A hard week: bad contractor break up & lessons learned

It’s been one of the hardest weeks of my startup journey thus far and concluded with a hard meeting. I had been anxiously waiting for this meeting for the past month. Every scenario of how it could play out occurred in my mind with all the anxiety-filled thoughts with each outcome I thought through. The actual meeting was just as hard and uncomfortable as I thought it would be. I spent so much time thinking about what to say in the meeting and how to get through the meeting that I didn’t prepare myself for how bad I would feel after the meeting.

Let me fill you in on the back story. As you have gathered, I am a technical founder and have learned to sell through my experience building this business. My process is based on all the blogs, books, and advice I have received. It also means my process is not standardized, efficient, or productive. I know that at some point, I would need extra help to accelerate the company’s growth. By the end of 2021, I knew that the time had come. So I sought a Sales and Business Development contractor to accelerate our deal volume and close additional partners. After months and months of interviewing, I finally found and hired a Sales/BD Contractor who I believed was the best fit.

This meeting I just had was the result of that contractor who had a bad breakup with the company. I will spare you (and the contractor) all the details about the relationship and how it unfolded, but I want to share my reflection on the situation and lessons learned.

Before I share, I want to reiterate that every decision I have ever made with the company is in the past. I repeatedly tell myself and believe that I made the best decision possible with the information I had at the time. This mantra clears my consciousness and gives me the space to reflect, learn, and grow, so ultimately I can become better because of it.

Lessons Learned

1. Before hiring a Sales/BD contractor
   1. Clearly define the goals, metrics, milestones, and reasons you are hiring a Sales contractor
   2. Determine what type of selling skills this contractor needs to have to be successful. What stage of maturity are you at?
      1. A product has already been sold to a few customers and a defined playbook (defined could mean many different stages, from a few notes to exact personas to sell to, etc.)
      2. There is a product that has no playbook and needs to figure out how to sell
      3. There is a product in development, and pre-orders are needed, resulting in a lead time
   3. If you say the product is in 1 or 2., then have 100% confidence that it is. If not, say something in the pre-hiring discussions to set the right expectations.
   4. For the best results, the product should be in 1. and have already been sold by the founder to early customers.
2. Managing and working with a sales contractor
   • Clearly describe to the contractor and ensure understanding of the steps are clear for what happens after a deal is signed
     • What blockers could arise in delivering the product to the customer promptly?
     • Who in the company is responsible for delivering the product?
     • If an order isn’t completed through the process, it takes too long, or there is an error along the way, then have a post-mortem. Talk it through with your team and fix it for next time.
   • Have a minimum of weekly sales calls to understand each deal in the pipeline in detail
     • What deals are you working on, and in what stage are they in?
     • What are the drivers for the customer? Why is the customer interested in this product?
     • What are the blockers for the customer? If you could remove all those blockers, would they sign tomorrow? What else is holding them back?
   • If issues arise, have a check-in and figure out what is happening with “Aaron Cooper’s Famous 3.”
     • The contractor understands the goal. Enough to repeat it back to you and gets it.
     • The contractor disagrees with the goal or feels negatively toward the goal.
     • The contractor doesn’t have the skillset or ability to reach the goal.
   • If an issue keeps coming up or can’t be resolved in a check-in, it is time to let the person go.
     • Don’t feel shameful, guilty, or unsure. If you have a gut feeling about the situation, just let the person go. It will save you from all the challenges later.
3. Ending the relationship
   • Make sure the paperwork is clear.
   • Get a status report or hand off and move on.
   • Let it go, this is the hardest part, but you have to let go and let the control go. Learn from it and move on.