Fix Your Sales Team in 90 Days

When it comes to revenue, a B2B CEO really only needs to answer two questions to themselves, their board and their stakeholders:

1-How much are we going to sell, and by when?

2-How are we going to sell more?

If you can’t answer these two questions with confidence, the most common instinct I see is to push harder on the sales team. Sometimes this is the right move but about ~40% of the time it isn’t. At the wrong time, pushing harder on the sales team can waste a quarter or more of time turning a bad quarter into a bad year or more.

Before you try anything, you need to know if the problem is with your sales team or is upstream in marketing, positioning, value proposition or product-market fit.

To know, ask this question: “If we could only do one thing to increase sales, would it be more appointments with qualified prospects or winning more of the deals already in the pipeline?"

If the answer is more appointments, you have a lead problem, and this isn't the piece for it. If the answer is winning more of the deals you already have, the problem is your sales team and the rest of this is written for you.

Your Sales Forecast Is Probably Built On How Your Salespeople Are Feeling About Their Deals, Not On What Their Prospects Are Actually Doing

Here's a sales standard practice that most sales teams get wrong without knowing it that distorts your forecast.

A prospect says to one of your reps: "My boss asked me to get information and pricing, please send a quote." Your rep asks their questions, sends the quote, and then moves the deal odds to 90%, Quote Sent in your Sales Process. They’ve sent the quote. The ball is now in the Prospect's court and your sales forecast shows the deal at 90%.

The problem is that it's probably a 10% deal. Nobody on the buying side really understands or has communicated to your rep the Business Problem that they actually need to solve, who needs to sign off on the decision, and what it will take to get a yes. Instead, a quote was requested and a quote was sent. That's it. 

The deal feels advanced because your rep took an action. But the customer hasn't done anything that predicts a purchase.

That gap between what your salespeople feel about a deal and what the customer has actually done is the biggest gap in most B2B sales organizations.

Deal odds are based on feelings. Feelings become deal stages, deal stages become a pipeline, the pipeline becomes a forecast, and the forecast becomes a committed number. In the worst case you then have to stand in front of your board and commit to a number that is built, at its foundation, on how a handful of people felt about their deals. 

And when your forecast misses, you can't even troubleshoot why, because the data was never real to begin with.

The fix isn't more discipline or executing harder. It's reorienting your Sales Process to observable buyer behavior instead of how your sales reps and leaders feel. Everything you need to do to get control of sales follows from this one shift.

Your Buyer's Decision Process Doesn’t Match Your Sales Process

The second blind spot is structural. Most sales processes are built around how the company sells. Typically your Sales Process is a sequence of stages that make sense from your side of the table. But the deal is won or lost on the buyer's side, and the buyer isn't following your sequence. They're running their own process.

A B2B buying group is usually doing three jobs. They are:

• The Researcher gathers information, costs, and quotes. They are typically tasked to “Get some information” or “Get pricing”. They’re typically easy to reach, pleasant to talk to, and are frequently mistaken for the buyer. They're not.

• The Champion recommends your solution and, in doing so, spends their own career capital to advance your solution internally. Their career improves or degrades based on how their recommendation and outcomes are perceived by their bosses. The Champion typically leads the buying group. They need to be equipped to sell internally, win their internal argument and politically de-risk the decision for themselves and the other members of the buying team.

• The De-Risker exists to protect the company. Finance, IT, and Legal are all incentivized to say no. Their job is to limit financial, security, and legal exposure. Their default answer is no. You need to give them as few reasons as possible to question your proposed solution.

Notice who isn't on this list: a Decision Maker. There may be one. But the larger the organization, the more likely the role has quietly morphed into a Decision Approver. Your Champion will recommend your solution to them and and they in turn will approve it, not "make a decision". Technically, yes, the Decision Approver is deciding yes or no, but funcaitonally what is happening is that all parties are positioning for denying that they are responsible if it turns out to be a bad decision.

Reps selling in this situation often don’t give the Champion the context, value proposition, and the risks of doing nothing that they need to get their deal approved.

When your sales process doesn’t satisfy the needs of each of these roles, your reps take actions that feel productive but don't map to how the purchase actually gets made. They send quotes to Researchers. They pitch features to De-Riskers whose real question is risk, not capability. They wait on a “Decision Maker” when one doesn’t really exist.

The Five Inputs That Actually Grow Sales

Now that you know about these two key blind spots, here's a way to diagnose your team and their performance that doesn't depend on anyone's gut feelings. 

There are only five inputs that determine sales performance. They build on one another, so they're listed in order. 

1. The Sales Leader. One person must own execution and the number for the team. This might need to be you until you can hire or grow the Sales Leader you need. To be successful, your Sales Leader needs to execute on focus, coaching, and accountability for your team. 

Does one person own the quota, do they produce a forecast you can actually trust, and are most of your salespeople hitting their targets? If the answer to those is yes, execution isn't your problem. If it's no, then improving these issues with yourself or your Sales Leader will grow sales faster than anything else on this list.

2. An accurate Pipeline and Forecast. This is your source of truth for how much will we sell and, by when. It needs to be right, consistently, within +/- 10%. Accuracy needs two things: a clear methodology (clear criteria for what puts a deal in each stage) and the accountability enforced by the Sales Leader that the stages recorded by the Sales Rep are accurate.

When a forecast is unreliable, one or a combination of both of these are the cause. Either the stages don't predict what happens next, or no one is holding the team accountable to calling the deals as they are. Both are fixable, but the Sales Leader needs to own monitoring and correcting the Pipeline and Forecast.

3. Sales Stages based on what the Buyer does. Your stages should mirror the buyer's decision process. Research, evaluation, decision and justification, and implementation. The criteria for each sales stage should be set by what the customer has done, not what your team feels. When you address the needs of the Researcher, Champion, and De-Riskers in your Sales Process your team will win more deals and shorten the sales cycle.

4. The right people selling to the right people. Two questions here. One, can your reps help a customer make their own problem clear enough that the customer understands what they need to do before you ever mention your product? 

People hesitate when the problem is fuzzy or unclear. A fuzzy or undefined problem makes every solution feel risky because there is not a clear connection between their problem and your solution. 

Two, are your reps reaching the person who can actually create or command budget? Or do they spend their time talking to the pleasant, available contacts who can't advance the deal? Selling to the easy-to-reach instead of the able-to-decide is one of the most common ways sales reps waste their time and lose deals.

5. Enough leads to make quota. If you haven’t addressed the four inputs above you’re losing sales because your team is not closing as many of your leads as you could be.

If your funnel doesn't put enough qualified appointments on the calendar, you're leaving revenue on the table and increasing CAC (Cost of Acquisition). 

Salespeople do need to source their own deals but there are tradeoffs. The time your salespeople spend hunting leads is time they're not spending winning deals, which is the only activity that actually books revenue and generates cash for your company.

The more you can shift their time to advancing and winning deals, the more deals they will close and the more revenue will increase.

The Bigger, Unaddressed Issue: Unspoken Agreements And Hard Conversations

Inside many teams there is an unspoken agreement not to have the hard conversations that are holding back their growth and transformation. 

This is not a formal agreement and nobody decided to avoid it. This unspoken agreement that avoids the discomfort of naming the real issue, to a colleague or a direct report or yourself, is real and it stops the critical conversations quietly so they don't happen. 

The consequences include expectations that stay fuzzy because pinning them down means admitting a hard truth or telling someone their role is changing. Deal stages stay inflated because calling a 90% deal a 10% deal means admitting the forecast is wrong, and that maybe we’re not doing as well as we’re telling ourselves, or the forecast stays unreliable because holding people accountable to accuracy feels like micromanaging.

But this isn't micromanaging. It's an act of respect to help your team have a clear view of their expectations, priorities and where to spend their time on the deals they can actually win. 

Too many companies can't get there without the conversations the culture has been organized to avoid. This is why sales problems persist in companies full of smart, capable people who can see the symptoms perfectly well but don’t know how to change them.

What You Can Do

Use this article as a blueprint and start this week.

Score your five inputs red, yellow, or green. Then review the two blind spots: is your pipeline anchored to what buyers actually do, or to how your reps feel? Do your stages mirror your buyer's decision process, or your company's sales process? You'll learn more about your revenue engine in an honest afternoon than most CEOs know about theirs.

Then start with your biggest red, make a plan, and fix it.

Then there’s the harder half. It’s the reason these problems survive in rooms full of capable people. Scoring the inputs is the easy part. The hard part is that your reds are protected by those unnoticed and unspoken agreements and the hard conversations they might lead to.

Calling a 90% deal a 10% deal means that your sales rep no longer has a story about how they’re going to make their number this quarter, or admitting the forecast number you gave your board was wrong. 

Telling your Sales Leader the role is changing means naming a truth you've both worked around. If you're inside the agreement, it's very hard to name the thing from inside the room built to avoid naming it.

Do your best to see things as they are, and have the hard conversations, respectfully. As the CEO you can create and enforce the rules that allow your team to operate through the discomfort, have the hard conversations and change the behaviors they need to change.

Going Forward

Let’s end where we began, here are the two questions you need to answer for yourself and your board. 

How much are we going to sell, and by when? is answered by inputs one through three: a leader who owns the number, an accurate pipeline you can trust, and a sales process anchored to the buyer. 

How are we going to sell more? is answered by four and five: the right people selling to the right people, with enough leads to make quota. 

I've done this work from both sides. I grew a bootstrapped B2B sales team from $750K to $5M in ARR in 36 months, and I've spent the last eight years helping more than 30 founders and CEOs with companies from $3M to $85M do the same with their own teams: Diagnosing the problems, naming the conversations nobody scheduled, and rebuilding the process around what buyers actually do.

If you want to fix your sales team in the next 90 days, here's the fastest way to start:

Join the next group Fix Your Sales Team in 90 Days CEO Session (click here). We walk through the full five-input diagnostic, how to fix your sales team, and the hard conversations that unlock each red. And answer your questions about how to do it for your own team. Click here to reserve your seat in our next session.

Already know you want to learn more to work together? Click here to book a call and spend 30 minutes understanding your key issues, what you need to accomplish, and the details of how we will work together.