Getting Comfortable with Being Uncomfortable

Tito has grown from four to ten people in the last couple of years which is something I’m very proud of and humbled by. But when you look at our About page something that is immediately obvious is that we lack any sort of racial diversity in the team. This has been increasingly uncomfortable for me as the months and years have gone on. And this is the story of how we are addressing what I see as a serious issue for us going forward.

Tito is headquartered in Ireland, where at the last official count in 2016 over 94% of the population was classed as white. Combine that with the global lack of diversity in tech and it’s no surprise that we’ve ended up with a team of white folks. No surprise, but no excuse.

With our last two engineering hires I pushed for circulating the roles outside of our normal circles and bubbles. We did some outreach and posted on a couple of PoCiT job boards but ultimately we received few applications at all, let alone from a diverse group. The two hires we made were perfect for the roles and have been a huge asset to the company.

At that point it would be easy to say “we tried” and leave it at that, but at best that felt lazy. It didn’t sit right with me.

There are no shortage of articles, hot takes and think pieces on why diversity in a company is good for business. It really is a no-brainer. But to me, it’s nothing to do with the potential for increased revenue. It’s everything to do with getting different perspectives on our product, our marketing, our approach to business, and any other aspect of our work. Tito has customers around the globe and I just don’t think a homogeneous team can serve them effectively. We all have our biases, whether we are aware of them or not.

Waving the D&I flag is nothing without action, but to be honest I had no idea how we could have done better. I knew that this would get worse as the company grew, but since we weren’t planning to hire any time soon this was pushed down the priority list.


Admission was a small conference we ran for event organisers last year in Chicago. In planning the event where possible I wanted the speakers to be Tito customers  and so I asked the team for recommendations. Maria suggested Kim Crayton. I wasn’t previously familiar with Kim’s work, but I did a bit of research, liked what I saw and we asked her to join the lineup.

Ticket sales for the event were nowhere near what we were hoping for and for a while we went against our better judgement and started inviting anyone and everyone trying to bump the numbers with discounts and complimentary tickets. However we quickly realised this wasn’t working and we’d rather give the smaller audience an amazing experience rather than simply put bums on seats. You can read more about that decision on our blog.

During this period we had an unpleasant interaction with an individual who we invited. He took offence to our outreach and was offered a comp ticket but after downsizing and subsequently realising he was pushing his own agenda we rescinded the offer.

Once uninvited, this individual then took it upon himself to @reply all of our female speakers on Twitter telling them that participating at our event would harm their reputation. Not good.

I tried to get ahead of this by emailing all the speakers, sending them a full transcript of the conversations with him and recommending that they didn’t engage. I left my phone number and said that I was available if anyone wanted to talk.

30 seconds after I sent the email, my phone rang. It was Kim.

She told me in no uncertain terms that this wasn’t something she could ignore and she would be responding. She wasn’t going to let some random person publicly talk about her reputation.

I was apprehensive, but I understood. Before we ended the call Kim said something that I will never forget. I quipped that it was these kinds of interactions that had made Twitter a terrible place to be. Her response?

Twitter is only a terrible place for you privileged white dudes. Twitter has given me a voice I would have never had.

If that isn’t a perfect example of a lack of perspective, then I don’t know what is.

I was already learning.

You’re a racist

The day before the conference I found myself in a small group chatting with Kim and a couple of others. She talked about her work and some of the many issues that are prevalent in the tech industry, and the wider world in general, from her perspective as a black woman in the U.S.

After nearly 20 years in tech, this was the first time I was able to hear firsthand about these issues of race from someone who had experienced them. It was also the first time I had been called a racist.

“You all are”. There isn’t an ounce of bullshit with Kim.

I was shocked. I felt defensive. She doesn’t even know me! But I listened to what Kim had to say. She commands attention and her statement was followed by an explanation.

Kim believes that until white people are willing to open up to the idea that everything we understand about race and diversity is a lie then there’s no conversation to be had. Racism is ingrained in our society. We need to start recognising it. It’s going to get uncomfortable. And we need to be okay with that.

Next steps

Kim’s talk at Admission was a powerful wake-up call. That, and having spent a couple of days around her, I knew Kim could help with our lack of diversity at Tito.

Her first suggestion was to attend her job fair for marginalised groups in tech. Although we weren’t actively hiring we would be there to coach and to talk to a more diverse group of individuals.

Secondly she invited us to be the first sponsor of her popular podcast, again, with the idea of getting us in front of a more diverse audience. 

Both coaching at a job fair and sponsoring a podcast were things that were new to me, and to be honest, a little uncomfortable and intimidating. Particularly as we are a company of white folks. But—as previously mentioned—until you are willing to get uncomfortable, nothing is going to change.

As part of the podcast sponsorship, Kim offered us a number of weekly leadership coaching sessions over video chat. I personally found these incredibly helpful and it was the first time since the company had started that we had made time for these kinds of discussions.

For example, Tito now has three clear core values—integrity, excellence, delight—that Kim helped us solidify from our hand-wavy notions we had previously. This has been something that we’ve brought into our day-to-day work. Every decision, every piece of copy, every code or UI change, can all be measured against the three values.

We’ve decided to continue with the coaching. As a company we try to act ethically in what we do, but while intentions are good, as one of two white males leading the company, we’re aware that our perspective is limited to our lived experiences.

Any of this sound familiar? I don’t think our story is particularly unique, and in the industry we serve, for all the talk of D&I in events, I still see mostly white faces at the events I attend. There’s still a mountain to climb.

Our plan is to share what we learn as we go. Hopefully some folks will find it useful. As always, please feel free to get in touch if you have any questions or comments.