Episode 436: Bridging the Gap Between Challenges and Desired Results: A Salesperson’s Guide to Success

Intro:
0:00:18 – (Bob Woods): Welcome to the Making Sales Social podcast featuring the top voices in sales, marketing, and business. Join Brynne Tillman, me, and Bob Woods as we each bring you the best tips and strategies our guests teach their clients so you can leverage them for your own virtual and social selling. This episode of the Making Sales Social podcast is brought to you by Social Sales Link, the company that helps you start more trust-based conversations without being salesy through the power of LinkedIn and AI. Start your journey for free by joining our resource library.  Enjoy the show!

Bob Woods 01:12
Great. So, let’s get into today’s subject. Understanding your clients’ needs and aligning your solutions with their desired results is the key to success. It’s not just your success as a salesperson, but also your company’s success as a solutions provider—and of course, your clients’ success.

The goal is to position both yourself and your solution at the intersection of your clients’ challenges and their desired results. This is how you, as a sales professional, become truly essential to your clients’ success.

Brynne Tillman 01:57
Thanks, Bob. That’s awesome. This is a different topic than we usually discuss. Most of the time, we focus on the top of the funnel—how to start initial conversations. But today, we’re talking about what happens after you’ve earned that conversation.

As Bob mentioned, when your solution sits at the intersection of their challenges and desired results, it means you’ve already earned the right to show how you can help. This is further down the funnel.

I want to add a quick framework we used years ago and recently dusted off: CHIRP, Challenge, History, Impact, Risk, and Priority.

• Challenge: What problem are they facing?

• History: What have they tried before? What worked or failed?

• Impact: How is this affecting their business today?

• Risk: What happens if they don’t make a change?

• Priority: Even if the challenge is real, how important is it compared to everything else?

If their priority is low, they may never move forward. So CHIRP is a great foundation to help us align with clients.

Bob Woods 05:03
Absolutely. Before we dive in, we’re giving away our Salesperson’s Guide to Success ebook. It’s free at socialsaleslink.com/success. If you’re watching live, you’ll see the link and QR code on your screen. If you’re listening to the podcast, check the show notes.

The ebook breaks down frameworks and shows how LinkedIn and AI can help deliver tailored solutions. With that said, we’ve got four main points on our agenda. The first is social listening. Lightning round—who wants to take it?

Stan Robinson Jr. 06:08
I’ll start. Social listening is about tuning in to what your audience is talking about online. LinkedIn, and especially Sales Navigator, makes this easy. With features like Account IQ and Lead IQ, you can quickly learn about a company’s revenue drivers, competitors, and challenges.

Social listening gives you insights into your audience’s priorities and what’s top of mind for them.

Brynne Tillman 07:30
Exactly. Social listening goes hand in hand with research. Once you gather insights, the next step is making them actionable.

This is where AI comes in. For example, take data from Sales Navigator, Lead IQ, or even a PDF of someone’s LinkedIn profile. Upload it to your favorite AI tool along with their website. Then, ask AI to highlight likely challenges, industry trends, and competitors.

You can even feed AI your typical discovery questions and ask it to tailor them to that specific company. That way, when you go into a call, you’re well-prepared to bridge their challenges with potential outcomes—rather than leaning back with a notepad and asking, “So, what keeps you up at night?”

Bob Woods 10:59
Perfect setup. That leads to point two: focusing on their desired results.

Your solution should be tied directly to their goals. That means being outcome-oriented in every conversation, not just talking about features and benefits.

LinkedIn can help here, too. Share case studies, testimonials, and success stories that let prospects envision the results they could achieve by working with you. This builds credibility and helps them connect your solution to their desired outcomes.

Stan Robinson Jr. 12:41
Exactly. Buyers don’t care about features; they care about outcomes. If you’re unsure what outcomes they might value, you can use AI tools like ChatGPT, Gemini, or others with deep research features. Give them a company’s website and details, and they’ll analyze dozens of sources to surface likely results the company would prioritize.

Brynne Tillman 13:47
Great points. I want to add the idea of the reverse timeline. Ask the client:

“In a year, if we were celebrating a big win, what would that look like?”

This helps them visualize outcomes and connect emotionally to what success feels like. Once they’re invested in that vision, you work backward: “If we want to reach that point in 12 months, what needs to happen at six months? At three months? Next week?”

This creates a clear path that ties their challenges to the solution, and it becomes much harder for them to say no once they’ve defined success themselves.

Bob Woods 16:41
Exactly. Let’s move to point three: your solution as the bridge with the power of personalization.

One-size-fits-all doesn’t work anymore. Your solution must be positioned as a tailored bridge between their challenges and outcomes.

Brynne Tillman 18:26
Personalization starts with the reverse timeline but goes deeper. Every stakeholder has different goals—the CFO, the CEO, the head of sales, and the board. Each needs to see something specific in the solution.

Personalization also means aligning with their existing processes. For example, I once worked with a client using another training firm focused on cold calling. Instead of competing, I integrated our LinkedIn strategy into their process so it became “lukewarm calling.” That alignment made the solution far more effective.

Stan Robinson Jr. 20:39
Yes—and personalization should also connect emotionally. People may claim to make decisions based on logic, but emotions drive decisions, and logic justifies them.

Some people are motivated by career advancement, others by competition, and others by stability. If you understand those motivators, you can personalize your approach in a way that truly resonates.

Bob Woods 22:02
Exactly. If you talk to marketing the same way you talk to IT, you’ll push people away. Tailor your message. That leads us to the final point: alignment.

Brynne Tillman 22:46
Alignment means integrating with the client’s current processes, tools, and resources. Identify bottlenecks early and make sure your solution complements what they’re already doing.

My friend John Stopper teaches a model where sellers align peer-to-peer—CFO to CFO, IT to IT, CEO to CEO. This builds trust and ensures everyone speaks the same language, which strengthens alignment across the board.

Bob Woods 25:13
Exactly. Alignment brings everything together. Sales isn’t just about pushing a product—it’s about aligning your expertise, insights, and solutions with the client’s goals. That’s how you create long-term trust and sustained success.

Before we wrap, one last reminder: download the free ebook at socialsaleslink.com/success. It’s a great companion to this episode.

Brynne Tillman 26:33
Solve problem, not product sell.

Bob Woods 26:38
Love that! Thanks for joining us for this episode of Making Sales Social Live. We do these weekly, so join us again.

If you’re listening to the podcast, hit subscribe or follow, drop us a like, and leave a comment. We also interview leaders in sales, marketing, and business, so check out those episodes too at socialsaleslink.com/podcast.

Until next time, make your sales social!

Outro

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