How My September Went – Mishaps and Challenges

This was probably the most challenging month I've had in sales so far. I closed fewer deals than I projected and wanted to, which leaves me with a bitter taste, but more things to improve on going into October. I finished the quarter over target but was one deal short this month. On the bright side, I can learn from the mishaps and challenges and not let this month go to waste.

Here are some things that I learned along the way, speaking to mentors and coaches who's expertise and experience, helped me define new strategies for the coming quarter.

Pipeline Solves Everything

To protect yourself against the possibilities of unexpected roadblocks with key deals, focus on constant pipeline generation. Ultimately, what hurt me this month was the lack of pipeline generation in the month prior. On the other hand, the conversations I had in June/July led to won deals in September, even with accounts that had previously decided against us as a provider.

Sometimes people need time to change their minds and come back as their alternative strategies didn't play out. At the end of the day, you can let randomness, like sickness or unexpected budget cuts, work for or against you — circumstances can also shift in your favor, and prospects suddenly come your way, as their original objections turn into buying signals. You make your own luck by generating a healthy pipeline.

Talking to a mentor, a VP at a big SaaS firm in the UK, he reminded me that pipeline generation solves everything. Don't focus on what comes your way or doesn't at this moment, because it is more random than you would like it to be – constant pipeline generation will allow you to let an abundance of deals choose you as a provider. Lots of deals in your pipeline will give you swagger and the needed coolness in challenging conversations to ultimately bring the deal across the finish line. Lack of pipeline can cause needy and pushy behavior, which repels deals.

"Pipeline generation solves everything."
- a mentor

Disqualification is important!

It's not just about quantity. You want a big pipeline full of people with pain and urgency to solve the problem you can address. Talking to window-shoppers and deals that don't show true intent to go with you is an indication that the problems they have are not worth solving at this present moment. So on the one hand, talk to a lot of people with pain and urgency, and disqualify those that don't demonstrate the ability to execute on the project. Disqualification is painful because you let the chance of a conversion die, but some deals just waste your time and give you nothing in return. These deals can kill your momentum.

Inbound Dependency

Treating inbounds as a bonus was also a big learning for me this month. You can't depend on the quality of inbounds. Some will just place an order right away, and some just want to take a look. There is always a possibility that the cost of acquiring a lead becomes too high for your company's marketing budgets, that the market demand shifts and fewer inbounds come in. Or, your marketing department might try a different campaign and it doesn't go as planned and generated fewer MQLs. There are a lot of factors outside of your controll and sphere of influence. "Eat, sleep, and breathe" outbound pipeline generation, my mentor said. You can never do enough.

Key Learning in summary: Control the controllable. Focusing on your sphere of influence, pipeline generation, upskilling, and reflecting on things you could have done better helped me generate some last-minute momentum that ultimately leaves me in good spirits for the coming months.

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