Authenticity, Transparency, and Vulnerability: Learnings from this year’s Costanoa CEO UnSummit

If ever there was a time to unlearn all that we “know for sure,” it feels like 2020 is that time for obvious reasons. This year has upended our expectations and plans – but it’s also opened the door for leaders to be more human as they help their teams through a crisis that’s testing us all personally and professionally.

Earlier this month, we held our annual Costanoa Ventures CEO Summit, which we rechristened the “Unsummit” in service to the important goal of unlearning to become better leaders. As Bob Tinker, Former CEO of MobileIron, taught us last year, what gets you from A to B, won’t get you from B to C. We must all continue to unlearn and relearn.

And even though circumstances dictated a virtual gathering, we still felt there was great value in bringing our portfolio CEOs together to learn from each other and other CEO and industry experts. We were honored to host speakers Kierna Mayo, Nick Mehta, Yvonne Wassenaar, and Dave Kellogg and were thrilled to bring in portfolio company alumni Rob Reid, Steve Carpenter, and Todd Vernon to lead breakout discussions. 

Here are just a few of those key learnings.

DIVERSITY + AUTHENTIC LEADERSHIP – Kierna Mayo, 25-year veteran writer/editor, content strategist, and brand architect

“Don’t just talk about it, be about it.” 

If you want to have a diverse company, don’t just pay lip service to the idea, Mayo says. Actually hire diverse candidates. Unsure where to start? Get to know the Black community – what their actual, everyday reality is. Get curious about where they are – look at TikTok, Twitter and Instagram – to do recruiting differently and authentically.

“Authentic leadership means being vulnerable and transparent.”

You don’t always have to have an answer, Mayo points out. That will feel uncomfortable at first but it’s also going to make you more approachable as a leader, opening the door for others to have hard conversations. You have to signal to people that it’s okay to engage and have those open-ended conversations where there is no right or wrong answer. Do that by leaning in and being the first. Don’t wait for them to bring it to your front door. Be the person in the room who says, “You know what? I was thinking about XYZ. And I don’t know the best way to approach this but I want to let you all know it’s on my mind.”

CEO MANAGEMENT – Nick Mehta, CEO, Gainsight 

“If you’re the CEO, you’re the driver of the car and you control whether the backseat passenger gets carsick or not.”

Like drivers, who rarely get carsick, CEOs have the benefit of knowing what they’re about to do, to anticipate what’s happening as they make different choices, says Mehta. But just as  backseat passengers have less visibility into the road ahead, employees don’t know which way you’re turning the wheel and why — and it can make them anxious. 

They’re riding the emotional wave of constant change and decision making, looking to you for cues to interpret it. They’ll amplify the emotions they pick up from you, he points out. So be thoughtful about that. It’s not that you can’t show emotion but you have to be aware and purposeful with them to drive an outcome. 

“Know your strengths.”

One way to understand your own strengths – as well as your executive team’s – is through formal assessment. Mehta uses the Enneagram to help people understand who they are and how they fit in with others. Having a framework creates a similar language across the company so people can quickly understand each other. This understanding also helps fuel a CEO’s interaction with the exec team. Mehta says that you need to give them the oxygen to go do things without you being there all the time.

“Make sure your manager mix is one of college and pro coaches.”

Mehta draws a useful analogy of ensuring your leadership team is one of both college and pro coaches. “College coach” managers are great at molding people earlier in their careers — like the college coaches helping young athletes hone their skills on the field and in the classroom, they’re looking at the whole person and all the things they have to do to be successful in the workplace. In contrast, Mehta points out, pro coaches assume the person’s fully formed so they’re emphasizing leveraging that experience to get the most value. 

PURPOSE, PROCESS, AND PLANNING – Yvonne Wassenaar, CEO, Puppet

“Your company should have true and authentic purpose.”

When you have that true authenticity that’s front and center in all you do, Wassenaar says, everything is easier because why you exist is clear. She recommends keeping a hard focus on that purpose and ensuring your team understands it and is bought in every step of the way.

“Build process after the pain.”

Technology is what enables a good process or way of communicating, observes Wassenaar, but putting a process in place in advance doesn’t necessarily solve a problem or forestall one. In fact, if you put process in place too early, you can kill what’s possible. You become too slow. And when you’re new and small, your strength against the mindshare and brand power of big companies is your speed and innovation.

“Establish a no-regrets framework.”

Scenario planning is crucial, advises Wassenaar. Look ahead to three or four likely futures as a way of evaluating the outcome of potential decisions you need to make now. Instead of debating if a future is likely to be true, you think through the choices you would make if that future came to pass. Thinking through “What would we do if…” in advance gives you a playbook to use, she notes, and ensures no regrets.

NO ‘DISPOSABLE’ EMPLOYEES – Dave Kellogg, former CEO of HostAnalytics and MarkLogic

“Re-ployable employees, not disposable employees.”

The old accepted truth that the employees who got you here aren’t necessarily the ones who will get you to the next level is true, comments Dave Kellogg. But that doesn’t mean you should dispose of them – in fact, you should generally try to “re-ploy” them elsewhere in the organization. Done correctly, you can create a culture of loyalty, where people feel valued and you have institutional knowledge to draw on. As an added bonus, this kind of culture gives you the ultimate flexibility to move resources and people where they make the most sense for the business.

There were so many more learnings from this year’s UnSummit, but the one throughline all of the speakers emphasized was the importance of authentic, transparent, vulnerable leadership in driving change, knitting teams together, and building successful companies. It’s the right message any time, but in 2020, it’s exceptionally resonant. There is so much room for executives to bring their whole selves to their roles right now — and so much to be gained from that honesty especially in a challenging time.