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You’re Doing It All Wrong — Choose A Leader Not A Company.

Image Credit: The Ringer

I’m a naughty boy — I’ve been window shopping for careers.

What I’ve done for the last six months is meet hiring managers and hear their pitch. Normally people do it the other way round. We look for company perks, the layout of the office, working hours and maybe even how far we have to commute every day.

This criteria is ridiculous. These factors will not give you long-term fulfillment from your work.

There’s an X Factor in your career that you’re missing: Choose a high-quality leader and nothing else will matter.

Why does the leader you choose matter?

That’s an easy question to answer.

The leader you choose matters because they decide the following:

  • Whether you get to move up in your career
  • Whether you get to make decisions
  • How your day is structured and whether they have a say over that
  • Who else will end up working with you

Crap leaders breed more crap leaders.

Crap leaders bring rookies in who have no grasp of how important the responsibility is of being a leader. These same rookies abuse their power and make your work life hell.

You get a shit laced buffet of inflated egos, toxicity, complaining, backstabbing, micromanagement and then sprinkled on top you get my favorite: revenue, revenue and more revenue talk.

In my experience, the more you talk about revenue, the less you get it. Focusing on revenue dehumanizes a business and makes us subconsciously feel like robots with a quota.

Leading is very different from being led.

Choose a leader that lets you take the lead rather than being told what to do and being led.

My first leader.

He was the one that made me forget about window shopping for companies and to choose a leader instead. Why?

Well because he taught me about positivity, leadership and doing the work. Every week we’d sit down and talk about work and life. We’d then watch one TED Talk video each week.

The company and product I was selling was a piece of junk yet he showed me that none of that mattered. In the twelve months I worked for this leader I learned more about myself than any other time in my career.

He taught me there are no shortcuts; he stopped me from complaining about some of my underperforming colleagues; he showed me kindness.

While everyone else was laughing at my decision to take a break from entrepreneurship, he was building me up.

That’s a leader I want to work for. Finding a quality leader will stop you caring so much about the company.


The other thing I learned is that good people follow leaders around from company to company. I once heard of a leader in the advertising space that migrated across more than 100 people from their previous company.

When I asked one guy why this occurred, this was his reply:

“Wherever she goes, we go. She gets us.”

The choosing a leader process.

When I met each leader over the last six months, I narrowed my criteria down to four things:

  1. Do they value output or hours worked?
  2. Do they understand emotional intelligence?
  3. Are they obsessed with experience or do they understand that a YouTube Video can teach most skill gaps?
  4. Do they value people? Not like how every bullshit startups says that culture is king. I mean really value people — to the point where they understand that the main difference between companies is the people.

These four questions led to some interesting results.

The concept of time (1).

I typically started out by asking about whether a four day week was an option. Many leaders tripped up on this question and instantly said no.

This straight away tells you that they are obsessed with time, not output. There are people I work with currently who work three days a week and achieve more than those who work five or even six days a week.

“Choosing a leader is about finding one that is going to let you have the freedom to pursue side hustles, hobbies and even take advantage of personal development opportunities”

Strangely enough, when I have time to do things outside of work, my workday excels. The obsession with time is the old world of work and you don’t want to work for a leader that values this way of working.

What if you have kids and need to work less?

What if your side hustle takes off and you need some extra time back in your day?

What happens if you decide to do a startup?

Image Credit: Alexander Kosolapov

Real leaders don’t care about time because they understand that everyone has an expiry date. One leader that really impressed me loved an idea I told him which I believe in.

I told him that anyone that works for me is going to leave or replace me and I’m going to help them to do so. After 1–2 years, if they aren’t growing, they’re unlikely to build up the skills to replace me.

I told him this:
“I’m intentionally looking for people to replace me. I have no interest in being here forever because then I’ll become stale. I want new challenges and I want to breed more leaders.”

The hiring manager I shared this idea with loved it. It’s not surprising that he made it onto my shortlist.

A strong grasp of the superpower which is emotional intelligence (2).

Many leaders do not understand emotional intelligence.

These hotshots piss off customers, suppliers, internal stakeholders and other leaders. I’m obsessed with working for people who get emotional intelligence because they tend to be the ones that understand compassion, kindness and dealing with human emotions which affect results.

Image Credit: TheLadders

I didn’t discover the power of emotional intelligence.

In fact, Google has been hiring for this trait for more than a decade. Brilliant leaders get emotional intelligence.

The hilarious idea of experience (3).

One particular leader said to me that I couldn’t work for them because I didn’t have enough contacts in the retail industry.

Thanks to LinkedIn, you can message almost any decision maker you want and get in front of them with a bit of emotional intelligence and an understanding of mutual value.

Another leader said to me that they want five plus years experience. The role was leading a team that sets up Instagram ads. As a joke, I told them I had the experience and then spent a few days learning how to run Instagram ads.

I did the interview and by magic, they thought I was experienced enough. What they didn’t know was that I’d Googled Instagram ads the week prior and self-taught myself.

Experience is overrated. Many of the worst people I have worked with have loads of experience and yet they are closed minded.

Because these individuals have the experience, they think they know it all. This makes them closed minded and they often miss new revenue opportunities, new innovations within their industry and completely different ideas which don’t line up with what their experience tells them.

Experience is nice, but open-mindedness is even better.

I can remember meeting a CEO once in the education space and he said to me that his ideal candidate would be someone that comes from a left of centre field like aviation. He’s obsessed with knowing how someone with no experience, who’s done nothing but pilot planes, would teach millennials about business.

Photo: Nathaniel Goldberg

How would they think?
What would dealing with crisis’s look like?
How would a pilot monetize knowledge?

Now there’s a leader you want to work for. Abandon these leaders who are looking for square pegs that go into square holes. People are not that simple and business is definitely not that easy.

Truly valuing people (4).

The number of times I hear in the business world that “We value people” blows my mind.

These same leaders are the ones that haven’t spoken to their direct reports or their front line sales team in over twelve months. It’s easy to attach a people first statement to your company motto and then just never talk about it again.

You can pulse check the culture of your company all you want, but it’s still not enough. An understanding of people trumps everything in business.

What I’ve learned as a leader is that when you help people achieve their personal and professional goals, the KPI’s take care of themselves.

Let me say it another way:

“When people feel like you give a shit about them and they know you’re helping them to make their life better (and grow) they’ll fucking bend over backward to do whatever you need them to do, no matter what it takes”

Valuing people is not about corporate jargon, or slogans or mission statement: it’s about actually giving a crap about people and most of all demonstrating it to them. Talk is cheap.

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Tim Denning

Tim Denning

Aussie Blogger with 500M+ views — Writer for CNBC & Business Insider. Inspiring the world through Personal Development and Entrepreneurship — timdenning.com/mb