The Leader-as-Coach: 10 Questions You Need to Ask to Develop Employees

Guest Post by Paul Falcone

Reprinted from 

Finding new software engineers is very difficult for most companies, and retaining them is equally if not more challenging. For Louis, a Chief Human Resources Officer (CHRO), attracting and keeping Millennial engineers is a particular challenge since tenure within that age group at his organization is averaging less than 18 months.

As an added challenge, Louis wants to transition his organization’s culture from a focus on individual contributors to team accomplishments. His plan is to reward leaders based not just on their own individual contributions but also for growing the next generation via coaching and development. However, he isn’t sure where to start or how to create this shift in organizational focus, given that his company has adhered to its individual contributor culture for decades.

“It isn’t easy, but you can definitely move your organization in the right direction,” said Shara Fisler, executive director of the Ocean Discovery Institute in San Diego, a nonprofit that supports underserved communities by offering inner-city students opportunities in the fields of ocean science, research and environmental stewardship.

Employee retention and talent management are hot topics in today’s business environment because great workers are so hard to attract and retain. “I’ve found that asking the right questions rather than telling employees what to do creates a sense of empowerment, professional growth and ownership that most employees respond well to,” Fisler said.

Fortunately, employee relations experts agree that turning departmental leaders and front-line supervisors into coaches, rather than allowing them to be unilateral decision-makers and disciplinarians, is a culture shift that can be achieved subtly and in a fairly short amount of time.

Coaching Questions in the Interviewing Process

The employee development paradigm can actually begin during the pre-employment process when candidates are being interviewed for a position. The three following questions can go a long way in forcing career introspection and helping job applicants articulate what they’re truly looking for in their next position:

1. What’s your primary reason for considering leaving your current company, and how would joining our firm help satisfy that need?

2. What criteria are you using in selecting your next opportunity, and what would joining our organization do for you in terms of building your resume over the long term?

3. If you were to accept this position with us right now, how would you explain that to a prospective employer five years from now? In other words, how would this role provide a link to your future career progression?

“No, these aren’t easy questions to answer, but they’re challenging in their own right because they require a certain amount of critical thinking on the candidate’s part, and most [candidates] will walk away being very impressed by an organization that takes such an interest in them personally and in their career needs,” Fisler said.

Coaching Questions for Stay Interviews

Too many companies spend time and energy tending to the lowest 10 percent of performers via progressive discipline, failed annual performance reviews and the like. Maybe a good amount of time spent on these employees is warranted in the sense that all leaders want to avoid or at least minimize the chances of being sued for wrongful termination.

“But every organization’s focus should be on leveraging the top 20 percent of talent because building on strengths is a far more lucrative game than shoring up weaknesses,” said Bill Milowitz, CEO of Turf Care Supply Corporation in Cleveland.  Don’t neglect your top performers only to find yourself struggling through a counteroffer once someone has given notice. Instead, consider conducting stay interviews where you focus on your top performers’ needs and then build individual development plans to help them leverage their strengths by contributing more broadly to your company’s overall success. Simply hold a one-on-one meeting with the top 20 percent of your team members—your “keepers” in the truest sense—and ask them:

4. How would you rate your overall job satisfaction on a scale of 1 to 10, with 10 being the highest? How would you grade yourself in terms of doing your best work every day, finding a balance in terms of the company’s needs and your own career and personal development interests, and feeling like you’re firing on all pistons in terms of your overall performance? (Follow up with further questions, such as: Why are you an 8? What would make you a 10?)

5. Which of the following five categories holds the most significance for you career-wise at this point?

(a) opportunities for promotion and advancement

(b) rotational assignments to gain a broader understanding of the organization’s operations and key players

(c) additional training, certification and acquisition of new technical skills

(d) money and other forms of compensation

(e) work/life balance

(Follow up with another question: How can I support you on building on that?)

6. How can you and I partner as co-leaders to make things better for the rest of the team?

“Making your top performers a critical part of your team’s performance turnaround is just good medicine,” Milowitz said. “Your top performers will always be resume-builders, so placing them into shared roles of key turnaround areas allows them to gain traction and thrive in their own unique way while increasing accountability and engagement.”

Coaching Questions for Employee Development

Building accountability stems from a combination of trust and expectations of high performance. Telling your employees what to do, micromanaging or otherwise holding their hands won’t get you very far. In comparison, stretch assignments, goal-setting and allowing employees the freedom to execute in their own unique way will often beget high levels of loyalty, appreciation and trust. The development of a strong talent bench stems from leaders who trust and respect their workers, as well as those who create an environment where employees can motivate themselves. Try these coaching questions to strengthen the muscles of your top performers:

7. What makes you stand out among your peers? How do you differentiate yourself from your competitors, and how can I help you prepare for your next career move in terms of building up your resume and LinkedIn profile?

8. What professional or career-related opportunities are you most excited about pursuing? How can we make one of your annual goals about or build your individual development plan around what’s most significant to you at this point in your career?
Leader-coaches are typically focused on helping high-performers get even better. But they should also be thinking about what can be done as a team to move the middle of the bell curve—in other words, how can we work together to make some of our good performers great, and who should we focus on?

Don’t underestimate the importance of this concept of “moving the middle.” Minor shifts in overall team performance can have tremendous results, especially when you’re partnering with your top talent to get there. Similarly, condition your team members to come to you with two possible answers for each question they raise.  “That will get them used to thinking constantly about solutions rather than simply passing the buck to you and expecting you to provide answers,” Milowitz recommended. But the most critical method that will force a healthy sense of introspection and also build confidence is simply this—and provides the last two of our 10 questions to develop employees:

9. When an employee asks you what to do, simply ask right back, “What do you think we should do?” And when he or she smiles and politely says, “I don’t know—that’s why I’m coming to you,” you can politely smile and respond back:

10. “I know you don’t know what I think. But if it were up to you, what would you say we should do here?”

Voila! You’ll quickly find that employees will volunteer exactly what you were going to recommend in 90 percent of the cases. “Even when they’re off a bit,” Milowitz said, “asking that magic question gives you an opportunity to guide and mold their response so they understand the why behind the logic of your recommendation. It also helps them realize that they knew the answer the whole time, which builds their confidence and decision-making abilities.” Coaching by asking appropriate questions may take a little getting used to, but you may just find profound results over time with this simple shift in leadership focus.

Creating this kind of learning culture may go a long way in engaging candidates’ hearts during the interview process and stemming the tide of turnover among your earlier-career Millennials. After all, it’s true that people “join companies and leave managers”—that is, of course, unless your leadership team members see themselves as leader-coaches who are helping to strengthen those who will be following in their footsteps. “Selfless leadership is the name of the game,” Fisler said, “and nowhere does it show itself more than in your current leadership team’s willingness to foster and grow the next generation of talent.”

As for CHRO Louis, he realizes that this soft change in leadership strategy may be a fairly easy sell to the rest of the senior executive team, and it may very well be just what his company needs to transition the culture to being more team-oriented and selflessly focused. This all begins with the questions you ask and your willingness to guide the responses you get. Don’t be surprised if your Millennials respond particularly well to this shift in energy as well: After all, leaving your company for another may be a less attractive option if they feel that you are developing them and meeting their career needs.

The article is reprinted with permission from, c 2021. All rights reserved

Paul Falcone


Paul Falcone is the Chief Human Resources Officer for the Motion Picture and Television Fund in Los Angeles. He’s also served as the CHRO of Nickelodeon and is the author of the bestselling book, “101 Tough Conversations to Have with Employees.” Paul is a long-term contributor to HR Magazine and an instructor in the UCLA Extension School of Business and Management.  His newest five-book set, “The Paul Falcone Workplace Leadership Series,” will be released in the spring of 2022 by HarperCollins Leadership.


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