10 Things Every Leader Needs to Learn the Hard Way

“You learn by mistakes. When you make those mistakes, you try not to make them the third time or the second time. You learn from them. Sometimes you learn the hard way. In football, if I held on to the ball too long, I got my butt kicked. You better make that decision quicker.” ~ Ron Jaworski

It’s something of a cliche that we learn from our mistakes, but it is true. We learn the most from our terrible bosses. And we learn the hard way from our mistakes.

Learn the Hard Way

We reflect more deeply, we ruminate. Even, sometimes, we despair… We are mortified, or embarrassed. We may even be fired or forced to resign.

But through it all, we come out stronger than before.

So here are ten things that every leader needs to learn the hard way… by getting it wrong first.

And by extension – here is permission to fail faster so that you can get on with the lesson.

Embrace complexity and contradiction, but strive for simplicity

Most people are naturally talented in one or the other of these… If you know your preference, that’s great. But you need to get stronger at the other – you need to be conversant in both.

I like understanding what makes things work, I’m what’s known as a system thinker. I almost (but not quite) see problems in images, rather than words, inside my brain. Usually, though, people who make decisions don’t want to know something’s complicated, they just want the solution – and fast.

As a leader you need to let go of the technical competence that got you promoted – you have a team to handle that for you, but you can’t shy away from it completely either. Your job now, as a leader, is to communicate things in simple language, so that anybody – your board, your customers, your stakeholders – can readily understand it. But the ability to explain things must come from deep understanding, not from a cursory glance, otherwise you’ll lead people astray.

Meditate and journal

These big jobs are hard. If you neglect your mental wellbeing, it will come back and bite you. I came to meditation and journalling after a pretty rough patch as a leader, where I was struggling to get my team motivated, and frustrated at our lack of progress.

Learn the Hard Way

As I became more mindful, and reflected more on my own contribution to the problems, I realised that the way I was delegating work was playing a significant role in the situation. Furthermore, my own frustrations at the lack of progress was resulting in me distancing myself from my team, at the very time they needed me most. I was behaving hierarchically, when they needed me to serve them.

Get to know your team

It’s easy, especially when the pressure is on, to start seeing your team as widgets rather than people. But therein lies the slippery slope to disengagement and poor performance. Sometimes small talk is actually a big deal. People are complicated multi-dimensional beings, with emotions, and desires, and feelings, and wants and quirks and – well – messiness.

Embrace it. Take the time. It will repay you umpteen times.

(By the way, this doesn’t mean you need to be best mates – just professionally collegial.)

Nobody is thinking about you… Except you

Because you’re in your own head all the time, you presume other people think about you as much as you do.

Well, bad news my friend. They don’t.

Do you know why? Because they’re thinking about themselves just as much as you are thinking about you.

This is definitely one I learned the hard way – I returned from maternity leave certain that I’d just slip right back into work like I’d never been away… but I didn’t. And here’s the thing. Work was still the same, but I had changed. My whole world had changed, so me and work had got out of kilter with each other.

I became convinced my colleagues were talking about what a poor job I was doing…

The minute you start worrying what others are thinking, you’ve lost the day.

They aren’t. So relax.

Unhook from praise and criticism

I can’t claim credit for this very pithy description (I’ve borrowed it directly from Tara Mohr’s fabulous Book, Playing Big. But the idea is important, so I’ll share it with you).

If you spend your time seeking feedback from others, you’ll get paralysed by indecision. Accept that feedback is only useful insofar as it tells you something you didn’t already know about the person proffering it – what they like, what they don’t like, how they like to be communicated with etc.

It tells you nothing intrinsic about you. Useful, but it shouldn’t be the fuel you need to keep you going, or the death knoll of your exciting big idea. Gain your motivation from internal sources – not external.

Unleash feedback

So having just decried the value of feedback about you, that shouldn’t prevent you from giving it, generously, to others. Especially when you are grateful for something that someone has done. Just remember that what you chose to provide feedback about is revealing something about you – not the other person.

It is giving them a message about what you like and don’t like. So be mindful and choose carefully. Because you should expect to see more of the things you express gratitude for, and less of the things you express dissatisfaction or dislike for.

Feedback should be a many times a day thing – not a twice a year thing.

Get a coach

You can’t fix what you can’t see. You don’t know what you don’t know. But you should always be trying to grow.

So, (feeling a bit like Dr Seuss with all the rhyming going on here) find a coach you trust, and openly engage in an open-minded discussion about how you can be better than you are right now.

When coupled with meditation and journalling, this can be a game-changer. It can also be a source of genuine feedback about your performance (unlike feedback from your boss or team members as alluded to above).

It’s important you find a coach that feels right to you. Most should offer an introductory session of some sort, and hold some sort of nationally or internationally recognised accreditation. (I don’t, but will shortly!)

Invest in your communication skills

Written and oral communication, along with body language, are the most frequently used and undertrained tools in the leader’s tool box. Everything about leadership comes down to communication in some way.

Communication is intrinsically hard – yet we think it’s simple. We can talk, right? So how hard can it be?

Learn the Hard Way

The physical act of speaking isn’t what’s hard, it’s the ‘getting the other person to understand what you meant’ part that is tricky.

So invest in these skills or expect a dampener on your performance across the board: public speaking, influence, logical argument, persuasion, business writing, marketing, storytelling… It’s almost the whole job.

Develop an owner’s mindset

Even if you aren’t the founder of the company, you should treat it like you are. You should be just as willing to pick up rubbish from the lobby as you are to create the company strategy. To replace the toilet paper as you are to help design a new product.

You aren’t better than your employees just because you are more senior in the organisation. If anything, you should be finding ways to serve them better, so that they can serve your customers.

Make spending decisions as though it was your money. Think about the future, and the long-run consequences of your decisions. That way, your success is the company’s success, and vice versa.

Find your why…

What makes you tick? If you don’t know, it’s hard to be authentic, I found mine recently and it’s been a game changer for me. I’ve never had more energy, passion, and drive. I’ve never been clearer in my decision making, and I’ve never felt more comfortable in my own skin.

I strongly recommend Simon Sinek’s Find Your Why if this is something you need to do too – the sooner the better.


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