Digital Byte 79: Are Your People Staying for the Right Reasons?

May 5th, 2026

I have a close childhood friend who went straight into sales after she graduated from college. She was the one landing the calls, building the pipeline, getting people in the door. But the way her company was structured, her pay was tied to closing, and she wasn't the one on those calls. Someone else was. The system was broken, and she knew it, so she brought it up. They acknowledged the problem and kept promising her a raise.

When the day finally came, the offer was half of what they had discussed. She was their best salesperson, the only one meeting quota, and yet they undercut a promise.

Livid, she decided to stay a little longer anyway. There was a conference coming up, and if she hit her numbers, she'd walk away with a bonus. It felt like the smart move to wait it out, even though it was a few months away.

I asked her what she would do if the bonus wasn't met. Would she stay until the next bonus period came along?

She said yes. She'd stay.

That's the whole problem right there. The bonus was never really the reason. It was just the most recent excuse to delay a decision she already knew she needed to make. The company hadn't fixed the broken system. They hadn't honored what they promised. Nothing had changed, but she was still finding reasons to wait. That's not patience. That's a trap, and a lot of us have been in it.

So I asked her: if you'd stay anyway, what are you actually waiting for?

She didn't have a good answer. She gave her notice days later.

She's now working retail at a boutique store in Soho. While she took an initial pay cut, it's a role she can grow within, where her work is actually seen. She's never been happier.

This is what I see happen constantly among my friends in sales. Companies don't have to fix anything if their people keep showing up anyway. They dangle the next milestone, imply the next opportunity, and let time do the work of keeping people stuck. And talented people stay, not because things are good, but because leaving requires uncertainty and waiting doesn't. So they wait. And the company has no reason to change because the talent hasn't gone anywhere, but their business isn't growing like it could.

For the business owners reading this:

If your people are staying because they're waiting on something rather than because they genuinely want to be there, that should concern you. Not just because they'll eventually leave, but because of the work they're producing in the meantime. People who are waiting to leave are not building your business. They're running out the clock.

The fix isn't a better bonus structure. It's creating an environment where people don't need an exit interview to finally tell you the truth. Where the systems make sense. Where growth is real and not just implied. Where you're honest enough to ask whether your structure is working for your team.

Nurture your talent, and they will show up for you differently. They will sell harder, stay longer, and bring others like them through the door. This is not a culture talking point. This shows up on your balance sheet.

Talented people don't need perfect. They need honesty and room to grow. Give them that, and they won't need a reason to leave.

Stay Inspired,

Sydney