Vetting a Leader During Your Chief of Staff Search


Being someone’s right-hand person is a phenomenal opportunity to learn, grow, and develop. But if you’re at the hand of the wrong person, it can be disastrous—for you both. While you may have targeted specific opportunities because they fit with your work history or your interests, it is also critical to vet the leader you will be supporting. In fact, many Chief of Staff candidates identify prospective opportunities by their leadership as opposed to company size or industry.

So, how do you vet a company on its leadership? There is the more obvious homework—like researching the leader online, noting their community involvement, speaking engagements and other activities. But what about during the interview process? It is important to remember that you are interviewing the leader and company just like they are interviewing you. These seven tips will make it easier to ensure alignment between the leader’s values and personality, and your own.

1. Know your value

This is about assessing someone else, so why is this important? Because knowing yourself is essential to understanding how well you align with someone else. Understanding your own values, how you like to be motivated and rewarded, what work environments energize you—are all critical for knowing the kind of leader and workplace that will help you thrive. In addition, knowing what you’re good at and what you bring to the table helps you identify how you could work effectively as a right hand. When you get to know the makeup of the leader, you can then assess your yin to their yang to establish solid footing as you begin your COS role. Are they a big picture thinker? Perhaps your process orientation will help them incorporate structure into their ideas to drive results.

2. Assess self-awareness

When you meet with an executive, do they share their strengths as well as their shortcomings? How many of you have listened to an executive profess their greatness ad nauseum? Self-awareness has arguably become the most important leadership trait. And while it may be in short supply at higher rungs of an organization, it is an attribute you should strongly consider when working closely with someone else. Your leader may not come right out and declare their weaknesses, but when probed, what are they willing to share? Both the Chief of Staff and leader should have healthy doses of self-awareness—an important part of EQ—to form a tight-knit partnership.

3. Look for results

Any leader can say, “I am great at developing talent,” but the proof is in the pudding. Who has been developed under the leader’s wing? Find out if there have been other Chiefs of Staff at the organization and if so, where are they now? What about within the executive’s inner-circle? How many have been groomed by the leader and where did their careers begin? If the leader is brand-new to the company, ask to speak with someone they formerly worked with who learned under their direction. Seeing a leader’s results is much more effective than hearing about them.

4. Define success 

Discuss with the executive what success means to them personally, not just as their Chief of Staff. Don’t be afraid to ask hard questions, like “What are your ideal plans for this company and for yourself?” Remember, there isn’t necessarily a wrong answer to this question, but rather, answers that align better with your goals and trajectory. A results-oriented COS with a strong financial background may love the challenge of hitting the mark with improved efficiencies and strategic management. Another innovative COS may be excited by the idea of venturing into new territory with a passionate leader who’s got big ideas and perseverant spirit, regardless of the company they lead.

5. Corroborate the evidence

You have positive experiences with an executive in your conversations, but there are slight concerns or potential red flags. Don’t ignore your gut. Asking others for their points of view on the leader is extremely helpful for developing a well-rounded perspective on who they are. Don’t ask surface questions like, “Do you like your boss?” Instead, focus on their behaviors and get specific. “You’ve said the CEO is particularly strong at developing others. Can you share an example from your experience that demonstrates this?” If you have concerns, be sure to raise them appropriately with others. Of course, don’t ask, “Is the CEO ever a jerk?” Rather, “How does the CEO act on their worst days?”

6. Engage your periphery

Basketball athletes are very familiar with the phrase, “Keep your eye on the ball.” However, the most successful use their peripheral vision to understand greater context on the court. You can do the same during an interview to observe how the leader behaves and is regarded by others in the office. At the end of your interview, ask the leader for a quick tour of the office. Do they lead the tour or ask someone else to do it? Do they greet people when they walk by and know their names? How do they treat their administrative staff? If you are in another setting like a restaurant, pay attention to how they treat the service staff. Executives can put on a great face to you, but they should also consistently demonstrate it with everyone else to be genuine.

7. Get personal

Let’s be honest. You’re going to be spending a lot of time with this leader. Working with them is one thing, but consider if they are someone you’d like to spend time with outside of work. Not that you’ll be hanging out together every day after work, but travel and business dinners offer plenty of downtime for small talk. Do you have a connection that could sustain a personal relationship? For some it’s hobbies, such as sports, food, wine, or travel. Even if you don’t share the same love of Starbucks lattes, it’s important to evaluate what topics motivate them and if your personalities are a good match.

What questions do you find helpful when vetting a leader during the interview process? Share in the comments below.

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