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Sales Strategy
SalesProChat Transcript: Managing Millennials and Gen X Sales Pros
May 24, 2018 | Canadian Professional Sales Association

In the May 2018 SalesProChat, we hear from Neil Ryland, Chief Revenue Officer at Peakon. As the company’s chief revenue officer, Neil built teams in multiple regions and oversaw the rapid expansion of a UK basement startup to a global company. Neil offers his take on managing and motivating high-performing multi-generational sales team. 

Listen to the podcast interview and join us for the Twitter chat May 31 at 1 ET / 10 PT and read the edited transcript:


Bill Banham: Neil Ryland, Chief Revenue Officer at Peakon. Welcome to the show.

Neil Ryland: Cool, thanks, Bill. It's a pleasure to be here.

Bill Banham: So we're talking the topic of millennials in sales today, Neil. And I know you've got lots of great opinions around this that you're going to share with our audience today. So let's jump straight in.

Firstly, what's changed since you were in junior sales roles in the mid-2000s? How have sales leadership and the execution of sales developed and changed?

Neil Ryland: You know, I think it's changed a lot. For me personally, it's changed hugely. One, I don't have anywhere near as much hair as what I used to have, which is a killer. But I think for me actually what's really interesting is, I think that the workplace has definitely changed, the workforce has changed, but I don't think management has necessarily changed. The role of management is still to inspire and lead people to be better than some of them are today.

But I think off the back of the changes in the workplace and the workforce, what you've kind of seen as an explosion around the technology and the ways that we can communicate with buyers, with customers, with prospects, which has then naturally changed the way the sales are KPI'd and measured as well. I think that's a big shift for me, is that it was very boiler room when I joined, and you learn the hard way, school of hard knocks kind of sales approach. You know, how many dollars can you make in a day, how many followup emails can you do, how many demos do you get on. And I think that's changed hugely now compared to when I first started out.

Bill Banham: Okay. So today we have a generation of folk who are pretty much the majority now, and if they're not quite the majority, they're going to be by 2020. And that's the way it is. And they're associated with lots of unique character traits and motivations and so on and so forth. But do you think there really is a big difference between what millennials want out of their career compared to, say, Gen-Xers and boomers?

Neil Ryland: I think at the heart of it, no. I think we're all still human and we all still seek the same things under Maslow's theory that drive us toward stability. But I think there are characteristic changes that's happened with the workforce that's coming through, and I think, again, a lot of that's been driven by access to technology. And I'm a big fan of Simon Sinek and his views around instant gratification. I think that's influenced it.

And for me, leading a team of millennials and being put on the cusp of it myself, I look at what motivated me and I looked toward my bosses when I first joined. And I kind of distilled it down to three categories. I think if you go back a long period of time, if you go back, say, 40, 50 years, I talk about my dad and my granddad's generation to an extent. They really valued the value of having a job. And it almost didn't matter what the job was. It was the value of being able to work and go home and put food on the table.

And then you have, and I kind of buck at this kind of thing myself, which is I understand the value of hard work. I feel very fortunate that when I've worked hard, there tends to be the rewards that come off the back of that. And that gets me to keep my head down. I think the shift, when you look at managing millennials, is that they've actually done something quite clever, in my opinion, which is that they've discovered the value of time. And that means that it sometimes comes across like they don't care about their job. But it's actually opposite. It's just they value their time, I think, a lot more than what previous generations have done. Where you spend most of your time at work, that's where you spend more time than you do with your wife, your kids, your family, your dog, whatever it might be ... You spend more time at work. And I think they've started to understand the value of that time far more than what previous generations have done.

And off the back of that, what it seems to have inspired is that they want to be more, call it "T-shaped" people. They'll have their specialist role, whether it be in sales, whether it be in marketing. But they also want to have the T-shape; i.e. that they have understanding and knowledge around the influence of what their role has in other areas of the business.

So I think there are some fundamental changes in the way that they're inspired and how they're motivated. But sitting underneath it all, do they want the same things out of a career? I think yes. Definitely. I don't think there's any difference. I think we all want to have enough money to have an enjoyable and sustainable lifestyle and hopefully better whatever our parents did so that we can continue to improve the world, is kind of the bigger picture for me.

Bill Banham: So talk a little bit about the differences. Are some of the differences that do exist, are they more to do with the how and the why we choose the work? The purpose, the causes, the engaging with the employee brand, the use of technology to work smarter, not harder?

Neil Ryland: Yeah, definitely. I think the big thing is that they want to be challenged and they want to challenge back. They want to get to the heart of the question of start with why, and that's what drives their motivation. And I think the other big difference is that they're far more values driven. And I think, again, it's exposure to information. When you're exposed to a lot more, whether it be fake news on Facebook or not, they still have a huge amount of exposure to things that we didn't have access to at this juncture. You'd have to go and manually take the time to look it up. I always make the joke that it's killed a lot of pub talk, because you used to be able to just make a fact up in a pub and no one could challenge you. And in today's world you can be challenged, because someone just pulls their phone out and Googles it and says, "No, it wasn't. It was 1972 that that happened," or in our case, Ipswich did win a cup in 1978.

But I think because of that, and that generation has grown up with access to that information, they will challenge things, because they want to get to the heart of the truth. And that's not because they're being difficult. It's because they actually want to ensure that they're doing the right thing. And because they're very values driven as people, it's very important for them to understand the why.

And I think that's going to come up to my point at the start around has the workforce changed? Yes. Has the workplace changed? Definitely, whether it's the beanbag kind of style or the pool tables or just the work-life balance. The fact that we have had this shift in being incredibly values driven as a business means that millennials will be asking why to ensure that we're doing the right thing as a leadership team.

Bill Banham: Do you think that some of the stereotypes about millennials are maybe just older people complaining about young people?

Neil Ryland: I do, yes. And I think this because ... And a lot of people share this view, the generation above have always complained about the generation below. Whether it's linked to the music is rubbish or that they didn't work as hard, and the classic, "Oh, you don't know how tough it was." And I think that is just the nature of not being young and not being in the group any more.

But that doesn't mean there aren't differences. I don't think those differences are necessarily considered bad things. You could argue that working 10 hours down in a mine or working in terrible conditions, that was really, really bad. But people did it and no one said anything. Just because we now have a generation that is more aware and more conscious and has more corporate social responsibility as well, it doesn't mean that they're bad. It just means that they're challenging a work force above them in ways that they haven't been challenged before. And it's trying to figure out a way, how do you bring those two or even three generations in the workforce together to accomplish whatever the greater good is for the company they're trying to do.

Bill Banham: Just a side question. How many people in your office wear a tie every day, in terms of the chaps. Is that still a thing, or did that go out of the office five years ago maybe?

Neil Ryland: I think that pretty well went out. In our office, there's no one that wears a tie except if the sales team or there's one of the executives joining perhaps a meeting where we know that we're meeting like a corporate bank. And it's more about ... Like I've said to the team, it's more about playing the chameleon. When you're in our office, this is around you being totally comfortable and what makes you most productive. Why would I find a way for you not to be productive by making you wear a tie, not that we ever get any sunny weather here in London at the moment, but why would I do that? So you sit there uncomfortable all day wearing a tie. That doesn't make any sense to me.

At the same time, if you're going to meet a bank and it's all about an "excellence always" approach, which they know, they're passionate around their values and doing the right thing for the customer first, and the customer would appreciate that you wore a tie, then we would wear a tie. I wouldn't walk into a creative agency in a suit and tie. And I think that's another thing. The "there's one rule and this is the way we do it" doesn't work, anyway. I don't think it's a millennial thing, I think that's just a maturity thing of the workforce of the last five years, that we've started to realize that that's not the best way to maximize people's productivity.

Bill Banham: And so you've just touched upon another really interesting point. You used the word "maturity." Another way of putting that is "a stage in one's life." Could a lot of these stereotypes around millennials just be because people are seeing folk who are in an earlier stage of their life who've perhaps not had some of those experiences or some of that level of maturity from their perception, and therefore are behaving in different ways? Maybe, for example, they don't have a family or mortgage yet, and therefore they perhaps are a bit more casual when it comes to their career path?

Neil Ryland: Yeah, and I think, again, there's two parts. I think there's also an element of ... We've quite also created a self-fulfilling philosophy here, which is the more we talk about millennials doing certain things, I think the more they read about it, the more they feel like they have to live up to this stereotype of what it's like. So I think there's an element of that happening. So if you say something enough, it becomes true.

And when you actually sit down and have a conversation with an individual, regardless of whether they're a millennial or baby boomer or they're in the middle, like us, there isn't a huge amount of difference. It's always going to be linked to the stage in your life. We've all had our first job. And I remember in my first job, and he's still one of my mentors today, a guy called David Meade, he was the sales director at Capscan. And I came to the end of my probation period and I decided it might have been a good idea to have a few beers on a Wednesday. And I quickly realized by Thursday at 10 AM, when I was in his office, that wasn't a very good idea. And I think that's the nature of the stage that you're at. I wasn't branded at that stage as being a millennial and not understanding my career or anything like that. I was just so young and learning my trade, coming out of University.

So I think there are some things that are very, very similar. It's very much linked to your stage in your life. And I think it's also because we've raised the awareness and almost categorized these things about not just being immature and then being mature and experienced and senior. We've now bucketed it against the age and the year that you were born. And again, the only thing for me that's fundamentally driving a lot of that is the use of technology and access to information.

Bill Banham: So the younger generation is often perceived as expecting to progress their career at an accelerated pace compared to previous generations. You and I, we mentioned earlier, we were both born in 1983, and certainly when we left University in 2005, 2006, around that point, the student debts were nothing like what they are today. Apologies to our Canadian-American listeners here. The context is in the UK, student loans and the cost of tuition fees increased a lot in the mid-'90s. So now you've got, certainly, folk in their 20s in their career that are perceived as coming in and expecting a much higher salary to reward the fact that they're more qualified. But added, of course, perhaps that they've got this debt.

How can leaders manage millennials' expectations around that part of it from the get-go?

Neil Ryland: Yeah, I think that's a good point. I think, again, it comes back to one of my points around that management hasn't changed. I just think that management was able to get away with not being fantastic in the idea of career development, because often career development was linked to someone leaving that was above you, all purely on your performance in a set role, and therefore people didn't ask. It was just, if I keep working hard and I just do what I'm doing I'll naturally progress. And if I don't, I'll go somewhere else. And I think now what's been challenged by millennials is they wonder, well, what are all the career paths and routes I could take? Because I value my time and I want to be somewhere where I'm learning, I'm developing, and I'm challenged. None of those things are bad things.

If you think about when you interview someone, and someone says, "I really like being challenged. I'm very keen to learn, and I'm very willing to try new things." You thought, well, brilliant. These are all the skills we look for. And yet somehow when we then place them into the job and they ask for those things, it's seen as a negative. It doesn't make a huge amount of sense to me. And the first thing to do is to embrace it and not try to shut that down, because they are good traits to have in people.

So how do you address that? Well, I think it comes down to, I think, three key areas. One around the expectation management is sitting down as a group and in the teams, and we build what it means. In this case I did that at Huddle as well and now at Peakon ... What it means to be part of this business, and what are the core values that we hold ourselves accountable to. And some of those core values are around being excellent always in the task we've put our hand to. And if you start to create those kind of expectations, they know that until they've mastered those skills, which they're challenged by because they want to become masters at them, they know that they can't be CEO in the afternoon. There's a lot of things that go around it.

I think the other key parts of it are around clear communication. And it sounds a bit cliché, and I'm working in a data-driven employee engagement company, and telecommunication still comes out as often the number one reason people leave lead businesses, from the managers not communicating clearly. But that doesn't just mean telling people where they are and what they're doing well, what they're doing wrong. It actually means explaining all areas of the business and what different functions are and the roles and responsibilities of those people. Because then they become aware of the skills that they do possess and what they don't possess. So then they don't think they should be CEO tomorrow because they're fully aware that they haven't got the skill set to go and sit in front of the VC and present, they don't know how budget sheets work. They're not quite sure of the importance around churn, and ARR growth and difference between bookings, and how our marketing team do adverts.

And so there's so many things that you can do to communicate better to the workforce. And again, it's around an understanding. They're used to having instant access to information. So when you share the details around what makes your business tick, all the things that are really great, all the different roles and the skills that are involved in it, and build up career paths, you tend to find actually that the problem goes away because they'll self-learn and go and find out what they need to do to get to the next level, versus just saying to you, "I want to be promoted. I see myself as being here." Well, they probably only see themselves being there, as I pointed out earlier, if they're in the early stages of their career, because they don't have the information to know what it should be. They're just desperate to be better. They're ambitious. They're curious. And they're used to having access to information. So, to me, the role of management has changed around being clearer and very transparent around those skills that are needed to progress.

Bill Banham: What technologist are there to help us better analyze and understand top ways to communicate with and motivate our sales teams?

Neil Ryland: You know, I feel like I'm cheating because I'm about to plug Peakon here, Bill. But I think one of the reasons, if I step out, and let's just talk around what we do here at Peakon, which is fundamentally helping organizations to take a data-driven approach to managing their workforce by taking their feedback and finding new ideas of what would help to get the best out of your team.

But I think for me, it is around creating clear communication channels for getting feedback. We also have a situation where we have a whole load of managers that are looking after people that are very young, but are managers because we've got "expert promotion syndrome" and we didn't know how to manage millennials. And this is still in companies today, but very apparent if you look at even the last two years, because millennials will challenge the older work force. And what happens is we think they're great. Let's take the talented and just make them a manager. And the older ones are saying, just because you're very good at the individual contributor, you can very easily get promoted to manager on what you become as an expert manager of that function. You're not an expert leader. So I think technology such as Peakon really support, help people going into these new roles, what it takes to lead and manage people and motivate them.

The other things that we use and help with communication is that, I think a lot of this is around because they value time, they want to work in a place where they're working with people that they can learn from and that they get on with. So we've invested quite heavily in tools like Slack, tools like Workplace that have a social area, so they can interact and engage in things.

Some of it isn't even technology. It's the strictness that you apply around running your All Hands or your Fireside Chat meetings to share communication with the team. We run a panel with the executive team for Q & A, and prior to that we ask for questions. What questions would you ask Neil, what are the biggest challenges you see as an executive team in growing this company? And then get them to give us the questions and we'll answer them in an All Hands kind of forum.

Also, I've actually encouraged them to build their own social ground. So we encourage them to be on Twitter. We give them lessons around building a social media presence so they have their Twitter profile, their LinkedIn profiles. And we also encourage people to look at new ways of working. Like just because I used Sales Force and LinkedIn, that doesn't mean that's the golden way to do it. And they'll come forward, and through ideas from millennials, we deployed intercom, we deployed Trello, and we now use Tableau across a number of areas in the business to give better data insights to the team and encourage everyone from SDI level right the way through to the senior team to use new technologies to drive productivity and not be afraid of failing if the new tech doesn't work.

So there's a whole load of ways that you can use technology to support productivity for millennials and for the older workforce, as well.

Bill Banham: We could keep talking about this forever, I think, Neil. But unfortunately, we're running out of time. So just one more question for today. A big one, to recap. So millennials are the future of sales and the future of the workforce. By 2020 they are going to be the majority in most of the G7 countries. How do you motivate millennials? What are some of your top tips to leave us with for leaders of tomorrow, for [choppy audio 00:20:42]those of you who are looking to ensure that a millennial-dominated workforce are firing on all cylinders and [inaudible 00:20:52].

Neil Ryland: Definitely. No, it is. Well, I think I can just give my humble opinion in doing this. But I think there's four things that you really need to bear in mind when you're managing a younger workforce, a millennial workforce. The first one, like I said, is they value their time. And that means that they value their freedom, as well. And I think you have to question and work with them around, when do you actually need them to be in office and what freedom can you give them? And that basically means if you want to have a policy where people can work from home, which I have no problem with, but they also want an amazing culture to be part of. Then there has to be this balance and this mix. But allow and work with them and facilitate a conversation; well, okay, how do we build an amazing sales culture? And that wouldn't mean everyone working remotely all the time, because then you wouldn't have an amazing culture, sat on your sofa on your own.

If you or one of your core values is around how do we help you to drive learning, one is to give them enough room where they can learn and that they can fail in a safe environment. Again, then some of the attitude of "hey, we want to work from home and never want to be in the office" goes away because you've given them a reason that they want to be in the office which benefits the company and benefits them in the future. So give them the freedom and the time. Give them the ability to fail in a safe environment.

The other thing is they constantly want to be challenged in the right way, so I basically have a rule where I say to them, "Hey, 90% of your time should be on the bigger function, the bigger mission and the role that we play in that. But 10% of your time should be around how do you learn new skills." And that could be anything, from spending time with the marketing team, it can be taking Excel training courses. We encourage them, but we ask them to report back on it and say how are these new skills they've learned going to benefit your teammates. And again, they feel quite inspired around doing that. It plays into this T-shape personality that you want to build.

And then the last one I'm going to say is listen and communicate clearly. Don't think because you've done something in the last company, it's going to work in this company. Take the time to rebuild what it means to be part of your current function, your current company. Work with them to build a set of values that they want them to hold themselves accountable to. Because if you're a manager that only has accountability to you, the minute you're not in the office it doesn't work. If they only have accountability to themselves, then they're not thinking about the bigger team. If you can create this culture where you work with them to build a set of values, then they're accountable to each other. And that generation are very, very inspired around doing the right thing and being accountable. So that's worked very, very well for me around how do you channel this amazing energy, this willingness to learn, get them in the right direction that works for them personally and develops them as individuals, but also helps you as an organization to get to where you need to be.

So freedom, give them the ability to fail in a safe environment, challenge them, and listen carefully.

Bill Banham: Well, listeners, I hope you've been listening carefully today, because those were some awesome insights from Neil Ryland. That just leaves me to say today, Neil, thank you very much for being my guest.

Neil Ryland: My pleasure. Thanks for your time, Bill.

Bill Banham: And listeners, until next time, as always, happy selling.

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