Sales Leadership 101: Lessons From History

2024 will be my 20th year as a Sales Leader and looking back on it, life was never tougher than during those first couple of years running small teams.

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One moment, you are a top performer with awards and club trips, next moment you are working long hours while remembering with fond nostalgia lost treasures such as accelerated commission.

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To be honest, the player/manager role kind of sucks. It brings with it all the responsibilities of frontline leadership, but with little relief from the burden of individual contribution. You quickly realise that any attempt to take on two challenging roles at the same time will always bring with it the sense of failing at both. It’s incredibly tough, yet ultimately a rite-of-passage for all senior executives and an opportunity to discover if you really have what it takes to lead.

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Drawing from my personal experience, I have two pieces of earnest advice for any ambitious sales professional with management aspirations:

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1)???? Be careful what you wish for!

2)???? Take a lesson from history...

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Traditional siege warfare has followed the same basic formula for centuries; surround the citadel, make a breach in the walls and send your armies through that breach. This presents two problems; the first of which is that the defenders now know precisely where your attack will come and will have organized their defenses accordingly. Second, armies are no different from any other organization in that they will not move decisively without being led. So, there was always a need for a young, brave, ambitious leader to volunteer for the extremely dangerous task of pushing the attack forward through those breaches.

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Throughout history this was known as “The Officer of the Forlorn Hope”. The deal was that in return for exposing yourself to extreme danger, you would be given a promotion, a cash reward and maybe a nice medal...assuming, that is, you survived. If you are a first-time sales leader, this will be sounding very familiar.

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The image above depicts Colin Campbell at the Siege of San Sebastián in 1813 performing this difficult duty. I put a copy on my desk back on my first day as a sales leader and it is still there today.

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The bottom line: As a player/leader of a small team, it is your job to

EXHIBIT THE BEHAVIOUR YOU REQUIRE OF YOUR PEOPLE.

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Whatever it is you need your people to do, whether that’s adherence to a methodology, delivering a new message or perfecting a demo

LET THEM SEE YOU DO IT.

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This simple lesson from history reminds us of one of the basic principles of leadership

YOU CAN’T EXPECT PEOPLE TO DO SOMETHING YOU ARE NOT PREPARED TO DO YOURSELF.

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Be the first to get checked-off on that method. On the next sales call, take the wheel from your rep to deliver that new message flawlessly. Role-play that tricky demo yourself in your next team meeting. Do that well and your people will walk through walls for you.

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By the way, Colin Campbell survived and later became a Commander-in-Chief in the British Army. But if history isn’t your thing, then I’ll close with a footnote just for you: Once I was interviewing an exceptional enterprise sales candidate and I really wanted them on the team. When asked what they wanted from their manager, the answer was:

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“I expect my sales manager to be a superhero.”

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That was brilliant. It instantly became my default job description for any leader in sales, so if waving swords isn’t for you, try wearing your underpants on the outside and every day seek to perform super-human feats that make your people look on and say:

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“WOW! How are they doing THAT?!”

The rest is easy.

Steve Benton Steve Kraner Jarret McKallagat Sean Hector Michael Dyer Adam Clay Ryan Solway Stephen Oram Richard Q. Gil Alter Gal Tvila Cindy Sivan Bailey Everitt Sam Islam Chris Nielsen Kevin Potts Kevin Bland