5 Lessons from 500 Conversations with Sales Leaders

May 3, 2022

Rasmus Goksor

Someone asked me what I've learned about sales management since starting Ressemble. Looking back, I’ve talked to over 500 sales leaders in the last 5 months. Here are my top five takeaways. (Some of them were unexpected, maybe they will surprise you too.)

1) Sales leaders don't give enough feedback. I hear this all the time from reps, which is odd because sales leaders are in contact with their reps daily and say they are always available to help if something goes wrong. I have to wonder, is it not enough feedback or not the right kind of feedback at the right time?

2) Deal size is the most common filter for prioritizing where to spend time in a pipeline. What if we could filter for winnable deals? The real problem is that we don’t have better insight available to pick out winnable deals.

3) Sales intelligence is still all about tracking follow-up activity in a deal. “When did we hear from the prospect last?” I can’t help wondering if this is just us trying to find signal somewhere, anywhere… But follow-up activity is unlikely the reason the deal has or hasn't gone through.  Personally, I'd put my bets on working with my reps on the front end to improve their actual interactions with the prospect.

4) Pipeline stages are centered around our sales steps rather than the buyer's journey to consume our solution: “Connect, Demo, Price, Proposal” versus “Struggling with pain, Clearly defined solution image, Understands value of change, Clear visibility to ROI.” Seems like this should be solved by now.

5) We love tracking win rates in our funnels, but talking about loss rates could help us question some of our own biases and blind spots. Why is it ok to lose 80% of deals for which we committed to do a demo?

Where does it leave us? It is all about reshaping how we collaborate in our sales team to make the most of every sales opportunity. Stop wishing it were back to how it was, and start reimagining what your sales team needs now.