Practice doesn’t make perfect; perfect practice makes perfect. Practicing the wrong things over and over again without appropriate correction merely cements bad behaviour. To get better at selling your expertise you’ll require a certain amount of self-assessment at the points of interaction with the client so that you can improve future behaviour.

The good news is it’s easy enough to conduct a simple yet powerful self-assessment after each of these interactions, simply by asking yourself two questions. The answers will reveal your opportunities for improvement for next time.

The first question: What assumptions did I make?

The assumptions you make in the sale are the points of diversion that lead you down long expensive roads with few positive outcomes. The fewer you make the more effective a salesperson you will be.

Often, in the debrief after, it’s easy to spot where you may have made assumptions because they are the source of any friction you might be feeling between you and the prospect. The main areas where we tend to make assumptions are in the four qualifying areas where we are gathering information in order to assess the fit and determine the next step.

The first area is need. Did I make assumptions about the client’s underlying business need? Did I take the prospect’s description of a tactical need at face value without diving deeper? Did I assume I understood his need without asking him to validate my interpretation?

The second and perhaps most significant area of assumptions is decision makers. Did I assume the person I was talking to had decision-making authority or did I fully explore the decision-making process and the roles of those involved?

Then there’s timeframe, which is our surrogate for intent. Did I assume intent when maybe intent did not exist? Did I assume one person’s enthusiasm was shared by other decision makers?

What about the oft-neglected subject of budget? Did I assume because the company is large that the proper budget would be there, or did I ask directly if funds had been allocated yet?

The second question: Where was I uncomfortable?

The habits you want to develop include training yourself to go to the dark places. If something is left unsaid, say it. If you see something that might kill the deal, put it on the table. If you notice that a topic is causing you some stress, lean into it.

You’ll notice in an honest moment of self assessment afterward that it’s easy to identify the areas where you felt uncomfortable. You may also notice that your discomfort is tied to assumptions you made – places where you filled in missing information with guesses. You chose to guess (or hope) rather than explore a topic that made you a little uneasy.

Using Your Answers to Improve Right Now

Next time you will be better, but only if you do an honest debrief of the previous situation and ask, what would I do differently if I had this chance again? Repeat for three or four interactions and I promise your improvement will be noticeable.

The good news is that most of the time you do have the chance to, if not do it again, then make up for what you did not do. What can’t you pick up the phone now and say, “Hey, I’ve been thinking about our call and I realize now that there are a few things I should have said or asked you? Do you mind if we have a quick chat?”

Now go into those dark places. You’ll find after a while they’re not so dark and there aren’t nearly as many of them as there used to be.