When Your Skill Set Holds You Back


When Your Skill Set Holds You Back.

Dr. Jim Kestenbaum has been in my life for the better part of 10 years. A boss hired him to work with me for a year, and the sessions we engaged in changed the course of my career, how I worked, and how I saw myself.

Because of that, I asked him to speak to a group of sales leaders and to share his thoughts on growing as a leader.

Here’s what he shared.

The plague of sales leaders. (And most small business owners)

What’s in one’s head guides their behavior. Every professional has to create an initial skill set. It’s often something they like a lot. Most heads of sales got into sales because they liked it was good at it, and got paid well.

But eventually, he or she started to wonder, “What if I’m not supposed to be selling full time, or at all, anymore?” It’s a hard question to ask. The native skill set is selling. Psychologically, it’s hard to make that change.

Many sales leaders see the reps as assisting them in getting to the number, not as the ones primarily driving the number. The reps don’t get enough coaching, and the manager hustles harder in the leadership role than he or she did as an individual contributor.

What happens? The poor performers stay where they are. They don’t get better. And the leader starts owning the number and carrying the bag to get there. “Put everyone on my back – we’ll get it done.”

The title has a managerial connotation to it, but the leader isn’t leading: he or she is selling. The native skill set has become a trap.

It’s anxiety-inducing, being in this place. A leader has to transfer – confidently – what he or she does well to other people. “How do I do this?”

The next question that arises: “If I’m to transfer my skills, am I really that valuable anymore?”

Then: “If I’m valuable if I transfer my skills, do I have the ability to transfer these skills to others?”

This isn’t easy. But let’s pretend a leader can get past these initial concerns. The leader has to begin thinking, “I’m a resource to help my people get it done.”


Trust, the leader and coaching.

When the leader makes the shift to seeing himself as a resource for the team, he’ll ask, “How do I trust my people to do it as well as I would?”

Let’s be clear – trust is not a blank check or blind faith in people. It’s built on assessing their behavior and skills.

A leader can develop this trust by outlining for his people the top activities, that if done well, would predict success in their space or industry.

Here’s what you want to do as a leader:

Write down the 5, 8, 10, and 12 things that your people need to be able to do in your business to perform. Things like prospecting, presenting, building relationships, entertaining, talking about money, coming up with solutions, getting access to decision-makers, etc….
Create a grid.
Assess the behaviors of your people on this guide on a 1-5 scale
You’ll find 2 kinds of averages:
Averages across behaviors for each person
Averages across the organization
Then have each person do a self-assessment on the 10-12 behaviors

Once you have done this, you have a baseline for each rep between your assessment and theirs.

Here’s the truth: most leaders don’t know how to coach. But if you go back to the grid, you have a quantifiable way to know what to coach ON. This is the upside of the native skill set: sales leaders use their skill NOT as a seller, but now as a coach.


The sales leader and internal customers.

Too many sales execs don’t pay attention to the stereotype of the sales exec. With external customers, sales leaders are collaborative and charming. It’s where they get their juice.

It’s the exact opposite with internal customers. And those relationships are often very broken.

But sales, to succeed, needs other departments. And the sales leader needs to find a first initial internal relationship to develop. It could be distribution, purchasing, finance, operations, or customer service.

And sales often alienates other departments, and the sales leader ends up at odds with other execs. Internal meetings can be contentious.

What can you do as a leader?

You can sit down with the other party and ask, “What are our joint goals?” That discussion needs to happen to build trust. (Obviously, there has to be some trust that both people are accurately representing the truth in this conversation.)

In sales, we have to look hard to assess the need. The other person may be in conflict. They may be worried about money. Or time. We have to understand them.

With peers, we have to do the same: seek to understand. Even if we think they’re not competent. There’s a difference between someone being stupid and acting stupidly. In groups, people act strange. Groups elicit different behavior. They’ll defend their department, their people, their intellect, and their rights. In a group, they try to save face. So you have to get one-on-one time with them.

How do you do this?

You fall on your sword, go to them, and say, “You gotta eat lunch. I’m not connecting with what’s happening in a group. It’s my fault. I want to better understand what we do in sales that make you crazy. This will help me better understand myself.”

If they agree to lunch, what then? Let them tell their story. Guess what they’ll do? They’ll go quid pro quo and ask what they do that makes you crazy. It’s reciprocity.

Start small in terms of actions. See if you can build trust with them and move the needle.

You can do this with anyone on the exec team. As you build these relationships, you’ll be seen differently.

You will have other execs who either have never sold or haven’t in a LONG time. They’ll have all the answers for your department, or what and how sales should do. It’s easy to be defensive. Instead, reply with, “Sounds like you have some ideas. I’d love to get your take on some things. I want to hear what you’re thinking, and then I can share my thinking and how I’m approaching this.”

We have to remember, people are defensive for a reason. They put up walls to protect themselves. We have to ask, “How do I create enough safety for them to open up and drop their walls?”

And when you start doing this, your ability to impact not just sales, but the entire company takes off.

If you found this helpful and want to get in touch with Dr. Jim, you can email him at drjim@tsgdrjim.com.




Adam Boyd