Four Questions About Sales (Most CEOs Won’t Like Their Answers)
I’ve been doing this for twenty years. One thing I’ve noticed.
CEOs who have a broken sales organization usually know it. They just can’t name the specific thing that’s broken.
So they hire. Or they swap out the CRM. Bring in a new VP and wait to see if anything changes. Sometimes something changes. Usually it doesn’t.
Here’s a faster way to figure out where the problem actually is. Four questions. Answer them honestly.
1. Do you know your real close rate?
Not what your team reports. Not what the pipeline says. What actually closes, from a qualified opportunity, by the time a deal either signs or dies.
Most companies don’t know this number. And most of the ones who think they do are working off pipeline stages with percentages attached. Qualified is 20%. Demo is 40%. Proposal is 60%. Those numbers weren’t calculated. Someone set them as CRM defaults and the team accepted them. So reps mark deals at 60% because the deal is in that stage. Not because they have information that tells them the deal is likely to close.
That’s not a close rate. That’s a guess dressed up as a number.
If you don’t know your actual close rate, that’s the answer to the question.
2. Are you still in deals you shouldn’t be in?
Your VP should handle this. Your sales manager should handle this. But somehow the deal requires you. Your name has to be on the call. Your credibility has to be in the room. The prospect won’t move without you.
I see this constantly in mid-market companies. The CEO closes the big deals. Has for years. They’re good at it. So they keep doing it, and nobody develops the skill to do it without them. The sales team takes orders. They handle the small stuff. The real deals wait for the CEO.
At some point you need to be building the business, not closing every deal over a certain dollar amount. And buyers start to notice that your team doesn’t instill the same confidence you do. That’s a structural problem. It doesn’t fix itself.
If you can’t step out without deals slipping, the organization isn’t working.
3. Is your pipeline a forecast or a wish list?
I had a CEO tell me his team had $20 million in the pipeline. Two months later they missed their number by 30%. The pipeline wasn’t $20 million. It was about $5 million of real opportunities. The team didn’t lie. They just believed what they wanted to believe.
Here’s what usually happens. Reps put deals in the pipeline when there’s interest. Not when there’s a qualified reason to buy. Not when there’s a committed timeline. Not when they’re talking to someone who can actually make the decision. Just when someone says “yeah, we might be interested in that.”
So you look at 40 opportunities and feel good about the quarter. Then 15 push. Eight go dark. The ones that close come in lower than forecast. You miss by 30%.
The pipeline looked full. It wasn’t.
If you’re not confident your pipeline reflects reality, it probably doesn’t.
4. What does your sales manager actually do each week?
Not in meetings. Not in reports. In the actual development of the people under them.
There’s a difference between a sales manager and a sales leader. A sales manager reviews numbers. Runs the Monday call. Holds people accountable to activity. A sales leader sets the standard. Develops people. Listens to calls. Debriefs. Coaches reps on how to have the conversations that win deals.
Most companies have sales managers. They call them sales leaders. They’re not.
The tell is simple. Ask your VP of Sales: “When was the last time you listened to a rep’s call and debriefed it with them?” If they have to think about it, they’re managing. If they can name the call, the rep, and what they worked on, they’re leading.
If the answer is “reviews numbers” or “runs the Monday call,” you don’t have a sales leader. You have a sales manager.
If you answered two or more of those with some version of “I’m not sure” or “not well,” something in your sales organization is broken.
Most CEOs I work with already sensed that. They just didn’t have a name for it. So they kept making moves that felt productive. New hire. New comp plan. New kickoff. New playbook. More activity. More emails. More dials.
Those moves don’t fix it because they’re treating symptoms. The root cause is always one of four things. The people, the process, the skills, or the leadership. One of those is your constraint. Maybe more than one. But once you know which pillar is broken, the fix becomes a lot clearer.
I’ve worked with over 150 companies on exactly this. I wrote a book that walks through how to figure out which pillar is broken and what to do once you know.
It’s free.
Click here to grab it
Adam
