything that the Teams and Slack have enabled, I think is great as well. And I think one thing that isn't super tool related is just going overboard with your

Jeff Cullimore (42:23.242)

willingness to be available. You know, if you're rolling out something that's a significant change, just plan on spending the next couple of weeks on Zoom calls, on Slack, you know, whatever it is, whatever the tool is, just be overly available. Drop in randomly and ask people how things are going. Check in on reports, hey, I saw you recently completed this process, you know, help me understand what's going on there. I think that helps people feel less like they're bothering you and more like they can come to you and trust you and get a question answered.

Ken Babcock (42:52.51)

Yeah, absolutely. I think being, you know, we're on our team, very transparent with our calendars. You know, I always tell people, hey, if something's open, it's open, you know, it's open for a reason. You know, I'll try to block as much off as I can if I can't be contacted, but yeah, communicating that you're available. I mean, I think we've all had that hesitation where it's like, I don't want to DM somebody or I don't want to set up a meeting unannounced, you know, like...

make sure they're actually available. So I appreciate all that insight, Jeff. I do want to close with one final question. I mean, we've hinted at so many tools in this episode. So I do want to get your perspective on, you know, what are the three tools that you can't live without today?

Jeff Cullimore (43:43.519)

Three tools.

I don't know if this is cheating, but I am going to start with chat GPT. I'm not a developer. I'm not an engineer, but I have had a reason to need to do some lightweight coding recently with some integration projects and the extent to which chat GPT can serve as a springboard or a starting place is it's pretty insane. Honestly, at this point, how you're able to just use natural language and say, I need to be able to do this in JavaScript. And it turns around and spits something out. That's 95% of the way there.

I would say another one for sure is Loom, which we've talked about, or QuickTime. Honestly, I use QuickTime a lot for desktop recording for things that are longer than the five minutes. Anything that allows me to put a video together, Slack allows it, and Zoom as well. So anything that makes it easy to record videos. And then the last one I would probably go with is, I don't know if I'd be a true operations.

Pro if I didn't say JIRA as well. JIRA is keeping our team organized and up to date on all sorts of different projects that we have going on and some external things that we're doing as well. So a project management tool on JIRA is the flavor of choice for the team I work with right now.

Ken Babcock (44:58.01)

Awesome. Well, thanks for sharing that, Jeff, and thanks for spending time with us. I know the audience is gonna love this episode, so I really, really appreciate it.

Jeff Cullimore (45:08.746)

Yeah, thanks. Great. It was great to be here.

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