What this guide is (and isn’t)
This guide is meant to help you get started. It provides context, principles, and practical starting points for reaching out to business owners and brokers to find a good business to buy.
It is not a silver bullet formula. There is no one way to approach building a pipeline that guarantees results for all people.
The real progress comes from showing up consistently, learning from real conversations, and evolving your approach over time. Think of this as a framework you can adapt and make your own.
Step 1: Get Clear Enough to Reach Out
Before you send a single email or make a call, you need just enough clarity to explain what you’re exploring.
Not certainty. Not perfection. Direction.
You should be able to articulate, in plain language:
the type of business you’re interested in,
the general size you’re targeting,
your relevant experience or background,
and your timing.
The goal isn’t to sell yourself. It’s to make it easy for someone else to picture who you’re looking for and connect you to people they know. It’s okay if you interested in many different types of businesses to start.
You just need to be able to verbalize that in a way that’s clear, so as you talk with business owners and brokers, they can potentially help connect you to the opportunities that might align.
In reality, your clarity will evolve as you talk to real owners and look at deals. That’s expected. You just need a starting point for your outreach.
Step 2: Create Your Outreach Strategy (Warm to Cold)
Outreach works best when you move from warm to cold, not the other way around.
Start with the warmest options
Your existing network
Business owners you already know
Friends, former coworkers, or acquaintances who own businesses
Professionals who regularly work with business owners:
accountants and CPAs
attorneys
bankers and SBA lenders
financial advisors
commercial real estate brokers
These people are or know business owners, and they hear things early. They know who’s tired, who’s thinking about slowing down, and who just had something change in their life.
Even when they don’t know someone ready to sell, they can often make introductions or offer perspective. Keep in mind that “business owners know other business owners.” You will increase your chances of success by adding more business owners to your network that are familiar with what you’re looking for.
Businesses you already know and frequent
If there’s a business you already spend money with, respect, and believe in, that’s a strong starting point.
You already have a reason to reach out, and response rates tend to be higher when you’re communicating that you are a customer.
Warm-adjacent options
In-person owner communities
trade associations
industry groups
chambers of commerce
local business meetups
The goal here is to look for local groups and events you can attend that will give you the ability to meet business owners and the kind of people who know a lot of business owners.
These settings aren’t about pitching. They’re about proximity. Meeting owners as people can help you naturally build trust and expand your network over time.
Semi-warm options
Local brokers
Find out who the local business brokers are in your area and take the time to go meet with them. Be clear about what you’re looking for. Ask:
what they have now,
what’s coming soon,
what perspective they can share with you about what’s going on in your local market.
Good brokers have pipelines, not just listings. If they trust you and see you as prepared, they’ll often share opportunities before they hit the market.
Colder options
You can generate a lot of businesses for a list just by heading to the internet or getting in your car. Look at:
public business directories
Google searches by industry and geography
Google Maps searches in neighborhoods you like
Driving around areas you like to identify potential businesses
These options are cold because you don’t know these people. That doesn’t mean it’s a bad strategy. It’s just likely to have much lower response rates, so volume matters much more.
One tip to make these leads less cold is to visit these businesses as a customer. It will give you a more interesting lead in to your reach out message, and you may be able to meet the owner in person if you’re willing to ask.
Step 3: Commit to a consistent weekly time for outreach
Don’t fixate on how many names are on your list. It’s better to anchor on your time investment than list size, at least when you start.
Decide how many hours per week you can consistently commit to outreach. Even two hours per week is enough if it’s consistent.
Start with the warmest options and gradually layer in colder ones. This isn’t just because you’re more likely to make a connection with a warmer lead. It’s also because it will help build your confidence to make more reach-outs.
This is business development. The real objective is to expand your network surface area so opportunities, conversations, and referrals can find their way to you over time.
Tip: Use Your Time to Take Action
Research has a place, but it’s easy to hide in it.
If all you’re doing is adding names to a spreadsheet, you’re likely procrastinating.
Every week should include real reach-outs:
sending emails,
sending DMs,
making calls,
or showing up to events with the intention of meeting people and exchanging contact information.
Momentum matters more than polish early on. Set a weekly outreach target that’s small enough you know you can hit it every week. Consistency compounds, and once you start getting responses, motivation tends to follow. That’s when volume increases naturally.
Step 4: Prepare for the Conversation
Start with the Type of Meeting
Before you think about what questions to ask, the first step is to decide what kind of conversation you’re having. Not every meeting has the same purpose, and how you show up should reflect that.
Most conversations fall into one of two categories:
Advice conversations
This should be your default unless the stage has already been set (by your outreach or the person who referred you) that you are a buyer interested in potentially acquiring their business. In this approach, you are going to focus on gathering their perspective and potentially getting them to refer you to one or more people that could help your search. It’s possible they may tell you they are open to selling, but you aren’t going to aggressively go after that response.Exploration conversations
These are meetings that have already been framed around potential acquisition interest. This is common in cold outreaches, where the business owner has responded to your communication about potentially acquiring their business, or in broker-led introductions.
Getting this distinction right matters, because it will shape the structure of the conversation.
Advice Conversations: A Clear, Respectful Format
Advice conversations are about learning and network building, not evaluation. You’re not there to determine whether this person wants to sell their business or to deep-dive into their company. You’re there because you believe they can help you think more clearly about your search.
A simple structure keeps the conversation focused and respectful.
Start with your intro
Begin by briefly explaining who you are and what you’re looking for. This should take no more than two minutes.
Cover:
the type of businesses you’re exploring,
the general size you’re interested in,
your relevant experience,
and your timing.
This isn’t a pitch. It’s context.
Thank them and explain why you wanted to meet
Acknowledge their time and make it clear why you value their perspective.
For example: “Thanks again for taking the time to meet. I‘m excited to talk with you because I think you have perspective that could be really helpful as I think through my search.”
Set a light agenda
Let them know what to expect and signal that you’re being mindful of their time.
Something like: “I’ve prepared a few questions I’d love to ask, and I want to be respectful of your time since I know you’re busy.”
This lowers pressure and makes the conversation feel contained.
Ask your prepared questions
Most of the conversation should live here.
For business owners, your questions should focus on:
The realities of managing and operating this type of business,
Where they see opportunity,
The challenges and risks they see,
and their reflections on what may help you find a business to buy.
Examples of good advice-stage questions:
What does day-to-day ownership really look like once the business is running smoothly?
What parts of the business require the most attention from the owner?
Where do you see the most upside in a business like this if someone were taking it over today?
If you were starting over, what’s one thing you’d focus on earlier to grow or improve the business?
What do you think separates the best operators in this industry from the rest?
What are the hardest parts of running a business like this that aren’t obvious from the outside?
Where do you see new owners struggle most when they come into this kind of business?
What risks do you think buyers tend to underestimate in this industry?
If you were in my position, what would you pay the most attention to when evaluating businesses like this?
What would you want to understand about a business like this before getting too far down the path?
Are there any red flags you think buyers should watch for early?
Based on what you’ve seen, what kinds of owners tend to do well in this business?
Is there a background or skill set that you think gives someone a real advantage here?
Be curious. Be complimentary. Be human.
Avoid asking them if they want to sell or probing for financial details. You’re looking to add this person to your network, be able to tap into them in the future, and to have them know you are an active buyer, in case they get to a stage in their life where they may be ready to sell.
The goal at this stage is connection and perspective.
Close with reflection and an ask
As you wrap up, do three things.
First, reflect back a couple of things they shared that you found particularly helpful. This shows you were listening and value their input.
Second, make the referral ask: “Based on what you know about my situation, is there anyone you know who you think would be worth me talking to?”
Then pause. Let the silence linger. Give them space to think. If they mention someone, you can follow up by asking if they’d be willing to make a mutual email introduction.
Third, ask for permission to stay in touch: “You’ve been really helpful. Would you be open to me reaching out again if I have another question down the road?”
This keeps the relationship open and makes future follow-up natural.
Adjusting Your Questions Based on Who You’re Talking To
The core principle stays the same in every conversation: you’re there to learn, build credibility, and expand your network. What changes is who you’re learning from and what they’re best positioned to see.
Questions for Brokers
When talking with brokers, your goal isn’t to pitch yourself or push for listings. It’s to understand:
how they think about good businesses,
what they’re seeing in the market,
and how to position yourself as a serious, prepared buyer.
Good questions to ask brokers include:
What kinds of businesses tend to sell quickly in this market?
Where do you see buyers get tripped up most often?
What usually causes a deal to fall apart late in the process?
What do strong buyers do differently than everyone else?
Are there owners you’ve spoken with who aren’t quite ready to sell but might be in the next year or two?
These questions help you learn and quietly signal that you’re thoughtful, realistic, and not a tire kicker.
Questions for Accountants, CPAs, Attorneys, and Other Professional Advisors
For people who work closely with business owners, your goal is perspective and pattern recognition, not deal sourcing.
They often have insight into:
which businesses are healthy,
which owners are tired,
and what tends to trigger transitions.
Helpful questions include:
In your experience, what tends to cause business owners to start thinking about selling?
Are there certain types of businesses you see owners struggle with more than others?
What do you think separates owners who build strong, transferable businesses from those who don’t?
When owners do decide to sell, what usually surprises them most about the process?
Based on what I’ve shared about what I’m looking for, is there anyone you know who might be worth me talking to?
These conversations often don’t produce immediate leads, but they expand your understanding of the landscape and your access to people who matter.
Questions for Connectors and Network Introductions
When you’re meeting someone primarily because they’re well-connected, keep the focus on learning and referrals.
Useful questions include:
Who do you see doing really well in this space right now?
Are there owners you’ve seen start to think about stepping back or slowing down?
What kinds of owners tend to be happiest with their exit?
Based on what you know about my situation, is there anyone you think I should talk to next?
This keeps the conversation helpful, respectful, and forward-moving.
One Important Reminder
You don’t need to ask all of these questions in every conversation.
Pick a handful that feel natural, stay curious, and let the conversation unfold. The goal isn’t to run a checklist. It’s to leave the other person feeling heard, respected, and open to continuing the relationship.
That’s what builds pipeline.
Exploration Conversations: Clear Intent, Same Human Approach
Exploration conversations are about relationship-building and credibility-building.
These meetings are already framed around potential acquisition interest. The owner knows you may be interested in buying their business. Your goal is not to evaluate the business in this meeting. Your goal is to build trust.
You want them to leave the conversation liking you, seeing you as someone who could responsibly step into ownership, and feeling comfortable continuing the conversation. Ideally, that trust leads to a willingness to share more information after the meeting so you can thoughtfully assess whether an offer makes sense.
Start by acknowledging the context
Be clear and direct: “I’m actively exploring the acquisition of a business like yours and wanted to see if there might be enough of a potential fit to keep talking.”
Then explain why this type of business is interesting to you, and why their business in particular caught your attention. Do your homework. Find a few specific things you genuinely respect or admire.
That might be:
how the business is positioned,
how it shows up online,
the reputation it has,
or values the owner has made visible.
What matters most is that you acknowledge and respect the business they’ve likely spent years building. Keep it honest and authentic. Share observations you actually believe, not generic compliments.
Set expectations for the conversation
Let them know how you’re thinking about the meeting and signal that you’re being respectful of their time.
For example: “I’m not asking you to share any confidential information today, so please let me know if there are any questions you’re not comfortable answering. My goal is to learn more about you and the business, and see whether there’s a mutual reason to keep the conversation going.”
This helps slow the conversation down and lowers pressure.
Ask exploration-stage questions
Your questions should help you understand:
the realities of owning and operating this business,
where the owner sees opportunity and risk,
and what would need to be true for a sale to make sense.
Examples of strong exploration-stage questions include:
What does ownership of this business really look like day to day?
What do you think is the most important skill or ability for someone to be successful operating this business?
What’s the hardest part of this business to learn?
Where do you see the biggest opportunities for growth or improvement?
What parts of the business require the most involvement from you as the owner?
What do you see as the biggest challenges or risks in the business today?
Whenever you decide you’re ready to move on from the business, what do you want to see happen with the business and the employees going forward?
What would need to be true for you to seriously consider selling the business?
These questions invite openness without pushing into valuation or financial details too early.
Avoid asking for a price or any detailed financial information at this stage unless the owner brings it up.
Close with reflection and next steps
As you wrap up, reflect back a few things you learned that stood out to you. This shows respect and reinforces that you were listening.
For example:
“One thing that really stood out to me was how much of the business revolves around managing people well. That’s helpful context I hadn’t fully appreciated.”
“I appreciated hearing how you think about customer relationships. It helped me better understand why this business has the reputation it does.”
“What you shared about the seasonality of the business was really helpful. It gave me a clearer picture of what ownership actually looks like.”
“I found your perspective on growth interesting, especially how you’ve chosen to prioritize stability over expansion.”
The goal isn’t to summarize everything they said. It’s to highlight one or two insights that were meaningful to you and reflect them back in your own words.
That moment of reflection:
shows you were present,
validates their experience,
and helps the conversation end on a thoughtful, respectful note.
If you’re no longer interested in the business after this conversation, politely thank the business owner for their time. If they stop you to ask if you’re interested in acquiring the business, you can always share what about the business you learned that wouldn’t make it a good fit for you. Just be sure to also explain one or two things about the business that are intriguing and would likely draw the interest of a different buyer if and when the owner is ready to sell.
If you’re interested in continuing the conversation beyond the initial meeting, let the owner know.
You might say that you find the business intriguing and would be open to exploring it further, if they are. Then create space for them to share where they are, rather than guessing or pushing.
A simple way to do that is to ask something like:
“Can you help me understand where you’re at right now?”
From there, owners usually fall into one of three places.
Some aren’t interested in selling right now.
If that’s the case, keep things light and permission-based:
“Would it be okay if I checked back in with you in a few months to see how things are going?”
“If I have another question as I continue learning, would you be open to me reaching out again?”
This keeps the door open without pressure and respects their timing.
Others are curious about what you might be willing to offer.
If they express interest in that direction, you can offer to sign a non-disclosure agreement to help them feel comfortable sharing financial information. That allows you to take the conversation to the next level thoughtfully and professionally.
Some owners need time to think.
If that’s where they land, acknowledge it and suggest a follow-up: “It sounds like this isn’t something you’ve fully thought through yet. Would it make sense to reconnect after you’ve had some time to sit with it?”
Offering a specific follow-up creates clarity without forcing a decision.
The key in all cases is to let the owner set the pace. Your job is to signal interest, create optional next steps, and make it easy for the conversation to continue when the timing is right.
And even if they’re clear that selling isn’t likely anytime soon, the conversation doesn’t have to end there.
You can still ask the referral question: “Based on our conversation, is there anyone you know who you think would be valuable for me to talk to as I continue my search?”
Then pause and give them time to think.
This shifts the focus from their business to their network, keeps the conversation helpful rather than awkward, and often leads to introductions that wouldn’t surface otherwise.
It also reinforces that you value their perspective, not just the possibility of a deal.
Step 5: Follow Up Thoughtfully
For every conversation, plan to follow up in some way.
At a minimum, that might be a simple thank-you note. In many cases, it can be a small, thoughtful gift based on something you learned about them during the conversation.
The goal isn’t the gift itself. It’s the signal. Thoughtful follow-up shows that you were paying attention and that you value their time.
One idea a broker shared at a conference I attended was a coffee shop gift card, something in the $50 to $100 range. The reason it works is simple. It’s a gift they’ll have to use several times before it’s spent. He suggested getting one branded with your contact information, but it could also be as simple as writing thank you, your name, and phone number in Sharpie on top of the card. The idea is that you stay top of mind each time they pull it out. It’s subtle, but effective.
The specific gesture matters less than the intent. What counts is that it’s personal and genuine.
Just as important, follow through on anything you committed to during the conversation. If you said you’d send an NDA, send it. If you said you’d follow up in a few months, put it on your calendar and do it.
One of the fastest ways to build trust is to do exactly what you say you’re going to do. Over time, that consistency is what turns conversations into relationships, and relationships into real opportunities.
Closing: Build Relationships Before You Need Them
Many great businesses don’t sell because the owner is burned out or unhappy. They sell because something changes: a health issue, a family situation, or a new opportunity.
When that moment arrives, the buyer who already has a relationship is often the first call.
That’s what pipeline thinking really means.
This process isn’t about forcing outcomes or trying to shortcut your way to a deal. It’s about positioning yourself early, learning through real conversations, and steadily building a network that compounds over time.
Along the way, you’re developing the same skills that matter once you become an owner. Setting a clear direction. Showing up consistently. Paying attention to feedback. Adjusting your approach based on what the real world tells you.
There’s no perfect script for this. The most effective approach is the one you make your own.
Use this guide as a starting point. Adapt it to fit your style. Lean into what works. Adjust what doesn’t, and most importantly, keep showing up.
That’s how trust is built, and trust is what creates opportunity.