Where Good Leads Get Stuck: Why They Aren’t Becoming Clients with Brian Ondrako

EPISODE: 67


Talking to someone outside your network can feel like a very different kind of sales conversation. Brian Ondrako helps founders make that shift. After 15 years in software sales, he now works with early stage businesses that need to move beyond their first warm introductions and build a more consistent sales process.

In this conversation, Brian and I talk about what changes when you stop trying to sell and start helping someone buy. We get into the questions that uncover the real problem, the habits that keep a pipeline moving, and why a message with someone’s name in it still might not feel personal. Brian also walks through the numbers founders need to know so “I need more business” can become a plan.

In this episode, we cover:

  • Why sales is a skill you can practice, even if talking to strangers feels uncomfortable

  • How deeper discovery can reveal a different problem than the one a prospect first describes

  • The difference between personalized outreach and a message that shows you understand the person

  • A simple way to start prospecting with a focused list of 25 to 50 people

  • How deal size, close rate, and pipeline coverage help you plan for a revenue goal


LISTEN TO THE EPISODE HERE 👇🏻


MORE OF A READER? 👇🏻

For a while, a founder’s first clients may come through people they already know. A former colleague makes an introduction. A past client sends a referral. Someone who has followed their work reaches out.

Then things slow down.

You still know how to do the work. You may even have years of experience selling it. But starting a conversation with someone who has never heard of you feels different. I know that firsthand. Selling for someone else’s business and selling your own services can bring up very different fears.

Brian Ondrako works with founders at that point. After 15 years in software sales, he helps early stage businesses move beyond their warm networks and build a process for reaching new buyers. His advice starts with a shift in how we approach the conversation: stop trying to sell, and start helping someone buy.

When you’re trying to sell, it’s easy to lead with everything your service can do. When you’re helping someone buy, you need to understand the decision they’re facing. What problem are they trying to solve? Why does it matter now? Who else is involved? What would need to change for them to move forward?

That takes more than a few standard discovery questions. Brian gave an example I see often: a founder says they need more leads. A little more conversation might reveal that they already have enough inquiries. The difficulty is turning those inquiries into clients. More leads would give them more conversations, but it wouldn’t address what happens during those conversations.

You can only uncover that distinction if you stay curious long enough to ask what sits underneath the first answer. It also helps to know your clients’ industry. The more you understand the problems they face and the language they use, the better questions you can ask.

Of course, you need people to have those conversations with. Brian recommends making pipeline generation a regular appointment on your calendar. If you’re starting from scratch, begin with one or two industries you understand and build a small list of potential clients. Twenty-five to 50 names is enough to begin. You can add to it as you learn.

Then choose a way to reach out that makes sense for those buyers. That might be email, LinkedIn, a phone call, or an in-person introduction. Brian made a useful distinction here: an automated message can be personalized with someone’s name and title without being personable. A message becomes more useful when it shows you’ve paid attention to that person’s business and have a relevant reason to start a conversation.

The final piece is knowing what your pipeline needs to produce. If your annual revenue goal is $500,000, your average deal is $5,000, and you close a fraction of your opportunities, “get more leads” isn’t a detailed enough plan. Your average deal size and close rate help you estimate how many opportunities you need. From there, you can look at what’s already in your pipeline and decide where to focus your time.

None of this requires you to be born good at sales. It asks you to practice: learn about the people you serve, start conversations, listen closely, and keep track of what happens next. When you find an approach that works, do more of it.


✦ YOUR SALES AS SERVICE CHALLENGE

Talk to someone new this week. Choose one type of client you can help and make a list of five people or businesses outside your immediate network. Spend a few minutes learning about each one. Then reach out to at least one with a short message that reflects something specific you noticed and opens a conversation.

Put another block on your calendar to keep going. The goal is to start a habit you can repeat and learn from.


RESOURCES & LINKS


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TAM SMITH

I’m Tam Smith-Sales Growth Strategist and Founder of Studio Three 49. I help service-based founders find, connect with, and convert right-fit clients through predictable, sustainable outbound sales solutions.

No pushy pitches. No bro-marketing. Just simple, structured systems that turn connections into clients.


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