3 Things Creatives Taught Me About Coaching Smart People

by Sep 23, 2020Protip, Resoundcast

3 Things Creatives Taught Me About Coaching Smart People

by | Sep 23, 2020

We all want projects to run smoothly. But it’s hard to find good help these days, right? And yet, we will become more effective and useful if we learn how to manage these kinds of projects efficiently by helping people to help themselves.

Creatives. Innovators. Problem solvers. They’re not fundamentally different from accountants, doctors, or factory workers, all of whom may tend toward a linear process. Creatives simply spend more time in what researchers (and John Cleese) call the “open mode;” that mode where ideas and new solutions come.

To understand how to coach — and delegate to — creative, smart people, it doesn’t hurt to have a process. But to build that process, let’s build a foundation of understanding.

Principles for Creative/Innovative Work

Let’s take a look at how people work.

Task and Purpose

The military does a great job of defining task and purpose. They don’t just tell you what to do, also why you’re doing it. “Do this so that he is able to do that.”

We do the same thing in development work when we talk about user stories. “The user wants to fill in the email signup so that she can get the monthly email.” Defining this helps people to understand the scope. Because if I tell them why, they can understand the value of the task. He or she can then choose for themselves when to give up because it’s not worth it, and how to get the best result given the reason for the task. Read: they can make decisions without you

An Organized Mind Leads to Improved Focus and Time

Focused work doesn’t take as long. You get in, you get immersed, you finish and you deliver. And it’s satisfying. But how do you get there as a project worker? And as a leader, how do you help them?

You have to solve a few problems for them, and then they can solve everything else. Your project workers have problems:

  • They’re overwhelmed by the world. They probably filled their brain with emails, social media, and the news before they started work.
  • They’re overwhelmed by competing priorities. If the workplace asks too much of people — too many small tasks — for creative workers, they lose focus.
  • They get interrupted. It’s hard to work with interruptions, like people talking to you about other things when you’re trying to focus. This is especially true for strategists, writers, or developers — people whose work benefits from bringing a system of thinking into their short-term memory to play with.
  • They try to hold too much in their brains. They have a bad working process and think that fewer steps mean faster work. But skipping steps can make work take longer and lack depth.

Problem: Short-Term Memory is Limited

With short-term memory(STM) in short supply, it’s folly to build work practices that depend on it being abundantly available. The solution? Save all that short-term memory for the task they’re working on, allowing them to absorb the work and really get into it.

Why is it important to allow them to immerse themselves in their work? Because if you can protect their fragile STM, you will preserve their focus and prevent the disruptions that will cost them time, attention and frustration…and will cost you missed deadlines.

Problem: Task Switching Costs You

When you interrupt them, they have to break away from their thought and attend to you. Sometimes that thought took 15 minutes or more to develop. It could have been a Eureka moment, or it could have been building toward that.

This is the task-switching penalty you may have heard about. If you’re task switching (multitasking is actually not a thing; we’re just task-switching):

  • You complete fewer tasks.
  • You make more errors.
  • All this compounds for cognitively complex tasks.

This saps motivation, too, because it’s always motivating when your brain is immersed in a problem that you can solve.

Solution: Get them Organized

Most times, people need you to help them organize their thoughts. You can’t do anything about the news they saw on TV they (irresponsibly) watched before work or the social media post they saw that has become a distraction. But you can talk them through their tasks, giving them a shot in the arm.

Like a Counselor for Project Work

If you had a process for working people through a problem, you could use coaching to create the happiest, most on-time team. But let’s look at some objections first.


“Don’t I have to know how to do their job before I can coach them?”

Short answer: No. And this is the greatest thing about this approach: you only have to know the strategy and their place in the strategy to be able to help them. It helps if you know what the deliverable needs to look like to some degree.

“But I don’t have time to meet with people.”

Then create a team meeting where you help people help each other. It could be a standing meeting where you quickly go over things in a way that exposes misconceptions and insecurities about delivery.

At some point, if you don’t have time to manage people, you don’t have time to be a project manager.

“But I don’t care about people. Just the work.”

If you don’t want to help people solve their problems, you may be lacking an understanding of the value of people and possibly missing an understanding of how they help you in your job.

We all depend on each other, so it’s not just generous to help someone feel good about the work they’re doing. It also helps you by making them more competent each time they talk with you.

Because this isn’t about giving them a fish; it’s about teaching them skills that will help them not need to bug you as much.

Help Them Solve Their Problems

When you’re helping people solve their own problems, you’re at the same time moving them through a challenge and showing them how to overcome similar challenges. You’re taking the role of a coach.

Every industry benefits from this kind of thinking, but especially B2B businesses, where you see more technical, specialized work. In fact, this is where it shines, because so few people can help others do work they don’t understand themselves.

But this process does precisely that: it helps you solve problems in processes you don’t understand by using your own logic, knowledge of the big picture and information they provide.

Why this works

When everyone’s afraid to ask a “stupid” question — usually in highly bureaucratic cultures where you don’t dare to show weakness or ignorance — miscommunications hide and become buried, often causing a problem in the process that nobody seems to be able to find.

But by taking the unashamedly inquisitive approach, you question the very structure of the perceived problem, and like a surgeon, pull out the tiny cancer and show everyone. Often, there’s a “Wow, I can’t believe it’s that simple” kind of reaction.

So What’s the Process?

In a way, this is very Socratic. You just ask questions that work from the goal back to where they’re at. But so few people are willing to be good at asking questions. But for those who can, this becomes a superpower.

Qualifications: If you care about people, you understand the goal of a project, you understand how people work and if you can write a job description and hire well, you might be good at this process.

Let’s say a project worker is stuck. How do you ask them questions that will get them engaged? Here’s a good list to start with.

1) Get Them to Clarify the Goal

Creatives need to understand the goal. Clarify the goal and make sure you’re both in agreement as to why the goal is important. Remember “task and purpose?”

So what’s the goal? Why do stakeholders care?

  • Client
  • The client’s customer

2) Help Them Define Obstacles

Creatives and other smart people are valued because of their point of view. That means they miss stuff that others think is obvious, simply because they’re looking at it from a totally different angle and are probably preoccupied with a certain way of doing things or an insight they think is the most important thing. Your goal is to help them walk through what’s important and what’s not. But here’s the rule: you can’t tell them what to do or solve it for them. It’s best if they arrive at their own conclusion.

Why do people fail at this? They fail when they don’t understand that their experience doesn’t magically make something possible for someone else. Don’t assume they can follow your process. And although it’s tempting to tell them how to do it, you want them to own it, not you. So you have to understand the problem as they see it.

And while some ways of thinking and working are easier for you than for your creative, they can solve problems you can’t and in ways you don’t understand. And this is the goal: listen to them and get them to talk about the obstacles.

Have them define the obstacle: it could be something as simple as “I don’t like to make phone calls.” or “I don’t know what this deliverable looks like.”

They might not have understood their problem. But if you listen, you can start to see where they might be confused. Then get them to define the problem.

3) Help Them Define Their Task

Creatives, like many people, want to skip steps. If they think they get the obstacle, they’ll rush to a solution. But if you ask them to define their task — how they’ll solve the problem — it will help them work through problems without the time it takes to initiate another communication cycle with you.

This is usually some sort of plan or process. This can really help if there’s a follow-up meeting too since it helps you guide their goal-creation process. So if you realize they don’t really have a real goal that’s measurable, you can talk them through it.

Here are some sample questions:

  • Describe the process that comes after this for you.
  • More focused: What are your next 3 steps?
  • What has to happen before you hand this off or deliver?
  • What are your next 3 steps?
  • Describe your process.

This may take a few steps, and it may take practice, but this highly consultative approach matures people. It makes them more valuable people to work with. It’s a huge value for them as well, since it’s good for their career, and you’re helping them become stronger people.

Questions to Get Them Talking

Do they know they have a problem? Do they see a point of even talking with you?

If you’re not sure how to ask, here are some questions you can ask if the conversation stalls.

  • Process
    • What’s your next step? Or next 3 steps?
    • Why will you take that step?
    • What do you hope it accomplishes?
  • Drawing
    • Ask them to draw a diagram of the problem.
    • Ask them for a drawing of a user flow or data flow diagram.
  • Clear goal
    • Ask them to define the goal of the project.
    • Ask them what the client’s problem is.
    • Ask them about the client’s customer’s problem.

Congrats. You’ve Just Helped Someone Solve Their Own Problem

So how do you build your organization, make people happy and motivated and grow them so that they can replace you, even if you don’t know their job? You treat them like you’re a consultant. You audit their connection with the work, asking questions and exposing their disconnect.

You help them see their contribution in terms of their task and purpose, giving you someone who’s plugged in, interested and aligned with you in the desire to complete the project well. And that’s a great way to build a solid organization that can scale.

Creating a culture where this kind of coaching can thrive depends heavily on your brand. This month we’re launching a new opportunity for people to connect with a few of their peers and our CEO Mike Jones to discuss why branding matters and how to build remarkable brands as we dig into your branding issues together. Learn more and sign up for an upcoming session of Brand Roundtable Chats.


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