The Trust Dividend: How Great Sales Leaders Win in the Age of AI

I've spent the last 30 years of my career leading global sales teams and delivering billions in quota revenue annually. And yes, that's billions with a B. Most recently, I was with Microsoft. But I didn't start my career as a sales leader. I actually started as an MIT-trained engineer. Working for IBM in Silicon Valley. And a couple of years into it, I realized that I wanted to be out with customers, helping them use technology for business benefit, delivering value. And so that's been kind of a foundation of my whole career. And I'm excited to share the trust dividend that you get to win in the age of AI. So let's jump in. So in 2018, I used this exact slide in a keynote on sales transformation and what it means to sales leaders. Because the reality is technology is kind of the easy part, and culture and people are the hard part. Whenever we sell technology or services, we're often displacing something that already exists. Maybe it's not as effective, like CRM displacing spreadsheets or something like that. But it's the change management and the people side that really is critical to realizing the value from whatever it is that the customer is buying. And that's challenging. And in fact, when Satya Nadella took over as CEO of Microsoft in 2014, he made culture, changing Microsoft's culture, the number one priority. Because at that time, there was a lot of infighting. And we were fighting with, you know, across different organizations. And so he turned Microsoft into a growth mindset, also into a learning organization. And so culture, like we as human beings, We change much more slowly than the technology. And this has implications for AI. So we're living in massive disruption. And I don't need to tell you guys that with all of the AI advances, just, you know, people are being displaced. One of the people I read recurrently on LinkedIn is Jason Lemkin from Saastr. And he's replaced the bulk of his SDR our team with about 20 AI agents. And he talks about the learnings. For example, some of the agents go awry and they don't notice it right away. Or the person that is managing the agents has become less tolerant maybe, or find it more difficult to manage human beings. So there's a lot of things going on. And I love that Jason and his team are on kind of the frontier And so I learn a lot from reading that, reading his posts. So if you want to think about kind of what they're experiencing and then what that could relate to you and your journey using AI, I would recommend it. We also have social and political unrest, and people need to do more with less. So all of this disruption creates stress. Calm is not present. People are kind of running on few fumes. And when people are stressed and unsettled, they don't do their best work. So you as a leader have a responsibility to help your team de-stress. And I'm going to talk more about that. So I like to call AI as the bot we love to hate. So AI hallucinates. And I appreciate that AI ideates with me as a great thought partner, but isn't so good on the facts. And so trust in AI-generated content is eroding fast. And if you're using AI for outreach and go-to-market, your brand trust may be at risk. Personalized emails sometimes aren't so personalized. AI is sending emails at scale, clogging the airwaves. So if your human beings are sending personalized emails, it can be perceived as just adding to the noise. And in fact, I'm working with some early-stage companies on their go-to-market, and they're flat out not having success with digital outreach anymore. And so they're looking at and doing more cold calling. And in fact, I was talking to kind of a professional cold caller who makes his living cold calling, and he told me that he's now having people on the other side of the phone say, "Are you a human being?" And so that suggests that there's a lot of AI bots doing cold calling and impersonating being a human being without disclosing it. So I'd ask you, if your company is doing that, is that enhancing your value? Is that enhancing your brand or putting your brand at risk? And then buyers are doing a lot of research. We all know that. They come more informed. So it's really raising the bar for your sellers. Your sellers need to deliver value and be able to build trust with the buyers, with a customer every step of the way through every interaction because trust is the currency of B2B sales. And we've got to be cautious that AI is not eroding that trust. And the AI paradox is the more we use AI, the more we crave human interaction. And I love Tim's quote, his stat with Gartner that, you know, Gartner has shifted 180 degrees from buyers just don't want to interact with the sellers to now buyers prefer interacting with sellers. It's that human-to-human interaction. The other thing is, is, you know, In the olden days, we used to pay sellers to sell laptops. Now we just buy them online. A purchasing agent will, you know, have a list of laptops for the company employees to buy, and they buy it online. And the reason for that is it's not a risky purchase. It's been commoditized. But every time you are paying a seller to sell something, sell your product and service, and service by definition, it means that the buyers are risking something. And so you need your sellers to build that trust and close the gap. Otherwise it would be a commodity, a bot buying from a bot, and it's not so risky. So the irony here is that trust is becoming the differentiator in an AI world, and it matters hugely. So I'm gonna quote one of my favorite people, Chris Beale. People buy from people they trust to make decisions they don't trust themselves to make. Think about that. When we're selling something, does the buyer and the buying committee and the customer really understand what they're buying? Probably not. When I buy a car, do I really understand the car, the electronics? Absolutely not. Well, buyers are risking their career on purchasing decisions. Think about it. It's not just what they buy and the cost of what they're buying from you. It is also the change management, the disruption to their business. So trust is critical and foundation, and trust requires human-to-human synchronous conversation, not leaving a voicemail, getting a voicemail, sending an email, receiving an email. It's, you know, real time, can be virtual, can be in person, but synchronous conversation. And this also applies inside your organization. I used to see my sellers sending email to customer success on the account and having some conflict going back and forth between my team and customer success. And if I saw this go back and forth a few times, I'd call a timeout and say, wait a minute, let's get on a Teams call or a Zoom call and have a conversation and sort it out. The other thing of interesting fact I learned recently is The number one reason strategic projects fail is due to lack of trust, lack of trust across the team members. And so trust is really a huge currency, particularly more important in the world of AI. And as Gerhard mentioned in my book, Love Your Team, my book really is a lot about building trust and holding teams accountable But the foundation is trust. Connection over performance. It's all about trust at the start. So some of the principles, 3 principles of sales leadership directly from my book is building trust. So find out what your team members care about. Find out what you can do to support them, help them achieve their goals. Draw the connection between their ambitions and their goals to the job that you're asking them to do working for you, working for your company. Be consistent with your words and actions over time. And after all, you're modeling the trust that you expect your team members to be able to do with their prospects and buyers. And then be transparent. You know, don't tell them everything that, you know, obviously that's confidential in the company that it might not be appropriate to share, but they want straight talk. They want authenticity from you. And in return, you want straight talk from them. I mean, you want to know if a deal is going sideways so that it gives you the opportunity to step in and help them, help coach them, help them with the deal. And then your team needs to know that you matter to them, or they need to know they matter to you. And that's really key because this is all about them performing, creating psychological safety. Remember all the disruption and stress and chaos happening around them? It's up to you as a leader to create psychological safety, care about your team, support them, help them be successful. When I wrote my book and I reflected on what I actually do as a sales leader, I realized that what I do is have conversations with my team. And leadership is a conversation. That's it. It's nothing fancy, nothing mysterious. And so What conversations do you need to have with your team? How are you building that trust? And for me, the foundation of that is really one-on-one conversations, understanding what's going on with deals. Yes, setting clear performance indicators, you know, performance goals, tracking that, supporting them. Trust and loving your team is not soft. It actually is about holding people accountable as well, but doing it in authentic way as well as no surprises. So with AI, you get a trust dividend because the juxtaposition between AI and the rapid pace of technology and the disruption, it is putting a premium on trust. You are able to get a dividend from that. You start getting real intelligence back from your team. You get the truth. You can lean in on their deals and you help them with their deals, reducing the sales friction. So let's say a seller needs to meet with an executive, a prospect executive. They probably need your help. They need you as a leader to use your positional power. Maybe your network, maybe someone in your network knows that executive. Because let's face it, executives don't often want to meet with sellers. So there needs to be kind of a compelling reason, a bait in the bucket. And that's where you come into play to help them, support them to get the deal done. And deals as a result move faster. They close faster. And your top talent stays. And they recruit their friends. It also enables you to build your reputation and keep your job. So if you can't retain your top talent, it's really hard to make quota. And so that puts your role at risk. And attracting top talent is easier when people know your reputation across your team, other teams, people want to come working for you. And you get promoted. So in an AI world, you are the difference. As I said, connection before performance, setting trust with your team, enabling your team to build trust with customers. You are setting the context for, of expectations for your team, but you're also creating the context for AI and using it intentionally. So your job and what you're trying to do is build trust. Well, AI is kind of eroding trust. So you need to be super intentional about it and set that context. And, you know, it's— I love AI. I use it all the time. And there's appropriate uses for it. But how do you think about where to use it appropriately. I mean, Tim talked about research and others talked about research, researching companies and executives before you meet with them. Thumbs up on that. I use it to, I give AI, you know, a URL, a domain name, and I ask it to tell me what are, what's the ICP for that company based on what they have on their website and who are their top competitors. And I, I look at it, I validate it, I think about it. I, I don't just take it at face value, but it helps me with the companies I'm working with. It helps me understand how they're being positioned in the market. It also helps me help them define their ICP, make sure that they're reaching out appropriately and thinking through and testing their messaging against their ICP, doing some testing. So perhaps you want a little bit more. Let me ask these questions. Here's the 3 things I would recommend you do. Think about how will this, using and adopting AI, how will this impact my team and customers? Is it building or eroding trust? And what are the unintended consequences? I'm guessing right now you have people on your team, in your company, using shadow AI projects or products on their own. Maybe you have agents working. Maybe you're augmenting your team with AI. So how's it going? Because it's been a little bit— adoption's been excuse me, a little bit of the wild, wild west. What kind of controls and knowledge do you have about how AI is actually being used today and how it's impacting your team, impacting your customers? And if you want more, I have created a trust-first AI framework. And the way it goes is this. Take stock. Take stock of what you're currently doing today. And that can be pretty hard to do. Do. And by the way, I know IT is probably doing this and wants to officially certify things depending on the size of your company. But as I said, there's a lot of shadow AI happening and start to build a risk assessment, a risk map to think about what's this doing to my brand? Are you doing AI-generated outreach at scale? Are you doing cold calling without the bot disclosing that it's a bot and offering the person picking up the phone to connect with a human being? And then see what you can do to upgrade guardrails. That's the third step. You want to make sure that there's some framework of guardrails where you're— this is where we're going to use AI. This is where we're not going to use AI. And then, you know, look at your messaging and sandbox things. Always, whether it's human-generated messaging or AI-generated messaging, test it against your target market. See what resonates. And then track and tune over time. This is not a one-and-done thing. This is an ongoing process. So that's a quick little framework and some thoughts I have about winning and building trust in an AI world. And I'm happy to take questions. Any questions?

Yes, Helen. You are describing a habit that I haven't heard articulated before, which is shadow AI. So explain why is that happening?

It's happening because AI, because everybody feels the need to become somewhat AI proficient or they become irrelevant. AI is pretty inexpensive for employees to get a hold of and use. So they're paying for it themselves or an organization is paying for use of AI for some purpose without telling IT or what have you. So it happens with new technology that People on the front end of it want to harness it, use it. And so they do it kind of under the radar. And it can happen on an individual level or an organization level. And you'll see it with all sorts of tools, particularly, you know, if you're looking at wanting to get better insights and data, things like that. Organizations are using that today. And it may be fine, but you have the risk always of hallucinations. And AI is not a fact engine. And we kind of think about it that it knows what it's saying when it doesn't. It's just spitting out the next thing. So it sounds believable and we trust it and then we go with it. And then that might be fine. But if you're Using it to reach out to prospects, not so good.

That makes a lot of sense. Actually, there's a lot of buzz about your presentation online. And when— okay, Gary is asking, with AI transcription tools like Gong, where every client interaction is tracked, how does this degrade the trust relationship between leads and reps? For example, is there a feeling that AI is now Big Brother?

Is now being what? Big Brother?

Yeah.

Well, sure. Yes, for sure. However, here's the thing that I think people sometimes they literally take the transcript that that was what was literally said. And it might be. But also, that is AI doing it. Again, AI is not great with facts. I think the transcripts are a fantastic tool to use for coaching their reps. So for example, but take 50 transcripts or 25 transcripts that a rep has different calls, like a cold call or discovery call. Put that into AI and then ask for it to give you a skill set review. It'll give you indicators. And then, you know, ask it to identify where the skills shined and where they didn't. And then you can go and validate whether you agree with what the AI said. So I think it's a wonderful tool, and it can save leaders a lot of time. But you've got to fact check and look and make sure that you are trusting the output. But for sure, it might feel like, big brother. But you know what? In this day and age, I think we've already crossed that Rubicon that it's expected that calls are going to be recorded.

Somebody is asking about what to ask AI because it reminded me of what you said earlier. You ask AI about the ICP of the customer that you're calling on. So this person is asking, do you have a list of what to ask AI? About the customer?

Oh, so what I do is I just say, okay, you know, tell me about— I have like a standard script. Just tell me, look at this website, tell me what their ICP is and tell me who their top competitors are. And I do it all in one prompt. Like, you don't need to tell AI what those words mean or go into detail. And that will give you some information back. And then you can, if you want clarification, you can ask for clarification. I look and I go, does this make sense? Because I'm, I'm working with those, that account, and I know what they think their ICP is, but I'm also validating based on what I'm seeing and what AI is telling me from how they represent themselves on their website.

And I want to add that my friend Anthony Anovino is also asking two additional questions. Uh, give me the three headwinds the company is experiencing right now and the three tailwinds. Uh, and that gives you a lot of insight, uh, into the potential difficulty that your customer may be experiencing at this time. But again, you need to use your critical judgment, uh, whether to believe what AI is serving you and maybe test those assumptions with other AI tools. So you're not just asking, let's say, ChatGPT, but go over to Gemini and ask the same question and see what results you get. And then also ask to validate where does this information come from about the headwinds.

Right. Right. That's, you know, one of the things I learned. So I was, uh, working with Microsoft and my team was having difficulty reaching VPs of HR at Honeywell. And even though it was, you know, our account, they wanted to reach HR VPs that were responsible for employee engagement because we had a new product. I did all this research trying to figure out what the things were, and then I created a list and I realized that If you're cold calling, which I started cold calling, I set up meetings with 5 VPs of HR. I realized that I had done too much research, that the conversation actually was way more valuable in terms of the insights delivered than all of the research in the world. And this goes back a number of years, so really before Gen AI. But That's the other thing is I would say validate and talk to your market and find out what they really care about because they're the litmus test.

Right. Somebody's asking, have you asked for a SWOT question and see what AI thinks?

Yes, I have. Yes, I've done SWOTs for sure.

I think there's another really interesting question given the whole conversation of love, which is definitely a love language for me, having been an executive at enterprise-sized organizations and then taking the step out to, you know, being an entrepreneur in a small business. And it's Trip Braden that had this question about the soft side skills. And I'm curious what your thoughts are, Helen, on how those soft skills become more important. But the fact of the matter is what people went to immediately saying, oh, the AI will never be able to replace the relationship or the connection with human people. That's just not statistically basically that's not data true. The, the AI has a massive leg up on all of our friends and closest, closest relationships in terms of how the day went today, what it can do to solve the challenges, or how we're feeling about what happened in our day, just as a small example. So I'm curious how you think about that and how that connects with how you're leading your teams and supporting them effectively.

Well, I think it comes down to the perception and the reality of how the buyers feel in terms of how they trust and what they trust. So I get what you're saying for sure, but the litmus test is really in, are you getting the deals done, particularly in risky, strategic, high-dollar-value sales you're trying to do? Because the buyers are more critical now than ever before, and there's new people on the buying committee. So I do think that the human-to-human interaction and trust is required in B2B sales to win. And that at least at this point in time, AI isn't displacing that. And it might be a handy tool on the front end, but it will still require human-to-human interaction in order for that buying, risk-averse buying committee to pull the trigger and buy your product or service.

Well, thank you, Helen. That was outstanding, insightful, and actionable. So many practical ideas. But also head over to amazon.com and get Helen's book that is an incredible read, Love Your Team. Thank you, Helen.

Thank you.