The Gen Z/Boomer Sales conflict - can AI be a generational equalizer?

Why do Gen Z and Baby Boomer salespeople not get along? A new report from Clari + Salesloft sheds some insight into the conflict and how AI is both a symptom and a solution. 

As someone who has been covering Marketing and Sales tech for a while now, I've always thought Sales technology was way ahead of its Marketing counterpart in terms of AI capabilities. And because this category seemed to lead the drive to incorporate AI, that meant that all salespeople were diving in and taking advantage of what it offered.

But the new research from Clari + Salesloft tells a different story. The report, Inside the $56 Billion Productivity Hit from Generational Conflict — and How AI Can Fix It, is a survey of 2000 US Sales leaders across all generations that examines how they view one another and how generational dynamics are shaping how AI is used in Sales.

The generational approach to Sales

You probably don’t need to be told this, but Gen Z and Baby Boomers do not approach selling the same way. Boomers take a traditional, relationship-first approach, focusing on building personal relationships through in-person meetings, phone calls, and even social outings (yes, some salespeople still golf!). Of course, many are also likely leveraging Zoom and other online meeting tools as travel is not in the budget of many organizations, but there’s still that face-to-face aspect.

Steve Cox, Clari + Salesloft CEO, points out that Boomers often have the perspective that they've done this for years, why do they need to change?

On the other hand, Gen Z takes a digital-first, outcome-driven approach to selling. They are fully computerized, often work remotely, and leverage AI extensively. Relationships are still important; they just initiate and manage them differently. Cox says Gen Z’s approach is to meet the customer where they are.

Sales has always been considered a relationship-based business. […] The advent of technology kind of shifted that slightly. And then COVID and the advent of AI have really kind of shifted that dynamic a lot. [ ] I think we're in this interesting dichotomy now of two different groups, generationally apart. They have different views of how you build a good selling process and how you attract and convert end customers, and I think we're at an inflection point now where we're starting to see some impact to revenue and lost productivity.

With these very different approaches to selling, the report discusses three areas where these differences are driving significant challenges.

The technology challenge

It's no surprise that younger Generations like Gen Z are the biggest AI champions. It's not that older generations, like the Baby Boomers, don't recognize the benefits of AI; they just worry that overreliance on it undermines relationship-building.

In this study, Baby Boomers think the Gen Z's approach to using AI lacks relationship-building and strategic thinking, is not appropriate for complex deals, and is destroying customer relationships. On the other hand, Gen Z says Baby Boomers' resistance to using AI is making them less efficient, slowing the sales process, affecting the ability to close deals, and is killing innovation.

The communication challenge

From a communications perspective, Gen Z embraces digital channels like direct messaging (DM) and social media chat, but Boomers prefer in-person meetings for all deals, or even Zoom meetings.  It's interesting to note that 59% don't adjust their approach based on deal complexity, and 49% don't tailor it to customer preferences. In addition, eight out of ten say they've watched reps from the other generations lose deals because of mismatched communication styles.

AI is adding another layer to the mix with 83% in total believing it can enhance customer relationship building, but only 67% of Boomers buying into this. For example, 46% believe it improves responsiveness to customer questions, 40% believe it supports communication across touch points, 38% say it helps understand customer needs more deeply, and 36% say it personalizes outreach and follow-ups.

The work-life balance challenge

Work-life balance is a funny thing because it means different things to different people. In this study, 64% of Boomers think Gen Z's work-life balance demands take precedence over business performance, and 67% say they've seen younger sellers lose deals because of this.

But it's not true, according to Gen Z with 72% saying Boomers' fixation on long work hours doesn't translate into better results, and they believe Boomers value hours worked over actual performance. Gen Z also claim to have seen Boomers lose deals because they sign off at 5pm or refuse to work weekends.

Here the kicker: although Gen Z and Millennials prioritize work-life balance over a company's business needs, they spend just as many hours working as their older colleagues and report hitting quotas more consistently. They are also the most active with AI tools.

This generational conflict is costing organizations money

Eighty-eight percent of respondents work on cross-generational teams, or they manage salespeople from multiple age groups. 70% of these employees say generational conflicts hurt their productivity, costing each seller an average of 5.3 hours a week. I'm not going into the breakdown of that number (you can read it in the report), but it does make sense.

When people don't communicate well, misunderstandings happen, people get stressed, and morale drops. And all of that just makes collaborating on deals or accounts more difficult for any generation. The frustrations are so deep that 28% of Gen Z are looking for a job where they don't have to interact with Boomers as much, and 19% of Boomers are planning to retire early because they're tired of dealing with Gen Z. Is there an answer here that would make both sides happy?

AI is everywhere in the modern workplace

It's no secret that AI is in just about every technology in marketing and sales. So when 69% say their company is providing AI-enabled tools such as engagement, conversational intelligence, forecasting, coaching, and opportunity management, it's not really a surprise.

What may be surprising is that adoption is not universal.  According to this study, 64% of salespeople are not using the full capabilities available to them. Over half are not happy with the tools they are given because they're not integrated with existing workflows, offer limited customization options, provide weak reporting, lack actionable insights, or have poor mobile functionality. Cox suggests: 

“I definitely think adoption is a key risk and a key problem for everybody. There's a little bit of a feeling around AI at the moment that you just buy these AI agents, and you drop them in, and they do the work for you, right? There's an element of making people more productive using AI tooling than just expecting AI to do the work, which I guess kind of leads into my  AI managing Gen Z being next level. Because right now, we have an adoption problem around the technology stack that we've got.

The stat that said 39% of Gen Z sellers would rather be managed by AI than a Boomer is the one that really stands out for Cox: 

I had to take a moment to think about why that was. I think some of it came down to feeling like it was, the word I'm looking for, it was condescending, like the feedback and approach. There's this attitude of, look, I'm using the latest tool, I'm using AI, I've got all of the knowledge, I don't need any help. So, finding any kind of feedback and opportunity to be able to coach and guide or mentor came across a little condescending. And I think some of that stems from the fact that, if you've been successful in doing things a certain way for a number of years and never needed to adapt and change, and then suddenly you've got somebody coming along and saying, Hey, look, this is a much better way to do it. I don't want to hear what you've got to do. I think that feels a little dismissive. And so that's driven the wedge. That was the thing I found really surprising. And I've been trying to imagine how you would be managed by AI, in today's world.

AI as a generational equalizer

Why is this important to a conversation on generational approaches to selling? AI could be a way to bridge the divide.

First of all, let's just say AI is not the only answer to the generation gap in sales. But it can help a lot. Respondents in this study agreed they could learn from each other, and 79% were interested in being paired with someone from the other generation for mentoring or skill-sharing.

For example, Gen Z can teach Boomers how to use technology and AI tools. They can explain social selling and digital outreach, often have a better handle on data and analytics, and can help Boomers understand them better. Plus, if you don't have a personal brand online, you need to get one, and if anyone knows how to build a personal brand, it's Gen Z.

On the other hand, Boomers are very experienced at building long-term customer relationships and could share with Gen Z how you can do that. They're also very good at maintaining professionalism and resilience under pressure, and they know how to navigate complex negotiations.

AI is adding another level to this collaborative environment. First of all, and maybe most importantly, it enables knowledge sharing. 81% in the study said AI can improve the spread of best practices and 80% feel that AI can level the playing field, bridging experience gaps that happen between newer and older sellers. Also, 79% said it can enhance cross-generational communications. Cox notes: 

I think there's an element of  how do you take some of that pre digital experience, and turn that into some digital workflows and digital data sets that you can incorporate so that you can take the benefit of it? Because the human interaction piece is always going to be hard, right? [ ] But if you could capture some of that knowledge and insight and processes and put that into a model alongside all of the digital data you already have, I think there'd be an opportunity to bridge the gap and show either side that there is some benefit.

It’s not just about the tool

It's possible that one of the biggest challenges in implementing AI across an organization and ensuring equal adoption is how it's being implemented. If a company just drops an AI solution in or starts telling employees to use the AI capabilities in the tool they have, it's not going to work. Adoption is probably the biggest challenge to leveraging AI successfully. Cox says: 

This has been a problem in the software industry for the longest time. Because AI moves so fast and these tools spin up so quickly, it continues to just exasperate the problem. And one of the things that we think about is what do organizations do next. Take an audit of your technology and your AI adoption now and look for pockets where you've got different generational approaches to using it, identify the gaps, and then it's about focusing on what you have today. It's much easier to go out and think, I have to solve a problem. I'll go buy a new tool and another new tool and another two new tools, and then you end up with software sprawl, and it becomes impossible for anybody to use it. Take a stair-step approach, with cross-generational champions to drive adoption. And make it a way that it feels like a team effort to drive adoption, and then it becomes a team effort to drive results.

I honestly believe that if you take the extreme ends of the spectrum of Gen Z and Boomers; if you took the best parts of relationship building, and the negotiation skills from a traditional way of doing it, and then you took all the benefit of AI technology, and the speed and the performance and the productivity they can give you, and you can bring those two things together, I think what you'd end up with is an even better result than either generation could deliver on their own.

My take

This study included 2,000 salespeople: 20% were Gen Z, 45% were Millennials, 25% were Gen X, and 10% were Boomers. It's a good study, but we have to be careful not to lump everybody into these generational buckets. When you look at the bigger picture from this study, there are clear challenges that need to be overcome, and AI does have the potential to help

As Cox sums up: 

When a lot of people read this report, I think some people will think, oh, this is about age and saying certain people are not this or certain people that. And I would say, here's one thing I really think about when I read this. Is not about a generational shift. We see differences in approaches. And, like I said at the beginning, there are pros and cons. This is about having a clearly defined [AI] implementation strategy. I think if you deploy this stuff intentionally, it aligns and works across all generations, pulling in that knowledge that crosses teams. Really thinking about how you create an operating system that values not just everybody's experience in the way they work, but also kind of values innovation.

These challenges are not unique to Sales. When you look across Marketing, Customer Service, and Support, and even development teams, you will likely see similar generational challenges. It’s something every department in every organization should be thinking about.