When we met, I really hit it off with this executive. I asked her lots of questions. She shared some confidential information. And, because I'd dealt with similar issues when I worked in the medical field, I had lots of ideas about how to address the challenge.

It was a great meeting. She thanked me for my time and said she needed to think about what we'd talked about.

My initial reaction was that he'd probably spilled the beans too quickly. That's one of the most common problems I see. But honestly, he convinced me otherwise. They really had a solid peer-to-peer conversation. So I asked him, “What's the problem?”

“That was three weeks ago and I haven't heard from her since,” he confessed. “What should I be doing?”

Chris said that he'd called and emailed several times, mentioning that he was touching base or wanted to know her thoughts. As Chris saw the expression on my face, he justified his follow-up strategy, “I don't want to be too pushy.”

How holding back holds you back

If I've heard that response once, I've heard it a thousand times. No one wants to be pushy. I don't want to be pushy. But there's a big difference between being pushy and being professional.

That's when I decided it was time to turn the tables on Chris — to get him to think “as if” he were his prospect. Here's what I said:

Let's say you were the decision-maker. You'd just met with a savvy business person who truly understood your situation. You were impressed — and even relieved — because a solid resource had appeared.

Here's my big question, Chris. If you, as an executive, met this savvy person, what would you expect him or her to do next?

He looked at me thoughtfully. “I'd follow up—but I don't want to be pushy. It might turn her off.”

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Dare to be a leader and show your prospect the next logical step. (Photo: iStock)

“Chris,” I said. “Get over yourself. You're being a total wuss. Now tell me, what would you want this person to do? Put on your buyer's hat. Think. Then talk to me 'as if' you were this person.”

I watched Chris struggling with the question, then saw something shift. A new idea was emerging; deep down he already knew the answer. Speaking as if he were the buyer, Chris told me:

I'd want this person to take charge. I have a gazillion things going on here in my organization. I'm constantly jumping from project to project. I don't like to take big risks here either. I've seen too many careers get dead-ended.

I don't want this person coming to me with a big humongous plan to solve my problem. That would only throw me into overwhelm. What I'd really like is for the seller to suggest the logical next step.

I'd want to test him out on that to make sure that I liked working with him, that he delivered on his promises and that his work yielded results.

“Exactly,” I chimed in. “And what's preventing you from taking charge with this prospect?”

Chris said, “I don't want to be pushy. And, I guess I want her to want to work with me.”

How your own thinking holds you back

As I talked with Chris, I could see that his wish not to be pushy was overriding his sense of how he could help his prospect. “This is not about you,” I told him. “This is about helping a potential customer address their challenges and achieve their objectives.

“You need to focus on them, not you. Don't wait for them to come begging for your services. Help them. Show them the next steps. Now.”

With that, I took the last sip of my beer and said my good-byes. I honestly don't know if Chris ever dared to be a leader, to show his prospect the next logical step, to help them realize the value of making a change and to guide them through the decision process. But if he didn't, he was missing a big opportunity.

That's what it takes to win big deals this days.

Related: How to successfully follow up with anyone