Dear SaaStr: How Do Sales Reps Lose Deals?

And What Are Some Good Questions to Ask a CEO in an Interview

Dear SaaStr: What remarks have a salesperson said to you that lost them the sale?

A quick list here:

• “You are wasting my time”. I don’t think this was meant to be said aloud, but many B-tier reps say and think this all the time. No. A prospect’s time is always valuable. Sales is there to serve. If sales was routed the wrong lead, that’s the company’s fault, not the prospect’s.

• “Our product does [key feature]” — when it doesn’t. If I’m buying a product I haven’t used before, the AE is my guide. If he/she tells me things that aren’t true to close the deal, I’m out. I’m buying a solution. I need to know for real if it solves my problem — or not.

• Constant bashing of competitor. Not only does that make the company look insecure — it makes me want to go test the competitor instead. Even worse (see prior point) is when they say something about a competitor that isn’t true.

• Forcing me to talk to an SDR first. I don’t want to be qualified. I want to try, use, and buy. I lose patience here and move to a vendor I can just deploy without being forced to talk to an SDR that just wants to force me to get on the phone and screen me but doesn’t get me going now.

• Wrong / painful economic terms, even if price itself is OK. I’m basically an SMB these days. I don’t like annual contracts, and I especially don’t like being railroaded into enterprise-type contracts — multi-year with no outs. I don’t have patience for any contract that is so long it requires legal review. Let the buyer buy the way they want. And let especially SMBs out if you don’t deliver for them.

• “I’m turning off your trial” — and other threats. Yes, you have to do that. But a sales rep needs to do it the right way. Threats don’t work. How about “Your trial is about to end — I can extend it a week if that helps? Let me know what I can do to help you get going with us!”. Then — I’m in.

Use something like Gong to hear if your reps say stuff like this. Then — make sure they don’t anymore.

Most importantly: Founders and even VPs of Sales are almost always shocked what some sales reps say when they don’t audit and monitor calls and Zooms. Shocked. Especially if they don’t carefully train the reps.

Dear SaaStr: What are some good questions to ask a CEO in regards to their leadership?

A few thoughts. You may not be comfortable asking all of these in all circumstances, but I think they are telling:

1. What’s a key hire you made that didn’t work out? What lessons did you learn?

2. Who are the best 1 or 2 hires you’ve ever made?

3. What will the industry look like in [X} years? X=how long the company has been in existence.

4. Who are some of the folks who have grown their careers here? How did they do it?

5. What happens if we miss the quarter?

6. Who was the best boss you ever had yourself? The worst?

7. How strong is the competition? What do you respect about them?

8. How does the company incorporate diverse thinking and perspectives?

9. Why are you doing this?

I think that’s a pretty good start to learn about 10x more than you might otherwise learn. I think they are pretty good for VPs, too.

In fact, this is the list I am going to start using. And that I wished I’d used.