Guest Post: Jay Ryan, How CEO’s Can Avert a Sales Storm!

How CEO’s Can Avert a Sales Storm! is shared with us by our guest, Jay Ryan, Principal, Executive Sales Playbook Advisors

Jay’s first question to business owners is “Do you have a winning sales culture? The answer to that question should tell all business owners what they need to focus their efforts on! As a former Chief Revenue Officer, Jay has spent the last 25+ years working to build a sales culture that drives repeatable and successful revenue growth!! The first step is developing a unique sales playbook that will produce wins!


It is a stormy day here. It is dark and windy outside meaning an impending thunderstorm is on its way. I have always found it interesting that big storms send out signals like the change in the wind and  the color of the sky just before the downpour and thunder bolts strike. I am not a meteorologist , and I do not play one on TV, so I cannot say this happens all the time. Yet, I find that Mother Nature often gives us these warning signs to prepare for what is to come next!

Is there a storm brewing in your sales team’s pursuits? There are often signs from the team that a bad storm is coming and unless you prepare for all that it brings, the aftermath of that storm may be devastating.

I have found that salespeople are extraordinarily emotional people. They have different ways of showing emotions but believe me, they are stewing with emotion during the sales process. Selling and buying is an emotional transaction. To be good at sales, you need to plan for the emotional changes of the situation with the buyer(their personal pressure, connection to you and the application, and changes in the market) and for the sales associate as well (pressure to close in a certain timeframe, personal rewards, engaging and guiding the correct people on both sides down the same path, and then know when to demonstrate patience or when to push for a close). Being the guide to forecast these changes is where sales leadership earn their stripes.

Isaac Smith

I find many new sales leaders think that if they just hold their teams to statistical KPI’s in order to report activity, they are doing their job. Yet they do not earn the trust of their sales associates. Sales leaders need to use their past experiences to watch and listen for signs that a storm is on its way. They need to hold their team accountable for their actions, but they must also shed some light on the situation and illuminate the associates to other possibilities in getting the deal. Plan do not just react!

Sales leaders should be asking basic questions of their associates throughout the process to help forecast what will happen next. A basic question like:

“Why now?” Why is the client so motivated or emotionally attached to owning your services at this time? If there is no urgency in the prospect, look outside to see if the skies are turning to dark clouds.

Some other questions can further help sales leaders predict the future weather pattern of the deal.

“What is the client’s buying process? Who decides if they buy and who must approve it?”

“Is there a budget? Is it seven figures? Is it six figures? Is it planned for now or next year?”

“What is the timing to get started?”

“What is your competition?”

If the answers are unknown or as my kids say ‘sketchy’, check to see if the winds have picked up because a storm is coming and the forecast for deal failure is high.

When sales associates emotionally invest in a pursuit, a deal failure wreaks havoc for their confidence. Leadership needs to be there with an umbrella long before the storm hits in order to guide the sales associate to shelter.  We all know that when a storm is averted based on Sales Leadership’s insight and guidance, the trust and emotional bond between the team gets stronger and there will be many more sunny days ahead.

The experience of recognizing which storm clouds can cause the most damage comes through education and having lived through many sales storms. Finding such a leader can be tricky. You can go the less expensive route in hiring, which likely means less experience. The more experienced hiring route usually means a more expensive leader. Budgeting is an unpleasant fact!

An option that is becoming much more prudent for businesses that need that experienced sales leadership, yet at a fraction of their normal compensation are leveraging a Fractional/Outsourced VP of Sales. Most fractional Sales Leaders have over 20 + years of sales leadership and bring with them a plethora of resources, proven methods, process, and sales execution success.

Building a ‘winning’ sales culture is a mandate for success!!!

If you’d like to learn more and have a complimentary discussion and assessment, please reach out to me at Executive Sales Playbook Advisors (



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