If you’ve been to tech events in Toronto or have followed along digitally, there’s a high chance you’ve run into Johnathan and Melissa Nightingale. Tech veterans in both Silicon Valley and Toronto, they’ve run nearly every major department of a tech company.
In an industry marred by stories of awful bosses and the awful things they have done, a dedicated focus on good management is “Toronto’s chance to get in front of this issue – Silicon Valley is not good at this right now,” Johnathan reminds me emphatically. Just today, the Nightingales released their book, How Fucked Up Is Your Management?, tackling this very issue.
I had the chance to connect with Johnathan and Melissa at Elevate Toronto Festival in September, right after their conversation on Building Better Leaders, moderated by Borrowell’s Eva Wong.
We tucked into a corner and the Nightingales shared their story. They talked about their relationship, the moment they knew they had to start a company, and their source of energy to continue working — even when things get really bad.
“We’d been seeing each other for a few years long distance. I was working at Mozilla in PR in Silicon Valley, and Johnathan was in security in the Toronto office,” Melissa mentioned.
“The book was about reaching a new audience. Running a consultancy is more scalable than being an employee, but it’s still limited.”
“We did the math, and realized that a mortgage in Toronto was cheaper than paying rent in both cities plus flying back and forth. That, and long distance relationships suck.”
After they got married — but years before starting Raw Signal — the couple would host close friends at their house, drinking whisky and talking about management struggles.
So the couple would host conversations, which eventually led to their blog, The Co-Pour (so named for the co-poured whisky at their living room gatherings).
Both were still successful tech executives – Melissa at Wattpad and Johnathan at Hubba – while The Co-Pour was gaining steam and an audience. However, it was a trip to Mexico with their kids that led to striking out on their own, founding the organization now called Raw Signal Group.
On the trip to Mexico, the kids were in daycare at the resort, but Melissa and Johnathan were hesitant to go into town. The nearest town was more than a half hour drive away, and they were concerned about their young children needing urgent help.
“It was the first time since having kids that we could really just sit and think,” recalls Johnathan.
This was in January 2017, when newly inaugurated President Trump released his first executive order banning travel to the US from seven Muslim-majority countries. While scouring on “bad hotel wifi,” looking for ways to help and raise money, they came across Susan Fowler’s article on her year at Uber.
Looking at President Trump’s EO and Fowler’s article, the couple reflected on the horrible state of affairs that tech had, at in least in some way, helped to create.
“It’s hard to say, ‘we’re changing the world, but don’t look too closely because we’re abusive and exploitative in the way we do it,’” said Johnathan.
This was when they knew they needed to do something about it, and the issue was important enough to require them to leave their jobs to do it.
“My mentor told me to find out what I was truly passionate about and do something about that topic. For me, that became management. I’d heard so many tropes about meritocracy and the ‘best idea winning’ in tech, but the reality is that those beliefs are often only true if you are coming from privilege, whether that be class, identity, or another form,” Johnathan said.
After making the decision to go on their own, defining the brand was next. When it came to naming, they immediately crossed names like “Nightingale Consulting Group” off the list.
“I was a CMO,” said Melissa. “That simply was not going to fly.”
Johnathan suggested they try the French translation of ‘Nightingale,’ which is ‘Rossingol.’ “To my American ear, I just kept hearing ‘Raw Signal,’” joked Melissa.
“The name Raw Signal resonated because we are very direct and sometimes swear – so ‘raw’ made sense – and there’s a lot of noise in the management space so we thought ‘signal’ would be fitting.”
As well, the couple was clear that the business needed to be in Toronto.
“Silicon Valley had a feeling that something big was happening when I moved there in the early 2000’s during ‘tech nuclear winter,’” explained Melissa. “Now, in Toronto, there is immense energy from a lot of people who want to build things coming together.”
Johnathan nodded in agreement, explaining that the two events while in Mexico made them realize they needed to work harder to change the world in any way they could.
For them, it was building organizational leaders.
As an employee or organizational leader themselves, they could only help one organization at a time. As consultants, however, they could help multiple organizations at once, making a larger impact.
“Raw Signal, and HFUIYM, is about making people okay with being uncomfortable. It’s about having them question their sacred beliefs.”
The couple had the Co-Pour, had already been public speaking, and now had a consultancy. The missing piece was a book, so they wrote How F*cked Up Is Your Management? a Canadian business best-seller.
“The book was about reaching a new audience. Running a consultancy is more scalable than being an employee, but it’s still limited. Many folks who read the blog may not read the book, and vice versa, so we wanted to make sure we were reaching as many people as possible,” said Johnathan.
“Raw Signal, and HFUIYM, is about making people okay with being uncomfortable. It’s about having them question their sacred beliefs. This happens in a variety of different ways, and we want to make space for people to talk about what they need to do to improve their management skills,” added Melissa.
The couple is also a huge proponent of continuous learning.
Getting better, to them, is not necessarily about gaining skills to check off on a list, but becoming more attuned to where your weaknesses are and understanding what you need to do to compensate for them or acquire the necessary skills.
“And being strong enough to say you fucked up and need to work hard to get better without it being a personal failing,” adds Melissa.
I was lucky enough to get an advance copy of the book and read it in between interviewing the Nightingales and writing this feature.
Having the privilege to get to know the Nightingales – and having Johnathan speak at VentureOut, an initiative I co-founded – I was fully expecting to love the book.
So imagine my confusion when I didn’t like it.
I didn’t know why at the time, and couldn’t articulate whether I was angry, apathetic, uncomfortable, or something else entirely, but the book fell flat for me.
I was fully prepared to chock it up to nothing and simply move on with my life, but then I remembered that Melissa told me their goal with this book is to make people sit with, and question, their discomfort.
So I dug a little deeper.
I realized, perhaps, I didn’t like the book because one chapter suggested to me that I may have authored a lot more of my problems than I cared to admit. Suffice to say, that realization stung a bit, as someone who is well-intentioned and, by and large, felt I was doing a good job.
I’m still not 100 percent comfortable with the book – or myself – as I write this, but I am starting to think that’s the point.
The books tackles some serious topics, and gives a glimpse of what is going on in Johnathan and Melissa’s heads, hearts, and lives. These are issues that cannot be solved in a couple of weeks, or even a couple of months, but I can’t say I wasn’t warned before I read the book.
Now, neither can you.