"Sealing the Deal Without Selling Your Soul: The Art of Closing with a CIO"

Closing a deal with a CIO isn't just about hitting your sales quota; it's about composing a relationship that plays out in a series of trust-building movements and can last for many years to come. Let’s fine-tune our approach to ensure that the final note resonates long after the ink has dried on the contract.

The Finale, Not the Frenzy

Timing is Everything: Remember, the end-of-quarter sprint is seen through more skeptical lenses than a telescope at a UFO convention. I always take use these to my advantage.?

Pitfall Alert: Mentioning the end of the quarter is a red flag that screams "Sale on aisle five!" and I'm here to get the best value, not just clear your inventory.

Building Trust, Not Treehouses

Genuine Relationships: Coziness with the IT team should be comforting, not suffocating. Like a trusty old blanket, not a straightjacket.

Pitfall Alert: A team member lobbying for a vendor is as subtle as a marching band in a library. It doesn't just look desperate; it looks like betrayal. I watch for those things. So getting messages to me from them is often times a really big signal that might not work in your favor. I can see them a mile away.?

No December Dashes

Respect the Calendar: Pressing for a close when the holiday carols are playing is like asking for a dance when the party's over. I dont do it as a matter of policy and its the surest sign someone from my team has sold their soul when they are pushing for last minute deals.? I won't take the bait. I tell my own team members and especially in October that they better get their needs taken care of before December. The real reason is I can not go to the CFO looking unprepared or reputationally challenge who I work for. So if you have Q4 plans get them done in October and maybe November. December? It's a risk I can't take.

Pitfall Alert: Last-minute holiday hustles can leave me looking like I'm more interested in closing deals than opening presents. Let's not mix business with the eggnog.

The Uncontrollables

Factors Beyond Our Control: From budget cycles to product overlaps, these are the tides we cannot direct, only navigate.

Pitfall Alert: Trying to fit a three-year deal into a one-year space is like trying to download more RAM—it's just not possible.

Playing the Long Game

The Bigger Picture: Sales isn't a hit-and-run game; it's more like chess, with moves planned far in advance.

Pitfall Alert: As a CIO, I know you're not going to hawk the same wares until retirement. You're building a relationship Rolodex, not just a customer list.

Sowing Seeds of Trust: When you advise against an unnecessary upgrade or a premature renewal, you're planting an oak tree, not just sprouting a mushroom.

Trust-Building Examples:

"This model hasn't changed much. Squeeze more life out of it; it's still in its prime."

"The next big update isn't due till next year. Hold off on that upgrade—your wallet will thank you."

"Renew for a year now. Wait for the next wave of features to lock in a longer commitment."

"Our new product line is coming, but it's not a leap forward for your specific needs. Let's revisit when the tech catches up with your ambitions."

These things are more than just music to my ears. They show you are thinking like me and not like a QBSR. They show me that you, like me, are playing the long game. This will bless your career in so many more ways than you can say Presidents Circle.?

Closing with Class

The final act of the sales symphony should be harmonious, not hasty: Take your time get it right and hope its not Q4.

Understand the CIO's Priorities: Keep the score aligned with our strategic goals.

Long-Term Vision Over Short-Term Gain: Cultivate a partnership that grows robustly over time.?

Transparent Communication: Clarity is king; keep the lines clean and the intentions clear.

Collaborative Negotiation: It's a duet, not a duel. Let's create a melody, not a maelstrom. If it even starts to feel that way, pull back and start over.

No Last-Minute Surprises: Keep the surprises for birthdays, not business deals. No one likes any sort of contractual surprise.?

Due Diligence is Non-Negotiable: Skipping the details is like skipping leg day—eventually, it shows.

A Concluding Note: The Sales Tightrope

Let's take a moment to acknowledge the tightrope that sales professionals walk every day. Yours is not an easy job; it demands a blend of intelligence, subtlety, and tenacity that few can master. The rewards are commensurate with the challenge because, let's face it, not everyone is cut out for the balancing act you perform on a daily basis.

You have to be smart, but not a know-it-all; innovative, yet not so far outside the box that you become a red flag. It's a delicate dance of providing value without overstating, of being persistent without becoming a nuisance.

Here's the heartfelt truth: playing the long game will likely pay off more in the long run. Most of you will continue to navigate the world of sales, just as I will likely remain in the IT arena. Our paths are bound to cross again, and when they do, the trust and rapport we build now will be the currency that matters most.

So, as we close deals and build bridges, remember that the long game is not about the quick wins or the accelerators that so many of you love. It's about sustainable success, about being the trusted advisor who's called upon time and again, deal after deal, year after year.

In this game, the long game is the win that keeps on giving.

I sincerely hope this series was helpful in some way to you. If it was, that is great! Guess what, if it wasn't, It was all for my special first born at Presidents Club! I'll move to my next series of thoughts after the holidays.?

Sean