Delegating Tasks Versus Delegating Problems with Scott Drake

In today’s Live with Bottleneck, Leadership coach Scott Drake explains the difference between delegating tasks versus delegating problems. He also expresses why learning the difference between the two matters.

Scott Drake is a sought-after consultant and trainer who made every mistake when rising through the leadership ranks. After seeing emerging leaders on his teams repeating the same mistakes, he set out to find a simpler and faster way to grow leaders. When he couldn’t find a shortcut, he invented one.

So if you want to become an effective leader in your company, stay tuned to this episode.

Who is Scott Drake?

The conversation starts off with an introduction of Scott Drake. Scott’s background has always been in tech, and he started out his career as a computer programmer. But he has always aspired to do more and move into the leadership ranks.

“I have always liked the idea of being in control and being able to make decisions and some of those things that you think of leadership is about. Until you get into leadership (roles) and you realize it’s not.” – Scott Drake

He started his own development shop as a small business owner, but eventually went back to the corporate world. It was only in 2021 that he left Corporate America again to start his own venture once more.

The Struggles of Leadership

Scott Drake shares his struggles on starting his own venture again, mostly with his leadership and his delegation skills. It has hard to understand at first how he could work through others to get things done, as he was used to getting it all done on his own.

This caused a certain disengagement with the team, and burnout on Scott’s side.

So he started researching ways to improve his leadership and delegation skills. In the course of his research, he found that he was not alone in his plight.

“I started seeing leaders burning themselves out and being unable to delegate, being unable to work through other to get things done. I thought, “there’s got to be a better way to do this.” – Scott Drake

Delegating Tasks Versus Delegating Problems

That said, Scott Drake defines the difference between delegating tasks versus delegating problems to your team.

With delegating tasks, these are often routine work that is done on a schedule. The purpose of delegating tasks is efficiency, so you as a business leader can focus on other important and high-level stuff for the company.

The difference with delegating problems is that it is not a routine work. It is often irregular, something that needs time, patience, and creativity to solve. When you delegate problems to be solved by another individual, you should expect that there will be a learning curve to it, and It might not be done in one go.

The issue with most leaders is that they cannot differentiate within the two. So when people delegate problems to their team, they expect it to be done efficiency, and as soon as possible. That is where the disconnect lies, and it is one of the things that Scott coach leaders about.

“Where we really struggle in (problem) delegation is when we have to give somebody a problem and we don’t accept that we’ve got to build in learning loops and do these other things around it. We often lose patience and struggle to get value out of working with other people. So it’s really understanding that there are two types of things that we delegate: routine work versus creative work.”  – Scott Drake

To hear more from Scott Drake and learn about how you can properly delegate your work, continue listening to this episode.


Scott Drake’s journey into leadership was long, painful, and he made every mistake in the book. It took him 10 years to thrive as a leader and not feel like an imposter.

When he became a leader of leaders, he saw next-generation leaders making the same mistakes and having the same struggles. Selfishly, he couldn’t spend 10 years watching new leaders wreck his teams while they figured out how to lead, so he began searching for a faster way to teach leadership. That search turned into a five-year research project and the innovations that are now JumpCoach.

In 2021, Scott left an executive role in medical education and founded JumpCoach to make best-in-class leadership training available to everyone who needs it.

Connect with Scott!

Website | Email | LinkedIn

Want more Live with Bottleneck? Visit our website or go to our YouTube channel for more Live with Bottleneck episodes!

Jaime Jay

About Jaime Jay

Meet Jaime Jay – a man who wears many hats, and wears them all admirably. He's a master connector, an entrepreneur extraordinaire, and a published author who knows how to get things done.

Before he found his way to the business world, Jaime served his country as a brave paratrooper in the U.S. Army. But that's just the beginning of his many accomplishments.

He's the founder of the renowned Bottleneck Distant Assistant Services firm, and his book "Quit Repeating Yourself" has become a must-read for entrepreneurs everywhere.

When he's not busy building his empire, you can find him on his beloved Harley Davidson, cruising through the countryside and taking in the invigorating effects of Uitwaaien – a Dutch practice that involves facing the wind to boost health and relieve stress.

He enjoys spending his free time outside building stuff with his wife, Nikita the dog and their two kittens (for now at least) Tommy and Tater.

He is ‘over-the-moon’ happily married to his wonderful wife Sara, his amazing daughter, Jessica, who is serving our country as a United States Army soldier. Jaime and Sara are the proud grand parents of two beautiful little girls.


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