Find What's Holding Sales Back, Then Fix It With Your Team

Most sales problems get solved before they're diagnosed. Hire more reps, replace the CRM, bring in training, change the comp plan, buy a tool. Each can be the right call. The question is whether it fits the situation you're actually in.

I start by finding the constraint. Build the change with your team, on live sales work. Equip managers and sellers to keep it going after the engagement ends. Scope follows the problem.

The three diagnostics below are the same ones I'd start with. Use them on your own; they work whether or not we ever talk.

## Diagnostic 1: Which sales situation are you in?

Answer these four questions in order, using actual deals, manager conversations, and onboarding experience.

1. Can we explain how we win and teach that approach to another seller? If not, you're in a [**Build**](/build) situation.
2. Does that approach still fit our customers, offer, and buying environment? If not, you're in a [**Rebuild**](/rebuild) situation.
3. Can our people execute it without excessive manual work or missing information? If not, you're in a [**Modernize**](/modernize) situation.
4. Can we extend it without overwhelming management and delivery capacity? If you're ready to grow and this is the open question, you're in a [**Scale**](/scale) situation.

The first "no" usually tells you where to start. You may find more than one. An established account team might need to modernize while a new team needs to build. Keep it proportionate: one struggling rep doesn't mean the whole organization needs a rebuild.

## Diagnostic 2: Give practical AI a job before you buy it

Before buying or rolling out any AI tool, finish this sentence:

"We need to help **[person]** do **[specific job]** better, and we'll know it's working when **[observable result]**."

Two examples:

- "We need to help **reps** do **account research before first outreach** better, and we'll know it's working when **they form a useful account hypothesis faster and can show the evidence behind it**."
- "We need to help **managers** do **1:1 preparation** better, and we'll know it's working when **they arrive with an accurate view of recent customer conversations and one specific behavior to coach**."

If your team struggles to fill in the blanks, spend more time understanding the work. A clear job makes the technology decision easier.

## Diagnostic 3: The comp plan audit

Your comp plan is already telling reps what to do. This checks whether it says what you meant.

1. Write down your three biggest sales priorities.
2. For each one, walk through exactly how a rep gets paid for advancing it. Include the time, effort, and risk involved.
3. Compare that with what the same rep could earn by spending that time somewhere else.
4. Check for the common mismatches:
   - You ask for margin, but commission is paid on revenue.
   - You ask for new customers, but growing an existing account pays the same for half the effort.
   - You ask for a new market, but income depends on what closes this quarter.

Finish with one question: if a rep followed your comp plan exactly as written, would you get the sales organization you're trying to build? If not, the behavior you keep asking for may require reps to work against their own financial interests.