Episode 456: Create Trust-Based Conversations with LinkedIn and AI

Intro 00:22
What’s up, everyone? Thanks for joining us for Making Sales Social Live, coming to you from the Social Sales Link virtual studios. I’m Bob Woods, and Stan Robinson Jr. and Brynne Tillman are joining us as well today. How are you all doing?

Brynne Tillman 01:01
Gentlemen, how are you? Excellent. Thanks. I feel like I haven’t been here in a while.

Bob Woods 01:08
It’s been a minute, and it’s good to have you back in the saddle, as they say. We’ve got a really good one to talk about today.

Brynne Tillman 01:18
A really important one, right? This is often the core of everything we do.

Bob Woods 01:25
Exactly. That’s a perfect way to roll into this, because we talk a lot about trust here on the podcast, and as a company with our clients. Starting trust-based conversations requires intentionally creating a safe, open, and empathetic environment. That’s why we’re talking about creating trust-based conversations today with LinkedIn and with AI.

And yes, you can be trust-based with AI—100%. You can use it to lead with curiosity, empathy, and transparency. When you do this, you create a foundation for trust-based dialogue that can evolve into meaningful and productive relationships. Trust is the easiest and best way to do business. It’s also just the right way. Right, guys?

Brynne Tillman 02:27
Absolutely. A slogan we use occasionally is “Start trust-based conversations without being salesy.” For salespeople—and really for anyone—the key to building strong relationships and a solid reputation centers around trust. As human beings, if we approach things from this perspective, we’ll have success in every area of life, personally and professionally. I love this conversation.

Bob Woods 03:07
Stan, anything to add?

Stan Robinson Jr. 03:09
Just that it takes time to build trust. You can’t really accelerate it. That’s why we say, slow down your outreach to speed up your outcome, because trust needs time to develop.

Brynne Tillman 03:28
Exactly. I love that. When we push too fast, we don’t just lose trust and credibility—our reputation suffers. We also start coming off with what I call “engineered empathy.” It sounds like trust, it sounds like we care, but it’s self-centered. You can’t build trust when the focus is internal. Trust comes from providing value externally.

When we focus on trust-based conversations, it has to be sincere—heartfelt. We can’t fake it or engineer it. So I love that: slow it down. That’s key.

Bob Woods 04:39
Yes. And it has to be truly cooperative. I’ve been on the buyer side of conversations where things seem great, you’re building trust—and then suddenly you feel the hammer drop. That’s when their own interests come in, and it ruins trust instantly. It feels terrible on the buyer side. You don’t want to do that as a seller. Don’t shift from a genuine, two-person trust-building conversation into “Now let’s talk business.”

Brynne Tillman 05:28
That’s why one of our 21 Tenets of Social Selling—which is also an ebook—means so much to me. I kept it on a Post-it on my computer for years:
Detach from what the prospect is worth to you, and attach to what you are worth to the prospect.

That’s how you build trust—by showing up to solve a problem, not to make a sale.

Bob Woods 06:11
100%. Before we move on, we have a free ebook that encompasses everything we’re discussing today. If you’re with us live right now, it’s at SocialSalesLink.com/trust. There’s a QR code on the screen as well. If you’re listening to the recorded podcast, the link should be in the show notes. Just in case it’s not, again: SocialSalesLink.com/trust.

So with that, let’s get into some of the specific, nitty-gritty concepts behind everything we’ve been talking about. I forget who’s first—I think I’m first.

Brynne Tillman 07:01
You’re first. All right, what’s my first one? Reliability.

So reliability, from the ebook’s perspective, is consistency—what your audience can expect. But I’d also say reliability is ensuring your content is impactful and accurate. People should be able to rely on your advice. When you share tips or value—whether in messages, posts, videos, live shows, or podcasts—people should trust that the information is good.

Now, “good” is relative; it may not be for everyone. But we shouldn’t share made-up statistics or unverified information. There’s reliability in accuracy and in consistently showing up.

When you consistently deliver valuable insight without any expectations attached—value with no strings—you build trust.

Bob Woods 09:02
Yes, and when people go to your content, they should know they’re not going to be pitched. They should know they’ll get valuable information they can use. They should never feel like, “Oh great, here comes another pitch.” That’s the opposite of reliability.

Brynne Tillman 09:42
Content written with the intention of selling instead of helping is one of the fastest ways to lose trust. We have a comment—I’m not sure who it’s from—but yes, everyone should review their content before posting. Look at your content from an external perspective: if you read this with no other context, would it bring you value?

I get frustrated with posts that say, “DM me for the answer.” That makes me lose trust. Honestly, I’ll go to ChatGPT to get the answer instead, and they’ll never even know I was there. I’ll only DM if you give me a compelling reason beyond “message me for the answer.”

Reliability means that when I click something, I know I’ll get value—an actual answer.

Okay, next. Who’s number two?

Intro 11:32
That would be Stan.

Bob Woods 11:36
So I’ll blend honesty, which is number two, with what we just discussed about reliability. AI can help you be consistent, and as Brynne said, the goal is to reach a point where people anticipate your content. If they know you publish every Tuesday, they look forward to it.

Stan Robinson Jr. 12:08
Honesty is simply doing what you say you’ll do—and doing it well.

Bob Woods 12:17
And one thing we always warn people about is avoiding automation. Aside from breaking LinkedIn’s terms of service, if you tell someone—

Stan Robinson Jr. 12:37
—“I’m super impressed with your LinkedIn profile; we should connect,” and they check who viewed their profile and don’t see you—trust is broken before the relationship even begins.

That’s one aspect of honesty.

And another, as a commenter mentioned earlier: before you send anything, review it. If you used AI to generate it, read it out loud. Bob always says this—reading it aloud helps ensure it sounds like you. If you trip over a sentence, your reader will too.

Bob Woods 13:45
Yes—and sometimes people don’t even realize this. One of the simplest ways to destroy trust is claiming, “I read your profile and was impressed,” when the recipient can easily check and see you never viewed it

Brynne Tillman 14:19
I think that’s what Stan was saying. Yeah, that’s exactly right. That was exactly his point — if you’re not showing up…

Bob Woods 14:27
There. Right there specifically, too. Yeah.

Brynne Tillman 14:32
And the bottom line is: don’t send out a note that is not congruent with the truth. Whether you’re religious or not, whatever your God is, just picture he or she watching you. I know that sounds funny, but that’s my litmus test. Is this a lie? Because often in this outreach that happens, it’s this mass outreach: “I viewed your profile, I checked you out, I liked your content,” and then you see that it was scraped because your spelling error is there or your emoji got pulled in. I agree strongly that this is really important.

Alright, awesome. I guess that would be integrity then.

Bob Woods 15:38
I would be integrity. So integrity flows really well out of reliability and honesty — even though I can’t seem to say those words right now. If you’re reliable and honest, integrity comes from that and more. It means staying true to your values, whether you’re talking about a public post or private messages.

Some of the things you shouldn’t do… the big one is what Brynne said. You see that all the time on X (Twitter). You used to see it more on LinkedIn, and I think it’s going down now, especially because some of the latest algorithm updates show that LinkedIn knows that’s happening, and LinkedIn doesn’t like it. If you’re still doing it, just know the algorithm is taking a dim view of that. That’s one of the good things the algorithm is doing.

Other things: don’t bait and switch. No one likes that. We’ve all been victims of it. It still happens every once in a while. You lose integrity in the eyes of the other person even more when you get through their filters and then switch. Meaningful conversations cannot start from bait and switch. They can’t start with using engagement solely to pitch. You need to build meaningful connections by aligning your values with your stated goals — and actually talking about those as well.

By doing all of this and showing up consistently, you prove you’re a person who can be trusted.

Brynne Tillman 17:52
I think it’s so important. At the core of integrity are your moral principles. It’s who you are as a human being. Why, if we put such weight on our moral principles in life, would we not continue that on social? Why would we not continue that in sales? Why would we shift what we would never say or do to friends or family — and say or do that with prospects? They’re human beings. Integrity is continuing your moral principles in your business relationships.

Stan Robinson Jr. 18:47
Absolutely. And for anyone who isn’t familiar with the term “bait and switch,” since we’re in the world of sales: bait and switch is when someone tells you one thing and delivers another. Like, “I’d love to set up a call to learn more about your business,” and you get on the call, talk for 30 seconds, and then they talk for 29 minutes pitching their business.

Brynne Tillman 19:24
That happens so often — not just on calls but in messages, even in connection requests.

Bob Woods 19:34
Even in the connection request, which is the height of — I don’t know if arrogance is the right word…

Brynne Tillman 19:40
There are people teaching this. People selling programs with automated mass messaging, hoping someone says yes. That is not the way we want to go to market. We want to go to market with integrity, reliability, honesty. And what’s number—

Bob Woods 20:05
Number four. You also want competence, Brynne.

Brynne Tillman 20:08
Competence. It’s funny — I talked about this in reliability. Competence is bringing your expertise to the forefront. It’s sharing incredible value that is useful even if they never talk to you.

When you use AI the wrong way, you sacrifice competence because you’re relying on AI’s research on a topic, not yours. Competence comes from the value you bring based on your knowledge that has proven impact on clients.

The way we overcome this is: we use transcripts from trainings, coaching, client conversations, emails, blog posts — our own voice — put it into AI, and ask it to manipulate it into the type of content we want, but using our words. It’s AI ghostwriting for us, not as us. That’s how you highlight competence rather than using AI to sound competent.

Bob Woods 22:08
Great way to put it.

Stan Robinson Jr. 22:12
And for those who don’t like to write and think, “Well, thought leaders write books but that’s not me,” talk to ChatGPT using advanced voice mode. Just speak — that is absolutely your voice — and then ask the tool to work with it.

Brynne Tillman 22:42
Side note: I’m writing another book — because, well, I’m me — and part of my book references “Gap Selling” by Keenan. I had a question about the Ask-Offer Ratio, so I went to ChatGPT and said, “Based on Keenan’s book Gap Selling, tell me his definition of mastering the Ask-Offer Ratio.” It gave it to me quickly, slightly different from how I’ve used it, which helps me reference him accurately. It saved me from going through hundreds of pages. That happened yesterday, so I thought I’d share it.

Bob Woods 23:47
Very cool. So now Stan is going to take one that I think is huge — vulnerability.

Stan Robinson Jr. 24:07
Vulnerability is being willing to reveal a little bit of yourself. It may sound counter to competence because vulnerability often involves revealing a mistake or an area where you don’t feel strong. But you’re letting people see the human behind the performance. People appreciate that and relate to that.

Don’t worry about it damaging your competence. If you say, “This is something I need to improve; I’m working on it,” people relate to it.

Brynne Tillman 25:09
Some of the best stories and lessons start with failure. When something didn’t go the way we expected — a launch, a project — when you express that, you’re approachable. When you’re vulnerable, I believe your content more because you’re not showboating. And you can’t learn without failure. If you’re not talking about your failures, people don’t know that you grew or that your experience taught you something.

Bob Woods 26:16
The other thing about vulnerability is: if you’ve learned from that mistake, what did you do and how did it help? I guarantee other people have been through something similar. They want to know what you did. If you’re just starting the path of fixing it, write about that and maybe even ask your audience what they’ve done.

Brynne Tillman 27:16
Before we go to the next one, we had a question come in: “How do I develop the fastest communication and engagement?”

The answer is: slow it down.

When you focus on fast, it’s about what you need, not what they need. Fast is your goal, not theirs. So shift the mindset from “fastest” to “most meaningful and impactful communication that earns me the right to the conversation when the time is right.”

Bob Woods 28:01
Yep. Very important.

Now let’s move on to number six: empathy. Salespeople should have it. A lot of us do. It means understanding and addressing the needs and challenges of your audience, hopefully connecting with them on an emotional level. Listen carefully, respond with tailored solutions.

Being empathetic — genuinely empathetic — is acknowledging that what they’re sharing is important. This isn’t a time to dig at wounds, exaggerate pain points, or use old sales tactics. That’s not empathy.

Brynne Tillman 29:43
Empathy allows buyers to recognize that we understand their situation and the impact it’s having on their business.

The challenge today is engineered empathy — when we use AI to try to be empathetic. It’s not real. Don’t ever say, “Make me sound empathetic.”

Instead:
“Here is the situation. Here is my experience. How can you frame my perspective in an empathetic way?”

AI should ghostwrite your thoughts, not fabricate emotion. Engineered empathy is disingenuous — it breaks trust.

Armin asked: If you use AI to spark conversation on LinkedIn, how do you come across genuine and sincere while optimizing AI tools?

Use the CRISPY framework from our book Prompt Writing Made Easy. Quick overview:

C – Context (What are you writing?)
R – Role (Who should AI be?)
I – Inspiration (What’s the message meant to evoke?)
S – Scope (Format, length, structure)
P – Prohibitions (Words/tones you do NOT want)
Y – “Your voice” questions (AI asks YOU questions to write authentically)

The “Y” is what keeps it genuine — AI becomes the interviewer of you.

Bob Woods 33:04
And I dropped the link to the book in the LinkedIn chat if you want to check it out.

Moving on to number seven: accountability.

Brynne Tillman 33:22
Accountability has many meanings, but for me, it’s simple: I do what I say. I know we touched on this in integrity and other areas, but accountability is being responsible for the actions I take and the mistakes I make. Vulnerability fits into this, too.

If I state something that’s wrong, I correct it. I don’t hide it. If I send an email with an error, I apologize. I take responsibility.

I use God as my accountability partner — I’m always asking: is this what I’m expected to do as a human being? If the answer is no, I need to take accountability.

And what we fear is always worse in our minds. People appreciate accountability more than avoidance, even if they never noticed the mistake.

Perfect example: I called someone in our membership the wrong name for three weeks — long story — and when I discovered it, I picked up the phone. She thought the name was a little pet nickname. We laughed. The fact that I called made all the difference.

Don’t ignore it. Accountability also helps your own well-being. It’s cleansing.

Bob Woods 37:47
Yeah, you feel better.

Brynne Tillman 37:54
Okay, that’s a deep way to end.

Bob Woods 38:01
Yeah, we did get pretty deep there.

Stan Robinson Jr. 38:13
With accountability, you need someone to help you stay accountable — God, Bob, your spouse — because at least for me, I can’t do it alone. I’m too good at giving myself excuses.

Bob Woods 38:43
We went even deeper. Painful but worth it.

Brynne Tillman 38:53
We are significantly over time. Funny — when we set out to do this “Create Trust-Based Conversations,” I said, “This will be quick. Yep, 20 minutes.”

Bob Woods 39:06
I’ve totally dropped that phrase from my vocabulary for these shows. It’s always wrong. It just goes as long as it goes.

Before we wrap up: reminder of the free ebook at socialsaleslink.com/trust — very easy link this week. QR code is on the screen. If you’re listening on the podcast, again it’s socialsaleslink.com/trust.

Thanks for joining us on this episode of Making Sales Social Live. We do these every week, so join us. If you’re listening on the podcast, please subscribe. You’ll get all our previous shows and alerts for new ones.

Besides the LinkedIn Lives, we also interview leaders and experts in sales, marketing, business — lots of valuable perspectives. And we might get a little vulnerable occasionally too.

For more info: socialsaleslink.com/podcast.

When you’re out and about this week — and every week — be sure you’re making your sales…

Brynne Tillman 40:31
…social. Almost missed it.

Bob Woods 40:36
That was close. Thanks, everybody. Have a great week. Bye.

Outro:

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