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Danny Wood Enterprises, L.L.C. | Rutherford, NJ | 201-842-0055

Let’s say you’re the manager of a team and, for whatever reason, you realize that someone who reports to you is missing an essential skill. What do you do?

This is a common situation. One day, you notice that there’s a major difference between what this person needs to do in order to succeed in this position … and what he or she is able to do. Let’s say it’s a salesperson, and let’s say the skill has to do with conducting an effective initial discussion with the prospect. Let’s say that skill just isn’t there.

Let’s also say you’re also pretty certain this particular gap isn’t about willingness. The salesperson in question – we’ll call him Bob – does want to have better discussions. It’s just a matter of him not yet having learned and practiced the required skill.


If I was the manager, I had a good person like Bob on the team, and I knew that a key skill Bob needed wasn't there in an essential area, the first thing I would do wouldn’t be to sit Bob down and say, “Here’s how you run a meeting with a prospect. Pay attention.”

The first thing I would try to figure out would be the Pain – specifically, Bob’s Pain. This is a step that a lot of managers skip.

Bob’s Pain is his personal frustration, the thing that keeps him up at night. I’d be very interested in learning about that, and about all the possible side effects of that pain. I’d want to get a clear picture of what obstacles Bob was facing in life, and how his life and his sense of personal fulfilment were being held back. Let’s say, for the sake of argument, that the pain in Bob’s world is his uncertainty about how he’s going to pay for his daughter Kelsey’s higher education. She’s a sophomore in high school now, she’s deeply goal oriented (just like Bob) and she wants to become a lawyer. Bob supports that goal, and he wants to make sure Kelsey’s experience with higher education is a lot easier financially than his was. Bob got saddled with a lot of debt when he went to school, and he doesn’t want his daughter to repeat that cycle. Right now, he’s not sure he’s going to be able to keep that cycle from repeating in Kelsey’s life, and that’s stressing him.

A side note: The best way to get a clear picture of Bob’s pain – of anyone’s pain – is to take the time to get to know them as a person. This is best accomplished naturally and informally, over a series of events (such as going out to lunch together), not by means of a questionnaire or some awkward interrogation session featuring questions like, “Can you tell me what your pain is, Bob?”


Once I had a clear sense of what was missing in Bob’s life, I would want to get a sense of his Vision for his own life. Where does he want to be? The Vision is all about what the person wants to do, have, accomplish, or become. It could connect to a certain type of lifestyle, or to a specific

Bob’s Vision, as it turns out, is to get his daughter into, and through, college and law school without her having to take on any debt at all. That goal is important to him. That’s where he wants to be. Here again, the best way to get a fix on Bob’s vision is to spend one-on-one time with him and show interest in him as a person. This is likely to take more than one discussion. The point of all these discussions about Pain and Vision is to establish were Bob is right now – and where he wants to be.

The word to describe the difference between where Bob is now and where he wants to go is Gap – and that’s what I would want to focus on next. In other words, what's keeping Bob from getting to a position where Kelsey doesn’t take on a single cent of student debt? What is keeping him from doing that? And what are the things he would have to accomplish in order to close that Gap?

Knowing Bob’s Pain, Bob’s Vision, and Bob’s Gap allows me to bring up the skill issue in a very positive light during my one-on-one coaching sessions with Bob. I’m not going to say, “Bob, sometimes the truth hurts, but here it is: you don’t know how to run a decent meeting. Let me show you how it’s done. I’m coming on your next sales call. Stay quiet and watch me do it.” And I’m not even going to say, “Bob, I made a mistake in hiring you without realizing you were incapable of running a decent discussion with a prospect.” Both of those messages would send the conversation in the wrong direction. And yes, they would also send the wrong message if I made them sound a bit more polite. The same dynamic would be there: I, the boss, am the expert, and Bob, the subordinate, is not okay because of this skill gap that we need to fix.

Instead, what I’m going to say to Bob is, “Okay – given where you are now and where you’ve told me you want to go, does it make sense for us to work together to get your questioning skills up to a level where they support the right income goal – and your plan to get Kelsey through college and through law school without her having to take on any college debt?”

In other words, I’m going to ask Bob a question, based on what I’ve learned about his Pain and his Vision, and see if he agrees about the importance of closing the Gap. Then I’m going to ask other questions that continue that important conversation.

Notice that this is a conversation that puts the skill issue in a very positive light, not a series of instructions. And notice, too, that Bob and I are, so to speak, on the same side of the desk. I’m not saying, “Hey, you’re not doing your job.” I’m saying, “Bob, from where I sit, it looks like you’re not going to get to where you told me you want to go unless we close this Gap – so what would happen if we took a closer look at what’s standing in the way of you giving Kelsey the financial support you’ve promised her?” It’s a coaching discussion using Socratic questioning to get the other person to do the diagnosing of what’s wrong and what needs to happen next.

This approach has proved very effective in helping people to identify and close their own skill gaps. After this kind of discussion, Bob is invested! There are all kinds of things we as leaders can tell our people about what we have observed about their performance and abilities, and what we think needs to happen next. But by helping them get a clearer picture of the Pain in their lives, the Vision of what they want to achieve in their lives, and the Gap between where they are now and where they want to be, we enlist them as allies in the shared mission of expanding their skill base. And that’s where we want to be.

Check out this blog post to learn the importance of investing in employee development so you can build a successful team and business.



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