Balancing the Grind with Amy Benson, CEO at Diolog

Amy Benson is the CEO at Diolog, a two-way investor communication software startup.

Let’s start with your background! Can you share with us your career journey and what you’re currently up to?

From the moment I left school I’ve always been reluctant to commit to a specific discipline in fear that I would be limited and stuck on a certain ‘career train.’ My career journey is cross-disciplinary, explorative and still evolving. 

Currently, I’m the CEO of Diolog, a two-way investor communication software startup. Diolog was established about 18 months ago and most recently, we were lucky enough to win the SmartCompany x AWS Pitch competition ahead of our hard market launch in about a month’s time.

Diolog addresses the pattern of one-way communication evident in current investor relations practices where investors are left with little to no opportunity to reciprocate communication or build a relationship with the companies they invest in. 

I’m sure many startup founders would agree that CEO really means Chief-Everything-Officer. Each day I’m working between product design, customer acquisition, marketing and finance. It’s exactly how I imagined my dream role. 

Prior to establishing Diolog, I worked in a boutique venture capital firm as Digital Strategy Director working across a varied client portfolio managing socials, creating websites, investor communication, pitch decks and marketing channel strategy. 

My passion for startups began when I worked in a startup at university and was able to experience startup land (including a WeWork office) for the first time. I knew that working in a startup and leading a team was something I wanted to do, I didn’t know that in the future it would be my own startup!

We’d love to know what a typical day is like for you. Could you describe a recent workday?

Morning (on an office day)

• 6am: Wakeup, gym, or movement of choice.
• 8:30-9am: Start work, I usually like the first hour or two of the day to myself to set priorities, write my non-negotiables and assess any problems that have come up since yesterday. I am definitely more productive in the morning, so try to tackle any deep thinking requirements or urgent tasks as soon as possible. 
• 11am: Check Trello, make sure the team is on track, update cards and fill in gaps. (We love Trello!)
• 11:30am: Internal catch-up and collaboration on tasks in progress (e.g. content writing, website optimisation, socials, competitor research).

Afternoon

I try to schedule meetings and engaging activities in the afternoon, because it boosts my energy when the afternoon sugar low is real!

• 12:30pm: Have lunch with a friend from university who reached out wanting to learn more about Diolog.
• 1:30pm: Diolog software demonstration.
• 2:30pm: Daily tech team meeting. Discussing any issues, product questions or bugs.
• 3pm: Meeting with a potential VC partner.
• 4pm: Finish off any incomplete tasks for the day, approvals, team check-in and respond to emails. 

Working in a startup means fitting many disciplines into one day (i.e. sales, product design, marketing, finance). I never really know how many hats I might switch between throughout the day.

Evening

• 6:30-7pm: Get home, shower, dinner, relax!

Can you define work-life balance for yourself and share with us your approach in maintaining it?

For me a good work-life balance is the sweet spot where you can successfully manage (or fit in) your health, work and life priorities. What are your priorities? Mine usually revolve around getting enough sleep, exercise, feeling organised and having something to look forward to.

I have quite a strict approach when it comes to ‘work-time’ and ‘life-time’ and I encourage my team to do so as well. When you are passionate about building something great (aka Diolog), it can easily become all-consuming and bleed into non-work-related activities. This is a key contributor to burnout and by the time you realise this is happening, it’s often too late.

I believe that work-life balance is different for everyone and if you can find something that works for you that’s all that matters. 

Change is constant, and it’s essential for growth. Have you made any lifestyle changes in the past year to improve your work-life balance?

Most of my working and studying life I have definitely been a routine person. During school and university, my sister nicknamed me “robo” for my apparently robot-like nature in the way I would stick to my routine. However, in the last year or so, in an effort to balance both my creative and strategic output mindframe, I have found myself craving change and a lack of routine. 

On the days I go into the physical office I have a completely different ‘routine’ compared to the days I’m working from home. This has given me the flexibility of having multiple lifestyles in one and also takes the pressure off having to maintain a very strict daily routine.

Now, I focus on the non-negotiables I want to fit into my day or week then organise my life around that. I would encourage those reading this to learn about the 7 types of rest and question if you are allowing enough freedom in your ‘routine’ to achieve the balance you are after. 

As of June last year I also turned off all my phone email notifications. Initially it was because I was going on leave, but I’ve just left them off ever since. I dedicate time to checking my emails and they don’t take up any more time outside of that!

We’re always on the lookout for new resources! Can you recommend any books, podcasts, or newsletters that have helped you in your journey towards balance?

Podcasts I listen to frequently:

• The Diary of a CEO with Steven Bartlett
• Dare to Lead with Brené Brown
• Working Hard, Hardly Working with Grace Beverey
• The Inspired Unemployed (for a laugh)

Other newsletters/blogs I follow:

• How to CEO by Startmate CEO Michael Batko
• Overnight Success

Before we wrap up, do you have any final words of wisdom or insights on work, life, or balance that you’d like to share with our readers?

Whenever I share my experience working in a startup, especially with those who might be founders themselves or people working on projects that feel like they are never-ending, I remind them of a common phrase. 

Everyone is familiar with the saying “Rome wasn’t built in a day.” However, we don’t tend to acknowledge the second part of that saying which is “…but a brick was laid every hour.” 

This saying resonates with me because, as a founder, you have a clear and bold vision of what you’re working towards but damn, it can take a long time and a lot of hurdles to get there. I keep reminding myself that whether it’s work, mental health, lifestyle changes or social life, I might not see significant progress day-to-day, but I’m still ‘laying bricks’ every hour.

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