- Sales Skills For Founders
- Posts
- The Most Important "Follow up" Founders Miss
The Most Important "Follow up" Founders Miss
How to become a master at digging deeper to create clarity
Welcome to Sales Skills For Founders! One weekly, instantly usable skill that navigates you toward mastery. Think of it as your compass for founder‑led sales. Someone forward this to you? Subscribe here
Today’s Skill: Drilling down into the details
When I was early in my sales career I made mistakes I wasn’t aware of that cost me countless clients. Not because we couldn’t help them but because I wasn’t effectively diagnosing their problem. I only realized those mistakes from reviewing my calls and getting feedback on my blindspots.
Now that I am coaching Founders, I get the opportunity to help them do the same. And, although every Founder has their differences in how they sell, what they sell and the nuances of their clientele problems, there tends to be overlaps in the mistakes I see.
I’m calling out one glaring miscue I see too often:
→ Death by questioning
My guess, you make this mistake without even knowing it.
You either, 1. Ask too many surface level questions and/or 2. You skip from question to question without uncovering more.
Why This Isn’t Effective
You never get a deeper understanding of where the problem or pain lies which means you have a hard time tying value to the costs. (remember those “Costs” from a few issues ago)
If you review a recent call, I bet a pattern emerges like this:
You ask a question.
They give an answer.
You ask an unrelated different question.
They give an answer.
You ask an unrelated different question.
They give an answer.
…and so on this continues.
The questions tend to be “Yes or No” type questions or very broad and general, “What type of software are you using for X.”
You jump around from one area to the next thinking you’re covering ground. But, the problem isn’t just under the surface. It’s much deeper.
What You Should Do Instead
I want you to master the art of the follow-up question.
How? → It starts by recognizing 3 human patterns:
1. People tend to speak in generalities → Help them speak in specifics
If they say, “I’m getting a lot of leads” → I’m asking, “What is a lot?”
If they say, ”I’m closing around 30% of my leads” → I’m asking, “How do you know that number?”
If they say, “I want to get better at sales” → I’m asking, “What does better mean?” or “What would better look like for you?”
When someone answers your question you have to be thinking, “What am I unclear about with what they just said?”
2. People ramble → Help narrow the focus
When you ask a question, you may get a rambling monologue for 4 1/2 minutes with many pieces of information (that may be related or not)
It’s important to take a step back and reestablish a direction.
→ First, summarize what they said and confirm you captured the essence of it.
→ Next, pick one specific area and focus on drilling down to learn more.
→ Finally, go back to the other points, if relevant, and do the same.
What they said could end up being a 10-minute back and forth exchange of relevant challenges, needs or buying signals. You lose out on that if you just skip on to your next question.
3. People have different meanings for words → Help to define them
There are so many buzzwords floating around out there and you can’t be certain that the way you define them is the way they define them.
If they say, “We have to get approval from leadership” → I’m asking, “What does ‘leadership’ mean? Is that a direct boss, a board, etc? “Do you get to have a say in the vendor or do they make the decision with the details presented”?
If they say, “The costs are more than expected” → I’m asking, “Which costs are you referring to, the annual cost or the upfront?” or “What costs were you expecting?”
If they say, “We are looking to streamline our processes” → I’m asking, “What do you mean by streamline?” or “How would that look if done correctly?”
Think about how you can gain clarity
The most important thing is that you are speaking the same language, understanding what they mean with what they say, and finding specificity with the problem.
Founders that continually struggle with sales do so because they don’t effectively get into the nitty gritty details. They hang out at the surface.
You might have captured the right information to quote the project but you haven’t captured the right information to sell it.
Diving deeper into the details solves this.
Action Item
Pull out a recent sales call and watch it back.
See how you respond after a prospect answers your questions.
→ Do you jump to another “surface level” question?
or
→ Do you clarify and go deeper?
Start there. Having the awareness is the first step.
Once you recognize it, you can’t unsee it.
*** If you’re not recording every call, you absolutely need to be. I use Fathom and found it’s the best tool out there for recording and analyzing sales calls. And, it’s free!
![]() | That’s all for today! If you wanted to say hello, reply to this email or catch me over on Linkedin The best way you can support me is by passing this newsletter along to a fellow founder or shout it from the rooftops on your socials! until next week! just get started, Brian |