On Tough Conversations

“CTOs at Sunset” - October 11, 2019. ⊕This looked better on my phone. It doesn’t have a shallow-enough depth of field when focused on infinity for the shot I was trying to create.

I had the opportunity to attend my third 0111 Conference last week. This year’s emphasis was on creating a retreat-like atmosphere where CTOs and engineering leaders can let their metaphorical hair down and share their challenges and strategies for overcoming those challenges with their deeply-empathetic peers.

The final day had us break into small groups to go through an abbreviated version of Brené Brown’s Dare to Lead training. Leona de Vinne, a leadership coach and emotional intelligence consultant, facilitated the day’s events.

The group I was part of included a diverse collection of CTOs: Among others, there was 7CTO’s Growth CTO of the Year, Mr. Scott Williams of CDBaby (they still exist!), to a serial-entrepreneur-CTO, to a code-slinging, React-loving development agency founder, to… me, whatever I amServant-leader, jack-of-all-trades startup CTO on sabbatical?.

Mrs. Brown’s research led her to create a detailed list of 10 cultural issues caused by a lack of vulnerability, which the Dare to Lead book and training seeks to correct through both theory and practice. The #1 issue caused by “armoring up” and refusing to be vulnerable with your coworkers? Avoiding tough conversations! Other issues included spending unreasonable amounts of time managing problematic behaviors (#2), having a culture of shame and blame (#6), and not learning and growing due to perfectionism and fear (#10).

We had a chance to walk the room and use sticky notes to cast 3 votes on iconic corporate “flipcharts” labeled with each of the 10 reasons–which of the 10 reasons most resonated with us? Unsurprisingly, the top reason from Mrs. Brown’s research was far-and-away the winner with this crowd of CTOs. #1 was absolutely covered in stickies–43, to be precise–from a group of 70-odd people.

Each group was then assigned a cultural issue, with the instructions to, you know, just go ahead and solve the problem. Come up with some strategies to fix these problems identified across companies, cultures, and continents. No big deal, right? And, of course, our table was assigned the #1 problem: How do you stop avoiding tough conversations?

I was designated note-takerI’m definitely not a pen snob and brought my daily drivers to the conference, fully Nipponsei kit: A Midori A5 notebook, Uni Jetstream Alpha soft-grip pen with 0.7mm Uni/Mitusbishi Jetstream ink. and tasked with compiling my group’s whirling thoughts into something cohesive. After getting it all down on paper, I was asked to distill the fruit of a 20-minute discussion into a mere two sentence soundbite for the other conference attendees. Hardly room to expound on the problem. 😒

Without even more belabored introductions, here’s my notes from the group’s discussion. This is a mix of strategies to take the sting out of tough conversations and create space and context for them to happen:

• Creating a psychologically safe space to hold tough conversations encourages people to share their true feelings–creating vulnerability and letting you resolve root issues.
• Working to empower the “quietest voice” can make it easier to hold productive tough conversations, ensuring more introverted employees have their needs met.
• Anonymous employee feedback can provide direction towards what tough conversations we’re avoiding: What’s being swept under the rug or ignored?
• Separating facts from feelings, such as by having blameless post-mortems after experiencing problems, aids in creating a safe space to hold tough conversations.
• The CEO has to model having tough conversations. If this isn’t permeating the top of your org chart, you’re unlikely to see it happening between peers at the lowest levels.
• The RACIThis is an excellent tool, by the way. It stands for Responsible, Accountable, Consulted, and Informed. It’s used in product management to make sure everyone’s on the same page in terms of who’s responsible for what business processes and product development areas. Going over the RACI sheet with the senior leadership team, for the first time, is often painful. framework/exercise aids in peer-related tough conversations: Addressing perceived conflicts in who’s responsible for what.
• Similarly, having codified values/characteristics/traits/DNA for the company crates an accountability framework for conversations concerning violations of those principles. They give you a common language to aid in having a fact-oriented conversation, removing the feeling that this is a personal attack.
• Not permitting long delays between a principle’s violation and the ensuing tough conversation reduces the stress of having to hold that conversation. Reinforcing good communication practices (see Radical Candor for a treatise on this) aids this effort.
• And, I’m not sure what you could do with this one, but bold, Slack-obsessed cultures could consider adding a #tough-conversations channel. But if you’re willing to use that, it sounds as if you don’t have issues with vulnerability and humility in your organization. 🤔

Given more than the 20 or so minutes we had to brainstorm, there’s obviously a lot more strategies for creating more (healthy) vulnerability in an organization, and ensuring that those tough conversations our human nature drives us to avoid happen.

What have I missed? As ever, feel free to contact me and let me know what’s worked for you.