Building Strong and Cohesive Teams

Chuck Brotman: Hello, everyone. Welcome to the Talent GTM podcast. This is Chuck Brotman. I am posting an episode today. Fun fact for everyone. This is our final recording of calendar year 2023. We will be posting this sometime early in 2024. But nice to wrap up the year. We’ve had some great podcasts and I’m so excited to have on my former peer and friend Tiffany Jensen to our last recording of 2023. Tiff. Thanks for joining us. Great to have you on the podcast.

Tiffany Jensen: It is very good to be on and to celebrate this last podcast of the year with you.

Chuck Brotman: That’s awesome. I really appreciate you making the time between Christmas and New Year’s. And I’m looking forward to talking about building strong and cohesive teams with you. But to kick things off, I do want to tell our audience a little bit about you. Tiff has an incredible narrative over two decades of experience in sales and revenue leadership roles, including working at high growth startups like Parcel Perform and Topology and Andela. Prior to that she had a great career in channel organizations, working at PGI and then coming over to On24 where we met. Actually, we might have met when you were at PGI, but

Tiffany Jensen: Yeah, I think we did meet there.

Chuck Brotman: Tiff works basically running the global channel and strategic accounts organization. She did some of this while in Paris, some of on New York saw, ran these organizations all the way through On24’s IPO. And she’s currently managing a consulting practice, helping companies with GTM strategy development, promoting better cross executive collaboration and sales training. She’s a very active member of various professional organizations, including Chief, which is a community for C-level women. And Pavilion, where she is co chairing their Ciro group for New York. And she’s also an active investor in the investing syndicate and accelerator in the UK called Impact Ventures, which has a commitment to helping support women founders. When Tiff is not doing all of these things, she enjoys travel, cooking, eating, running, languages, reading, music, wellness and people studies or she studied cultural anthropology and music. I know Tiff was one of the very few people who had an actual authentic interest in my academic background. Fun fact of it, you mentioned here you, you were a cited authority in a Landmark Supreme Court case on intellectual property law. I did not know any of this. Can you tell me a little bit more about that?

Tiffany Jensen: You know what? this is a fun fact because it is actually fun. I googled myself probably 10 years back and realized that my sort of undergraduate thesis I’d written on, the History of Cinderella as a Folktale, which my thesis essentially, laid out that it’s not a European story as many think of it as, the Disney version, the Perrault version, a French story, but, Chinese in origin with some interesting mistranslations around glass slipper being first slipper and some sort of bride traditions. so I, Googled myself, saw my, thesis pop up and realized I’d been quoted in an intellectual property suit let, I think, and this is at the time, I don’t know if you remember when John Ashcroft, I think, was secretary of defense or secretary of state. So, apparently he used my thesis for his argument, which I don’t know how I feel about, but it was interesting to see like, wow, I’m a so excited authority. So I think it goes to show, going back to that academic work you do early in your career and it feels sort of irrelevant to the rest of your life, it makes an impact and you never know how,

Chuck Brotman: Well, I mean, yes, when you’ve done things well, I can tell you, I’ve googled myself and my results have been a little bit more disappointing than that. But that’s awesome hear.

Tiffany Jensen: I’m sure that’s not the case.

Chuck Brotman: Yeah, I will. I will definitely look more into this after our podcast here. But jumping into our discussion here. So I think as we shared with the audience, we met probably 15 years ago before, before you joined On24, I love to ask, our guests this question. And I’m particularly curious about you in light of learning more about, some of your, your interests. How did you get into sales in the first place? What’s your story there, Tiff?

Tiffany Jensen: Yeah, I finished school. Initially, I had sort of pivoted from culture anthropology to focus on opera performance. So I’ve always been a musician, very musical family and. I, graduated from school and was sort of looking down two different paths in life. one of them where I would be, like, auditioning every three months for the rest of my life for, music gigs. And you never, I mean, it’s hard to be the best of the best. There’s various, it’s, very limited sort of career path. and having an opportunity, I’d worked and put myself through school. And so I had some professional experience. But, something stable, something solid and something that paid six times what I expected to make as, a chorus music singer.

Chuck Brotman: Right.

Tiffany Jensen: And so I thought I’d take a chance and I, it just, I absolutely loved it. I felt like my interest in people. My interest in understanding cultures, what makes people tick, and also sort of larger macro market trends, what drives decision making, how to make things happen, all of these things, sort of came together in sales for me. So I started as an individual contributor, I was

Chuck Brotman: And was this that PGI out of curiosity? Wow.

Tiffany Jensen: It is actually a company that PGI acquired, called Clear One. So I think they still exist in some form or another, another division of theirs, but nice company. I was very quickly promoted to run a small kind of national sales team and that is, is where it all started.

Tiffany Jensen: I was given a really great opportunity at PGI to build their channel organization, something that was really important for the company at the time in terms of, being an initiative that needed to succeed that they were willing to resource. But, channel was very nascent at that time.
So it was a sort of like, figure this out. there aren’t a ton of benchmarks. There aren’t, there isn’t a lot of ground that’s already been trodden. and I love these types of creative projects where you’re bringing together people, ideas, and really being able to tap into a customer voice, market voice, and build something. So. Yeah.

Chuck Brotman: I’m sure you’ve got to be fascinated as well, seeing how interest in channels and partner ecosystems has become so, so fashionable in the market today. Right?

Tiffany Jensen: Yeah, different terms now but you know it’s ecosystems it’s near bounding it’s. Yeah, no, I, it’s, those of us who spent a lot of our careers in channel it’s we’ve always known it’s, it’s the way.

Chuck Brotman: Yeah, for sure. For sure.

Tiffany Jensen: Or it’s one of the important ways. As part of a strategy.

Chuck Brotman: Yeah, no, definitely going back to the narrative again. So when you first got into sales at the initial company, did you know that some of these other, like, your kind of people skills, your curiosity, your renaissance background. I mean, did you know these would be applicable in sales? Or was it more of a matter of like, Hey, I’m just like, I’m looking for opportunities to make, a good living. and like what did you know about sales at that time? I’m always curious about, like, cause I had my own preconceptions that were way off.

Tiffany Jensen: I mean, I think I’ve got a fairly strong belief that I can do what I put my mind to. So it wasn’t really, I don’t think I was trying to connect dots between skills and and the role itself. I am a big believer in work. I have a strong work ethic. I was sort of raised in a very entrepreneurial family and I just came in not knowing exactly what to do and rolled my sleeves up. and I will say there’s this kind of fake it till you make it element that all of us realize at some point in our life, there is kind of a grain of truth to that. Until I closed my first deal, I thought I was completely failing like, Oh, how many calls am I going to have to make?

How many presentations, what am I doing wrong? And then suddenly, it’s like one deal after another, things start to happen. And I realized there was this tie between, what I could drive what I can influence, and accomplishments that actually came. So, I think that moment for me was actually probably my very first deal, like, oh, wow. Okay, this is actually happening. And then the next one and then the next one and then the next one. So, yeah.

Chuck Brotman: That’s really, that’s really exciting. and I mean, certain aspects of my narrative, I feel are similar. I mean, I’ve always banked on my work ethic when everything else has felt more uncertain, right? Because it can get a lot. so I’m curious about like, where you see your own narrative fitting into how you think about, hiring for, successful salespeople.

Like, are there certain Kind of skills and behaviors. When you’ve been in roles where you’ve been hiring, either like, early-stage sellers or SDRs or, or just, where the market’s been more constrained. You needed to hire people that haven’t done it before. Haven’t done subscription software sales.

Are there certain constants that you look for in terms of behaviors or dispositions? or I know you might say it’s really role dependent, but I’m curious, like how you think about certain things that are more likely to tie to success in sales. 

Tiffany Jensen: Right. number one, I would say I love I like to understand someone’s thought process. So. I will oftentimes take an interview in a little bit less traditional direction at some point if I feel things are going well, and I’m getting, kind of the data that I need from somebody, and ask them about a challenge I’m actually trying to solve as a business and Just listen to their thought process.

Understand how they sort of take my feedback and we’re able to bounce ideas off of each other, how they sort of are able to intellectually process, challenges and you could have a very different background. But a very great, capability to come in and think about the way that an organization is growing or how we can be more efficient, or how to build a relationship with a customer that’s challenging. So it’s, there’s a component of sort of thought process, intellectual curiosity that is important to me. There’s the obvious stuff like, communication skills demonstrated, follow up the things that you want to see in an interview. I, again, I don’t know that this is untraditional or not, but I’m usually when I’m approaching, a hiring process, I’m also thinking about what I have on my team already.

That is where it depends each time. It’s I’ve got somebody who’s super organized, who’s super process driven. And who has a lot of experience in this particular industry, but I don’t have somebody that’s quite as good of a presenter or that is really a motivator for other people on the team or that has a desire to move into a leadership role.

I made balance what the team needs and that may vary each time, but intellectual curiosity, and I’d say some demonstrated way to think about problems creatively is the number one thing. And then the number two thing equally important is I listened for cues in an interview about how team focused they are.

So our topic today of building strong and cohesive teams, that’s not necessarily me building, that’s me facilitating. And so I’m trying to identify if I’m somebody I’m speaking with or somebody I’m considering for a role is able to come in and value the health of the team and the organization over their own professional short term goals sometimes.

Chuck Brotman: Yep.

Tiffany Jensen: And so that’s, I think that’s important to assess for me as well.

Chuck Brotman: That’s right. So I mean, you’re thinking about team in multiple dimensions here. I mean, the first you’ve talked about is like understanding if you’ve got certain like gaps or needs on your team and thinking team first, right? That will help with like leveling up the team as a whole. You’re thinking about.

They’re intellectual curiosity and coachability is kind of your relationship with them. And then the third thing I think you’re touching on here is like the traditional notion of are they a team player? Will they put sort of the needs of the whole versus their own personal needs when push comes to shove or in circumstances where you need, you just need a certain level of selflessness.

Is that a fair way to put it?

Tiffany Jensen: It’s a level of self-selflessness, or it’s the ability to think a little bit more long term and to trust that works on a reciprocal basis. Like the team will take care of you as well. And oftentimes it’s hard to count on that now with the company. So I know that this is not an opinion that everyone shares.

There are folks that I respect a lot and have worked with who are like, I want somebody with an absolute killer instinct who the only thing they’re focused on is comp and they’re fighting tooth and nail for every comp dollar they can get. I want somebody who’s very driven to succeed, but that in my experience, the person who’s a hundred percent, commission driven ends up being pretty hard to manage oftentimes, and burning bridges internally that I’m then sort of taking my focus away from to repair.

Chuck Brotman: It’s kind of like you’re thinking strategically about like, if you can have a team of folks who are in, who are sort of personally accountable for their goals and achievement and have that ownership mentality. You still have to think about are they going to do so in a fashion that helps level everyone up or they can actually be more of a drain than a contributor.

Right? So I think, I mean, as a recruiter, I can tell you, I think most companies like us. Aspire to hire collaborative people. I mean, that that word almost always comes up in intake, but where I find, people often lacking is like, what does that mean in terms of how you’re thinking about your ideal candidate profile?

And how do you balance that with other things that you’re looking for? And I’ve seen, our best clients, like tend to be like pretty good at balancing that right. Particularly for sales hiring. So, I think a lot of it comports with what you’re thinking about,

Tiffany Jensen: Building it into a process is what you have to do. It’s like building it into the right questions, being consistent about it. When I say, what am I missing on my team? it’s not a scalable recruiting process, hiring process, management process, if I’m having to think about this every time I have a conversation with a candidate.

So it’s sort of documenting and consistently working towards goals that are defined and understanding competencies on the team in a way that. my HR partner, my recruiting partner is also aware of, and that we’re able to sort of tweak, or push a lever for one role and not recreate the wheel every single time.

Like, well, what do I think my people are missing this week? it’s just, you gotta force yourself to be a little bit more long term.

Chuck Brotman: Totally. I want to come back to intellectual curiosity for a second. Then we’ve got other things to discuss, but I’m curious about this. and I mean, obviously just even going through your interest and what, one of the many amazing things about you is you’re, you are a non-traditional revenue leader.

We don’t have enough women in sales leadership roles. You’re passionate about women in leadership. I mean, you’re putting your money where your mouth is there in terms of your investment work and everything else. and you’ve got interests also that I think are, very nontraditional, right?
You’re very, you’re, an intellectual, right? And you’ve got a lot of interest in culture and music and opera. And these are not common things that you see in B2B sales. obviously, that that might suggest that for you, if you’re talking to somebody that has like similar interests, right?

It’s easier for you to build rapport much as for right. Right. A traditional stereotypical sales leader who’s interested in sports and traditional bro type activities, right? Might find easier to talk to somebody who’s got those kind of interests. I’m not being as elegant as I wanted to

Tiffany Jensen: No, you’re being totally real and I have bro interests. What do you mean?

Chuck Brotman: I feel like I fit in all these categories because I certainly do too. But how do you, sort of ensure that you are not letting your own ability to maybe build rapport with certain folks faster than others based on shared backgrounds like we talk about sort of getting to know people and tailoring your interviewing to their backgrounds and you’re sussing them out for their actual curiosity.
How do you make sure? That you’re able to assess people maybe have very different backgrounds in you, whether they’re more traditional, bro. You’re just different backgrounds altogether. Like, what’s your process there?

Tiffany Jensen: Yeah. I think it’s like when you asked me about my interests and I, think one of my answers there is I’m interested in people. I’m actually fascinated. By those differences in people. So, I, and I think I’ll say what my process in an interview and with hiring is also similar to sort of, I think that concept of building a cohesive team is I’m legitimately interested if somebody comes in and they’re just absolutely passionate about some random sport, they grew up, playing hockey, you or they grew up, playing well, who grew up playing pickleball this next generation of people
I don’t know that much about it. And I am, I want to learn. I will ask great questions. I’ll. Probe to dig deeper, because I’m legitimately curious. So, you know, I’ll sometimes, get to a dinner party or, good business dinner. And I feel like it’s been like 20 questions with Tiffany where I’m just what about this?
What about that? Tell me more about that. I kind of process information quickly, but I soak it. In and with interview candidates as well, it’s, I want to understand and I want to understand why those are their interests and their commonalities between everybody. and I do have some Brody interests as well.

Chuck Brotman: Right, right, right? That’s awesome. No, I mean, so so you are intellectually curious yourself and you let that lead. And I think that’s great. So let’s let’s segue talking about leadership. And so I’ll start with a question for you. I Curious where you think many traditional sales leaders get people management wrong and why, like what, when you look at your point of view and you may share more with them than others.

I mean, I, to me, I see you as very unique and what you think about it. But if many get this wrong, where are they getting it wrong? And why are they getting it wrong?

Tiffany Jensen: Right. Yeah. I have opinions on this. I’d say. First of all, they are leading the actual people out of the process a lot of times. So it’s the idea of we’re building a culture where, we want to drive teamwork, but there, there’s not a relationship and an understanding of the strengths and weaknesses of each individual team member, the professional goals of each person that they work with.

So the thing about being a people centric leader, about building a cohesive team, about driving culture is people are at the center of that and you have to take the time. You have to listen. I know empathy is kind of a hot word right

Chuck Brotman: Right. I don’t get why, by the way, but I’ve seen that.

Tiffany Jensen: I know, and I think actually managing a group of people as I would want to be managed sort of allowing for dignity respect while being able to hold very high expectations and be clear about those expectations. That’s the challenge. So, I can kind of talk about how I do that as part of my playbook when I come in with a new team, setting the expectations right at the outset, creating, a really strong management cadence so that I’m actually building time into my management cycle to spend one on one, usually documenting, my relationship with each rep is sitting down and talking about what do you want to accomplish? What are the things that professionally you see in front of you personally, what’s important to you, where do you want to be? And then we’re meeting, in our weekly one on ones on a monthly basis with some sort of longer term topics, and then as a team trying to facilitate interactions where others on the team are also very well aware of their team members, strengths and weaknesses so that they can lean into those, when needed and help each other kind of compensate and grow on points that may be lacking.

So I think that you can’t build a people driven culture. You can’t build a culture without actually doing the work and the granular work to understand who your people are and what drives them.

Chuck Brotman: I feel like most sales, if we talk about sales for a second, this applies well beyond that. But we’re talking about sales leaders. Most sales leaders claim if you press them that they are people centric, right?

Tiffany Jensen: Yeah.

Chuck Brotman: I mean, it’s not,

Tiffany Jensen: Oh, totally.

Chuck Brotman: almost cliche, right? and most of those when further pressed will tell you that they want to know their people as individuals. They want to understand their growth aspirations. Their gaps.

Tiffany Jensen: Right.

Chuck Brotman: They want to tailor coaching to those people. I feel like they’re still getting things wrong compared to what you’re doing. Like what?
Can you elaborate? Like for those folks? Like what makes many of them not people centric in the way that you’re? Describing your approach here. Like what?
What’s the gap there in a context? Let’s filter out the folks who like just don’t see their game that way because that they’re just not credible in my book at all. Right. But for those who do see them, where are they not at your level to be candid?

Tiffany Jensen: Yeah. Well, I mean, I, we, I always have room to learn. there was something when you asked me that question that I was thinking of, I went, I was at a conference, probably a year ago, go to market conference and there was a session on leadership, on hiring great people are building great teams and I was excited for the session.

There was a panel and very interactive room. and the main audience topic, like, the main topic of conversation ended up being how would a move out bad performers and how to put people on pips. So it’s like, even in this room where we’re all talking about, how to build a more people centric culture and how to get the best out of your people, really, people are just thinking about how do I get rid of these bad performers?
And I, it was very interesting to see what you just talked about, this disconnect between wanting to be performance focused, but people centric watching this kind of play out. Like we, the session topic is sort of morphing before my eyes. It was frustrating. I actually I don’t know what the gap is.
I know what the gap is as sort of on the receiving end of it, it’s the times this concept of sort of psychological safety or radical candor or being able to feel like you can actively participate and bring yourself to your job without fear of consequences.

There’s a trust building element. There’s curiosity. And there is a trust building element, so I think it’s, you can, a lot of leaders can talk the talk, but they’re not willing to actually advocate for folks and have their teams back with the expectation that you are going to meet this standard and this

Chuck Brotman: Right. Well, I think actually tell me if I think you are kind of getting to a gap right here, which is at a fundamental level. What you’re what I hear you saying is that Many leaders are simply too quick to assume a problem is a performance management one that in other words that there is this notion that even the best, people centric leaders that in any context, any time you’ve got X percent of your organization that needs to be managed out and if you are.
Like committed to exceeding your targets like you will manage those people out quickly for their own good. Am I correct in part? Are you saying like there’s something off about that? There’s a gap there. If that’s your approach, you may be missing some things that you could be doing to better up level the team you’ve picked up on day one is that am I putting words in your mouth? Is that a fair way to put it?

Tiffany Jensen: No, I think that’s a fair way to put it. this being said, as you’ve ever, there’s always going to be. Poor performers on a team and their bad performance is gonna impact other people. And you have got to be decisive and you need to be fair. and you need to be sure. So you know, people say, you know what?

Hire fire quick. Hire quickly. Fire slowly.

Chuck Brotman: Or the opposite, right?

Tiffany Jensen: Right, yeah, the opposite.

Chuck Brotman: Hire fast, fire slow.

Tiffany Jensen: Yeah, give people the benefit of the doubt. I’d say at least once throughout the process, give them an opportunity to explain to understand motivations. But yeah, when it’s time to manage somebody out of the business, if somebody doesn’t have the right intent, if they don’t have a work ethic, number 1, understand what’s going on.
Number 2, give them very clear feedback and the opportunity to address it, have a process in place that supports this work with HR, yada, yada. But, you don’t hold on to bad performers.
Chuck Brotman: If I’m hearing is that when you go in organization like it is incumbent upon you, it’s imperative for you to make sure that you actually that you do know your people that this is not lip service, not a talking point like do you know what you have, what you don’t do, your team’s motivations and drivers, right?
And if you haven’t done that well, if you’re making decisions about who needs to be managed out and by when that may be premature.

Tiffany Jensen: Right. I think it may be premature, I would qualify this by saying the number one thing is to dig deeper and understand what’s going on. And I think a lot of times it’s uncomfortable to do that oftentimes, especially if you don’t have the relationship and maybe you haven’t been as clear about your expectations.

So the clarity around your vision, how everybody fits into it, KPIs, all of that is needed. Assuming that’s established what is going on when you’ve got a bad performer being willing to dig deeper and to actually understand and to still, if needed, be the bad guy, do it in a way that it again, preserves people’s dignity, but I think it’s that willingness to dig deeper when it’s easier to kind of write it off and not have the discussion where maybe there’s a trap and to your point of organizations needing to be as efficient as possible right now and being needing to be able to pivot it is not efficient. Cycling through headcount, letting somebody, having to get somebody up and trained, that’s sort of this CAC payback on employees. it takes a long time to find a great person and bring them in. So if you’ve got, if you’re losing talent left and right, that’s a cost to the business,

Chuck Brotman: Totally. How much of being I want to ask a little more about like what you think, like being people centric, really means and how one does it in a uniquely compelling way. In part, what I’m hearing you say is part of being like people centric is having. The wherewithal, both the skill and the willingness to have, very uncomfortable conversations with needed with your people.

Is that would you agree is that kind of a key part of doing this? Like not just the ability to diagnose and understand but to address and conversationally with your people.

Tiffany Jensen: Yeah. I mean, I think it’s, important. And I think, I mean, I feel like I’m saying things that are obvious here, but as soon as you observe something. as soon as possible after observing something again, give feedback, but assume the best like, hey, I noticed this. I may have done it. I may have done it this way.

These are some thoughts. What do you think? Explain to me why rather than, waiting till the end of, 2 weeks later, you’re having your 1 on 1 and it’s just I noticed you’re, you’ve been, you didn’t hit this expectation or things don’t seem to be going well. So that kind of more consistent dialogue, I would say is where I agree with you.

Uncomfortable conversations. I’m honestly, when I’m looking at my teams, I’m not often having uncomfortable conversations. Like, it’s much more comfortable to have that dialogue to understand what’s going on and to address it quickly. You don’t end up in that many uncomfortable conversations.

Chuck Brotman: That’s really interesting. I think I do. And I’m thinking back to an experience of mine. as a people manager where I had a situation where somebody I hired, had not delivered in their own onboarding. And my initial instinct was to like, hold off on the conversation, kind of gather more data.

And I remember I talked to another 1 of my managers who sort of suggested getting in front of it faster and which I did and I realized like being able to balance like, readiness to have a conversation and to share specific examples. But to get in front of these things fast. It’s really important, isn’t it?

Tiffany Jensen: Absolutely. And also to be a leader who is very legitimately and sincerely asking for feedback all the time. Like, what do you think? What are your ideas? How could I have better supported you in that? how might we approach this opportunity together? and them understanding I’m thirsty for their feedback as well, and I’ll take it into account or I’ll disagree with it.

Sometimes I’m like, thanks. Totally disagree. Like, no, we’re not doing that. And here’s why.

Chuck Brotman: How do you do that? How do you prevent? I mean, do you have like structure time when you ask people to share that? I mean, I know some organizations obviously have, 360 review processes and formalize this. But if you’re an early stage company doesn’t have that. Like, how do you make sure if you’re asking for feedback that doesn’t, you’re not blindsided, doesn’t take you down a path you don’t have the time to go down at that juncture.

Tiffany Jensen: Yeah. I mean, I’ll give you a couple of examples. I’ve managed remote teams and I’ve managed in person teams and I’d still say like the same process applies. It’s are you debriefing like in a room? Are you debriefing on a zoom? So after a sales call, I’ll ask, especially if it’s a kind of a higher profile negotiation or an important strategic client, the expectation for the rep and or account manager is you’re setting up a 10 minute debrief for key stakeholders after the call.

And we’re all and that’s just part of the practice. We’ve got the 45 minutes booked for the meeting and you’re putting to the limit of being efficient with time, but it’s I’ll say it’s important to agree on any internal stakeholder, follow up steps to share feedback and to potentially identify opportunities that the group may have missed now with technologies like gone with and all of the variations and flavors of it.

There may be some value in sort of waiting. So you’ve got a transcript and any identification on that and doing a debrief slightly later, but like, the process can change, but it’s having a forum to exchange when it is known that there is going to be something worth discussing and sharing feedback on if it’s like, oh, hey, we were all in the break room. And I noticed you said that. And let me understand. I mean, that’s just seems like almost petty.

Chuck Brotman: Right.

Tiffany Jensen: But building in and scheduling debriefs pre briefs for things is, I think is one concrete way that I’ve done that.

Chuck Brotman: That’s really cool. I mean, you’re really kind of leading people forward in a way where it becomes. Like organic to how they’re executing in their roles. I mean, you’re teaching kind of skills to level up in practice and to get more comfortable sort of sharing feedback that in other contexts might be harder for individual contributors to share.

Tiffany Jensen: I mean, it feels natural, like for you and I can think of deals we’ve been in the past and we’re jumping on a call afterwards, but you’ve got somebody who’s earlier stage in their career and who was already nervous about, pulling product in and pulling marketing in for this presentation. And it’s like, no, here’s how we do it.

This is the collaborative process. And it also gives them an opportunity to get in front of peers, to share sort of their strengths and their perspective. and everybody gets better.

Chuck Brotman: Yep. There’s been a lot of talk, in the market. I mean, almost over this entire year, but this notion of doing more with less, and I think you see a lot of people, on LinkedIn and social networks suggesting that
And I think there’s some truth to that. Right. but at the same time, I think the concept resonates with me because it’s just the reality of our world today and our macroeconomic conditions. Maybe this will change, but companies need to focus more on efficiencies and bottom line. They did in the growth at all cost days of the past. I’m curious. how do you reconcile more with less with being a people centric leader, like, how do you balance those often competing necessities?

Tiffany Jensen: Yeah. I think there’s a thinking about this. There’s a few things that number one, you from a very practical standpoint during a time when you need to be as efficient as possible, you want to get as much productivity out of people as possible and people are more productive when they are rested, when they are happy, when they understand what they’re supposed to be doing, and when they feel like they’re making an impact. So you’re actually creating an opportunity and sort of a baseline and environment for your people to be as productive as possible by creating a positive culture and team environment. number two. I think one of the things is you as we see companies pivoting really quickly and trying to figure out how to be more nimble and to do more with less. I think of this return that I’m seeing right now across some organizations to this like full cycle.

And again, where I think you and I both experienced, you run sort of the deal from beginning to end. Even the idea of renewals was not as well formulated 1520 years ago when I started as it is now. And so now sort of bringing back to we don’t have an for this. An AE for this, and then somebody else takes over here and then there’s an onboarding team.
And then we’ve got this team doing expansion and they pull in, and great in, in a world where you’re pouring resources and you’re trying to get as specific and expertise levels as possible. And you’ve got money to throw at it and resources to throw at it right now, when companies are pivoting quickly.

Tiffany Jensen: And maybe returning to full cycle ease you by creating an environment where people are consistently learning from each other, where again, they’re able to tap into let’s say the knowledge or the expertise of a team member that they’re aware of. They know, hey, so and so is really great at spreadsheets. I need to do this. You’re sort of building an environment where people understand more about the business globally and are able to if needed, be a little bit more Swiss army knives, and it’s not quite as painful to pivot, like a renewals manager into a role where they’re now, the key or maybe only point of contact, and maybe also need to drive some pipeline for new business, if they’ve all been exposed to each other doing it. You’re just kind of building more competency, and more flexibility across the team and you’re building a muscle for better knowledge transfer when needed. So I think that network sort of form early.

Chuck Brotman: It’s kind of ironic.

Tiffany Jensen: You agree or disagree?

Chuck Brotman: Totally do that. I’m laughing here because This is like screaming for a sports analogy.

Tiffany Jensen: Specialists.

Chuck Brotman: Well, well, I think, I mean, tell me if you disagree, butit is so much like, like sort of feeling a competitive teams.

You talked about like, like the long game or like making sure your players are arrested. So thinking about NFL teams and look, you can if you’ve had a bad game, you can have your players do full pads workout the next day. But is that going to be more productive for the next game?

Right? So balancing urgency and needs with the importance of like rest and sustenance to short and long term execution. And then the scene that keeps coming up from you. That’s really fascinating me because I hadn’t really thought about it. But just this notion of really building great cohesive teams in a context where we are becoming more full cycle or moving away from like, factory level differentiation is you have to know your strengths and your gaps by people.

And if you do that and think about that less as like, a training deficiency, but more like, hey, we’ve got this person here maybe happens to be particularly skilled at like pre sales. Maybe they can help record like, a library of demos we can use to upskill people. Maybe they can help out on certain calls, right?

Versus someone else who’s like really thought leadership in maybe can help with some Some content that could be used for prospecting and maybe someone like, like an early test who like knows channels really well can help like build like a, an informal channel ecosystem or recommend tech that could be used to find like shared opportunities with key partners. Right?

Tiffany Jensen: I think I always love on podcasts and meetings when people give like really concrete examples of how to facilitate this. So I’m going to say, I’m going to give an example of something I’d done at a past company that ended up paying off.

I came into and I won’t name the organization, but came in, to manage a sales organization. And very first initiative was, like, we need to let a bunch of people go. We overhired and so I needed to build culture back with this team. And I also didn’t know strengths and weaknesses across the group yet.

And there is a lot of like I’d say it was a team of great people, but some sort of suspicion and is it going to be me? And is it them? And how, so I set a kickoff meeting with the team to set my expectations and then follow up meeting in our sort of team kickoff is everybody’s preparing a presentation about their superpowers. What are you great at? And then we built off of that a calendar of team led trainings where every week a different team member takes something. It doesn’t need to even be specifically related to the job, but something that they’re great at that. They think everybody would benefit from and they’re leading a session. And so, somebody is, turns out to be amazing at like graphic design and has been customizing their, these incredible client proposal, client proposals and
They’ve got higher conversion rates. And we realize it’s because he’s building these kick ass presentations and he’s super fast at it. So he teaches the rest of the team how to do that. And we wouldn’t have known that if he didn’t identify it as a superpower, have the opportunity to share it with the team and then teach everybody in a forum that was scheduled.
Everybody every week is learning from somebody else. Somebody else taught and taught us how to build a pivot table. I mean, you and I probably know how to do that. Well, but that’s a skill that some of the folks on the team of at least minimally, they know how to Who to go to in the future next time they need to do it.

So it’s that information sharing. And then everybody felt really good about being able to go in there and talk about what they’re great at and share a little bit more about themselves. And so it allowed the team to be more nimble, and to be more efficient by identifying where they can lean on others.

Chuck Brotman: That’s awesome. I mean, I think.

Tiffany Jensen: That’s a good one, right?

Chuck Brotman: a great one. Right? And I think it’s, I mean, this felt so challenging. And I think you, we’ve kind of, we’ve got a solution on our hands where I think this is, what it’s all about. And this is teamwork in action. This is teamwork that doesn’t get in the way in a properly structured, cohesive organization.

Like this drives more productivity and more efficiencies and more fulfillment. And it doesn’t have to be over complicated. Right. So nor does this necessarily become a. an excuse for overworking your people. Because again, as you’ve outlined that you’re looking at, you’re always looking at the long term game and making sure that your people are rested and fulfilled.

Tiffany Jensen: And ultimately, if there’s a tool, a sales tech stack tool that does that if you can get a marketing resource to assign, great. That’s like, that’s the dream. That’s best case scenario, but where everybody is super scrappy and just trying to be as efficient as they can.

Chuck Brotman: Well, also, I mean, these things are not, these things kind of work together, right? You’ve got somebody who’s like really good in specific areas, whether it’s graphic design or channel partnerships or something else like that. Yeah. Yeah. Now you’ve got an opportunity when there are dollars to invest and maybe bringing in tech or personnel.
Like, guess who can be a part of that panel or that vetting process to make sure that this will be additive versus, a distraction.I want to come back a little bit to the theme of, like, diversity and hiring.

I don’t think I had described it that way, but we talked early on about intellectual curiosity, assessing for it, leading with it in terms of how you get to know people and not being steered in certain directions. I think the DEI world’s kind of got interesting. I don’t know what your perspective is, but over the last 6-12 months, for a variety of reasons, I feel like we’ve heard less talk about its importance.

Tiffany Jensen: Right,

Chuck Brotman: I stil believe that diverse teams outperform non diverse ones. I also think that many organizations have not practiced the right way and maybe been at times too focused on checking boxes versus really thinking about it in terms of like the lowercase d, and really finding people that have the broadest set of backgrounds, even when they don’t increment numbers in a way that that makes you look diverse. I’m curious, like your general thoughts on DEI today and going forward. Like, again, you may not have a strong point of view on that but given some of the work you’ve done and also recognizing too, that we still have a diversity problem.

I still talk to many more male candidates than females. I certainly understand there are imbalances and I do think they overall, adversely impact execution, but what’s your point of view on all this?

Tiffany Jensen: Yeah. D-E-I, in and of itself is not an, a strong area of expertise for me, it’s, I am very passionate about diversity and very supportive of diversity initiatives. And I will say from a super practical standpoint, for naysayers, it’s, there is a strong ROI for diversity.
There’s a straw. I mean, there are a ton of stats, as you mentioned about more productive teams, more innovative products, better, more higher profitability levels for companies with diverse teams. So, in terms of just statistically and from a bottom line standpoint. It is the right thing to do.
I can say, having been really active in chief for the last couple of years, which, is an organization that is trying to help support women in sea level positions there. The statistics are pretty abysmal. I mean, I think now the Fortune 100 or 1010 percent of, CEOs or women for the global 500.

It’s lower. I think it’s five or five or 6%. And so, the idea of DEI becoming unpopular for, I don’t know, culture war reasons. if there’s a strong ROI for it, which there is, if you can build into your process ways that work for your organization, it will be effective, but there are so much gains to be made, in terms of productivity improvement and that ROI, and I think it’s really important to look at where we are when you look at where we are right now.

At least speaking from, from the standpoint, as I mentioned, of looking just at, female leadership for Fortune 1000 organizations. So I am passionate about it. I work with and interact with a lot of people where it is their specialty, which maybe makes me feel like I’m not qualified to even kind of talk about the state of DEI

I am not a DEI specialist, but I do believe in diversity and I think I’ve been fortunate or intentional about building very diverse teams throughout my career.

Chuck Brotman: It’s an interesting conversation. I mean, I’m struck by as you’ve gone through this and I know this would be a topic for another day and probably something you might not agree with fully, but I almost, feel like that the more we have leaders. Regardless of their demographics and background, they do operate the way that you do.
I kind of wonder if at a fundamental level, it lessens the need for, you talk about DEI expertise, like, I don’t know what expertise on top of what you are already doing. And now I grant, I know we have a long way to go. And this is just not the way that most functions practice. But if they do, right, I think, part of the challenges.

And there’s a physics metaphor here. I forget this is quantum mechanics or whatnot. But you can’t measure this, right? Like once you go down that path of trying to like, measure it. And I understand if you don’t measure it, you don’t know what you’re achieving. But to me that the measurements become problematic.

I think we’ve seen this and obviously there’s a lively debate in higher education about this recently for a variety of reasons.

Tiffany Jensen: Very lively.

Chuck Brotman: but I think at the end of the day for me, the more I know you’ve got it. Yeah. leaders like you who think the way that you do and who have that intellectual curiosity and recognize that you talk about ROI like that.
Ultimately, like, if you don’t, if you’re not rigorous about addressing bias and all of its formats, you are not going to build the kind of teams that can take you where you want to go.

Tiffany Jensen: Yeah. Agreed.

Chuck Brotman: You’re not gonna be successful. I am. This has been awesome. I’m so glad we closed out 2023 with you, and I appreciate you taking the time.

Are there any final things in terms of recommendations you have for listeners like, podcast books, boot camps, anything else that you recommend? You mentioned, or I think I’m assured you’re, you’re an active member of Pavilion. If you want to talk about things that they’re doing or anyone else that you follow or recommend to our listeners on LinkedIn or elsewhere.

Tiffany Jensen: I would be happy to so on a personal level. I usually I’m a fiction reader more than a nonfiction reader. I am not somebody who loves reading business books because my whole life is, business.

But I have loved this year and it’s been life changing in some ways. I really loved Atomic Habits. It’s by James Clear. It’s like highly recommend. I started running this year. It’s amazing. I, I can’t recommend it more. and just like very easy to read, very enjoyable. I, I was, Pavilion has done a great job building out, educational content and resources. So I attended this year, their CRO school, enterprise CRO school.
Definitely worth checking out if any of your listeners want to chat about it. I’m happy to to answer questions and help in any way I can. I don’t work for Pavilion, but I found it to be an excellent organization. I mentioned, Impact Ventures in the UK that I’m working with. I’m actually not 1 of their angel investors.

I’m helping teach 1 of the courses within their accelerator that’s launching in February. So. If there are women founders, and entrepreneurs out there, there’s really great sort of modules and high excellence in this course content that’ll be released as part of the accelerator. So that’s Impact Ventures Group.

And I always happy to share podcast recommendations, but again, not minor, not necessarily businessy recommendations. I tend to there’s one called follow civilizations that I find fascinating that I think he would like Chuck.

Chuck Brotman: Tell me more. I shouldn’t, we shouldn’t limit this. What’s that one

Tiffany Jensen: Yeah, there’s this. So it’s the gentleman who created it. It’s named Paul Cooper, and he goes into specific civilizations.

So, like the Mayan civilization, or I’m, trying to think there’s, I Greenland one of the one of the ancient civilizations. In Greenland and goes through and sort of tracks their entire kind of cultural history and tries to identify the reasons that various civilizations have fallen.

So, this idea of kind of Roman Empire crash and fall, and then gets really deep into kind of science and research, trying to understand was, were there black swans, so to speak on unknown reasons that may have, that may have led to declines. And I, just love like the granularity of the history and he’s a fascinating storyteller.

Tiffany Jensen: So it’s a, that’s a really

Chuck Brotman: Aliens a part of any of these declines? Any

Tiffany Jensen: No, not yet.

Chuck Brotman: Maybe an episode

Tiffany Jensen: Not yet.

Chuck Brotman: I’ll have to check it out. Well, Tiff, thanks for, thanks for being our guest. I really enjoyed the conversation. I think we’ve got hopefully an opportunity to do this again in the near future.

Tiffany Jensen: Wonderful. so much, Chuck. Have a great new year.

Chuck Brotman: You too. Happy New Year. Bye.