The Tao of Churchill in Sales

Tony Hughes

The Tao of Churchill in Sales

"I am easily satisfied with the very best." So are your customers so put your best foot forward and work to impress them with insight and genuine listening. General is the enemy of specific and mediocrity is the enemy of excellence.

"We are masters of the unsaid words, but slaves of those we let slip out." Listening is everything in enterprise sales. You learn nothing while talking so aim to speak only 25% of the time. When we wing it, we will never fly. Be prepared, prepared to actively listen and be fascinated by the customer.

"Courage is what it takes to stand up and speak; courage is also what it takes to sit down and listen." Sometimes the boldest card to play is silence. Sometimes the most powerful strategy is to take a conversation off-line and have coffees with other players in the deal, outside of the political power-base. The next time you sit down with a CXO, ask an insightful question about something you read in the annual report or in their social media stream. You'll impress them that you took the time to provide research.

"Never give in, never give in, never; never; never; never - in nothing, great or small, large or petty - never give in except to convictions of honor and good sense." Perseverance is critical in seeing major deals through. You must have the eye of the tiger burning bright, never faltering and never giving-in. Mastery of complex enterprise selling is hard, like climbing Mt. Everest hard. Those who have done it for decades make it look easy but make no mistake; they've earned the right to stand upon the mountaintop. It's a humble road and a lonely one at that. When in doubt, go with gratitude and return to the fundamentals. Build pipeline proactively and get in front of your dream clients by knowing what an ideal prospect looks like.

"There are a terrible lot of lies going about the world, and the worst of it is that half of them are true." It's imperative that you integrate new methods with traditional wisdom. Getting caught-up in the latest sales training that provides a silver bullet can really be latching on to a red herring. Respect the candor in your coaches; be open to constructive 360 degree feedback. It's the only way you'll truly be mentored and improve. I think this quote is also a call to leverage sardonic humor as a weapon for good.

"Courage is going from failure to failure without losing enthusiasm."In baseball, you only need hit the ball 3 times out of 10 to look like a hero. In cricket as bowler, you're only 3 deliveries away for completely turning the match. Keep that fighting spirit. Remember, the IASM in enthusiasm means: I Am Sold Myself. Champion salespeople give everyone their best. They refresh and restart each day treating each engagement as if it were their first or their last. Be fully there and give it your all when you're in the arena. You are the face of your company's brand. First impressions are crucial and the first experience she has with you, may have repercussions on all future interactions with her company.

"The price of greatness is responsibility." It's a very big honour to close a huge deal. You represent the precious brand of your company and your own reputation is also at stake. Understand that everything will rise or fall with delivery of the promise. Manage expectations all the way through. Closing the deal is the beginning of delivery - signing the contract is the beginning of a long-term relationship. You are only successful if your customer is successful and happy with your solution, service and support.

"History will be kind to me for I intend to write it." Humbly choose your own destiny by being intentional with the sales activities that actually make a difference. Identify and commit to the KPIs that create results. These include the number of calls you make, contacts InMailed, meeting planned and executed. Take control by creating three times pipeline coverage as a minimum. Focus on the leading measures that influence the static lagging measures. Incredibly, revenue itself is a lagging measure you really can't influence. Understand the causal relationship between your actions and the business outcomes that they drive.

"A pessimist sees the difficulty in every opportunity; an optimist sees the opportunity in every difficulty." If it were easy then they wouldn't need you. Be a problem solver who is positively paranoid... that may sound like a contradiction, breakthrough entrepreneurs like Steve Jobs were described as thinking this way. Optimism can actually positively influence revenue and prospects can sense it. Running through every possible deal scenario and fully mapping the account strategically will give you the confidence to run a winning strategy that you deserve to feel optimistic about.

"I'm just preparing my impromptu remarks." What I love about this quote is that even the extemporaneous can be planned. Be ready for what you will do off the cuff by role-playing with your colleagues. Never leave even the slightest detail to chance. Know the customer's organization soup-to-nuts and your own solution, inside-out. Most sellers go about 10 feet deep into the water. You must dive deep into the bottom of the ocean to get the pearl... and avoid the giant squid of the status quo or enemies in the account seeking to eliminate you.

"Continuous effort - not strength or intelligence - is the key to unlocking our potential." In the end, it will come down to work-ethic applied consistently over time, persistently and with tenacity. (See my post on sustained self-discipline.) Many would say that selling is a numbers game but it is actually a game of strategy and sequence just like Chess. You can move the pieces ever faster and keep playing the game over and over again. Unless you get smarter with pattern recognition, deduction and predictive analysis, you will not see an increase in winning. Over time you develop more skill and a sixth sense at prediction. The harder and smarter you work, the 'luckier' you will become so embrace Churchill's principle here.

"You have enemies? Good. That means you've stood up for something, sometime in your life." If you have a great idea about how to transform an account and you present in the boardroom to a dozen executives, rest assured a few may try to block you. You may have made some 'frenemies' along the way here. People can be duplicitous due to competing motives or politics in play within the customer organization. Press on - it's critical to crusade for ideas of integrity that are indeed good for the client. Have their best interest at heart and transcend negativity with cunning and goodwill.

"The farther backward you can look, the farther forward you are likely to see." We must learn from our mistakes and the wisest people also learn from the trials and triumphs of others. Be a student of history and of all those who have trodden the well-worn halls of your customer before you. Internal knowledge transfer is critical. Do not take a key account for granted. Take the time to study how it was won and why they bought - know the narrative and the hard data. Research the client's success and any challenges they've had implementing the solution along the way. Study the history of the deal to improve your future ability to grow the account.

"Please be good enough to put your conclusions and recommendations on one sheet of paper in the very beginning of your report, so I can even consider reading it." Such a genius example of the busy executive or world leader for that matter. Brevity is the soul of wit. Always write the executive summary first; well before anyone on the team starts providing detail. This keeps everyone on message and helps them link the 'what and how' to the 'why and when'. A forty-slide deck is a quantum leap backward. Never forget that the purpose of the first slide is to captivate the audience to move to the next. When communicating to key executives, use powerful imagery and brevity of words - practice economy of language. Have a document to leave behind that provides all the data and verbiage. The best advice I could give to sales people looking to ascend in their career is to take courses on writing. The pen is mightier than the sword and senior level executives with MBAs will very much appreciate relevant displays of emotive yet logical eloquence backed with evidence in an appendix.

"If this is a blessing, it is certainly very well disguised." There's something somewhat zen about selling. Sometimes something very bad occurs and turns out to be a stroke of good fortune. At other times, your 'happy ears' may deceive you. You're dead in the water by EOD but keep the boat steady. The best deals take time and build from a simmer to a boil. Count your blessings such as a warm referral but don't be too quick to mistake a curse for a blessing in disguise. I've seen an in-the-bag million dollar enterprise deal, shrivel up in an instant based on internal politics, external events or a competitor who hacked their pricing at the last minute. Success is about being the person worthy of it, learn form every failure and challenge - it makes you who your are. Remember, lessons in life are usually repeated until learned.

"I like a man who grins when he fights." Practice insouciance. Enjoy the negotiation. Enjoy the battle. When it gets grim, find the élan vital. Personally, the most fun I'm having is when I'm solving the biggest, thorniest problem. I love to coach teams who are in the heat of a major deal and need to find a way to get things unstuck. Just like a cycling professional in a grand tour, enjoy the suffering - it's what eliminates the competition.

"Attitude is a little thing that makes a big difference." A positive attitude, thriving in the face of adversity, is how careers are made. Leadership is an inside job. I can think of several major deals that incumbents lost based on attitude issues with their sales person. Skills and qualifications do not differentiate - they're just a ticket to the dance. Attitude and execution is what makes a person stand out.

"Difficulties mastered are opportunities won." The greatest challenge of your life will be mastering yourself, learning to keep cool, grace under pressure, wrestling your fears and self-destructive tendencies, doing what is needed at the right time whether you feel like it or not. Every time you conquer an insurmountable challenge, you build that mental muscle. Churchill understood that a diamond is created by extreme pressure. There is dark before the dawn just as he lead the world out of a darker chapter of history. If you're sitting at the tail end of the quarter feeling defeated, know that your luck is just about to turn if you've earned it. That's the fun of sales - the uncertainty and the unknown. The challenges make success all the more satisfying. If it were easy, it would not be as rewarding.


Tony Hughes is ranked as the #1 influencer on professional selling in Asia-Pacific and is a keynote speaker and best selling author. This article was originally published in LinkedIn where you can also follow Tony's award winning blog. Also visit Tony's keynote speaker website at or his sales methodology website at

Main image photo by Flickr: cliff1066™


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