Why Every Leader Needs a Challenging Cheerleader

I have a love-hate relationship with my personal trainer, Lucas.

I hate it when he makes me do one more round of burpees after I’ve already done four. And I have fantasies about throwing a pavlova in his face when he chirps good-naturedly to “keep it up, you’re doing great” as I ungraciously wheeze my way through the latest workout he’s concocted for me.

I especially hate it when he gets out those calliper ‘thingywatsits’ after I’ve had a weekend of one too many margaritas and a bucket of those amazing hot chips they serve at my local, Urban.

On those calliper wielding days, I glare at him over his fat testers and think he’s the biggest meanie on the planet.

But here’s why, in the same breath, I also love him to bits:

He’s my Challenging Cheerleader. He supports me when I need it, he pushes me on the days he knows I can take it, and he always shows up for me – and my fitness goals.

Although I’m sharing with you my Challenging Cheerleader in my personal life, I think every leader should seek one out in their professional life as well.

What’s a Challenging Cheerleader?

A Challenging Cheerleader is someone who holds you to account regarding the goals you want to achieve and the person you want to become. They always have your best interests in mind and genuinely care for you in the professional realm. They’re usually a colleague or mentor or even a previous boss, maybe an internal coach. They are someone who has your back. There’s no hidden agenda. There’s no obvious power differential. They’re someone whose judgement you trust. And you trust them.

Most importantly, they care for you enough to tell you the truth, not just what you want to hear. The challenging cheerleader is like Simon Cowell on The X Factor, who tells you that “actually no, you can’t sing”. Or in my case, that “actually, the extra margarita does count if you want to lose that extra kilo before Christmas.”

Particularly as you climb the corporate ladder, the number of people who will be brutally honest with you decreases, but the need for it increases. Hierarchical power packs a big punch – we just need to think of the fairy tale The Emperor’s New Clothes, to be reminded of how reluctant people are to tell the boss what they really think. Not so, the Challenging Cheerleader. They’ll support, value and challenge you in equal doses. And not only for your own benefit, but for the benefit of the organisation. They’ll not just tell you where you need to improve – they’ll work with you to uncover how to get better.

When is it a particularly good time to seek out a Challenging Cheerleader?

  1. When you’ve identified through performance appraisals or 360-degree reviews, feedback, or just your own self-awareness that there’s an area of your leadership you want to improve. Enlist a Challenging Cheerleader to give you feedback – when you’re making progress and when you’re falling flat.
  1. When you’re new in a role or an organisation.
  1. If you’re a CEO (Challenging Cheerleaders are especially useful for first time CEOs). This is where an external executive coach can play the role of Challenging Cheerleader.
  1. If you‘re leading a large transformation or organisation-wide cultural change. A Challenging Cheerleader can be someone to bounce ideas off. They can also function as a litmus test for the wider organisation or be someone who lets you know when you’re winning or when you’re getting in your own way.

In all cases, choose someone you trust, someone who you know will be honest with you, and whose opinion you respect. Extra points for your Challenging Cheerleader being different to you – diversity of thought, approach, and perspective can be extra awesome in a Challenging Cheerleader. Tell them your goals and give them permission to be honest, hold up the mirror and to hold you to account. Seek their counsel regularly.

Do you have a Challenging Cheerleader? How have they helped you become the leader you aspire to be? Have you thanked them lately? There’s no time like today.

And how can you be a Challenging Cheerleader for someone else? After all, that’s leadership in action.

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