Operator Spotlight: Talent leader Michael Kieran

Looking for practical help and advice on an operational area that may be outside your realm? Each month we spotlight one of our talented operators, who’ll share their expertise and offer insights and ideas that may help improve your own operations. This month we spoke to Michael Kieran, Head of Talent at Tray.io

As a Talent leader, you know this year’s intense challenges manifest differently in everyone. What are some ways your team at Tray.io is supporting employees

MICHAEL: This year has definitely had challenges, but it’s also provided a lot of opportunities for companies, teams, and leaders to show how much they care about their people.  

I think that part – genuine care and concern, as well as taking accountability for the well being of your people – has to be the foundation of anything programmatic, and one of the things that came easy for us at Tray.   

For anyone leading people, I highly recommend Brene Brown’s “2 emotions that describe how you’re feeling today” question. On first glance, it may seem a touch saccharine or unnatural, but after starting a few 1:1s this way, it was amazing to see others skip the surface level reactions and actually take a moment for real introspection with real vulnerability. Most importantly, people began to speak in specifics about what they wanted to solve for in the coming weeks and where they needed support.

In addition to being a Head Of Talent, you’ve also been an Executive Recruiter. What key competencies do you think are critical for success in early-stage tech executives?

MICHAEL: I think early-stage tech executives have to love the build, and want the keys to drive their function in the best interests of the company. Those doing the hiring also have to give them the keys, have to trust that they will build their function the best way possible for the company.  

I always think about Larry David when we start an executive search. Here’s a guy that created Seinfeld, the most successful sitcom of all time — and after that extraordinary success, takes a few years off, but just has to come back and write another show, Curb Your Enthusiasm. That’s another wildly successful show he’s “ended” multiple times and then come back to. He has to get back to doing what he loves. That “Larry David Effect” is a competency worth measuring, and something we seek to understand with growth executives: Do they love the process, or the win?  

Culture addition over culture fit. As a recruiting leader, how do you evaluate this in the hiring process? Can it be measured?

MICHAEL: We take a lot of pride in our structured hiring process that ultimately provides us with a data driven, fair evaluation of someone’s potential to succeed in the role they’re interviewing for. One of the areas we pay special attention to is desired soft skills, the subjective criteria in the hiring process.

Culture addition is a great example.  At Tray, we continue to lean on our values and pillars in how we get things done, interact with our customers, and show up for each other – and then reverse engineer those pillars into attributes, evaluation criteria. From there we create calibrated interview questions and high/low evidence indicators to determine if the candidate is a culture add.  

Another approach to move to culture addition over culture fit is, instead of a hiring team asking if the candidate is hiring a culture add, ask if they’re hiring a culture subtraction. That will steer hiring managers away from the typical subconscious bias that comes with ‘fit’ and allow them to get back to the real purpose of culture addition.

You recently took on some initiatives for diversity, equity, and inclusion (DEI) in your organization. What are some ways you’ve approached integrating these two People functions?

MICHAEL: From a Recruiting and Human Resources perspective, DEI has been a priority for some time and continues to evolve as a core focus across the technology industry.  

The problem with that is, like most areas of activism for good, you typically have an active, intentional group that makes up 5-10% of the population, another 5-10% that detracts from the cause, and a middle 80% that is not against that effort, but also not held accountable for any progress.  

In 2020 that 80% of employees in the tech industry had a realization that they need to be active, and accountable for progress in DEI in their respective organizations, and across technology to fix the problems we have today.

Our approach has been to leverage this interest by shifting the positioning of HR/Recruiting as owners of DEI. This helps us support the broader business as they work toward their team objectives of building a diverse and inclusive environment.

To support this, we launched a Diversity & Belonging council with a particular focus on avoiding the usual suspects that raise their hands for something like this. We worked hard to recruit a highly diverse group across gender, race, sexual orientation, department, geography, and more. Equally important, this council is diverse in the sense that some were brand new to this kind of effort, still learning about problems, biases, and potential solutions in order to better represent the 80% mentioned above.

Hiring a diverse executive team is key, but remains a huge challenge. Do you have any advice on how to think of diverse hiring on the executive team in the early days?

MICHAEL: It all starts with your why. Most early-stage tech companies are maniacally focused on getting to a “next” stage, which also means they’re especially focused on hiring the absolute best people that are willing to bet on their opportunity.  

Where most companies trip is that at their core they lack the understanding that building a homogenous executive team fundamentally limits their potential. As HBR notes, there’s a huge amount of evidence showing that diversity unlocks innovation and drives growth, which should only intensify efforts to ensure your executive staff embodies and embraces the power of differences.

Once the understanding is there and the purpose validated, the next step thing is to start thinking in cohorts, the executive hiring across the nest 12-18 months, versus “this role must be [insert specific underrepresented group here]”. The behaviors a micro approach to diversity drive are ugly and will deteriorate the intent to provide equal opportunity and with time erode any established purpose.  Instead, map out the growth of the team and set goals around the next 4-6 hires. 

From there, be intentional about a structured hiring process that evaluates the candidates future and their potential to succeed in the role versus their past and previous accomplishments.

While betting on growth experience across your future stages is important, it does perpetuate a cycle where there are no new entrants. If you are excellent at hiring, you can spot the person that hasn’t done it before, but very well could do it better than anyone ever has.

AOC often talks about the skills she picked up as a bartender, and others talk about what they learned working retail. What were one of those formative jobs for you?

MICHAEL: Selling Christmas cards door to door when I was 10. It was a crash course in selling and marketing a product you truly believe in, plus I raked it in. Best. Christmas. Ever.

What’s the one condiment you could never live without? 

MICHAEL: Is wine a condiment?

We believe culture, diversity, and operational excellence are a key part of building truly great companies. Learn more on our website or on Twitter and LinkedIn.