Powered by Planning: How SkySail Technologies Found Clarity, Confidence, and Steady Growth with Doug Diamond Coaching: An Interview with Darren and Stacey Gratton

When Darren and Stacey Gratton of SkySail Technologies first crossed paths with business coach Doug Diamond, they weren’t actively searching for a sweeping transformation. They were simply trying to steady the ship. Their small IT services company in British Columbia had grown in fits and starts, fueled mostly by instinct and grit. But as the business expanded, so did the fog around where they were headed and how to get there.

“We weren’t business planning at all,” Stacey recalled. “We’d set goals, but without structure or checkpoints. Everything ran on gut feeling, and we had no way to know whether we’d actually achieved anything.”

That uncertainty carried a cost. Time slipped into tasks that didn’t move the needle. Growth stalled. Hiring felt reactive instead of intentional. And long-term visioning stayed stuck in the realm of “someday.”

The Moment They Needed “Someone Outside the Jar”

The Grattons had been active in their peer group, where business planning was a recurring theme, even if not one they’d fully embraced. But watching Doug present, and later meeting him one-on-one, planted a seed.

“He’s the kind of guy you just love to talk to,” Darren said. “There’s this presence, this knowledge, and this genuine interest in your well-being. Trust wasn’t earned over time. It was almost instant.”

They weren’t looking for a drill sergeant. They were looking for a guide.

“Some people want to be yelled at,” Stacey laughed. “That’s not us. Doug is gentle, even when he’s giving tough love. He says things in a way that brings you back to center, reminds you what’s most important, and calms the panic.”

So, at the end of 2023, Skysail officially joined Doug’s coaching program and entered the world of structured quarterly and annual planning for the first time.

Exercising a New Muscle: The First Months

If business planning had been a low-priority item before, Doug quickly moved it to the front of the line.

“He had us skip Q4 and go straight into our 2024 annual plan,” Darren remembered. “It felt like exercising a new muscle. It wasn’t always fun. But it started creating this subtle shift we didn’t even notice until we looked back.”

For the first time, SkySail built:

• Metrics that actually meant something
• Quarterly and annual priorities
• Clear benchmarks to measure progress
• A habit of thinking ahead, instead of reacting

That clarity changed their day-to-day. The Grattons found themselves spending more time on the business instead of being swallowed by the daily whirlwind.

“It was costing us growth not to plan,” Stacey said. “Now everything is intentional. Our time, our decisions, our hiring, our goals. That’s huge.”

The Wins They Didn’t See Coming

There wasn’t a single lightning-bolt moment; instead, progress accumulated quietly until they looked up and realized how far they’d come.

In 2024, SkySail closed more new logo business than ever before.

They also hit over half of their Emerald goal, a milestone they wouldn’t have believed possible two years earlier.

“It’s starting to change how we think,” Stacey said. “Even when we don’t hit every goal, we’re achieving more because we’re aiming with purpose.”

Doug’s influence wasn’t limited to growth, though. When unexpected turnover hit in recent months, the Grattons handled it with steady hands instead of spirals.

“I don’t think we’d be smiling through it if we hadn’t spent two years learning Doug’s methodology,” Stacey said. “We know why things happened, how to navigate it, and how to rebuild with the right people in the right roles.”

Culture, Communication, and the Team Behind the Metrics

SkySail’s internal communication also began to shift.

Through the Culture Survey and conversations around metrics, their employees gained a clearer window into why certain expectations existed and how leadership made decisions.

“It helped us have deeper conversations,” Stacey said. “‘Why are we tracking this? What does it tell us? How do we know when to hire?’ Before Doug, I don’t think we would’ve known to talk about any of that.”

And in hiring, the impact has been enormous. Instead of rushing replacements after burnout or crisis, SkySail now predicts staffing needs months ahead, giving them time to find the right people.

“That alone feels like a superpower,” Darren said.

Powered by Doug Diamond

It’s no surprise, then, that Darren occasionally wears a homemade T-shirt that reads Powered by Doug Diamond.

“That one was my idea,” Stacey laughed. “We wanted to show how much we value the way he’s helped us.”

Doug didn’t ask for it. In fact, he’d probably prefer not to be the center of attention at all.

“He makes us the hero,” Darren said. “He’s just the guide. But he’s aptly named—he’s a gem.”

What They’d Tell Anyone Considering Coaching

“If someone’s sitting on the fence,” Stacey said, “I’d tell them: Get off the fence. What’s the holdup?”

Her message to other business owners is blunt and heartfelt:

You keep putting business planning at the bottom of your list. And we are proof that you won’t get there on your own. This is an investment that moves you forward faster, with enormous value for the spend. It’s something that should never be last. It should be where everything starts.

Darren didn’t hesitate to add:

Doug helps you get out of your own way. You just have to let him in.

From Fog to Foundation

Today, SkySail Technologies runs with greater clarity and confidence than ever before. They’ve weathered client loss, staff changes, and growing pains — but instead of reacting, they now rely on the structure, tools, and mindset that Doug helped them build.

“We know how to dig out,” Stacey said. “We know how to shift, redirect, and move forward. That’s what business planning gives you. It’s not just about hitting goals when things go well. It’s the foundation you depend on when they don’t.”

For SkySail, Doug’s coaching wasn’t just about planning. It was about building a better way of running their business — one they’re committed to carrying forward.

And they’ll tell anyone who asks: They’re never going back.