Grow the Deal™ begins with understanding how your customer actually feels about working with you. Getting the Grade™ is my technique for making that conversation specific: ask the customer to give your company a letter grade, explore the reasons behind it, and agree on what would earn a small improvement. Start early, repeat the conversation, and build a stronger relationship before pursuing expansion.
A signed contract tells you the customer chose you. It doesn’t tell you how they feel about that choice a month later.
The original salesperson may have moved on. A new account manager may have inherited the relationship. The customer is now experiencing the product, implementation, and support rather than evaluating a promise.
And somewhere inside that experience, expectations are being met, exceeded, or missed. You need to understand which before the renewal becomes an urgent conversation.
Account teams can become comfortable with an absence of complaints. There are no alarming support tickets, no angry emails, and no requests for an executive meeting. An occasional check-in produces, “Everything’s fine.”
That can feel reassuring. It still leaves important questions unanswered.
The customer may be pleased. They may be too busy to discuss a problem. They may have stopped expecting a resolution. Different people inside the same account may have completely different experiences.
Waiting until renewal to investigate creates two competing conversations. You’re trying to learn whether the customer is happy while asking them to commit more money.
That timing can make both conversations harder. The customer knows you want a signature, and you may find yourself responding to concerns with concessions before you fully understand what is wrong.
I run a business, which means I spend time on both sides of the sales conversation. I work with many vendors, and a substantial group of those relationships comes up for renewal near the end of the year.
I’m generally happy to keep using a vendor that serves us well. Switching takes work. A modest saving doesn’t automatically make that disruption worthwhile.
But the renewal approach many account managers use gives a buyer room to negotiate.
Imagine an account manager named Laura calling in October. She introduces herself, mentions new developments, asks how things are going, and notes that the renewal is coming up.
By November, her message has become more focused on getting the renewal completed. By December, she’s warning about a possible interruption in service.
I’ve described this pattern because I’ve been the buyer letting those messages pile up while already intending to renew. When I finally speak with the rep, I can ask for a discount against the pressure of an approaching deadline.
The rep has spent months wondering whether the account is at risk. The conversation now revolves around price and timing.
The missed opportunity was earlier in the relationship. Laura needed a meaningful reason to speak with me in March or June, when neither of us was staring at an expiring agreement.
Getting the Grade™ gives that conversation a purpose.
Whoever owns the customer relationship after the sale should get involved within the first 30 days.
That applies whether the original account executive keeps the account or hands it to another person. Your internal structure shouldn’t leave the customer waiting months to establish a relationship with the person responsible for helping them succeed.
The early conversation is an opportunity to understand what the customer believes they purchased, what has happened so far, and where expectations may already be drifting.
After the introductions, ask: “Could you give us a grade as a vendor right now? A letter grade, like in school.”
The customer may point out that implementation isn’t finished. That’s fine. You’re asking about their experience at this moment, based on what they can reasonably evaluate.
Explain that you want a starting point. You’ll return to the question as the relationship develops.
Your customer may initially say, “You’re doing fine,” or, “No problems so far.”
Politely ask again for a letter grade. A specific grade creates something you can explore more closely than a general reassurance.
Once they answer, keep your reaction neutral. Don’t celebrate an A or become defensive about a C. Ask why they chose that grade.
Then ask, “Why else?”
Give them room to think. The first answer may describe the most obvious issue. A later answer may reveal the concern they weren’t sure they wanted to raise.
A customer might begin with an unresolved support request and eventually explain that their team feels unprepared to use the product. Those are related concerns, but resolving the ticket alone may leave the larger problem untouched.
Keep listening until you understand the experience behind the grade. You’re giving the customer permission to be candid, including about things you would rather not hear.
A comfortable B can deserve more attention than you initially think. Early in a relationship, a middling grade may reflect disappointment the customer is softening out of politeness. A C deserves prompt investigation.
The explanation determines what you do next. The letter helps open the conversation.
When the grade reveals problems, thank the customer for being direct. Acknowledge the frustration they’ve described and make improving the experience the immediate priority.
Then ask for a manageable next step.
Suppose they give you a B-minus. You could say, “Let’s speak again at this time next week. What could we do between now and then that would move your grade from a B-minus to a B?”
That is the size of improvement I’m looking for: one-third of a letter grade. A C-plus becomes a B-minus. A B-minus becomes a B.
Jumping straight from a C to an A can suggest you haven’t understood the seriousness of the concerns. It also invites a wish list you may have no ability to deliver.
You cannot promise a new product feature in seven days because someone wants it. You may be able to arrange useful training, resolve a specific issue, or clarify who owns the next action.
Agree on something meaningful and realistic. Confirm who will do it and when you’ll review the result.
The modest target keeps the conversation focused on progress you can demonstrate. It also gives the customer a clear way to tell you whether the work helped.
At the next conversation, ask the same question. Get the grade, ask why, and explore what else contributed to it.
Don’t assume that completing your task automatically improved the customer’s experience. The customer gets to tell you whether the work made a difference.
If the grade improves, find out what mattered. If it stays the same, learn what remains unresolved. Then agree on the next small improvement.
This may take several conversations. Some relationships need weeks or months of work. Some may never reach the standard you’re trying to achieve.
That is information you need.
Keep a record of the grade, the reasons, and the action you agreed to take. That history helps you see whether the same frustration keeps returning or whether a new issue has appeared. It also gives a colleague something more useful than “the account seems healthy” if responsibility changes. Capture the customer’s own explanation accurately. You want continuity in the relationship, so the next person can understand what was promised, what was delivered, and what still needs careful, specific attention.
Grow the Deal™ requires judgment about where expansion is appropriate. An account with unresolved disappointment needs attention to that disappointment BEFORE another sales proposal.
My rule is to earn an A relationship before making major expansion or advocacy asks. You want the customer to be able to explain why they value working with you.
An A or A-minus deserves the same curiosity you brought to the lower grades.
Ask what earned it. Ask what else improved. Let the customer describe the changes they’ve noticed and the value those changes created.
Those details help you understand which parts of the relationship matter most. They also prevent you from assuming that the work you found hardest was necessarily the work the customer valued most.
Thank them for the candor that helped you get there. Their willingness to explain the problems gave you something useful to act on.
Then, where the relationship supports it, introduce a different question:
“Would you like to know your grade?”
By this point, the customer understands the routine. You’ve listened, acted, and returned for their judgment. There’s room for a conversation about participation on both sides.
In this exchange, I often use B-plus as the starting point for discussing how the customer could participate more fully.
The explanation needs to connect to real opportunities or prior commitments. Perhaps they agreed to introduce you to another team and haven’t yet made the introduction. Perhaps there’s a relevant event or customer story they’ve expressed interest in contributing to.
This is a conversation between partners who have done useful work together. Keep the tone appropriate to that relationship. (Nobody needs detention from their software vendor.)
A customer’s obligation to pay the bill doesn’t automatically obligate them to become your reference or case study. Make a reasonable request, explain its purpose, and give them room to decide.
An introduction may lead to another department that could benefit from the product. A discussion of future needs may reveal an appropriate expansion opportunity.
Grow the Deal™ becomes more practical when these conversations follow demonstrated value. You have a basis for asking the customer to consider what else the relationship could accomplish.
Becoming a trusted advisor also involves how you support your customer’s standing in their own professional world.
Once you’ve earned the relationship, look for opportunities to help their expertise reach other people. Invite them to speak at a relevant event, participate in a council, contribute to an article, or share experience with peers.
Choose opportunities that suit their interests and responsibilities. Your customer may have something valuable to teach that goes well beyond your product.
Your logo doesn’t need to appear on every opportunity. Helping them share a useful perspective can have value even when the audience never sees a sales pitch from you.
Follow through with practical support. Make introductions, help them prepare, or connect them with a suitable organizer.
The relationship has more room to grow when both people can point to useful contributions.
Getting the Grade™ gives you a recurring way to discuss the customer’s experience before a commercial deadline dominates the conversation.
Start within 30 days. Ask for the grade. Understand the reasons. Agree on a small improvement, do the work, and return to hear what changed.
When you earn an A, explore the next opportunity with the same attention to the customer’s needs.
Grow the Deal™ starts with knowing where you stand. A customer who says “fine” has given you very little to act on. A customer who can explain their grade has given you a place to begin.
Happy Selling!®, Jeff