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Rodrigo Caetano from the Strategic What Podcast provides tips on how to improve your management skills, become a better leader and improve your productivity. 

Discover how to better plan your projects, inspire your team and take control of your work. On each episode, Rodrigo will share his practical on-the-ground experience and provide you actionable tips on how to be more innovative, get more work done and enjoy your management work.

Do you want to go the extra mile and achieve better results? Let’s hit the ground running!

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May 18, 2017

In this episode, learn a strategy I use every time I delegate tasks.


I always had issues with my team doing things in a way different from what I expected.

It was very frustrating.

We had meetings. We agreed on the results. But, when my team went back to their desks, they went off the course and did things in a way I thought it wasn’t the best one.

During that time, I was always wanted to jump in and do their work.

Then, I learned this technique…. That if you ask asking a simple question, it would help solved many of the issues I was finding.

What question is that?

The most powerful question you can ask to your team is “How?”

You may say, “Oh, no! That can’t be right.”

I challenge you to give a try. 

Let me explain why.

Let’s say you are in a meeting with your team.

Everyone is listening carefully to what needs to be done.

Everyone knows what to do and is aware of the project deadlines.

But, how many different ways they can come up with what you want them to do?

Every one of them has a picture of what needs to be done in their minds.

If you don’t ask them, you’ll never know if they are in line with the approach you think is the best. 

If you have a feeling that they may do things differently than you expect,  like your team is going on a tangent,

… Try asking “how”.

Let me give you a few examples on how I use it:

“Ok, John, I guess we are clear on what needs to done, right?….
Now, just for the sake of completeness, can you tell me How you plan implement these changes?”

“Ok, Sarah, you know the timelines for the project and what needs to be done.  Could you please briefly tell me how do you plan to implement this, so we are in sync?”

“Now, Lucas, could you please give me a rough overview of how do you plan to work on this task?”

You get the idea.

Why use “How?” and not “What?”

You may notice that there is a very subtle difference between asking “how” and “what”.

“Tell me how do you plan to do it?”

“Tell me what do you plan to do?”

You may argue that this is only linguistics, semantics, grammar...

No, it’s not.

When you ask “How”, you force the person to think in terms of steps.


An answer to How usually comes with some type of sequence or logic:
“How? Well, I’m thinking about doing this, then this, then that.”  

An answer to a What question tends to get you answers in terms of deliverables, end results:
“What? Module A, Module C and D.”

I know it’s subtle, but from practical experience, using how is an opportunity to find gaps and fix them, before your team starts working.

If you notice any holes in the approach the person is planning to use,

It’s better to catch them sooner than later, before everything has already been done.

By asking How? you are effectively avoiding future headaches.

Besides, you create an expectation that you have a certain level of control over how things will be done in your project.

If someone tells you they are blindly delegating because they trust their team and not having any problems – using the typical delegate and forget approach – they are most likely lying to you.

Either that or they may be in bigger trouble than they think, but just don’t realize it.

Give it a try and see the results for yourself. 

Here is how this strategy works for me:

  • I explain to my team members what needs to be done and make sure each person knows what’s required of them.
  • If I’m not confident about the approach used by someone on my team, I’ll ask a How? question: “Ok, could briefly explain to me how you plan on doing xyz?”
  • Listening to the person, I’m able to find out where the gaps in understanding are and correct them before the work even starts.
  • Asking How? saves me a ton of time checking and micromanaging my team.
  • At strategic milestones, I’ll ask them how things are going.

This is neither about micromanaging your team, nor using a delegate-and-forget approach. Far from it, this is an approach where you agree on a suitable approach and plan how things should be done.


Summarizing: ask How?

Remember that, even if something seems obvious, you better to have it spelled out.

Whenever you sense that the details are not clear, ask “how” in order to gain better control. I guarantee you will have far less problems using this approach. 

Have a great day wherever you are.