Coaching Strategies for Busy Leaders (Develops Others)

Photo: Pixabay/Geralt

Deborah sighed and looked at her phone. “David, I’m sorry, I need to take this.”

She paused the strategy session I was helping her work through and answered the phone. The employee on the other end needed help. She answered his question and got him back to work.

After she hung up, she looked at me and frowned. “He should be able to figure that out on his own.”

I smiled – having been there myself many times. “Looks like he’s got it figured out pretty well…”

“What do you mean?” she asked.

“Well, if he has a question or hits a roadblock, he’s figured out a surefire way to get his answer.”

Deborah chuckled. “Him and the rest of the team. But I want to be helpful, supportive…have an open door. Right?”

“Right,” I said, “and you can be the most helpful and supportive by helping your team develop their own critical thinking and problem-solving skills.”

“That would be great,” she said, “and give me more time to get my work done.”


What do you do when an employee asks for help?

For many years, I made the same mistake as Deborah, and I’ve watched thousands of managers do the same thing. Someone comes to you for help and you give them the answer.

Because you want to be the hero, or you want them out of your office, or you want them to like you. Whatever the reason, when you give them the answer, you’ve taught them to depend on you. But you need a team of people who can think critically and solve problems on their own, right?

Your good intentions have gone wrong and they’re keeping you from developing the team you need.

In my experience, managers and leaders often struggle with how to develop their people. You might vaguely know you’re supposed to…you’ve heard of ‘leader as coach,’ but what are you supposed to do?

The good news is that you can do it and it doesn’t take very long. In a few conversations that take a few minutes each, you can enhance a team member’s ability to take responsibility and solve problems.

Often, your team doesn’t need you to solve problems for them. What they really need from you in are your questions.


Asking good questions is critical to freeing up your own time and increasing your team’s ability to think and solve problems on their own. In these situations, a good question or two can quickly move the conversation back to the employee owning the problem and analyzing potential solutions – but they do have to be good questions.

Poor questions place blame, dwell on failure, and are followed by an implied “you idiot!” Examples of poor questions include:

  • Who screwed up?
  • Why did you do that?
  • What were you thinking?

In contrast, healthy questions focus on learning and on the future to generate ideas and solutions. Examples include:

  • What is your goal?
  • What did you try?
  • What happened?
  • What did you learn from that experience?
  • What else do you need?
  • What would you do next time?
  • What do you think would happen if you tried that solution?
  • What will you do?

Assuming that your staff has the basic skills, training, and materials they need to do their jobs, this conversation doesn’t have to take more than a few minutes. For a complex project, it might take the time required to drink a cup of coffee, but it shouldn’t take much longer than that.


Now, you might be wondering what to do if the person replies to one of your questions with, “I don’t know.”

No problem – it’s time to use the super-bonus question. When a team member says, “I don’t know,” most managers will then jump in and supply the answer, but not you!

“I don’t know” can mean many things. Rarely does it mean the person has zero thoughts about the issue.

More often, “I don’t know” translates to:

  • “I’m uncertain.”
  • “I don’t want to commit before I know where you stand.”
  • “I haven’t thought about it yet.”
  • “I don’t want to think about it.”
  • “Will you please just tell me what to do?”
  • “I’m scared about getting it wrong.”

Your job as a leader is to continue the dialogue – to ease the person through their anxiety and train their brain to engage. This is where the super-bonus question comes in.

With one question you can re-engage them in the conversation and move through “I don’t know” to productivity.

When someone says, “I don’t know,” your super-bonus question is: “What might you do if you did know?”

Before you laugh, try it.

Try it with your children, with your co-workers, or with the person next to you in a coffee shop. In any conversation where someone says, “I don’t know,” respond with a gentle, “What might you do if you did know?” and watch what happens.

It’s like magic.

The person who was stymied two seconds ago will start to share ideas, brainstorm solutions, and move on as if they were never stuck. It’s amazing and hard to believe until you try it.

The super-bonus question works because it addresses the source of the person’s “I don’t know.” If they were anxious or fearful, it takes the pressure off by creating a hypothetical situation: “If you did know…” Now they don’t have to be certain or look for your approval and they become free to share whatever they might have been thinking.

If they hadn’t thought about the issue or didn’t want to think about it, you’ve lowered the perceived amount of thought-energy they must expend. You’re not asking for a thesis on the subject, just a conversational “What might you do…”

Our brains can do amazing work when we remove the emotional blocks. When you do this for your team, you train their brain to engage, to push through their ordinary blocks, and increase their performance. Ultimately, they will be able to have these conversations with themselves and will only need to bring the very serious issues to you.


You’ll know you’re succeeding in asking healthy questions when a team member tells you: “I had a problem. I was going to come and talk it over with you, but then I thought, you’re just going to ask me all these questions. So I asked myself all the questions instead and I figured it out.”

Celebrate those moments and encourage them to start asking those questions of the people around them. You’ve just increased your team’s capacity for problem-solving, freed up time to focus on your work, and…you’ve built a leader!

Remember, when a team member has trouble thinking through a problem, good questions are your best solution.

Be the leader you want your boss to be,


David Dye, President of Let’s Grow Leaders, works with leaders to achieve transformational results without losing their soul (or mind) in the process. As a former executive and elected official and nonprofit executive he inspires audiences with practical leadership inspiration you can use right away. The award-winning author of The Seven Things Your Team Needs to Hear You Say and Winning Well: A Manager’s Guide to Getting Results Without Losing Your Soul, David is a sought-after leadership speaker, and believes everyone can master the essentials of influence.