2. Choosing the Right Broker – What to Ask Before You Sign

A story about trust, instinct, and letting someone else take the wheel.

James stared at the business card on his desk.

He’d collected five over the past two months - brokers, advisers, accountants’ cousins, a guy someone from Rotary vouched for. All of them said the right things. They knew the market. They had "buyers lined up." They’d “make the process easy.”

But only one of them, Sarah, asked the kind of questions that made him think.

In their first meeting, instead of launching into a sales pitch, she asked, “What matters most to you in this sale - freedom, price, your staff, or something else?” He’d paused, caught off guard. “I’m not sure yet,” he admitted. “That’s okay,” she said. “Let’s figure it out together.”

That sentence stuck.

It wasn’t just what she said, it was how she said it. No ego. No hurry. Just a calm certainty. Like someone who’d done this enough times to know that the hard part wasn’t selling the business. It was letting go of it.

Now, with the decision looming, James knew what was at stake. Choosing the wrong broker wouldn’t just waste time. It could cost him trust, money, and the legacy he’d spent 19 years building.

The Psychological Perspective

At this stage, most owners feel vulnerable, whether they realise it or not.

Inviting someone into the sale of your business is like giving a stranger the keys to your home, your diary, and your bank account. That’s why psychological safety matters. A broker must not only be competent but trustworthy, someone you can be open with when things feel overwhelming or uncertain.

Owners like James often feel a quiet pressure to “be businesslike.” But this process isn’t business as usual. It’s personal. It’s tender. And the wrong broker can make you feel either bulldozed or abandoned.

A good broker earns trust, listens more than they talk, and gives you a sense of steady ground beneath your feet.

HR Best Practice

From a leadership standpoint, the broker is more than a service provider, they’re an extension of your reputation.

The way they present your business to the market will shape buyer perceptions and staff reactions when the time comes. If confidentiality is broken, if the tone is wrong, if buyer conversations are careless - it reflects on you.

HR best practice here is about vetting for alignment. Does the broker understand your values, your people, your team culture? Will they protect your brand, not just your numbers?

Ask yourself: Would I trust this person to represent me to the world?

Sarah had already met two of James’s senior staff, discreetly. She’d asked them thoughtful questions. She hadn’t promised anything she couldn’t deliver. James noticed how relaxed they were around her. That mattered.

Red Flags To Be Mitigated Against

In hindsight, James realised how close he’d come to making the wrong choice. Some of the brokers he’d met had raised quiet red flags -

• They spoke more about themselves than his goals

• They were evasive about fees or performance metrics

• They pushed urgency (“This opportunity won’t last”)

• They were vague about how they’d market the business or screen buyers

None of these were deal-breakers on their own, but together, they signalled a lack of depth, or worse, a transactional mindset.

The biggest red flag? One broker said, “Don’t worry, I’ll handle everything - you just sign the papers.” It sounded great. But James knew better. This wasn’t a hand-off. It was a handover. And that required partnership.

Ideal Owner Mindset

Choosing a broker isn’t about finding someone to fix everything. It’s about selecting a guide who can walk with you through one of the most vulnerable journeys of your professional life.

The ideal owner mindset here is -

• Willing to ask uncomfortable questions (and expect clear answers)

• Ready to partner, not delegate blindly

• Conscious of alignment—not just competence

• Willing to trust instincts alongside due diligence

James didn’t need someone to sell his business. He needed someone to respect it and to respect him while they were at it.

Key Takeaway - A great broker doesn’t just know how to sell businesses - they know how to earn your trust. Choose the one who sees the person, not just the profit.