Picking Sides: Choosing the Right Players for Your Leadership Team

Steve Schloss
6 min readMay 11, 2022


There’s a small and busy highway running through the middle of my childhood town in northern New Jersey. Transporting commuters to New York City and shoppers to the malls of Paramus, it runs past an open field parallel to the eastbound lane. Surrounded by towering oaks and bordered by a line of Tudor homes, the field sits on a small incline. While non-descript to most, I considered it hallowed ground as it was home to many football and baseball games back in the day with friends.

In a recent moment of symmetry, I drove past that field while listening to the struggles of a CEO coaching client who was searching for a chief revenue officer. I was also reminded of a crucial skill set which never lost its importance and right up to this day plays an important role in the lives of boards, CEOs, and executive leaders everywhere: selecting who you want on your team.

I thought about the selection process applied those early days. Two friends were chosen (or decided with little push back) to “pick sides”. You had choices to make based on speed, height, throwing arm, catching ability, or just the general availability of talent based on whomever happened to be around that day. Or maybe, it was sticking with the friend who had supported you and had your trust and favor. The impact of your decision was typically measurable: it concluded with a winner and a loser.

Sound familiar?

Selection in the Real World

Assessing and selecting the right leader or leaders to fulfill key roles on an executive team is the most important decision any board or CEO will make. Yet, many of these accomplished leaders often underperform as interviewers, discerners, and selectors of talent. More often than not, the commitment to a disciplined selection approach is minimized or usurped by an array of inputs and distractions. They consider evidence from past performance, add in personal observations, personality assessments, and biases of fit, difference, and potential. They navigate politics and transparency among key deciding stakeholders, and their decisions factor elements of timing, leadership style, and the need for specific or unique skills.

A few years back, I worked with a group of executive leaders in media as we navigated our digital business and culture transformation. As we worked to recruit and introduce new capabilities and behaviors for a rapidly changing market environment, it was clear that we needed to “up” their interview and selection game. These executives were outstanding communicators and loved to hear themselves talk. They often forgot that an interview was not about themselves, nor was the time spent proportionally focused on the person sitting across the table. These leaders did not consider that how they conducted themselves, made it about themselves, and offered the candidate an unintended window into their potential boss or colleague.

Today, when coaching or advising C-level executives, the topic of selecting and acknowledging that one has the right people on their team is an ongoing “what keeps me up at night” conversation. And, for most board members or CEOs, the stakes have been raised. Their ability to be effective interviewers and selectors of talent (even with help from great search firm partners) is an essential skill set that requires commitment, focus, and practice.

The common thread between past and present is the need for a disciplined approach. To be clear, discipline does not mean rigidity nor inflexibility. It does mean a commitment to sustained and open-minded processes that consider talent sources, slates, and the continuous evolution of required strategic skills and behaviors. It also considers how a board or CEO conducts themselves toward making the best possible decisions.

At one point in my career, I became a “certified” talent selector and assessor supporting a global process of executive-level hiring and succession planning. Based on a GE 9-box influenced methodology, I was observed by (and observed) a group of peers for a week’s worth of actual selection and assessment interviews. It was an intimidating but highly effective approach. I introduced a similar idea to the media executive group in the form of interview shadowing, allowing a third party to observe their interview style and effectiveness, and to offer feedback as part of their learning process. While initially resistant, these leaders learned that discipline makes a marked difference in the form of role clarity and profiling, preparing key questions around areas of importance, being present through active listening and probing … and yes, talking less. Their willingness to be critiqued, receive feedback and recommendations on their approach, and the commitment to greater preparation translated to more effective interview and selection experiences and decisions, for both parties.

To gain a little more perspective on this topic, I reached out to my friend and colleague Keith Meyer, Global Practice Leader for the CEO & Board Practice at Allegis Partners. Below are his thoughts and perspectives on some of the challenges and opportunities of modern executive interviewing and selection:

S: Keith, how would you assess the current state of interviewing and selection capability at the board and CEO level? How have these key decision makers adapted for the better?

K: Overall, interviewing and selection capability at the top remains a mixed bag among boards and CEOs. With interviews shifting to video from in-person during the past two years, there has been an interesting set of tradeoffs –it has been much easier to schedule multiple rounds of conversations with key stakeholders leading to a faster time to hire. But we also see CEOs and executive interviewers struggle to accurately assess key skills like empathy, self-awareness, or communications made far easier when sitting face to face.

S: When you consider examples of CEOs who are great interviewers and selectors of talent, how do they differentiate themselves in their preparation, practices, or behaviors?

K: We observe several practices that are consistently a part of the best interview processes — utilization of structured, rigorous assessment criteria for the role which are defined before the search starts and are embedded in each interview; a clear understanding of the team’s overall assessment of the candidate from the individual interviews — this should generate a prioritized list of potential areas to probe further by the CEO; and, the ability to engage the candidate in an open, candid conversation that reveals their true character and personality, along with the prerequisite evaluation of areas to probe further — this typically involves some level of mutual disclosure and an opportunity to exhibit vulnerability, awareness, and perspective during the conversation.

S: What advice would you give to a CEO who is looking to identify and interview a new member of their executive team? How should they approach that process?

K: I would suggest they establish a central “clearinghouse” role to ensure all interview feedback is documented consistently and shared with future interviewers as the process moves forward. References should be conducted before the final “decision” interview and incorporate the findings into the CEO/candidate conversation, and during the “pitch” portion of the interview to unlock candidate motivations, personal biases, and decision-making acumen. Finally, I would recommend knowing when it would be helpful to retain an outside resource to conduct a candidate assessment to supplement the internal interview process.

S: What trends or practices would you recommend that same CEO avoid or stop doing based on your experiences of bad examples?

K: As you shared in the article, the most common pitfalls are a lack of listening or lack of engagement with the current executive team who are both beneficiaries and owners. CEOs must get more comfortable with virtual interviewing, as we have found that video drives a better experience and decision-making process for the next generation of executive leader. Still there needs to be a balance between live and in-person conversation, especially at the C-level. Finally, while I situationally support candidate assessment tools, I encourage CEOs to tread carefully if they do not have a history of using such assessment vehicles. However, as a data point, assessments can be helpful so long as that process is transparent to candidates at the start of the process.

While for me — and so many of us — the “field of dreams” experiences from our football or baseball days may be long past, the lessons — and implications of choice without a disciplined approach — at the top of any organization carry the same win and lose outcomes. The differences may be stark, but the rewards from picking the right players for your team, are every bit as satisfying.



Steve Schloss

Coach and advisor to CEOs, executive leaders and teams. Sharing thoughts, observations, and ideas around leadership and culture. Trying to break 80 more often.