One of the things I enjoyed most about my conversation with Shannon Mattern, founder and CEO of Web Designer Academy, was how willing she was to share the lessons she’d learned about running a business… the hard way.
As Online Business Managers, we spend a lot of time talking about how we support business owners. We talk about creating systems, leading projects, managing teams and bringing order to the day-to-day.
But what struck me most about this conversation was something much bigger.
Shannon wasn’t describing someone who simply “helped” her business. She was describing someone who helped her become a better leader.
If you’re an Online Business Manager (or aspiring to become one), I think this episode offers one of the most valuable reminders you’ll hear this year: the strongest OBM relationships aren’t one-sided. When they’re built on trust, accountability and mutual respect, both people grow.
Click here or on the preview below to watch now:
Prefer to listen? This episode is also available on the OBM Show Podcast here.
What Changed Wasn’t Another Hire. It Was the Right One.
One of the most refreshing parts of Shannon’s story was her honesty about her flaws as a CEO.
She openly admitted that even though she wanted to delegate, she’d often find herself jumping back into projects she’d already handed off. Not because she didn’t trust her team, but because she genuinely believed she was helping. Looking back, she realised she was unintentionally preventing people from fully stepping into ownership.
That’s such an important reminder for OBMs.
Sometimes what looks like micromanagement isn’t a lack of trust at all.
It’s a business owner learning a brand-new leadership skill.
Delegation isn’t always intuitive, especially for entrepreneurs who have built every system, solved every problem and worn every hat inside their business.
As the conversation evolved, Shannon shared something that perfectly captures what operational leadership looks like.
Her right-hand person didn’t simply organise projects or manage deadlines.
She challenged Shannon.
She encouraged her to stop “fixing” everything herself and instead give feedback that empowered her team to grow.
She helped systematise the business so they weren’t making the same decisions over and over again, creating more space for Shannon to focus on leading the company instead of constantly operating inside it.
The Best Partnerships Go Both Ways
My favorite moment? Shannon said one of her goals is to empower her OBM to “be the boss of her.”
Not to hand over her company. It’s because she’s realized the right operational partner brings back the one thing every founder loses in the weeds: perspective. The nerve to ask the hard question. The standing to say “I don’t think that’s the best use of your time” and actually be heard.
A partner like that doesn’t just take things off your plate. They protect your time, hold you accountable, and catch the blind spots you can’t see from the inside. And when you find that person, both of you get better.
The Next Step
If this conversation resonated with you and you’re ready to build the leadership, operational and strategic skills that businesses are looking for, I’d love to invite you to explore the OBM Accelerator.
And if you’re on the other end of things looking to hire just the right OBM, we’ve got you covered.
At OBM School we connect business owners with carefully vetted Accredited OBMs who don’t just manage tasks, they become trusted strategic partners. You can explore our Directory of Accredited OBMs, or let us match you directly with the right person through our Matchmaking service.
It’s time to step back from the day-to-day and get back to leading the business only you can lead.
Connect with Shannon (Web Designer Academy)
