Become a Creator today!Start creating today - Share your story with the world!
Start for free
00:00:00
00:00:01
S3 Ep22: Navigating Sales Leadership Challenges with Rebecca Gebhardt image

S3 Ep22: Navigating Sales Leadership Challenges with Rebecca Gebhardt

S3 E22 · Dial it in
Avatar
30 Plays2 days ago

In this episode of the Dial It In podcast, hosts Trygve and Dave converse with guest Rebecca, an accomplished sales leader and president of Rise Up Consulting. They discuss the challenges and strategies of transitioning from high-performing salesperson to effective sales leader. Key points include understanding strengths and weaknesses, data-driven decision making, recruitment strategies, and the importance of continuous leadership development. Rebecca shares insights from her new book ‘Leaderboard to Leadership’ and emphasizes the value of aligning individual strengths with organizational goals to achieve sustained success.

Connect with Rebecca
LinkedIn
Leaderboard to Leadership Book
Beyond the Board Book

DII Episode Sponsor:
Fractional Tactical

Dial It In Podcast is where we gather our favorite people together to share their advice on how to drive revenue, through storytelling and without the boring sales jargon. Our primary focus is marketing and sales for manufacturing and B2B service businesses, but we’ll cover topics across the entire spectrum of business. This isn’t a deep, naval-gazing show… we like to have lively chats that are fun, and full of useful insights. Brought to you by BizzyWeb.

Links:
Website: dialitinpodcast.com
BizzyWeb site: 
bizzyweb.com
Connect with Dave Meyer
Connect with Trygve Olsen

Recommended
Transcript

Podcast Introduction and Valentine's Day Special

00:00:08
Speaker
Welcome to Dial It In, a podcast where we talk to fascinating people about marketing, sales, process improvements, and tricks that they use to grow their businesses. Join me, Dave Meyer, and Trigby Olson of BusyWeb as we bring you interviews on how the best in their fields dialing it in for their organizations.
00:00:26
Speaker
Let's ring up another episode.
00:00:30
Speaker
i don't really have anything funny this week because the last time we did a podcast, you called me out on the same joke of mis misunderstanding the guest. Oh, sorry. Do you have something funny this week?
00:00:42
Speaker
I always have something funny. We're recording on Valentine's Day, so it's a lovely day. our guest is dressed in red, as am I. And I think if I'm looking correctly, you've got a little bit. I have a little bit of red the red in the gingham today. So we're all feeling the love.
00:00:57
Speaker
And we have a fantastic guest today, so I'm super excited.

Guest Re-introduction and Sponsorship Message

00:01:00
Speaker
a longtime friend, we had recorded a podcast with her nine months ago before her book came out. And her book is out now. And she kept saying, hey, that podcast that we did, can you fix that? and turns out her her her audio was with Richard Nixon's Missing 17 Minutes. So we had we had a really nice hour and a half conversation of you and I talking with extended silences in the middle. So we're excited to have her back today.
00:01:27
Speaker
So you have a do we have a sponsor? We do. Let me dump into our sponsor for just a moment and then we'll get to our guest. As a fractional CMO, your number one goal is to deliver success to each of your clients.
00:01:41
Speaker
With limited time and resources, you need marketing solutions that are data proven, easy to execute and repeatable. BusyWeb understands this unique challenge that marketing executives face.
00:01:52
Speaker
That's why we offer customized solutions for our fractional CMO partners. You tell us the results you need, and we create the strategy and Martech stack to get you there. You have the concrete plan, your clients have measurable results, and you look good.
00:02:06
Speaker
We hope to get there. Everyone wins. Visit fractionaltactical.com to find your marketing partner today. You get strategic, we get busy. Excellent.
00:02:19
Speaker
I'm super excited about our

Meet Rebecca: Leadership and Authorship Journey

00:02:20
Speaker
guest today. it's As I said, longtime friend, somebody that I have called on in the past who typically personifies the Henny Youngman school of coaching. The old Henny Youngman joke where the guy goes to a doctor and says, hey doc, it hurts when I do this. And the doctor says don't do that.
00:02:36
Speaker
So she's usually the person I call when I need that advice. she iss She is the president of Rise Up Consulting and an accomplished sales leader with over two decades of experience. I don't believe that because i she there's no way that she started in her teens.
00:02:50
Speaker
As a creator of the transformative leaderboard to leadership program and book, Rebecca specializes in guiding top performing sales professionals into impactful leadership roles. Our mission is to help organizations bridge the gap between individual sales success and sustainable team growth by equipping leaders with data-driven strategies and actionable insights.
00:03:12
Speaker
Her passion lies in empowering sales leaders to rise to their full potential, making her a sought-after coach and mentor in the field. She's the author of the newly minted Leaderboard to Leadership. Don't ask about the subtitle. Oh, I wasn't supposed to read that part out loud.
00:03:28
Speaker
Shoot. Hi, Rebecca. Welcome back. Rebecca? Hello. Excited that this round two will work. Fingers crossed. And I was going to wear that shade of lipstick today too. So I'm glad that I chose not to because then it wouldn't have been awkward. So what if you're a freshly minted author? What's that? and How's that going?
00:03:46
Speaker
Yeah, freshly minted two-time author. Yeah, my first book was about goal setting and that was released on February 29th of 2020. Nothing bad happened a week after that. Nothing at all, yeah.
00:04:00
Speaker
And yeah, released Leaderboard to Leadership How to earn and excel in your first sales leadership role. That's the long subtitle. That was released in September. And i wrote that to scale, I think, some of the the issues we have with our clients and some opportunities. I just feel in the sales enablement world to level up leaders because they don't get trained and we can make it as complicated or as simple as we want.
00:04:29
Speaker
And through some research and stories and work, There's just a few little levers we have to pull to then get some momentum going and then nail down. But it's going well.
00:04:39
Speaker
The launch party was a ton of fun and it's exciting to see the impact that it's making. I was scheduled to go to the launch party and the launch party started at 4.30 and I didn't get finished with it. I did until 4.15.
00:04:53
Speaker
and jumped in the car and I drove and then I got 15 minutes away from my house and then I actually checked Google Maps and it said that I would be there in an hour and 10 minutes. So I would have made it for the last 20 minutes of the program.
00:05:07
Speaker
Darn. I'd love it. It was really nice of you to like change your RSVP for me. The car. And I was genuinely excited. Thank you. Thank you. Yeah.

Transitioning from Salesperson to Leader

00:05:15
Speaker
That I was there for that. So what, when a, when a salesperson is, are are they usually thrust into the role of management or do they, does the salesperson typically ask for the step up? Right.
00:05:27
Speaker
both. There is a assumption that really great salespeople are rewarded for a job well done with a brand new role in a role they've never done before. That's what's happened. Some salespeople want to be sales leaders.
00:05:44
Speaker
Others need to be coaxed into it. And there's actually some conflicting data about what the next generation of leaders really want. So we look at Gen that you don't it's not just um younger people. Right. there There are seasoned professionals that are still elevating in sales leadership roles at the next level who have never done it. And they're not trained either. It's like this massive problem.
00:06:11
Speaker
But the average age of someone getting their first promotions into leadership is age 30. In sales, it's a little younger. But Gen z they expect to be promoted within their first 18 months on the job.
00:06:25
Speaker
So whether that promotion is from an entry-level salesperson to maybe an account, exactly yeah it may not necessarily be into leadership, but they expect it.
00:06:35
Speaker
There is also research that says most Gen Z don't even want to get into leadership because they just want to do their own thing. So i think taking what we know, what people want from work and what makes people successful is when it's first of all, just doing sales leadership.
00:06:54
Speaker
80% of sales leaders were given zero training once being promoted. We did some research on that back in I don't know, 23, 2023, I think could have been 21.
00:07:05
Speaker
It's been a while, but they're not given that. So I think having leadership development where you're inspiring people who want to lead and then providing them specific development that's not leadership development in general, but it's specific to them and their strengths.
00:07:23
Speaker
And that really sets organizations up to be massively successful.

Balancing Sales Management and Direct Selling

00:07:30
Speaker
What do organizations succeed or is it, what's the challenge when you ah have your sales manager also being an active seller?
00:07:39
Speaker
Yeah, the dual role, the player coach role. I i think that started as a way to cut on cut down on corporate bloat. It was like, hey, this really great salesperson, they can do their job. We'll just give them one or two one to three people to manage.
00:07:55
Speaker
And that is a very common thing, but it's my belief. And I think most consultants, most research will show that's not really a sustainable position.
00:08:05
Speaker
Although it's honestly where a lot of people find themselves. These frontline sales leaders find themselves still managing a book of business and managing a team, but it it dilutes their attention.
00:08:17
Speaker
And I did that myself for about maybe 10 years in different companies, but for 10 years. And then I finally made the switch just into sales leadership. It's really hard.
00:08:28
Speaker
It's what are we going to do today? Are we going to sell? Are we going to lead? Are we going to go recruit? What's going on? Or how am I going to time chunk my time? And and time management's the number one issue for sales leaders.
00:08:40
Speaker
It's the number one differentiator for salespeople who figure out how to utilize their time and do income producing activities. right And so that's just a really tricky situation.
00:08:50
Speaker
I think it depends on the the company. I get pushback from people who say, that works for us. I'm like, okay, it works. But how well is it really working? And it could it work better?
00:09:02
Speaker
do Do your sales leaders really have time to coach salespeople are they just deal coaching? i I just don't see when you add up all the hours someone has to do in a player coach role, it doesn't compute.
00:09:13
Speaker
Yeah.

Advice for New Sales Leaders

00:09:15
Speaker
So, what is that is so as somebody is thrust into sales leadership. I know you taught, what's a good, and I know obviously people need to buy the book to to get the specifics, but what are some of the parameters around teaching and and advocating for that person that you'd recommend that a company start with?
00:09:31
Speaker
Yeah. There's a chapter in the book It's also a keynote that I do called New Role, New Rules. And it really is about anywhere in in the pipeline of evolution and growth throughout your career. But the book is about that first level, right? Going from the leaderboard in sales to sales leadership.
00:09:50
Speaker
So I think number one is actually saying, what does success look like in this new role? What actually needs to happen? And then where do I need to be spending my time?
00:10:02
Speaker
Those are, i you need to look at what, and you need to look around your current company and say, what are the most successful sales leaders here doing? And collecting that and then saying, okay, with my strengths, because everyone's different, but with my strengths, what could I do that could also be doing these behaviors that the most successful sales leaders is just, you want to create this duplicatable process but customize it. And I know that's a little bit confusing and it might be a cop out of advice, but I feel that a lot of new leaders just go, okay, I'm going to look around. I'm looking at all these people I really respect.
00:10:42
Speaker
I'm going to do what they're going to do, but we're not working with the same skills and the same capacity, the same mindset. And I think that's really a mistake.
00:10:53
Speaker
I know when I was a new leader, i had a phenomenal female sales leader and most 80% of sales leaders are men. Most of my clients are men. I was blessed to have a really great female sales leader and she was empathetic and she was emotionally mature and everyone loved her. And I was like, I'm going to be her.
00:11:13
Speaker
but I'm a little rough around the edges and I like those skills she had, i didn't have them. And so it finally it took me a while to realize, all right, Beck, there are some things you're good at. Why don't you lean into that instead of trying to be fake and someone else.
00:11:28
Speaker
And I did learn how to emulate her in ways and just expand in areas I was short on that I needed to be successful in order to effectively lead a sales team. But messed that up and I see that happen all the time.
00:11:41
Speaker
So I think, i hope that kind of answers your question on what to do, but just get an assessment of what does success look like? What is everyone else doing? Where do I have to spend my time?
00:11:52
Speaker
Who am I identifying as? If you're still identifying as a salesperson, you'll spend your time there. You'll think like that. You'll deal coach. If you identify as a sales leader, you'll spend your time coaching and looking at the data and forecasting and doing all the things that sales leaders are supposed to be doing.

Essential Activities for New Leaders

00:12:11
Speaker
Are there some table stakes activities that every new sales leader needs to take into account? Yeah, you need to know your team. You you need to be having one-on-ones. You need to make sure you are communicating with your manager if you have one.
00:12:26
Speaker
I feel like some people, when they get promoted, they're really good at managing up Sometimes not, but you have to do both. You have to manage up and you have to man and you have to manage down. You got to know the metrics.
00:12:38
Speaker
You have to know what activities, skills, mindset, what what needs to happen for every person on your team to produce produce the results you want. Your mindset has to be of urgency.
00:12:51
Speaker
If you are a... You can be laid back. I don't mean false urgency, but you have to bring energy to the table and ignite that excitement and purpose in your team. But without those, it's you You might get some results, but it won't be sustainable. And then you're going to wonder why, oh I'm looking for a new career.
00:13:11
Speaker
Especially a sales leader. So as everyone under your team is going to react the way you do. And if you don't respond for half a day, that could be the difference between a closed one and a closed loss deal.
00:13:25
Speaker
Totally. yeah You mentioned a couple of interesting things of which I want to drive a through line from. I think you talked about ah even understanding your own strengths. How do you assess what, as you brought into a new leadership role, how do you assess really, what are your strengths? Because I think most salespeople would say, I'm good at everything, but I hate cold calling.
00:13:45
Speaker
And I'm good at relationship building and relationship development. I'm good at the lunches and I'm good at the happy hours and I'm good at the closing. I just really don't like cold calling. That's not even true because in an interview, everybody will say they love cold calling. in Everybody says that.
00:13:58
Speaker
Nobody actually does. Yeah. As someone who cold called, not on the phone, but face to face for 15 years, I can tell you I like to cold call. That's not possible.
00:14:10
Speaker
i I do with the networking and i I do it. But the so this is there is a difference between how we feel about how we assess ourselves and our current reality. There's always a gap there. We all have blind spots.
00:14:23
Speaker
I think that thinking through what you were just saying, trigby of saying, OK, what am I good at? What do i like to do? and that's actually important by getting feedback from others.
00:14:34
Speaker
So I suggest what I had done before I was ever certified in assessments that you have to pay for. There's like different varying levels of it. But before I even did that, what I did when I went into consulting is I went back to the people i had worked with, friends that knew me for years. And I flat out asked them, hey, what do you think I'm good at?
00:14:55
Speaker
And they were a little taken aback at first. They were like, what? And I was like, I'm trying to assess where I should be focusing my consulting business. And since I'm so good at everything, just kidding, I wanted to see what they actually thought.
00:15:08
Speaker
And some of the things that they said to me, I was like, Oh, you think I'm good at that? I didn't notice it. Things i thought I had that I had on my list, I thought they would say they didn't mention.
00:15:19
Speaker
So I thought maybe my ego is a little inflated or there might be a misalignment from my perception and reality. And it was just information that I took in. 360 degree feedback can be really powerful, but you can also there's plenty of set of assessments on the market. I'm certified in a Colby assessment, which is there's three parts of the mind.
00:15:42
Speaker
There's a think part. That's how smart you are. That's your experience. There's the feel part. And there's a ton of phenomenal assessments here, like um get Gallup StrengthsFinder, Enneagram, Predictive Index, DISC, Myers-Briggs. There's a lot of good ones there.
00:16:00
Speaker
But at the end of the day, it's like, how is someone going to be successful? Like, how are they going to do it? What's their MO? And that's the conative part. And it's subconscious. So we don't do anything about it.
00:16:11
Speaker
So for example, if you as a salesperson were just really talented and you didn't really follow a system because you just cut to the chase and you didn't need to use a CRM, that might have...
00:16:23
Speaker
worked for you there. But as a sales leader, you're going to have some consistency and a structure to how you scale your team. And there's, if you need someone who who has to cold call, they're going to have to be high in their tolerance for risk. Some people don't get their best results there. It's not even about hating change. They're just like,
00:16:43
Speaker
I do my best when I stick to what I know. They maybe shouldn't be in a cold calling kind of situation. So that's just an assessment. So when you're hiring people, you're aligning what they know, how they're motivated, their values, how they feel, and actually what they're going to do.
00:16:59
Speaker
And there can be mismatches in there and you don't want that. So there's a lot of assessments. There's all it. There's also like when you hire someone and we do this for salespeople, not all the time, but we definitely don't do it for sales leaders, actually assessing what do you know?
00:17:14
Speaker
i was on the phone earlier this week with a HR professional. We were talking about Onboarding. And I asked, have you ever actually done this? And the answer was no, not in like the capacity that it was.
00:17:30
Speaker
And we just assume because people are talented and competent that they'll just figure it out. And this person will figure it out. But it's also nice to see how it's done and figure out all those things. So that might have been a long answer.
00:17:45
Speaker
i was che good at yeah you i did you You need to use some data and these strengths of people and stop pulling successful people into roles they're not going to succeed in because there's a mismatch of their motivations and their values and their strengths.
00:18:01
Speaker
One of the other things that you made vague mention of that I want to spend a lot of time on is recruitment.

Recruiting and Assessing Sales Talent

00:18:06
Speaker
What are some good strategies that you can employ to find talented salespeople? Because I would imagine most talented salespeople are not looking for a job right now.
00:18:17
Speaker
they're now They're not unemployed, I should say. Some might be. I've actually seen just some of the layoffs recently where I'm like, oh my gosh, that person got laid off. They're so good. So there there are some of that because I don't want people to think listening to that only the crappy people get laid off because there's some very talented salespeople.
00:18:36
Speaker
But to your point, Trigby, they are usually picked up rather quickly, not always looking for a job. The part about recruiting from a sales perspective,
00:18:47
Speaker
Part of being a sales leader is actually owning the responsibility to recruit high caliber people. Some sales leaders are still under the assumption that is what HR does.
00:18:59
Speaker
And they don't fully realize the power that they have. So ways to recruit great salespeople, have a brand, have a heavy brand where you are able to showcase your company's culture, your own leadership aptitude, how nice you are. There's a ton to do there. That's not something that I had done.
00:19:21
Speaker
back in the day, but I always showed up to events and dripped on people. And when you need to have a drip campaign, just like you have a drip campaign for sales and that pipeline, the pipeline to prosperity. I did a course years ago when I was just focusing on teaching sales and about the size of your bank account isn't how successful you are, it's the size your pipeline, right?
00:19:45
Speaker
Pipeline to prosperity. The same concept holds true in sales leadership where you need to have a pipeline of candidates and sometimes you recruit them in a week. Sometimes I took it took me years to recruit some of my top people through intentional following up and, hey, look how much fun we're having on this incentive trip and check out the national sales meeting and all of this stuff.
00:20:09
Speaker
And I think just listening. So it's you've got to be focused on doing it. And then you need to know. It's not just the person you think is going to be successful because they look like they play the part.
00:20:20
Speaker
Surprise. Not everybody is who they are. Right. Professional actors are not the only ones who should be given Oscars for their performances. um and But making sure that it's aligned and and they're going to do well and whatever they really feel is important, that ah those opportunities exist at your organization. So if you've got a great person you can bring in for sales, but their goal is to have this impact or they've got some, their purpose outside of work is this big vision.
00:20:50
Speaker
First of all, getting to know that it's a deep separator because and not everybody is there like, how much money you want to make? Come join us. It's a new technology. And it's just like these tactics. with strategically recruiting with some depth to it will definitely separate you as a recruiter, as a salesperson.
00:21:07
Speaker
Is that outreach mostly done over social media usually then? Because I would imagine one of the problems with recruiting is that email addresses change a lot. it's This is about personal relationships for people. Yeah. So it might start on social media, but there's that you should be getting now you should have cell phones of people. Sure. Yeah. yeah you should be in a conversation i think It's like a dating process.
00:21:34
Speaker
you don't want to You don't want to be asking for numbers and emails but before what happens. But I think showing up where your prospects are is the best thing to do. So whether that be your customer prospects or your recruiting prospects, just show up, build relationships with people that they know.
00:21:54
Speaker
Having several ways to increase the strength of the relationship ah by the connections with other people, not just things you have in common is really important. But this is going to depend on, this is going to be different based on which technologies come out and and getting really good at that. But I just think sales leaders is just first understanding it's your job to recruit great people and your value goes up tremendously, tremendously, tremendously.
00:22:24
Speaker
It's right. yeah I like both. That's even better. Okay. But your value goes up, not just because you can sell or you can teach someone how to sell, but you can bring top talent into the organization. That is a promotable skill to go beyond where you're currently at.
00:22:41
Speaker
And part of the problem with doing that is if you get a bunch of salespeople together, it's like going to a gambler's anonymous meeting. so therere they'll never remember their win. They'll always remember all the ones they looked lost.
00:22:53
Speaker
And so some of that you have to listen in between the lines of what's a legit problem that you could solve by moving the salesperson somewhere else versus what is this just fish stories at the bar?
00:23:06
Speaker
Yep. and there is It's a long game and it's just you have to keep dripping until they get to a point where they are very dissatisfied with their current situation.
00:23:19
Speaker
And salespeople are emotional people. Some they'll make a decision emotionally, justify it rationally, just like their customers do, which is why they're so good at their jobs. Right. They can connect to that and they understand motive.
00:23:30
Speaker
But if you think about it, it's just sometimes it can be this moment of you've been talking to me for three years and I just I'm not happy with my boss. I'm willing to talk to you right now.
00:23:41
Speaker
And then you need a plan to talk to them and not just interview them, but really listen to them and what they want. And there's ways to distinguish what you're doing. And I think that what's similar about recruiting salespeople to sales is if you connect with their heart first.
00:24:01
Speaker
you'll connect with their mind. We sometimes just go to the mind and here's why we're awesome. And this is what our company has. And it's very like to do all this like stats and people like, oh, okay, that doesn't mean anything.
00:24:13
Speaker
So if you start with the heart and you do that by listening and asking really great questions and connecting with their purpose, you can get to the rational side. You can figure out how passionate they are, how excited they are. You know you don't want someone who's talented, but not really excited.
00:24:29
Speaker
about what's going on because they're not going to be able to have the energy to be successful in the long run. But but I would say those types of things when you're recruiting would go a long way. And it's not what people typically do.
00:24:42
Speaker
When I interview salespeople, I have a practical exercise that I do, and but I'm curious to know, are there practical, and and I'm happy to talk about it here, but are there practical exercises you can ask salespeople to do to demonstrate talent?
00:24:54
Speaker
Because I'm of the opinion that your resume gets you in the door and, okay, you've done some stuff and you're going to tell me so you're going to tell me a story in an interview, which is great, but that's your whole gig, whole zhuzh. I want to see what you'll do with something. Yeah. Yes. I don't think in the first interview, though. So I i think that how to structure and it depends on how many you know interviews. And I'd love to hear what those exercises are. Sure. trick be But the the first interview is all about the cultural fit. And I know this is a huge problem. People like cultural fit. You're not going to hire people who are like you.
00:25:27
Speaker
I'm not it's not I'm not talking about are you in the same organizations as I am thing, but do their values align? Are they, who who are they as people? It's really about them as a person.
00:25:39
Speaker
And there are specific questions you can ask to uncover that. Second interview is about job fit. And so hopefully you've done an assessment or two, not all are legal to do in the um hiring process.
00:25:51
Speaker
The Colby one is, which is partly why I got ah certified in that. Because you don't want to discriminate unintentionally based on their strengths. But There's questions you can ask. So for example, if you need to be able to negotiate or structure deals, financial deals, right? You need to know what the net profit's going to be. There's parameters that salespeople are given and there's maybe some leg room.
00:26:15
Speaker
You need to give them an example right there in the interview. Can they do the math? Can they? If you don't need to do the math, you need to give them an exercise to do the math. When they talk about things like, oh, this is, or you answer a question, you go, how would you do that here?
00:26:32
Speaker
So they may say, here's how I've done this in the past. How do you think you'd do that here? i think asking the how question is a great follow-up. And then the why question in that second interview, what are, I'm really curious, what are some of the little, cause you want to put people through

Interview Techniques and Cultural Fit

00:26:47
Speaker
scenarios.
00:26:47
Speaker
Yeah. So the first interview that I typically have with somebody, I'm just trying to figure out, A, do I like this person? Would I want to spend considerable amount of time with this person? and B, are they funny?
00:26:58
Speaker
Because ah for me, if if you're not funny and you don't have a good sense of humor, or at least you can't appreciate humor, yeah, we're going to have a bad time. because I've gotten to the point in my life where I'm not apologizing for being funny. And the people I work with, they're all fun people. They enjoy a good joke. They enjoy funny things. Right.
00:27:19
Speaker
And so, to be fair, it's part of the brand too. It's a culture that if if you don't, if you're not very funny or you don't think something's funny. Like when when my son was very little, we had a pastor at my church who asked my son what his name was. And but what is and he said, oh, my name is Linus.
00:27:37
Speaker
and And she said, what's your middle name? And he said, ah my middle name is Joseph. Do you want to know what my dad's middle name is? And she said, sure. And she said, yeah, my dad's middle name is Danger. And then he left and then she and I were sitting there and she's so Danger, is that Czech?
00:27:54
Speaker
It's actually pronounced Don Gere. Yeah. Yeah. No, it's not. has that. That was not, just she is no longer my pastor, but what I do is if I like somebody and I feel like they're a good fit, I put them through an exercise and say, I want you to, I'm going to give you a scenario in which I want you to go get me a piece of information.
00:28:10
Speaker
If you can get me the piece of information, you can have the next interview with the the head of the company. They say, okay, what is it? I say, there's a woman who lives in Lagos, Nigeria. Her name is Debbie A. And she's a very, I give her the actual last name. Debbie has a daughter.
00:28:26
Speaker
and want you to tell me what Debbie's daughter's name is.
00:28:32
Speaker
And they're like, what? What? Is this true? Is this really a thing? Is this a Nigerian prince thing? So really what I'm asking somebody to do is evaluate the problem. I've given you a piece of information. What can you do with it?
00:28:46
Speaker
So first of all, is it a little harebrained? Yeah. So are you okay with the little harebrained things? Okay. Yes or no. If the answer is no, then you i don't know how good you are evaluating other things.
00:28:57
Speaker
Second is how would you respond to solving the problem? Why is middle-aged white guy in Minnesota asking about somebody who's halfway across the world? There's got to be a connection there. So i what I would do is I would go to Google and type in both our names.
00:29:16
Speaker
And if you did that, very quickly you would find out that she and I teach a class together for HubSpot. And I spend just as much time with her as I do with Dave on a consistent basis.
00:29:29
Speaker
And it's just, she's just eight hours ahead of me and lives in Africa. So then, ah okay so now you've figured out how we're connected. And the the next question is, can you do an approach? And to me, that's not really hard to me. That's, Hey, we know Trigby in common. I wanted, he thought it'd be good for us to meet.
00:29:48
Speaker
Great, you do that's a LinkedIn request. That's it. the If you are curious and wanting to solve a problem, I'm 10 minutes in before I've gone in. And then as you try and develop a relationship with somebody, oh, do you have family? Oh, do you have and ah your daughter? What's your daughter's name? Oh, great, great.
00:30:04
Speaker
Any part of that process is developing a relate is is doing basic level research and basic social media research and developing the relationship, but it starts weird.
00:30:16
Speaker
And if you're not willing to go down that, you're not getting an in interview because you can't demonstrate to me that you can do that level of process. but yeah That's of mine. Yeah, that's awesome. it's with their're severe The critical thinking and persistence that's needed in sales is high, and it's just going down culturally.
00:30:35
Speaker
my I was teaching this to my kids. So we were in church, and my daughter was serving at mass, and the father came over, and he I was like three people in. They don't sit on this. Anyway. but The ah priest came over and asked something, mumbled something. I had no idea what he said. And now he's looking, he he looks at me he's like this. I'm like, why do you want? And I'm like, he didn't have his microphone. He needs us We don't know where the microphone is.
00:31:01
Speaker
And was like, I'll go get the microphone. You know what mean? I almost said damn microphone in church. but And I didn't know where it was, but then I started of asking. And so after church, I said, Violet, people are just not willing to ask a question or go figure it out on their own. And I said that if you want to be successful in life,
00:31:20
Speaker
You've got to take the initiative

Initiative and Humor in the Workplace

00:31:22
Speaker
to do it. And so it was like both of the kids, they're 10 and 12. I was like, you need to learn how to do this. The I don't know or whatever. And especially in sales. And so what I love about that trivia is you get these objections.
00:31:34
Speaker
The first time you hit a wall, you give up. Are you not willing to put in five, 10 minutes of research when you're going to have to do more that research than that on future? So there's a lot of different aspects there.
00:31:46
Speaker
i understand the funny part of it. I was like, you need to be a cultural fit to be fun. I think, though, not a warning, but we we hire people who are like us.
00:31:58
Speaker
And sometimes we need that. And sometimes we need difference. Now, you don't need a bump on a log. You guyss don't need a bump on a log. But we do need people who complement our strengths. And what happens is we just naturally will go to the person who's like us. We're comfortable. It's I can't even tell you. you You're the best.
00:32:16
Speaker
Gosh, Relator is my number one strength finder. So I am very guilty of this as well. But I think it's like critically thinking what you need, what the company needs, what the sales team needs, what the future pipeline, leadership pipeline needs. But I love that exercise you have people do.
00:32:32
Speaker
Yeah, it shouldn't take them too long. does Does Debbie know that you send people her way like this? Yep. And I've told her if you're not comfortable giving out your daughter's name, don't do it. If somebody gets the name out of you, then then that's the that's the prize. Don't just give it because somebody's asked. Because a guy about a year ago went through that and his approach was, hey I'm supposed to ask you what the name of your daughter is.
00:32:57
Speaker
yeah that's not how the work bro yeah Yeah, that's not how this works is that's not how you're going to approach a prospect in terms of you had to bring an interesting point because I have a guy who works for me that I think thinks a lot of the ways that I do, but personality wise and how he enters the world is completely different.
00:33:17
Speaker
And he appreciates humor, but doesn't always get it. So as means of example, one of the things that we did at BusyWeb last summer is I got Dave to give me ah half a day off because in BusyWeb, we get half days off in the summertime. so What I did is I assigned everybody in the company got a country and then your country, because it was going on during the Olympics, I did a daily medal count on a Slack channel.
00:33:46
Speaker
And then if your comp your country got the most medals, you would have the last day of summer off and you would have a four day weekend. And so ah some of them I gave just like, we had we have a guy who was from the Ukraine, so he got the Ukraine and then everything else I just did randomly. But the guy who i worked works for me, um he i gave him Norway just because I thought it was really funny.
00:34:11
Speaker
and who got holland i don't know who got holland but there's somebody who works with us who really doesn't like the the dutch so we don't talk about that so he got norway and nori got three medals and he was like he was living and dying and because of the way he thinks he he is incredibly fastidious and he will learn everything about it in case you ask him about it the offhand So he knew everything about the Norwegian summer Olympic team that you could ask. And he knew who was up today, up for a medal in whatever. He could tell you everything, chapter and verse.
00:34:47
Speaker
So he obviously didn't win. And as a consolation gift, I bought him a giant Norwegian flag. That's seven foot long. and hes And he hangs it in his home office.
00:34:58
Speaker
And he is very much not Norwegian. And i i I constantly have to remind myself that things that I say as offhand jokes, I i don't think of. So as recently what happened, I don't even think Dave knows this, is recently somebody I'm trying to get into a relationship with ghosted me for three weeks. And so what i want my reaction was what I was going to do is I was gonna i went on YouTube and I looked for clips of Anna king Kendrick from Pitch Perfect singing Don't You Forget About Me.
00:35:31
Speaker
And I really couldn't find that. So I was like, I mentioned to this guy who works for me, I was like, Hey, it' since you're the Norway guy, could you learn? Don't you forget about me in Norwegian? And he's, oh yeah, no problem.
00:35:44
Speaker
And I didn't really think about it. Two weeks later, he said, he came to me and said, oh yeah, by the way, I have the first two verses down, but I'm having trouble with the chorus. Is this something?
00:35:55
Speaker
was like, what do you mean? And then he sang the first two first as versions of Don't You Forget About Me. So it's always- Norwegian. In Norwegian. And he's very much if not not Norwegian.
00:36:05
Speaker
So it's always a constant memory of me that- I have to be mindful of what I say because things I can say that are funny, sometimes people take very seriously. and So one of the things I do is I absolutely will never joke about somebody being fired or a power play of I'm better than you because people often take that seriously.

Building and Coaching Leadership Teams

00:36:27
Speaker
But yeah, if you know somebody who wants to hear ah Simple Mind song in Norwegian, I got a guy for you. I'll keep in the back of my mind in case anyone has any random requests. Dave, does anything I said, is any of that an exaggeration? Could you examine if you expect all of that to actually happen?
00:36:43
Speaker
That is a very tricky thing to have happen. Yes. Well, my feeling in sales is it's my job to get people to respond and just sending and a follow-up email, that's not going to do it. You got to do something else.
00:36:56
Speaker
You got it. But that just brings to a really funny and interesting perspective to leadership skills of communication and just just the assumptions or what.
00:37:08
Speaker
And I don't necessarily think it's maybe like frontline sales leaders necessarily, but sales directors or VPs of sales, they say something then they forget about it. And then three weeks later, someone said, did the thing you asked me to do.
00:37:20
Speaker
and you're like, how much time was spent? Doing that or we what happened or oh, i forgot I asked you that. I do that. I'm very I change my mind a lot. I'll just say I'll just say that. And so it's got to be like, oh, I don't know if I'm serious about this. Check back in two days.
00:37:36
Speaker
Right. Yeah. Yeah. And I've gotten to that point. And I've told them after the whole norregian Norwegian singing incident that if I ask you something like this, I need you to, because i I have done things like that in the past that have usually been pretty successful with customers. But if I ask you that, maybe wait a day and then double check before you start learning a foreign language.
00:37:58
Speaker
If an organization is trying to bring somebody up into the next level and they they understand what their issues are and understand what they're good at versus what they're not good at, what, how do they then, what's the next step of that? So in terms of building around that person's strength, and is isn't that a danger then to have that person and building an organization who's around one person's ah leadership strengths?
00:38:25
Speaker
Because you talked a lot about replicating success. Yeah. I think the thing to remember is that companies are led by leadership teams. So when you're promoting into a first leadership, sales leadership role, there's very there's different ways to be successful, but you're not going to be successful doing what you're bad at. You're going to be successful using your strengths,
00:38:48
Speaker
And also going beyond your comfort zone. But when you look at, so your question of being a in the pipeline, you first want to look at, you got to get your list together of your high potentials.
00:39:01
Speaker
ah Some companies have very specific agenda items or things they need to do. They need to sell X amount. Some people are saying, no, they just have to achieve quota and they have to be a team player.
00:39:12
Speaker
but you need to get a list of what behaviors, what sort of mindset and the results that someone needs to have within these. I think I getting a clear picture of that. You don't have to be so specific and and knock everyone off the list, but it's get specific about that. Then double check with those people on your high performing list that do they indeed want to get into a sales leadership?
00:39:36
Speaker
think there's a disconnect where people like, we found this high potential. The executive puts extra time into that person. The person loves it, but I don't want to get into leadership. I just like working here.
00:39:47
Speaker
And so figuring out what their goals are, And then giving them small assignments. I think what happens with some of this whiplash of, I didn't know this was what I was expected to do, or I didn't think it'd be like this in this new role, is they never had a preview. You can give people previews.
00:40:05
Speaker
It might simply be, hey we're going to ask you to work alongside the the rookie salesperson for a couple of hours. Can you listen to their calls? Or can you analyze the call records right with different technology?
00:40:17
Speaker
Hey, can you maybe do a one-on-one where it will teach you how to do a one-on-one, a coaching session, but do you mind helping out with these two people? They really look up to you and then following up with what they're doing and coaching them, giving them little projects and wins.
00:40:35
Speaker
you want it You want to test them, but you want to make sure that they're finding success. Because in those projects, what happens is sometimes they give um these high potential leaders these really difficult projects and they don't win. And now you've lost a potential leader because they didn't win.
00:40:53
Speaker
This is what happens all the time. You have a salesperson who's great. You get them the role. They don't win. They're like, i'm going to go back to sales where I was winning. And there's some research about this that you need. John Cotter has written several books on change management and urgency. and And he had quoted a study and I'd have to find it. i'm I'm not a details person. I remember the gist of things that's for the most part.
00:41:16
Speaker
But he was saying you need two wins to build momentum. You need to win. And so what are those? the And so when you give people these projects, even before they're promoted, they get a win.
00:41:27
Speaker
And then what's really important to your point is it you don't want everyone just being like this one person. How does that sales leader fit in with the other sales leaders at your organization, the other leaders? Because leadership teams,
00:41:43
Speaker
can get dysfunctional when the team aspect isn't thought through. but That's a bigger deal when you get to the director in C-suite. You don't promote someone because they're good. You actually promote, you should promote them as well. not It's not an either or, it's an and.
00:41:58
Speaker
You should promote them for how they can amplify from a team at teamwork perspective. who You don't want to have too much of a good thing on a team. it It just falls apart. And and so does that kind of answer that question of what to do with them?
00:42:14
Speaker
Yeah, that's exactly what was hoping for. for As we're closing out, because you've been fantastic and this has been super cool, the big thing that I think I'd like to hear is for those sales leaders, those rock stars that have gone through and they're really crushing and now they're going to get into their sales role,
00:42:37
Speaker
Data is one of those things that it seems like maybe sales leadership needs to pivot on and understand, but not necessarily something that a solo salesperson might need to be super good at.

Data-Driven Leadership and Final Thoughts

00:42:50
Speaker
So are there some tips or training wheels that you give folks to, okay, well you're going to have to lead by numbers now. So here's how you get started. Yes.
00:43:01
Speaker
With one caveat. So data is very important. You can't just manage by, us this is not what you were saying. Right. But it's, um people think they go, okay, I'm in sales. Now I'm going behind a desk and I'm just managing numbers. It's an and thing.
00:43:16
Speaker
So there's this whole debate between managers are this and leaders are that. And you need to manage and you need to lead. We we need both in order the organization. And sometimes within the same role.
00:43:29
Speaker
But as far as the data, getting good at pattern recognition, which is a strategic thinking muscle that is built, not necessarily made, is going to be a key differentiator.
00:43:41
Speaker
Now, there is some technology that helps amplify that, but get really good at recognizing patterns and looking into the The lead to the leg factor, getting good at recognizing, okay, we've been successful doing it this way, but could we be more successful doing it another way? there's the The metrics, understanding your your own and numbers, this forecasting. I had an organization I worked with that they're just they're doing phenomenally well, but they tracked, this is like just data, for example. What they did is they tracked what the new sales, what the rookies were doing.
00:44:21
Speaker
okay, rookie is going to do this much activity and then they're going to produce this. This is their closing percentage. This is what we do. We call on schools. They do fundraising for sports teams at high schools. What they didn't do, because they didn't take a step back strategically, they didn't actually track.
00:44:37
Speaker
They tracked that the results of their experience, but they didn't track what was what they were doing. And what they found is that the experienced salespeople were better relationship builders. They did more referral.
00:44:49
Speaker
They landed more meeting, the success rate of the meeting happening. And then the closing percentage drastically went up. And then the results that were given, the the package size, right the deal size went up.
00:45:01
Speaker
So they went, oh my gosh, we're do So they use the metrics to change what they were doing and they 3x their growth, not actually doing more work. So a sales leader's job is to use that data, but then to not just receive the data, but to ask questions about it and to see what's missing.
00:45:22
Speaker
That's really important. Super, super important for for someone. And that can get it they can get really complicated depending on what industry you're in. But I think that the message is don't just rely on your gut feeling or and don't just rely on what the numbers say using them together.
00:45:39
Speaker
It's a weird art form to get a lot out of high performers and be a high performer at the same time and have data and sales management and meteorologists are the only people who are really judged by how well they predict the future.
00:45:56
Speaker
And it's certainly a challenge. I get smarter every time I talk to you. I feel great every time about myself. Every time I talk to you, I have the book. I want more people to read it. Where can people find the book?
00:46:08
Speaker
And then where can people find you? Yes. So the best place to find me is on LinkedIn. My my tag is RiseUp, so you don't need to look for Rebecca. The book is on is in paperback, Kindle, and audio on Amazon.
00:46:24
Speaker
I went through the torturous process of actually... turning the book into audible version because the market, we listen to books, right? We are multitaskers. We're insatiable appetites for learning in the sales realm. So that's where you can find it and me.
00:46:41
Speaker
Perfect. Dave, any final thoughts before we wrap up? it's It's just always so great talking to Rebecca. And the big thing that I think hopefully folks are taking away is that having sales as a role is completely different than being a sales leader.
00:46:59
Speaker
And you do have to level up and be okay with... expanding, getting outside of your comfort zone and being accountable in ways that you never have before. So Rebecca, thanks for sharing this. And I can't wait to read the book.
00:47:12
Speaker
Thank you. Thank you for having me. Thanks, Rebecca. This has been another episode of Dial It In, produced by Nicole Fairclough and Andy Witowski. He's Dave, I'm Trigby. And with apologies to Tony Kornheiser, we will also try to do better the next time.