What If Selling Could Feel Like Helping? (Because It Can)
Why the “win-win” approach to sales works better (and feels better) for small business owners
Let’s be honest, most of us didn’t start our business because we love “selling.”
We started because we wanted to do good work. Help people. Make a difference. Maybe solve a problem we’re passionate about. And somewhere along the way, we realised that running a business does involve selling; whether that’s promoting your service, having discovery calls or following up with enquiries.
And that can feel… uncomfortable.
For many small business owners I speak to, selling brings up a weird mix of resistance, pressure and awkwardness.
You don’t want to come across pushy. You definitely don’t want to be salesy. But you do want clients. The right ones, of course.
So how do you find a middle ground?
That’s where win-win selling comes in. A different way of approaching sales that focuses on connection, collaboration and real value.
It’s Not About Convincing
In traditional sales models, it’s all about closing the deal — fast. There’s often a power imbalance, where one person is trying to “win” the sale by overcoming objections and using tactics.
But that’s not how I work. And if you’re still reading, I’m guessing that’s not how you work either.
In a win-win model, the aim isn’t to convince someone.
It’s to understand where they’re at, figure out if you can genuinely help and have an honest conversation that benefits both of you.
If it’s a good fit — great.
If it’s not — that’s okay too.
Here’s What a Win-Win Conversation Looks Like:
You ask more than you pitch
You listen to understand, not just to reply
You’re transparent about what you offer, and who it’s for
You’re okay with someone saying no
You’re excited when it’s a “yes” for the right reasons
Why It Works (and Feels Better)
When you show up with a win-win mindset, everything softens. The energy shifts. You’re not trying to push something. You’re simply offering support in a way that honours both your time and theirs.
Clients can feel the difference.
That trust? It builds stronger relationships, better referrals and longer-term partnerships.
The Power of Real Conversations
One of the things I love most about what I do is connecting with small business owners and hearing their stories — what lights them up, what they’re struggling with, what keeps them going.
Sometimes I offer ideas or suggestions to help them think outside the box. Sometimes it’s just about seeing a way through, together.
That kind of connection is incredibly motivating — and it’s where the magic happens.
Learning flows both ways.
The energy of someone passionate about what they do? It’s contagious.
Final Thoughts
Selling doesn’t have to be scary, awkward or sleazy.
When it’s done with heart, honesty and curiosity, it becomes something so much better:
A win for them.
A win for you.
And a business that grows through genuine connection.
Need help making those win-win conversations easier in your business with better systems, clearer messaging or support behind the scenes?
Let’s set up a time to have a chat 📧 assist@tailoredvirtualsupport.co.nz
#SmallBusinessSupport #HelpingNotSelling #WinWinSelling #TailoredSupport #RelationshipFirst
