10 Things I Learned About Sales the Hard Way

Every new salesperson stumbles. Despite what many of the “gurus” will try to sell you, sales is a craft that must be learned. If your goal is to be a top level, trusted advisor sales professional, you understand that there are skills, strategies, disciplines, a certain mindset, and a lot of other skills that you must continue to hone to get to the very top level in sales.  You will learn a lot along the way, and some things you will learn the hard way. But not every lesson needs to be learned through your own mistakes. You can learn valuable lessons without paying the price if you are willing to learn from other’s mistakes.

Bad mistakes, I’ve made a few:

  1. Book Your Next Call While You Are in the Meeting: There was a time when I would leave a sales meeting without having booked another sales meeting with my prospect or client. I discovered that doing this made it nearly impossible to schedule the next meeting; it took dozens of phone calls and months to accomplish. Booking the call when you are sitting with your prospective client is the very best way to ensure you gain that commitment.
  2. Lead With Your Higher Price: It has become a common misconception of the ignorant and fearful that it is a good strategy to withhold your pricing until your prospective client wants what you are selling. It takes a while to learn that the sticker shock your prospective client feels when they see a higher price makes it far easier to justify the delta between your price and your competitors. Leading with a higher price, with confidence, makes justifying the difference between you and your competitors’ price easier, not harder.
  3. Don’t Present Anything More Than You Need To: When I was young, I worked for a company that provided me with an 84-page presentation. I literally read my prospective clients every page of the 84 pages, oblivious to the fact that I was turning them into zombies. It took me time to learn to pare down my presentation to only what was necessary and to only present what the prospective client needed to see to say yes.
  4. Ask for Your Money: I’ve had clients that spent millions of dollars with me and my company who believed they had a right to ignore the agreement we had made around payment terms. It can be difficult to ask someone to pay you hundreds of thousands of dollars, especially when you are young. At some point, I recognized that we had earned the money and we had a right to collect it.
  5. Assume You Need the Support of More People: I have felt very safe in a relationship with a single stakeholder who I believed was all that was necessary to win an opportunity. Later I was surprised that people I had never met, and who had nothing to do with the opportunity, had killed it. It is easier to get consensus when you include people in the process from the beginning rather than springing it on them later. Make sure you have all of the stakeholders involved from the beginning.
  6. Deal With the Elephant in the Room: Problems don’t age well. Many people will sit in a room perfectly content to avoid the most difficult and important issue. This is especially true for salespeople who believe they jeopardize an opportunity by bringing up the challenges in generating the results their dream client needs. But you win your prospects trust when you’re willing to “go there” and tackle the big issues.
  7. Leadership’s View of the Problem Is Often the Problem: At one point in my career, I was thrilled to be working with leaders of companies. They would share their sophisticated and nuanced view of their strategic challenges. It was fun and exciting. When it came time to execute, I found out that the ground truth, the real challenges, were very different than the leader’s view. A holistic view of the presenting problem and the root cause is easy to discover when you work North and South through your prospective clients or chart.
  8. Sustained Success is Found in a Full Pipeline: Early in my career, I had three major clients that were generating a massive amount of commission. I sat on these accounts like a mother hen sits on her eggs. All I wanted to do was keep them warm and safe. Over the course of a few months, I lost two of those accounts, cutting my income by about 70 percent. The only way to sustain success in sales is through a full pipeline of opportunities.
  9. You Have to Lead Highly Compensated Employees: When I became a leader I thought the easiest thing to do would be to hire people, pay them well, and that would be enough to prevent me from having to lead and manage them. That strategy failed every time I tried it. It turns out that everyone on your team needs to be led.
  10. Delegate and Help People Grow: Throughout my work life I have done a lot of work that I shouldn’t have because I believed I could do that work better and faster than anyone else. Even when this was true I was wrong. By doing the work myself, I wasn’t doing the most important work, the work where I was the primary value creator. I was also depriving my team of the experience they needed to grow and become even better than I was at that work. You help people grow when you delegate–including you.

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