Welcome to Grind Season (Money Monday)

Welcome to Grind Season. This week, we enter the most pivotal period of your entire sales year. From now until mid-December, how you choose to invest your limited time will determine whether you end your year strong, hit your income goals, make it to the winner’s circle at President’s Club, and start next year with a full pipeline OR wallow in mediocrity, miss your number, and damage your career. 

Write Your Sales Comeback Story

If you’re ahead of your goals, this is your time to build an insurmountable lead and give yourself an unfair advantage as you enter next year. Do not rest on your laurels and coast. Grind it out and build a massive pipeline for next year.

If you’re on track, this is your time to accelerate, finish strong, and propel yourself into the President’s Club. 

If you’re behind, this is the time to shift from being defense to offense.

Most salespeople who are going to miss their annual quota already know it by now. They can feel it. See it in their pipeline. Sense it in their gut.

But what separates winners from losers is that winners use this moment as a wake-up call, not a death sentence. 

Stop making excuses about market conditions, difficult prospects, or bad luck. Start taking complete ownership of your results and your future.

Stop thinking like someone who’s behind. Start thinking like someone who’s about to write their own sales comeback story. 

Your energy and confidence level will directly impact your results during Grind Season. If you show up defeated and desperate, prospects will sense it. If you show up confident and focused, prospects will respond in kind, and you will sell more.

But whatever your situation, this is not the time to coast. This is the time to get serious about finishing the year strong.

The Grind Season Mindset

“Grind Season” is more than just a motivational catchphrase—it’s a winning mindset grounded in the unglamorous, but essential, embrace of this crucial period with intense focus, hard work, discipline, and consistent, intentional activity. 

It’s about ignoring distractions, drowning out the noise, being stingy with your time, and using every moment of your sales day to identify new opportunities and actively advance those deals through the pipeline.

This isn’t about activity for the sake of activity. It’s about deliberately and proactively getting back to the basics and fundamentals of prospecting and sales at a time in the sales year when it matters. 

Your Pipeline Reality Check

Here’s the key gut-check question you must look into the mirror and answer right now: Where do you stand relative to your year-end number, and based on that answer, what will be your next move?

To fully answer that question, begin with a pipeline reality check. Your current quota attainment tells you where you’ve been. Your pipeline tells you where you’re going.

Far too many sales professionals look at their pipeline and see what they want to see, not what’s actually there. This is especially true at this time of year when we allow baggage from the first half of the year to remain in our pipeline, hoping that somehow we might close it. But here’s the deal, during Grind Season, hope is not a strategy. 

The truth is, those deals have been dead for a long time. The stakeholders are ghosting you; they never commit to next steps, and most haven’t returned your calls in months. In the words of Sales Gravy University trainer and author Kristie K. Jones, “stalled” is not a step in the sales process.  So start by getting brutally honest and ruthless with your current pipeline.

• First, clean house. Go through every opportunity and ask yourself: “If I had to bet my own money on whether this deal will close by the end of the year, would I take that bet?” If the answer is no, move it out of your active pipeline and replace it with something else. Stop lying to yourself and counting on it for this year’s numbers.
• Second, calculate your real pipeline coverage. Take your remaining quota and multiply it by four. That’s how much qualified pipeline you need to finish the year strong. And if you don’t have it, get fanatical about building it. 
• Third, assess your pipeline velocity. Get real about how long deals are actually taking to close. This number will tell you exactly when you need to get qualified opportunities into your pipeline to close them before the year ends. You should also use the assessment to find ways to increase velocity and shorten the sales cycle. 

Recommit to Fanatical Prospecting

Too many salespeople are trapped by hope. They hope that inbound leads will be enough, that a few referrals will carry them through, or that their existing accounts will magically deliver new opportunities.

Grind Season is the antidote to this passive approach. It demands a recommitment to consistent, high-impact Fanatical Prospecting. This means establishing non-negotiable, daily prospecting blocks with a focus on creating new opportunities with a vengeance.

The No. 1 reason for missing quota is an empty pipeline, and the No. 1 reason you have an empty pipeline is that you are not prospecting consistently, using every possible communication channel, every single day. 

Advance Deals With Unwavering Decisiveness 

Once an opportunity is in your pipeline, the Grind Season mindset dictates that you move it forward with intention and purpose. This means confidently asking for and securing clear and calendared next-step commitments in every sales conversation. This decisiveness prevents deals from stalling in the pipeline, which you cannot afford at this time of year.

Likewise, you cannot afford to waste time with uncommitted buyers or unqualified deals. Do not be afraid to ask tough questions and address objections directly, because this process eliminates tire-kickers and keeps your time and energy focused on truly qualified deals that you can close. 

Embrace the Grind Season Suck

Grind Season is hard. If you want to end your year strong, then you’ll have to embrace the suck and accept the discomfort that comes with hard work and running headlong into the grinder of daily rejection.

The essence of Grind Season is an unwavering commitment to outworking the competition. It’s about the mindset that no one will out-hustle you. 

For me, this means adopting a “blue-collar” approach to a “white-collar” profession—come in early, stay late, face adversity head-on, and always make one more call. Repeat this daily and you’ll gain a significant competitive advantage.

Time is Short, Act Now

The clock is already ticking on Grind Season. It feels like you have time, but you don’t. End-of-year judgment day will be here sooner than you think. This short window of opportunity will close soon, so you have a choice to make right now.

You can keep going the way you have been and take what you get OR you can decide that this will be the most focused, disciplined, and productive period of your career.

The choice is yours. But whatever you choose, choose it now, because time is running out.

And remember, when you’re tired, worn out, and ready to go home, always make one more call. Because that one more call might be the one that saves your year.

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