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“Be compassionate.” With Mitch Russo & Bill Flynn

People do not care what your product does. They only care what your product does for them. If you can understand their struggles and what kind of progress they are trying to make, you will be a welcome partner in the process. You also have to have integrity and not sell them something you know […]

People do not care what your product does. They only care what your product does for them. If you can understand their struggles and what kind of progress they are trying to make, you will be a welcome partner in the process. You also have to have integrity and not sell them something you know will not work… even if they ask for it. That will always come back to bite you in the end.


Asa part of my series about how to be great at closing sales without seeming pushy, obnoxious, or salesy, I had the pleasure of interviewing Bill Flynn.

Bill is the best-selling author of the book Further, Faster — The Vital Few Steps that Take the Guesswork out of Growth.

He is a multi-certified growth coach, with certification in Foundations of NeuroLeadership, and a Certified Predictive Index Partner. He has more than thirty years of experience working for and advising hundreds of companies, including several startups, where, as head of sales, he developed or revitalized five sales teams in five unique industries.

He’s had five successful startup outcomes, two IPOs, and seven acquisitions, including a turnaround during the 2008 financial crisis.


Thank you for doing this with us! Before we dig in, our readers would like to learn a bit more about you. Can you tell us the “backstory” about what brought you to this career path?

When I was 22, I worked as a Shift Manager at Papa Gino’s slinging pizzas. I knew I did not want to do this for a living and asked my uncle, who was a local venture capitalist, for help. He introduced me to several companies. One of them was Alloy Computer Products. They hired me as an inside salesperson, my first of many sales roles, supporting regional and national distributors and resellers. I enjoyed the work immensely which mostly revolved around supporting the purchasing agents and sales teams.

From there, I had a few sales jobs before I ended up at a hot Boston startup called Open Market — one of the early darlings of the budding world wide web. I was one of the first salespeople hired and by then had honed my sales skills. I was consistently a top performer winning several awards and accolades. I continued my sales career until about five years ago when I became a leadership coach.

Can you share with our readers the most interesting or amusing story that occurred to you in your career so far? Can you share the lesson or take away you took out of that story?

At my first internet startup, we went public long before we should have, transitioning quickly to a quarterly numbers rhythm. In our first public quarter, we were going to miss analyst guidance by 50%. This would have been disastrous to the stock price. I had signed a large computer manufacturer earlier in the month but we could not recognize the revenue until we passed a number of their internal tests and they signed an acceptance letter.

Due to our dire public market situation, we asked them to test sooner than they wanted and they reluctantly agreed and dragged their heels. On the last day of the quarter, we came up with a plan. My boss drove to their facility to shepherd and monitor testing from their side while I worked with our team on at HQ. Luckily, this company was local. Over the entire day starting in the morning, we coordinated the testing, patches and guidance we needed to provide them during the testing process. A little after 5pm, much to our relief and jubilation, we received a signed letter saying that we passed their battery of tests and made our quarter — a nearly $2M deal!

Are you working on any exciting new projects now? How do you think that will help people?

As mentioned above, I just published a book called Further, Faster which became an Amazon best seller. It was written to help leaders build healthy and thriving businesses with less effort and time. Here is an excerpt:

“I am committed to the day when every leader can predict their business metrics and customer preferences years in advance with startling accuracy. The key is not to be a great “guesser,” but to intentionally commit time and attention to a few important long-term decisions and actively manage a system for predicting these metrics and preferences within the business process. The most successful leaders create their future! Barring impactful unexpected events, I believe this is achievable because I have seen it.”

As we are in the midst of the COVID crisis, I think this book can help leaders plan to be better prepared for future events and accelerate their recovery and growth. I have also worked with my peers to provide resources and guidance to manage the economic and human impact of the COVID crisis. They can be found on my website — www.catalystgrowthadvisors.com.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

Blair Heavey, my VP, Sales and eventual CEO, taught me to focus less on products and features and more on how those can help the prospect. The prospect’s main goal is to solve a problem or lessen a current struggle they have been wrestling with. In essence, he taught me to be compassionate and curious to be a better salesperson. He also taught me to be self-reliant, and to not accept what others said was the way to do something. Finding solutions through the “art of the possible” became etched into my mind and I carry that lesson to this day.

For the benefit of our readers, can you tell us a bit why you are an authority on the topic of sales?

I am a focused student of topics for which I have a keen interest. Sales is especially interesting for me as it is a psychological puzzle to figure out. For the first few years of my sales career, I was not very good at my craft. Once I engaged my curiosity and tried to figure out why and how people made buying decisions things changed dramatically for me. I learned that it was not what the prospect told me that I should focus on, rather what was going on in that three-pound organ between their ears.

I learned that when the brain makes a decision, the limbic system is the primary region that lights up in an fMRI machine. The limbic system, it has been said, is where a lot of emotional activity is managed. Also, I learned this “internal” decision was made outside of and prior to conscious awareness. That means the buyer based his decision on emotion first and then made up reasons to justify that decision after the fact. With this superpower, used for good, I was consistently the #1 or #2 salesperson everywhere I went. I now knew where I needed to focus the majority of my time.

I also made sure that I was selling a product I truly believed in as we give off subtle cues that are picked up by the subconscious and work against us if we do not believe what we are saying.

In summary, the combination of how the brain makes decisions and a strong belief that my product or service could truly help my customers were the primary factors that made me a successful salesperson no matter what I sold, who the customer was or what industry it was.

Let’s shift a bit to what is happening today in the broader world. Many people have become anxious from the dramatic jolts ofthe news cycle. The fears related to the COVID-19 pandemic have understandably heightened a sense of uncertainty and loneliness. From your experience, what are a few ideas that we can use to effectively offer support to our families and loved ones who are feeling anxious? Can you explain?

As I mentioned above, I have created two documents to help leaders — a planning framework and an execution checklist. The main gist of these documents is for leadership to focus first on whatever you can reasonably do to keep your teams, their families and customers safe.

Next, you must help give your team more things they can control. Re-connecting them to meaningful work goes a long way to doing that through daily huddles and reminding them how their efforts tie to the company purpose and vision.

Third, focus on cash — saving and finding new sources. Here is an example of some things I am suggesting:

  • Review your current forecast for the fiscal year
  • Update your forecasted P&L down to cash in the bank for the worst case, best case and most likely case scenario. Please note all assumptions for all 3 scenarios. Your own KPFM is a good place to map this out and then work it back to your P&L Forecast.
  • Know how many weeks of cash reserve you have at all times (minimum of 1X/day).
  • Know how much revenue decline you can cope with and when/how to take action for each scenario.
  • Know what supply chain lines are going to impact your revenues and when.
  • Negotiate with large creditors now to preserve cash.

Review local, state and federal government assistance plans (e.g. small business loans and funds made available during crises.

There are a several other things I recommend in the two documents I mentioned. They can be found here and have been downloaded over 200 times in the past couple of weeks.

Ok. Thanks for all that. Let’s now jump to the main core of our interview. As you know, nearly any business a person will enter, will involve some form of sales. At the same time, most people have never received any formal education about how to be effective at selling. Why do you think our education system teaches nearly every other arcane subject, but sales, one of the most useful and versatile topics, is totally ignored?

Our current and arcane US education system was designed just after the Civil War based primarily on what came to be known as Taylorism. Frederick Winslow Taylor was all about efficiency. He saw the system as superior to the individual. This coincided with the need to consolidate education nationwide and the US government seemed best suited for this consolidation. The government embraced Taylor’s vision. The artistry of sales was likely not something that could be routinized so, I believe, it was not even a consideration. I also believe, along the way, sales was viewed as a necessary evil and did not warrant a pedagogy as it was (and arguably still is) beneath scholars and educational institutions. Basically, we don’t rate.

This discussion, entitled, “How To Be Great At Sales Without Seeming Salesey”, is making an assumption that seeming salesy or pushy is something to be avoided. Do you agree with this assumption? Whether yes, or no, can you articulate why you feel the way you do?

Yes. Compassion. People do not care what your product does. They only care what your product does for them. If you can understand their struggles and what kind of progress they are trying to make, you will be a welcome partner in the process. You also have to have integrity and not sell them something you know will not work… even if they ask for it. That will always come back to bite you in the end.

The seven stages of a sales cycle are usually broken down to versions of Prospecting, Preparation, Approach, Presentation, Handling objections, Closing, and Follow-up. Which stage do you feel that you are best at? What is your unique approach, your “secret sauce”, to that particular skill? Can you explain or give a story?

There are many different names of stages that I have come across over 30 years of selling and leading sales teams. I see them breaking down into three main areas — pre-sales, decision, and closing (including negotiation). As an essentialist, I always focused my and my team’s energy on the front end of the sales process. If you do that well, your close ratio will increase dramatically, decision processes will be easier and the closing and negotiations will be much less contentious.

I learned at LiveVault when I interviewed 17 of our best customers and asked them what the most valuable thing our service did for them. Over 70% used the same words, “Set it and forget it.” Prior to this, we thought the main reason was “Insurance”. That is, we were a cloud-based data backup company. We thought they saw us a way to ensure that if they ever did lose their data, they could get most, if not all of it, back quickly. We were selling insurance but they were buying time. That revelation was a game changer that proved to me that focusing on the front end made all the difference. We were purchased by a large partner for 10X revenues about 18 months later.

Lead generation, or prospecting, is one of the basic steps of the sales cycle. Obviously every industry will be different, bt can you share some of the fundamental strategies you use to generate good, qualified leads?

Work with marketing to understand why our core customers purchase our solutions — not every customer, just the ones who drive the most profit but are also great to work with; not what they tell you, but the real reasons why. Context creates value and contrast creates meaning as Bob Moesta states. If you can get to the bottom of the context and contrast, you will be able to speak the language the customer uses like I discussed in the LiveVault example above.

I believe that we do not generate leads, per say, we excavate them. The best leads are those who have already been struggling with the problem that you are solving. Your primary job is to find them and pass them on to a sales person. When you call up a prospect and can say confidently that our best and happiest customers work with us for these reasons and that person recognizes that in herself, you have found a great prospect to move towards an opportunity and often a customer.

In my experience, I think the final stages of Handling Objections, Closing, and Follow-up, are the most difficult parts for mny people. Why do you think ‘Handling Objections’ is so hard for people? What would you recommend for one to do, to be better at ‘Handling Objections’?

  • Poor training and poor pre-sales work especially needs analysis. Too often, we are impatient and insensitive.
  • Hire the best salespeople based on your current ones and train them every week on all aspects of the sales cycle helping them to improve on a regular basis.
  • Build a sales playbook that can be used as a guide to help accelerate and hone their learning. I think it is okay to apply your own strengths (e.g., relationships, technical, technique) to the sales process but not for each person to create his own sales process from soup to nuts.

‘Closing’ is of course the proverbial Holy Grail. Can you suggest 5 things one can do to successfully close a sale without being perceived as pushy? If you can, please share a story or example, ideally from your experience, for each.

  1. Do a great job upfront. Am I a broken record yet?
  2. Find the best possible prospects.
  3. Be compassionate.
  4. Be curious.
  5. Be rigorous and consistent in the pre-sales process but allow for flexibility based on different contexts — the art of selling

Closing will improve tremendously if you spend more time upfront.

When I used to meet with a prospect, I would try to identify what I came to call the “bully with the juice” and ask her to describe a great meeting and great buying process outcome to help them make the best possible decision. I would then ask the other people in the room what else was important to them. Another key was to identify the people who would be using the product as they could kill the deal if they weren’t happy. Lastly, there may be others whose job or part of their job your product threatens.

I was at a meeting in NYC with a very large advertising company with my CEO and her hand-picked “sales guy”. The meeting went well according to them as they focused on their main contact who was the big cheese. However, someone two levels below him kept sharing her concerns during the meeting. The CEO and sales guy ignored her and plowed ahead. We left and they felt great since the big cheese gave strong buying signals. I was skeptical. We never got the deal. The skeptic killed it and rightly so. It did not make her life any better. It actually would have made it worse.

Finally, what are your thoughts about ‘Follow up’? Many businesses get leads who might be interested but things never seem to close. What are some good tips for a business leader to successfully follow up and bring things to a conclusion, without appearing overly pushy or overeager?

Sorry, but I am confused by this question. Are we talking about a business leader or salesperson? Please clarify and I will answer appropriately.

As you know there are so many modes of communication today. For example, In-person, phone calls, video calls, emails, and text messages. In your opinion, which of these communication methods should be avoided when attempting to close a sale or follow up? Which are the best ones? Can you explain or give a story?

I believe these are best to worst in order — F2F, video call, phone call, email, text. Having said this, context is key. If your prospect prefers texting as a way to interact through the sales process, you may have to adjust. However, I would always try to get in front of people since emotion is the biggest factor in the decision. Our brain uses external and internal feedback to make decisions so getting in front of them so they can “see” your enthusiasm, interest, compassion, you have greatly increased your chances of closing the deal and/or moving it forward. You also have the benefit of seeing their reactions to help guide you through the non-verbal minefield that is a sales cycle.

Ok, we are nearly done. Here is our final “meaty” question. You are a person of enormous influence. If you could inspire a movement that would bring the most amount of good to the greatest amount of people, what would that be? You never know what your idea can trigger. 🙂

There is a saying that the purpose of humans is to love and to work. My core purpose is to spend each working moment helping to advance the human condition through having enlightened leaders focus on the few things that truly matter to their customers and teams. I wrote a best-selling book about it. Let me know if you want to me send you a copy.

How can our readers follow you online?

www.catalystgrowthadvisors.com; [email protected]

Thank you for the interview. We wish you only continued success!

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