6 Things You Suck At When You’re A Newbie CEO (But You’ll Get Better At)

You don’t need to know the answers; you need to know the questions.

My whole life I’ve moved forward. From exec to manager. From senior manager to head of department to associate director. On and on, until, one day, I found myself accidentally at the top. I was leading a start up. I was a CEO.

This was a dizzy height I’d never in my wildest moments dreamed I’d reach. Me! A freakin’ CEO! And, as so often happens, when I reached that goal, I found things not quite as I’d expected.

For a start, no matter how many blogs you read, how many inspirational entrepreneurs you follow, how many ‘how-to’ manuals you pore over, nothing — NOTHING — prepares you for CEO-dom. But we all have to start somewhere, right?

So, here are a few of things I really, really sucked at when I first landed the gig. And that I’m still trying my darndest to get better at (feel free to share your tips, encouragement and commiserations at the bottom of this post).

  1. You don’t need to know the answers; you need to know the questions.

You spend your entire career going “Look at me! Look. At. ME!”. Vying for your boss’ attention, striving to have the right answer, the best answer. Forget all of that. The most valuable thing you can do now is to start guiding the process of finding the answer.

Course, to do this, you have to know the question. This has been my biggest learning and the one I struggle with every day. Instead of diving in to fix things in my typical gung-ho way, I’ve had to learn reflection, patience, and let the smarter people around me uncover the solution.


By asking them the right questions. It’s not my natural state of being, to be more meditative in my approach. I’ve found memorising a handy list of questions that gently prompt my team to an answer has saved me time and time again.

Which leads me to my next point…

2. Stop thinking you need to be the smartest person in the room (in fact, you shouldn’t be).

This has been the most freeing, exhilarating revelation ever. I’m not alone in this! I have a team of kick-arse thinkers and do-ers that are far smarter than I could hope to be. They know their shit inside out and backwards and aren’t afraid to challenge me or each other.

By fostering a culture that encourages free thinking, that respects one another’s skills and knowledge, we’re already ahead of the curve. We collaborate more effectively, challenge each other robustly (but respectfully) and we continue to move forward.

More importantly, my business is made stronger by the people I surround myself with.

I don’t subscribe to the notion of “to be a great leader, get out of their way”. All teams need a unifying vision, a sense of purpose and the safety net of knowing they’re not alone, either.

I’m always around to gently correct the steering wheel when needed and offer advice when it’s asked for (pretty often it’s me that actually needs the advice).

My team knows they’re not alone and we build a stronger bond of trust.

3. Have a vision and share it. Every. Single. Day.

Before signing on to be CEO, I kinda thought that if you have the prerequisite smarts and the passion, you were already winning.


Turns out that actually, your vision, your personal and business beliefs, your holy raison d’etre trickles from top down to create a culture that shapes your entire business. I mean, I knew this, but I didn’t KNOW this.

It’s a responsibility that I hadn’t anticipated but that I’m conscious of, every day.

My vision defines our values, our attitudes and our behaviours toward each other and our customers. Our business achievements. Failures, too. But by consistently trying to live those values, the culture begins to take form.

Keep reminding yourself and your team of why you do what you do. I’m learning to be true to myself and to be ok if it doesn’t always resonate with another team member. It’s not everybody’s walk, but it’s mine. And that’s important to me.

4. Slow down and learn how to have conversations.

As CEO, you’ll often be left grappling with the broader picture stuff. You’ll reach out to Bob or Susie or Rachel and distract them from their important work so they can help with a concept you’re considering.

What the hell, they (rightly) ask, does she want this for? Without context, you’re not leading; you’re demanding. If you want your team onside, be honest.

Share as much information as you can. Help them see what you’re trying to achieve. Communicate. As a fast and impatient thinker, I find it the hardest thing. I assume too much knowledge of what’s in my head and wind up with a team that are confused or, worse, waste their energy delivering something that wasn’t what I wanted.

Take more time than you think is required to brief them fully. Give them the opportunity to contribute and chances are that together you’ll come up with a better solution.

5. Give yourself permission to think.

This bigger picture stuff is fascinating and seductive. But it also needs head space #lotsof. I used to feel guilty about taking time out of ‘doing’ things in the business. My thinking time was pretty much from 2am to 4.30am.

Not healthy for anyone.

Nowadays, I’m pretty good at giving myself slack to spend a half day or more reflecting, planning, reading and researching. Without this time, how can I possibly steer the business forward?

As every leader worth their salt will attest, to succeed you need to be working on your business, not in your business.

6. Make sure you’re having fun (because if you’re not, sure as shit nobody else is, either).

I really struggled with having to be the grown up. For some reason, I equated being CEO with having to be mature, reserved, sensible.

But that’s not me.

I mean, I can be, but I’m happier being energetic and positive. And that’s the kind of culture I want to work in. Where a positive mindset is encouraged, where we care for each other, where we do things as a team. I don’t want to sit in a silent sterile office for nine hours a day, everybody head down.

Who does?

OK, maybe the tech guys would kind of like that, but even they’re starting to warm up to my Spotify list.

So, make sure you’re having fun — even when things are hard. In fact, especially when things are hard.

There, that’s my list. I could actually write about a hundred more items here, but that’s probably enough for now. Thanks for reading my article. It’s my first Medium post, so I hope you like it. If you do, just hit the heart.

Oh, and please share your learnings and experiences as a newbie CEO in the comments below.

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