How to Win Trust and Advise People
Advice on becoming a trusted advisor.
tl;dr - Your sellers want to be seen as trusted advisors, but rarely earn that right from buyers. What follows are some words for sellers on why that is and how to change it.
Buying = risk. Most sellers don’t appreciate how much risk buyers take to shake up the status quo and buy something. Sellers must earn buyer trust for them to take that risk.
The foundation for trust starts with the fundamentals: preparation, attention to detail and follow through.
True advisors collaborate with buyers on an evidence-based POV, even if it means no deal. This starts with a hypothesis about why a buyer would change anything at all.
Elite sellers act with empathy and respect. They never forget that buyers are humans and that building a career is a long game.
I’m not the world’s best seller. I started my career as a software engineer. I’m a 2x founder/CEO so I may be unemployable. I messed up GTM pretty badly in my first startup because I didn’t truly respect sales, but I’m trying to do better at Gradient Works.
I’m not entirely without sales credibility. I’ve run a large RevOps team. I’ve closed quite a few 5 and 6-figure deals with some very big companies. I’ve also sold a company for a lot more than that. Not bad, but plenty of sellers have better resumes.
However, I do have one advantage that most sellers don’t have. I’ve been a buyer—both as a CEO answerable to a board and as an SVP of RevOps at public company. That puts me in a unique position to understand what buyers have to go through.
This part of my background has come up a few times recently. I got a chance to talk about it on the Elite Selling Podcast. I also got invited by a Gradient Works customer, SPINS, to speak at their SKO on the topic of becoming a trusted advisor.
What follows is my attempt to share what I think sellers should know to earn the chance of being treated as a trusted advisor. Hopefully after reading it, you’ll feel like you can trust my advice.
It starts with actually understanding what buyers have to go through.
Buying = Risk
Every one of us who’s hunting new logos is trying to get someone to reject the status quo. It’s simple—if your buyer doesn’t already have the thing you’re selling, they’ve got to disrupt something to get it.
That means one big thing for buyers: risk.
Most people hate risk. After all, risk implies downside—we might lose something we already have—and our brains hate that. It’s called “loss aversion”. Psychologists Daniel Kahneman and Amos Tversky found that the negative effect of losing something is more than twice as powerful as the positive effect of gaining something. That’s not rational, but it’s how people actually behave. Discovering humans aren’t perfectly rational was so shocking to economists that Kahneman won a Nobel Prize.1
It’s not just people. Large organizations are conservative by design. They’ve got something that works, so disruptions to the status quo face scrutiny.2 Noted muckraking multi-hyphenate Upton Sinclair3 said, “It is difficult to get a man to understand something when his salary depends on his not understanding it.” That sounds like every CFO reading every ROI case ever.
So, the deck is psychologically and systematically stacked in favor of the status quo. Since sales is inherently about taking a risk to change the status quo, it’s a wonder any of us ever sell anything.
But we do! We sell things because sometimes the status quo really isn’t acceptable. We’re all trained as sellers to “implicate” pain4 and talk about the cost of inaction, etc, etc. These are all attempts to find a compelling reason to change the status quo.
Sellers tend to forget that even if real pain exists, the road buyers have to travel is dark and full of terrors. Buying your solution means they’ll have to repeatedly stick their neck out—and 99.9% of the time you won’t be in the room when it happens.
I used to run RevOps for a public company that was really a PE rollup. The US Salesforce org was the unholy offspring of two others that had been, shall we say, inelegantly smashed together in years prior. The duplicate data and general unhappiness had become painful even for the CFO. By the time I arrived (via another acquisition, naturally) several past leaders had promised to solve this problem. They had not.
Thanks to the acquisition that brought me in, I needed to integrate another Salesforce org and tackle the data problem. Despite the clear need and the obvious pain for the CFO, it took months of work to get the budget approved—months of data analysis, vetting vendors and building an ROI case.
When I finally chose a vendor I took a genuine risk that I wouldn’t have a job if the project failed. At no point during this months-long ordeal were any vendors in the room, but one vendor had earned my trust.
To repeat: buying = risk.
The only way you convince a buyer that the status quo isn’t acceptable and that they should risk changing it is by earning their trust and proving that you’re someone from whom they should take advice.
Most sellers don’t put in the effort, which might explain why most sellers don’t make quota. For those teams that really want to achieve, here are the three things I’ve seen elite sellers do that earn them the right to be a trusted advisor:
Do the fundamentals
Develop a point of view
Operate with empathy
Let’s dig in.
The Fundamentals
To me, “the fundamentals” means preparation, attention to detail and doing what you say you’re going to do. These are the foundation of everything else and they’re fully within your control. If you put in the right inputs consistently, you’ll get the right outputs.
Let me (re)introduce you to one of my favorite basketball players: Tim Duncan. This man won 5 titles and 2 MVPs. He’s considered the best power forward of all time but he’s not a household name. Why? He was boring! His nickname was The Big Fundamental.
To fully appreciate Tim Duncan and his fundamentals you need to know one quick thing about basketball stats. Sometimes a player plays a lot (close overtime game), sometimes they play a little (blowout). Because of this, “per game” stats don’t tell the whole story, so basketball nerds look at “per 36 minutes” stats—for every 36 minutes a player is playing, what do they contribute?
Let’s look at The Big Fundamental through that lens.
This is what Tim Duncan did every 36 minutes. For 16 seasons, from his rookie year until his last championship, he would get you 20 points and 12 rebounds like clockwork. He prepared, he paid attention to detail and he delivered.
How could you not trust putting this man out on the floor? Do this for your prospects, and they’ll trust you too.
Now, here’s a much less inspiring story about another young person in Texas around the same time: me.
Not too long after Tim Duncan and the Spurs won their 4th title in 2007, I started a company. At the time Twitter was just blowing up and crazy ideas were flowing. My cofounder and I had the idea to search Twitter for coupon codes. We called it CheapTweet.
Like many dumb ideas at the time, it worked. We got mentioned on the Today Show and did a deal with Best Buy. I figured we were on to something, so I started calling other B2C tech companies. Lo-and-behold, we landed a meeting with Dell.
I spent a week prepping a presentation. The day of, I put on my best business casual and drove up to Dell HQ. I was a little intimated. These were the “dude, you’re getting a dell” people—clearly they knew more about marketing than me. But, I still felt pretty good because I was prepared.
They stuck me in a big conference room. Six Dell folks dutifully filed in, setting their laptops down. It was Inspirons as far as the eye could see.
I reached down into my bag to grab my laptop so I could present. And then I saw it… the Apple logo staring up at me. That’s when my soul left my body. I had no choice but to plop that 2008 MacBook Pro up on the conference table—glowing Apple and all.
I remember 12 eyes glaring at me, but not much else after that. Let’s just say we didn’t land Dell. I’d done everything right up to that point, but not thinking through that detail killed the deal because I immediately lost their trust. Don’t be like me. Get all the details right.
Point of View
Most people believe a Point of View (POV) is some fixed thing like your grandpa’s political opinions. This is partly because developing a good POV starts with… already having a POV. But it really means adapting that POV as you learn new things.
Your job as a seller is to collaborate with the buyer to develop and communicate an evidence-based POV for why your solution is worth the risk of change.
To do that, let’s take a brief detour into the science of making predictions based on beliefs. A POV is really a statement about what you think will happen based on what you believe: i.e. “If A is true and you do B, then I think C is the likely outcome."
When it comes to predictions like this, there’s one person to know: a Presbyterian minister from the 1700s named Thomas Bayes. He thought a lot about probabilities and ways to answer the question of how much we should believe in something given what we observe about it. Here’s how he summed it up5:
Simple right? Unless you’re a statistician, not so much. Let’s ignore the math and just walk through the concept.
We start out believing something: P(A). Then we learn something new: P(B | A). We take into account how common that new thing is regardless of what we believe: P(B). Finally, we put all that together to change our minds about what we now think given what we learned: P(A | B). That’s our new POV. The next time we learn something, that updated POV becomes our starting point: P(A).
Here’s an example from Gradient Works. We believe commercial sales teams should use dynamic books instead of geographic territories. Let’s say we talk to a prospect and they tell us they use geographic territories and they’re working fine. We wouldn’t update our POV very much—most companies use geographic territories. But if they tell us that 90% of their revenue comes from the Fortune 50, then we’d pretty quickly change our beliefs about the suitability of our solution since they’re mostly doing enterprise sales. In fact, we might think we’re not a fit at all.
Most sellers don’t do this systematically. Consider discovery. Anybody can ask discovery questions. The best sellers use discovery to learn things that meaningfully impact their POV, regardless of where it leads. Sometimes it’ll lead to no deal. When it does, you have to let go. Being genuinely open to take what you learn to a logical conclusion is a big part of how you build trust.
Instead, most sellers use discovery as an exercise in confirmation bias. They want to believe in the deal, so they seek out information to confirm there’s an opportunity while ignoring anything to the contrary. Prospects get a bunch of empty questions. Sellers get a bunch of empty pipeline that will be closed/lost in three months with “not responsive” as the reason.
So, how can you do it differently and form a convincing POV? It starts with forming a hypothesis about the answers to some questions. Specifically, these questions that tell you if an opportunity’s any good:6
Why anything?
Why us?
Why now?
The first one is the most important for hypothesis purposes. If there’s no good reason to change anything, then there’s no good reason to buy anything.
Your job is to go into your first call with a hypothesis about the prospect’s answer to the Why anything? question. You’ll need to combine what you know about common challenges with whatever concrete information you can learn about the prospect beforehand. Write it down in 3-4 sentences.
At Gradient Works, a Why Anything? hypothesis might look like:
Company X serves a large TAM, is growing quickly and just raised a large round. Their website is geared towards self-service so most of today’s pipeline is probably from PLG or inbounds. That must be working, but the new funding means bigger targets—which likely means new headcount and adding an outbound motion. They’ll probably struggle with qualification, focus and rep attainment as they try to shift their outbound contribution to pipeline.
As a bonus, we could use this to form an initial Why Us? hypothesis:
The lead routing portion of our pipeline platform could help them with inbound volume but, being inbound-driven today, they probably already have a point product for lead routing. We think adding outbound is a strategic priority, in which case we have a unique offering with the combination of our account selection and dynamic territory capabilities in addition to lead routing.
This gives us a strong framework for discovery. We’re starting with a POV about how their company works and the challenge they might be facing. Now we can tailor our discovery towards finding out which of those assumptions are accurate.
We can even just state those assumptions right out of the gate. If we’re right, we build credibility. If we’re wrong, we learn something, but we still build credibility because it shows we studied the situation and drew reasonable conclusions.7
This hypothesis-based approach gives you and the prospect a way to start building a joint POV that evolves over multiple meetings. Combine that with an overt willingness to learn new information and follow wherever it leads—even if that’s to no deal—and you’re well on your way to becoming a trusted advisor.
Empathy
Remember when I talked about Kahneman and Tversky shocking the economics world by discovering people weren’t rational? Well, they’re right. And so far I’ve been spent a lot of words talking about rationally updating bayesian priors and such. Let me not make the same mistake as those economists.
People buy things. People form relationships with people, even if they’re commercial relationships that are initially built around a transaction. In fact, I’ve got some lifelong friends that I met because they sold me things.
Your champion is a person. They’re going to need to put their budget, their reputation and in some cases their career on the line to buy from you. If you’re not aware of that, then you’re not doing your job.
Make their job easier. Do the extra work to prepare some talking points they can drop in with their boss, some tailored slides they can incorporate into their presentations or do some truly deep analytics for an ROI case. You can’t (and shouldn’t) do all the work for them but you can help mitigate their risk. Never phone this in. A great way to lose trusted advisor status if you respond to a request for help with some one-size-fits-all doc that sales enablement hands you.
Communicate with no ask. And I don’t mean sending them the latest blog post from marketing. If you see something interesting that’s relevant to their business, share it. If you see they just had a layoff, ask if they and their team are doing ok. Don’t ask for anything in return—not even an update on some next step. Just be a human.
Finally, there will come a time when you’re under pressure. This usually comes at the end of the deal when you’re trying to get a signature. Stay respectful of their time and priorities. Maintain a consistent even-keeled communication about timelines and next steps. Never demand that they make time for you in the evening, on a weekend or a holiday and always thank them if they do.
Your job as a seller isn’t to make friends—it’s to sell. But I guarantee you that you’ll close a lot more deals over the long term by treating your buyers with respect and empathy than you will with short-term manipulation. Once you’ve destroyed trust, you won’t get it back. Your career is a long game. People that trust in you and your advice will come back time and again.
Understand your buyer’s risk, do the fundamentals, develop a real POV and operate with empathy. If you do those things, you’ll earn the right to be a trusted advisor. Your customers and your bank account will thank you.
Their research is known as Prospect Theory. Unfortunately, Tversky didn’t get the Nobel. He died a few years before and the Nobel people insist you gotta be alive to get one.
Any of us who have ever answered a 37 page infosec questionnaire in addition to providing a 100 page SOC 2 Type 2 report while also arguing about worldwide IP indemnities with legal will feel this pain. And those are the easy parts.
He’s most famous for The Jungle (1906) which exposed how horrible the Union Stock Yards were for workers, cattle and general sanitation. If you like not (frequently) getting listeria he’s one of the people you have to thank. He also ran for governor of California.
Why this is the “I” in MEDDPICC is something I’ll never understand. You’ve got a P right there in your ridiculous acronym, freaking use it.
We actually have Pierre-Simon Laplace to thank for this interpretation but I’ve only got so many words here.
Shoutout to my friend Sam Spetalnick for opening my mind to these questions. I’ve come to love these questions to diagnose the quality of any given opportunity.
This has some similarities to the Challenger Sale but with more emphasis on the “mind reading” part to establish credibility and less about building to a big reframe moment.