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From WTF To FTW: The Sales Playbook Cure
Nothin' turns what should I do next, or how do I answer that question around faster than a sales playbook - even if it is only you selling
Tim Kilroy
April 25, 2025
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It's Fri-YaY - Let's Learn Some Stuff
Free Style Jazz Is Cool, But It’s Hard To Dance To Improvisation
Back in the olden days (the 1990s) I thought I was pretty snappy at sales. I could think on my feet - every once in a while I was funny - and people generally seemed to like me. I thought I was so fetch. (I know, it’s not gonna happen)
During the dot com boom, I had the opportunity to work with guy, Tim M, and he & I were working on a potential deal with Microsoft. I was the subject matter expert and he was THE sales guy. My boss asked me if I was ready for the meeting. I told him what I had planned, and my boss said, “Sounds good!” Tim M, asked me the same thing, I told him the same answer, and he looked at me and said, “Cancel your next two days. You aren’t ready.”
Over the next two days, he blasted all of the business unit battles that were happening at Microsoft. He jammed product strategy & market strategy into my face until my ears bled. He pummeled me with questions about our product (I didn’t know half of the answers…and I was the “expert”.) Every time I went searching for an answer or didn’t have a benefit at the ready, he would just shake his head in disgust. At the beginning of the second day, he shouted at me:
“This isn’t f*cking improvisational jazz. We are doing choreographed dance moves that match their rhythm exactly.”
We had the meeting. It was like a Viennese waltz. He lead, they followed. They added a wrinkle, he shifted effortlessly. They threw irrelevant blockers, and he stepped over them without so much as a raised eyebrow. After that meeting, it took another two months for the paperwork to get done, but he closed the deal with his prep and focus. After the meeting, he updated his sales pipeline on the plane, and marked “commit”, meaning that finance and management knew that the deal was as good as closed.
Forecasting? Hmm…Don’t Think I Know How That One…How Does It Go?
Over the years, I have still channeled my inner Miles Davis and done a lot of improvisational jazz while selling. The obsessive planning and preparation that Tim M showed didn’t often seem worth it for deals that were smaller, or ones where I could just “feel” that someone was going to close. I got lazy.
A decade later, I was trying to sell my agency to a much larger agency. Their CEO and CFO wanted to see our sales forecasts, and they wanted some detail on how we constructed them. Well, I didn’t have a CLUE. They were asking me questions that I wasn’t prepared for. They were asking for future surety based on proven logic and process.
Apparently, during that time, I went to my wife’s family reunion in Vermont. I honestly don’t remember any of it because I spent 14 hours a day constructing and reconstructing the future of my agency in a defensible way in a spreadsheet. Then the next day being challenged my the CFO on my data or thinking. It sucked. (BTW, I’ve seen myself in photos from that vacation and have no recollection of ever being in that place!)
My “vibe” forecasting & my lack of repeatable, dependable sales process punched me in the face SO hard that it was a miracle that the acquisition ever closed and I am sure that my lack of rigor cost me somewhere around $100K in lost value because apparently, serious business people didn’t work on vibes back then.
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The Sales Playbook Isn’t A Map. It’s an Epic Poem, Like The Odyssey.
A handful of years later, when I fired up my next agency, I knew that I wanted to capture some bigger fish. We had some nifty technology ideas that would only work with big budgets and lots of data. And I had the notion that this tech stack and thinking was going to be worth A LOT. I wasn’t going to let this magnificent vision in my head be defeated by jazz or vibes.
I started by planning every week with target outcomes. At the end of the week, I would map my actions to the target success or failure. I started building a process so I had the best chance of repeating the things that created positive outcomes. (BTW, you might know that I am a full steam ahead ADHDer, so this kind of tracking and mapping was torture.
So I quit that sh*t hard.
The micro focus on actions to success is probably great for some people. But for me, it was a killer. So, I thought about the things that made it easier for me to pay attention. I’ve always been a writer. I’ve always been pulled along by a narrative arc.
So, I decided that it would be easier to write the bones of a great story that I wanted to follow and enjoy. So what started as a narrative that kept me on track and engaged in the process got more complex.
So everyone who reads your book knows the plot, you start with the characters - your agency and the target clients - it’s a love story against all odds. You send your agency on a quest to find their true love. How are they going to find the customer? What do they need to pack to survive the harsh mountain overpass? When they see their true love for the first time, what are they going to say? When the bad guys come along and threaten to break up the love story, what does your hero agency do? When your true love is unsure that they want to run away with you…how can you grab their hand and lead them to even greater adventures?
Want A Sneak Peek At The Bones of A Sales Playbook?
I’ve outlined an epic love story, full of passion, obstacles and magic check it out.
🎧 Cool Podcast Episodes (with extra sass)
How to Run a Sales Discovery Call (80% Close Rate) – Selling Made Simple Podcast
“If your discovery calls feel like a bad first date (‘So uh…what do you do?’), this 13-minute episode will punch you in the face with structure and actually make you sound like a professional instead of a desperate magician pulling rabbits out of hats.”
A Discovery Call Masterclass – Punch B2B
“Finally—someone admits that discovery calls aren’t about ‘building rapport’ over your shared love of Labradoodles. They’re about finding business pain and politely sticking your finger in it.”
Why Most Salespeople Fail at Discovery Calls (And How To Fix It) – 30 Minutes to President’s Club
“Listen to this before you waste another hour being the ‘friendly neighborhood salesperson’ who forgets to actually sell. Spoiler: You’re not Batman. You need a plan.”
How To 10x Your Discovery Calls – Sales Playbook Podcast
“Discovery call feeling flatter than gas station sushi? This episode shows you how to prep, listen, and ask questions like you’re building a million-dollar lawsuit, not ordering coffee.”
📚 Nifty Blog Posts (now with 100% more attitude)
Sales Playbook Guide: Examples & Templates for Success – Salesforce Blog
“If your sales playbook is a sad Google Doc no one’s opened since 2021, congrats—you’re normal. Salesforce shows you how to build one that doesn’t suck and actually makes your team some money.”
How to Build Your Sales Playbook – RAIN Group
“Because ‘let’s just wing it’ isn’t a sales strategy—this guide walks you through building a playbook based on what your closers are actually doing, not what some McKinsey intern thinks they should be doing.”
How to Create a Sales Playbook That Sticks – Spekit
“Breaking news: Your dusty 97-page ‘sales manual’ is trash. Spekit shows how to build a ‘living’ playbook that salespeople don’t immediately pretend doesn’t exist.”
Enterprise Sales Playbook 2024: Strategies & Templates – Docket AI
“Got a sales team big enough to make Slack look like a food fight? You need a real grown-up playbook. This one’s for the companies whose sales orgs have org charts thicker than War and Peace.”
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