When the Selling gets Tough, the Tough get Selling

Gerard O'donovan
7 min readOct 13, 2017

Here at the-Coaching Blog-run by Gerard O’Donovan, our aim is to constantly bring value to those seeking to improve their lives. Therefore we have a policy of publishing articles and materials by guest authors whom we value and appreciate. Today’s guest author is Silvia Bailes (South Africa).

As human beings, we are born to sell. We do so from the day we are born to the day we die. We sell ourselves, our services, and our products because our personal and professional survival depends on it. Selling is a tough act that requires hard work, time, focus, resilience, and perseverance, least of all a thick skin to overcome the fear of failure and rejection.

Take my very dear friend Richard who has been chasing that ‘big deal’ all his life. Richard is a heavy-hitter who has served on the boards of some big multi-nationals. He has excelled as a business strategist, a financier and entrepreneur in various industries over a 50 year-or-so career that has spanned the five continents. Coming from a finance background, he is technically skilled, cognitively able and analytical. Yet, as much as he has collected accolades and successes, Richard has, on more than one occasion fallen, lost his fortunes, dusted himself off, and started over again. As he did again seven years ago when another chapter of his life ended abruptly with the demise of Lehman Brothers with whom he worked.

Richard pops up unexpectedly every decade or so when he visits my hometown in South Africa and regales me with the rich narratives of his travels, his life, and work. He has recently put together an international consortium to launch a new concept, at personal risk. The purpose of his last visit was to sell the concept to the consortium and to close the deal. His excitement was palpable as he described the transaction and then, somewhat out of character, he pondered: “What the hell am I doing…..here I am putting together the deal of a lifetime when I should be retired and taking it easy?”. So being a coach and with great interest in learning from my friend’s experiences I asked the obvious questions: “Richard, what makes you do it?” and “What keeps you going? “ Then his eyes lit up, because deep inside he recognized that he lived and loved his art — the art of being the ultimate salesman.

So, how does he do it and why does he keep coming back for more?

For him, it’s about busting the challenge and using his strategic, business, finance and development skills to do so. The tougher, more diverse and complex the deal, the more he stretches himself. Despite the odds, the risk, the pain, the hard work and the effort. He engages fully and perseveres with tenacity and resilience because beating the challenge is what makes him happy and satisfied. That is the ultimate love of the deal. It is what drives and motivates him and keeps him going back for more. That makes sense because he is in the flow and obviously having fun.

He adds that, in addition to challenge and skill, he knows his values — respect and integrity, because it is through these that he works and honors his relationships with others. He would not compromise his values, even for the sake of the deal. He lives his values by walking his prospective partners through the entire ‘selling’ journey — making a point of personally telephoning them to arrange meetings, driving them to and from hotels and airports, and facilitating their interactions. A genuine effort, commitment, transparency, and humility engender trust, enabling us to connect and maintain sustainable long-term relationships. Being aware of what is important to us and aligning with our values provides a framework, particularly in times of trouble and stress, which guides our behavior and decisions.

He knows who he is. Living to and being comfortable with ourselves, our ‘authentic self’, is evident in our presence: how we carry ourselves and come across to others. This shows up inconsistent behavior and actions that enable others to connect with us because they trust us when they see we are genuine.

He researches his prospective associates’ motivations and needs, is the deal about profit, or legacy, or both? He then connects to and sells to their sense of purpose. Ask yourself, does the product you sell serve the customer and the greater society and does it meet the customer’s sense of purpose? Do you satisfy your customers’ values or their sense of greed? What does this say about you?

He is adamant that he never loses his cool during negotiations, knowing when to stand back and when to take a stand. So, he manages conflict by staying cool, calm and collected when others lose it. Not only does he know how to apply the hard skills, which are imperative to structure the deal, but he has mastered his EQ, the soft people skills — effectively managing self and others. He steps in with solutions in the face of obstacles by refocusing discussions around the best interests of all, without casting blame or being judgmental. Despite being a type-A personality, Richard has learned to curb his demons as an overachiever by avoiding the tendency to dominate and demand. In its place, he has developed empathy and the art of patience which sets him and others up for success. As a result, he is the ‘go-to-guy’, the facilitator of the deal.

Because he listens, opportunity favors him. Listening is free and an ever-present gift of feedback. By encouraging safe conversation, we hear what needs to be heard. When we listen deeply we hear of problems and opportunities before anyone else, bringing us closer to our customers.

He believes in himself, his ability and the products he promotes. Finding reasons to believe in ourselves is healing because it frees us from previously perceived limitations such as fear, anxiety or negativity, opening us up to new opportunities. Our beliefs can and do dictate the direction of our lives.

He is a survivor who fosters a positive mindset. When in trouble, he hums to the lyrics of Gloria Gaynor’s ‘I will survive’, strong and positive words have encouraged him through tough and difficult times. An outlook that envisions desired outcomes keeps us focused, energized and on track. Positive attitudes, in turn, spiral and ignite similar moods and passion in others. A mindset aimed at positive, realistic outcomes, win-win and compromise is imperative from the outset where any type of negotiation is concerned. This enables us to open up to each other, abandoning vulnerability, creating acceptance and trust, building a space from where we can communicate through language that is grounded in fact, not emotion.

Richard makes effective use of his networks. He enjoys the support of an expansive international network of personal and business relationships built over time. Such a network can comprise trusted colleagues, professionals, family members, and friends with shared histories of experience, values, and purpose. They can be called upon in times of crisis for support, or, as is the case with Richard, to collaborate and work together, ad hoc, for reciprocal benefit.

And last, but not least, he never overpromises on time. The ability to deliver on time and on budget builds credibility and trust. Given too many options can be confusing. Yet, offering a limited but realistic choice of product or option is a sign that our best interests have been considered, encouraging us to make informed decisions. Recent research indicates that stating more than three benefits of a product makes people suspicious and likely to think that we are not telling the truth. So, keep it simple, real, stay grounded and avoid making false promises.

In conclusion, we summarise 10 insights from Richard’s journey:

  1. Find a challenge that stretches your skills, have fun ‘selling’ it, and persevere;
  2. Work out what is really important to you– walk your customer through the ‘selling’ journey with your values and do not compromise your values for the sake of the sale;
  3. Discover who you are, find comfort in being yourself — engender trust;
  4. Satisfy yourself that whatever you are selling serves the best interests of the customer and of greater society then sell to your customer’s sense of purpose;
  5. Remember your soft skills because they are as important as your technical skills and using both makes everyone a winner — work on your emotional intelligence and develop your self-awareness and empathy;
  6. Listen more than you speak and let opportunity find you;
  7. Find reasons to believe in yourself and your products ….what other choice do you have?
  8. Foster a positive mindset — it spirals, helps everyone to broaden and build and gets you closer to where you want to be;
  9. Nurture your relationships — your network will support you and is the key to your success;
  10. Always deliver on your promises — keep it simple, real and stay grounded.

Applying some of these insights, be it to your personal brand, the services you provide, or your products, may just help you take the ‘tough’ out of selling, and put the ‘tough’ back at you!

About the Author

RECURVE Professional & Leadership Coaching was founded by Silvia Bailes in 2010 following a 30-year career as a group executive and governance specialist in the international hospitality, gaming, and leisure industry. Silvia believes that leaders need to change old mindsets if they and their organizations are to survive the challenges of the 21st century. She would dream of changing the world by changing the mind-sets of leaders.

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