Management Isn’t a Soft Skill. It’s THE Skill.

Ashley Waddington didn’t start Ponder This Consulting to land speaking gigs or scale fast. She started it because no one ever taught her how to be a manager—and she wasn’t the only one.

Before launching her business, Ashley spent years moving through the corporate world: customer success, HR, hospitality, advertising, staffing, and sales. She’s seen every flavor of leadership—and every painful consequence of bad management.

“I’ve sat in the seat of the undertrained manager,” she says. “And I’ve also had to report to the ones who made my life miserable. I knew there was a better way.”

But it took a layoff to push her into building it.

Ashley was working for a large staffing agency in a sales and consulting role. She liked the work. But leadership turnover made the job harder and harder. And when she was unexpectedly laid off, she faced a choice: start over somewhere else—or bet on herself.

“If I’m going to rebuild either way,” she thought, “why not build something for myself?”

At first, she did what most people do after leaving a job: she built a version of what she already knew. Recruiting. Staffing. It felt safe. Familiar. But something didn’t sit right.

Two months later, a coach asked her a simple question: “Are you building what you want—or just what you know?”

That’s when everything changed.

Ashley scrapped the original plan and zeroed in on the problem that had followed her from one job to the next: poorly trained middle managers.

It’s a blind spot in most organizations. Senior leaders get the executive coaches and offsite retreats. Individual contributors get onboarding and tactical training. But the people in the middle—managers who oversee most of the day-to-day work—are often left to figure it out themselves.

Ashley knew how damaging that could be. So she built the program she wished she’d had.

Her company, Ponder This, delivers a 120-day management incubator designed specifically for lean-growth teams. It’s not a workshop. It’s not a course. It’s an immersive, customizable experience that combines microlearning, hands-on activities, group coaching, and one-on-one support.

It’s tailored for companies with 10–20 managers—especially those not quite ready to build an in-house training function, but serious enough to invest in developing their people.

“I don’t want to be their forever resource,” Ashley says. “I want to get them on track, give them the tools, and help them build something internal that works for their culture.”

Her philosophy is simple: management isn’t optional. It’s not just about putting out fires or giving annual feedback. Great managers drive productivity, retention, and culture—especially when the rest of the team is running full-speed.

Most of the companies Ashley works with have stretched HR teams. They know training matters. They just don’t have time to build it. Ashley fills the gap.

“You send me the names,” she says. “I’ll handle everything from there.”

It’s working. But getting here wasn’t easy.

Ashley had to learn every piece of the business from scratch: content, operations, outreach, pricing, delivery. There were no shortcuts. No one to call. Just her, doing the work.

“I’ve probably grown ten times in ten months,” she says. “When there’s no accounting team to call, you figure it out. You become more valuable—whether this business lasts forever or not.”

And even though the business is growing, Ashley’s not chasing headcount or clout. She’s chasing results.

She lights up when a manager tells her something finally clicked. When a tense relationship calms down. When a feedback conversation that used to take an hour now takes ten minutes.

“It’s those tiny wins,” she says. “That one line from a manager: ‘This made everything easier.’ That fuels the 14-hour days.”

Ashley didn’t build Ponder This to create a new category. She built it to solve a problem that most companies are too busy to name: bad management costs more than training ever will.

Now she’s helping companies fix it—one manager, one moment, one team at a time.

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