The vulnerability deficit


I don’t write here much anymore. It’s not for a lack of wanting. Perhaps it’s mostly a lack of time. Perhaps it’s mostly a lack of creative energy when everything is poured into work. Perhaps it’s mostly a lack of habit. One thing’s for sure is that the longer it goes without documenting the journey via the written word – the harder it is to get back into it. When you stop expressing your raw thoughts and feelings in a public forum, you go a long time between syncs. Then there’s almost so much to say, so much that’s missed, that it’s easier to say nothing at all. I’m calling this an accrued ‘vulnerability deficit’.

My vulnerability deficit ramped up when I became a true CEO. CEO in that you’re an executive of a corporation, have stakeholder expectations to manage, employee salaries to make happen, customers to satisfy, ongoing goals to achieve, and so forth. You become so careful and mindful of what you say, what you do, and how you do it that it’s better to delay your vulnerability. One day I’ll share more things in a book, I say. One day…

So, you end up focusing on communicating the wins. On curating digestible leadership qualities like being strong and cordial. You don’t want an investor to think you’re weak (heck, especially when you’re a female founder), and you don’t want your team to stop believing in you. You basically want to be a good, consistent, likable robot. But all the time, you’re just accruing more vulnerability deficit.

Melbourne-based Richenda Vermeulen, a founder of a digital agency, discuses this phenomenon in her recent post: ‘Why I’m-not scared anymore‘.

… I stopped writing publicly about personal things.

It’s was easy to talk about my passion for digital, my love for our team and the pride in our work. It was always true. It’s also safe. It’s freaking terrifying to share my heart, my intimate thoughts, my beliefs. Especially when I know that what I share can affect our income.

She was especially scared people would find out she was a Christian and that her personal opinions would affect her professional reputation.

It became easier to just stay silent, to limit my opinions to private, off-the-record conversations over coffee when it was safe to share.

As a manager, however, it’s sometimes hard to know what experiences you can and can’t talk about.

At the start of this year, I read Ian Bicking’s post on ‘Being A Manager Is Lonely‘. In it, Ian writes about his transition from programming to management, and how somewhere along the way the ability for him to talk freely about what he did diminished.

“This is a long digression, but I am nostalgic for how I grew into my profession. Nostalgic because now I cannot have this. I cannot discuss my job. I cannot debate the details. I cannot tell anecdotes to elucidate a point. I cannot discuss the policies I am asked to implement – the institutional instructions applied to me and through me. I can only attempt to process my experiences in isolation.”

As someone who loves to write and who’s also an entrepreneur, I want to find this balance and close the vulnerability gap. We’re in a time where hearing what people really think is refreshing and needed. The explosion in personalities like Elon Musk, Amy Schumer, and Donald Trump, is a testament to appreciating honesty regardless of whether you agree with what’s said or not.

So, here’s hoping for lots more content here in the coming months. :)

Image credit: Picasso

How to give and receive better feedback as a remote team

Screen Shot 2015-06-04 at 10.02.43 PM

I’m mixing things up this week with a guest post from our happiness lead at CloudPeeps, Tessa Greenleaf, about how to do one-on-ones well in distributed teams. 

From the very beginning, CloudPeeps has been committed to creating a culture of transparency, which means sharing consistent feedback — and that’s a huge part of why I wanted to join the team. It’s important to us that we keep open lines of communication on a daily basis. So far it hasn’t been too much of a challenge, as we’re all pretty tight-knit. However, even though the culture has been instilled, now is the time to cement it.

That’s why we felt very strongly about implementing pair calls [hour-long Google Hangout feedback sessions] with different team members each month. I was excited to take the lead on organizing these calls, and am happy to share how we’ve begun implementing them.

Pair call vs. performance review

If you’ve spent any time at all in the corporate world you’re familiar with the dreaded performance review. Every year at the same time you sit down in your boss’s office and listen in on how you’ve performed and how you can improve. It’s old school, it’s painful, and I don’t know anyone who gets excited for them – I never did. Not to mention, experts have been debating their effectiveness for years.

How is the pair call different? You’re not sitting in a one-way monologue listening from your supervisor. Instead, you’re in a dialogue with your peers talking about ways you can help each other be better team members.

We’ve set up a round-robin schedule where each person schedules two calls per month with two different team members. That way, we have a dedicated time to catch up with another member of the team who you might not otherwise chat with outside of daily work tasks.

So what do you talk about?

Each pair call starts with a two question feedback loop:

  1. Share two positive characteristics:
    • What about your teammate helps you enjoy working with them?
  2. Share one constructive criticism:
    • How can your teammate improve in one aspect of their work?

We chose these questions because it’s important to us that we’re always challenging one another to grow and improve, while reinforcing the positive traits we see in one another. I know what you’re thinking: pretty touchy-feely, right? At first it feels very revealing to dive into these types of questions, but we’ve found that the more we learn about one another, the better we work together.

The second half of the call is a bit more free-form. We suggest that each person chooses two-three questions from six provided talking points (below) to answer with their teammate. If they want to address other questions instead, that’s totally fine too. The point here is to get conversation flowing in a constructive way.

Suggested discussion points:

  1. How’s your workload?
  2. How do you feel your work/life balance is right now?
  3. What are the top 3 things that you feel waste your time during the day?
  4. Are there any projects you’d really like to work on if you had the chance?
  5. Are there any big opportunities you think we’re leaving on the table?
  6. Do you feel like you’re on the same page with the team as a whole?

Note: Thanks to Josh Pigford at Baremetrics for sharing their 1-on-1 call guide as the inspiration for these talking points, as well as Courtney Seiter from Buffer for sharing some of her insights from their team.

Initial outcomes

Since we’re a fully remote team, we spend most of our time online talking to one another on Slack. One challenge has been that personal connections aren’t forged quite as well when you’re always heads down on work, which is why we decided to build a little structure around getting to know teammates.

My first pair call was with our CEO and co-founder, Kate Kendall – and no, it wasn’t a performance review. What was great about having her as my first pair call teammate was that we could really test out the format. Most companies don’t instill a culture where you can provide your boss (let alone CEO) with constructive criticisms, so being in a position where it was encouraged to share feedback on a two-way street was incredible. We both identified ways we can help one another be better teammates, as well as how we can adjust our own workflows to better contribute to CloudPeeps’ overall mission.

All in all, I’ve really liked the format Tessa’s introduced and found her initial feedback practical and really liberating. The pair call questions are still applicable to face-to-face teams, and also to freelancers who can team up with an accountability buddy, so I’d recommend everyone give them a go.

Image credit: Colors of Tibet by Leona Craig Art Gallery

Startups and the freedom myth


I’ve just finished reading Ryan Hoover’s post: Startups ≠ Freedom.

He writes:

People start companies to become “their own boss” for the same reason — they seek freedom. But in most cases, it’s ironically the exact opposite. As a founder, you’re responsible to your investors (assuming you take money), your team, and your users. There’s no “two week notice” like in a regular job. It’s empowering and scary. Many romanticize startups and ignore this reality when pursuing entrepreneurship.

This came at a poignant time for me.

When I first started doing entrepreneurial things, the driving factor was about creating freedom: freedom to focus on building things without constraints; to solve problems I was passionate about and to work with people I wanted to. Freedom to work to my own productivity rhythm and schedule. Freedom to say no, and yes to new things. Freedom to experiment and explore.

Five years ago, I quit my management job, sold most of my possessions, travelled the globe and lived in Airbnbs. I was consulting and bootstrapping my first company. It was an extremely liberated state of being – highly independent with full freedom of expression.

Being the CEO or founder of a investor-back startup is a very different experience. You taste a different sense of freedom. Like Ryan says, you’re empowered and have a ton of responsibility, but you aren’t free. It’s a huge commitment and you have to really want to do it. The desire to do it is innate.

I’m lucky in that while my day to day has changed since raising funding, our product is all about putting the ‘free’ in freelancing – connecting marketing, content and community professionals with remote work gigs. If I wasn’t working on CloudPeeps, I’d actually be a Peep! I’d work on clients like Beather, be a nomad like Briana in South East Asia and start fun side projects like Tom. Witnessing people take the next step on their journey and going independent inspires me all over again.

While this post is less to do with recommendations (asides from suggesting you read this related Paul Graham essay), one of the things I’ve found helpful in my funded startup journey is allowing myself the time to still ‘live’ and have fun. If you’re going to give everything to your startup for five-plus years, you may as well do it in a format that energizes and fulfills you.

For me, that’s getting out of the city now and then to work remotely. I’ve just spent 10 days in Mexico where RescueTime tells me I’ve been more productive than at home, where I’ve checked out local coworking spaces, got on an early-riser schedule, Slacked with my team, shamelessly Instagrammed, and still enjoyed the odd comically-touristy piña colada. :)

Celebrating character and what we do when no one is watching


Last Friday evening I got the chance to see The Theory of Everything starring Eddie Redmayne as Stephen Hawking. My friends know me as being particularly obsessed with the gloriousness that is Redmayne but I point to this movie not for his talent alone.

You see, I’ve been thinking a lot about character, relationships and giving recently. What I liked about this film is that it portrays the love, support, care and commitment Jane Wilde gave to her partner as he battled motor neuron disease. The story is as much about compassion and sacrifice as it is the career trajectory of a physics genius. In a way, the hero’s journey refreshingly revolves around Wilde as the carer, not Hawking.

This brings me to character. We very rarely highlight certain attributes of the people behind the scenes – especially in the entrepreneurial or business press. I’ve been reading Susan Cain’s book Quiet: The Power of Introverts in a World That Can’t Stop Talking and early on, she discusses personality traits that were celebrated prior to the explosion of ‘the salesman’ type. Attributes that were revered pre-1920s were described by words like: “citizenship, duty, honour, morals, manners and integrity”. After this time, etiquette guides focused more on being: “attractive, fascinating, dominant and energetic”.

The book has made me more conscious of what qualities I naturally value in people. It’s given me confidence to see through the ‘jazz hands’ exterior into someone’s core character set. I’m especially inspired by those who do good deeds but don’t share them. In the days of social media, we often broadcast actions for vapid reasons like attention. It’s what we do when no one is watching that counts.

You can easily judge the character of a person by how they treat those who can do nothing for them. ~ Malcolm S. Forbes

I’m also intrigued about the future of work, with the advent of distributed teams and technology as more and more of communication is going to be based online. Therefore, it’s not those who are the loudest or most self promotional in the workplace arena – verbal orators battling it out – but rather, the writers, the listeners, those with great awareness and perception. These people might not have been heard much in the past but they can be now when our days are spent on tools such as Slack.

The environment is changing from being optimized for extroverts to one where introverts can thrive too. How we hire and vet candidates will evolve as a result. We’re moving into the reputation and trust economy, led by the influx of review-filled marketplaces, where character is center stage.

I’m excited about where things are heading. :)

Image credit: The Theory of Everything

10 ways to win at professional time etiquette

time I think of the last year and a half I’ve spent in New York as professional finishing school. If there’s anywhere on this planet where people are stupendously busy, it’s this place. It definitely took me a few months to settle into the rhythm. Combine this experience with recently fundraising, and I now feel incredible mindful of everyone’s time. So, without ado, I wanted to share 10 tips on how to win at professional time etiquette:

1) For the love of humankind, be direct with asks

Growing up in England and Australia, I was taught to be the opposite of direct. Skirt around issues, don’t address things head on, be tirelessly polite and pad lots of superfluous info around a lone ask. What I’ve now learnt is that one of the kindest things you can do for someone’s time, is to be as direct as possible. Don’t ask someone for coffee if you can put something in a one-sentence email.

2) Do double opt-in introductions

When I receive an email with the subject line: “Introduction…” my heart sinks. Connecting someone to another without asking the person if they want to opt-in, in a professional context, isn’t a favour to the recipient – it’s often a burden. In the days of overflowing inboxes, managing requests and day-to-day work – we can be plagued with guilt of not being on top of it all. The best referrers understand signal over noise – what each party is looking for. Over time when you build up trust in a professional relationship… use it wisely.

As Fred Wilson writes on AVC:

“When introducing two people who don’t know each other, ask each of them to opt-in to the introduction before making it.”

If you’re the one asking for an intro, include the context and a blurb that the introducer can easily copy across. Make it easy for people to help you.

3) Bcc the introducer post introduction

Once you have that intro, reply! It sounds super obvious but there’s been countless times when someone has sent an intro to me and the requester didn’t reply. Don’t be that person! When you do reply, move the person introducing you to bcc so they see you’re on it but you’re not clogging their inbox. Simply say thanks and that you’re moving the introducer to bcc in the email copy. No more getting stuck on irrelevant back and forths.

4) Don’t ask questions that you can easily google

Please don’t ask what someone’s email address is via social media when you can easily find it on the web. The same goes for other minutiae like addresses. If I’m sending a calendar invite through for a meeting, I’ll find the office address online (if it’s not on the website, look in their email signature, Foursquare/Yelp data and so forth).

If you’re reaching out to someone for advice, make sure you’ve read what’s out there first. Every man and his dog seems to have been interviewed about their journey or write a blog with their thoughts these days. Don’t make people repeat themselves.

5) Don’t abuse Facebook messages

This depends on personal preferences but I’m less of a fan of using Facebook messages for work comms. In a way, I’m glad Facebook is now splitting out the messenger app so I don’t have to install it and can switch off from another inbox to manage. If you want to say something important and have a request, don’t send it via Facebook. It’s likely just going to sit in someone’s ‘Other’ section unnoticed or just annoy them while they’re busy wading through the latest click bait in their feeds!

6) Calendar invites or it’s not happening

If you’ve arranged to meet someone or are hosting an event – calendar invite that thing up! Forget Facebook events invites or group text messages, New Yorkers send Paperless Post invites that you add straight into your calendar. It often takes weeks to get on people’s schedule here – you’ve got to make sure you’re literally on it. If you’re finding scheduling is taking up a lot of time, check out services like Zirtual or

7) Do phone calls

I have to admit, I used to hate phone calls… I’d much prefer an email. When I first moved to New York, I was surprised at all the phone call suggestions verse in-person meetings. The thing is, getting around the city takes a lot of time so why spend two hours out of your day commuting then having coffee, when you could fit it in an half-hour phone call. The same goes for email – if you’re forming work relationships, don’t ping emails back and forth, New Yorkers pick up the phone and hustle.

8) Do your background research

Preparation and research beforehand will make your meetings. Don’t spend time asking basic questions – the more you can deep dive, the livelier, more interesting and memorable the conversation will be. If you’re fundraising, for instance, go in knowing what companies/founders someone’s invested in, what their investment thesis is and if you’re at the right stage (e.g. What’s their average check size?). It’s likely not worth both of your time, if these things don’t align.

In terms of insights, Refresh is seriously a great app – it offers a nice (and often a bit too ‘stalkerish’) overview of the people you’re meeting with. It’s actually made it onto my phone’s homescreen it’s been that useful.

9) If you’re not 10 minutes early, you’re late

Australians are known, well, for being casual with time. It’s quite okay to ‘rock up’ five to 10 minutes late to a meeting there. I mean, it’s obviously not great manners but most people do it. Fast forward to when I moved to New York, and started working with my team member who preaches arriving well beforehand. Over time, I’ve stopped scaring her by arriving in the nick of time – and now give myself 10-15 minutes before any meeting.

10) Follow through

Pipeline’s Natalia Oberti Noguera recently said at a conference:

“Fortune is in the follow up.”

All of the above tips are nothing if you don’t follow up and follow through. Following up makes it worth it and is the ‘getting stuff done’ part – make sure you get your follow ups done within a few days post-meeting.

Anything else to add? Leave a comment below!

Image credit: The one and only Salvador Dali’s The Persistence of Memory

The Daily Gratitude: a complement to the stand-up meeting


I recently started a new company where I’ve been heads down doing a lot of testing and building. Part of this experience has been working with a new team that works remotely.

From day one, we’ve started to think about our culture – and the focus on culture has been inspired a lot by our advisor Joel Gascoigne and the crew at Buffer. (You can view their culture deck here.)

Among many things, like kindness, humility and authenticity, we deeply value gratitude. The thing about gratitude though, is that it’s not just an attitude – it’s a practice.

Vulnerability research professor and TEDster Brene Brown discusses the cultivation of gratitude in these videos here and here.

“These folks shared in common a tangible gratitude practice. They either kept gratitude journals, they did a ‘1234’ every day, they said something out loud that they were grateful for, or they said grace at dinner.”


“It’s gratitude that makes us joyful.”

Joy is an incredible emotion to harbour while building a company as there’s always more that needs doing and moments of pure contentment are fleeting. Joy is like an energy snack you can pull out when you’re exhausted by the startup marathon.

There’s been a lot of focus on the practice of mindfulness – meditation, yoga, breathing and so on – but I’d say the practice of gratitude has as much of an impact on the balance and outlook of ‘self’.

Gratitude also has a scientific relationship on happiness. You may recall this Soul Pancake video that went viral last year.

With all this in mind, we’ve formalised our gratitude practice at CloudPeeps via ‘The Daily Gratitude’ – a verbal or written note of thanks we share at the end of the day. While our standup meetings in the morning talk about achievements, tasks and blockers, mostly related to work, it’s our gratitude sessions that reflect back on our progress and joy.

Here’s two examples from our sessions:

“I am feeling a deep resilience and confidence with what we’re doing – and that feels so good.”

“I am grateful to be able to completely trust you. Really awesome.”

What’s nice is that we’ve begun to incorporate some personal moments (like simply enjoying a walk in the park on a sunny evening), which means the process is more holistic and contextual.

So, have a go at practising a Daily Gratitude session – I’d love to hear how it goes.

Image credit: Oil Painting of the Dog Star, Deb Anderson

I can’t decide if I want to write in British or American English anymore so bear with me.