5 questions every senior leader should ask their new managers

Emerging leaders are the most enthusiastic, excited group of employees I’ve encountered. Of course, you have to get to them very quickly, before burnout, disenchantment and bitterness seep in. Which, from my observation,  usually occurs between 6-9 months. 

Image created by Today's Leadership Solutions via
Image created by Today’s Leadership Solutions via

Of all the types of employees I’ve gotten to work with, coach, and/or lead, the ones I enjoy the most are the folks who are new to management. Emerging leaders are the most enthusiastic, excited group of employees I’ve encountered. Of course, you have to get to them very quickly, before burnout, disenchantment and bitterness seep in. Which, from my observation,  usually occurs between 6-9 months. That’s about how long it takes the new manager to realize that a) they really aren’t able to implement all the changes they dreamed about making, b) they aren’t still friends with pretty much any of their former colleagues, c) all that management training they were promised turned out to be aspirational more than actual, helpful material.  Most emerging managers are quickly overwhelmed with the pressure to maintain a high level of individual contribution in addition to a whole bunch of new (and mysterious paperwork), and financial reporting that they may or may not understand.

Of course this is a huge generalization and may not hold true at all for your organization. For the other 99.9%, though, I think there are significant gains to be made by investing in your new managers early and often. If it’s too late for early, it’s not too late for often, so don’t despair if your folks are past that 9-month mark. My experience is that most are salvageable, no matter how badly you’ve ignored them (you know I’m only teasing because I love you, right?)

I’ve found the following questions incredibly helpful to gauge where my new managers are at, where they’d like to go and what they need from me. Please remember as you consider these that tone and context are everything. Never forget that most leaders feel unqualified for their role on some level and that’s doubly true for new leaders. In many people’s minds, it’s an incontrovertible fact that if you haven’t had these conversations with your boss before and then she suddenly starts asking them that you’re about to be fired.

The goal with these questions is to establish an honest and trusting relationship so that you will know your new leader’s expectations of their role and of you. I’ve learned over the years that frustration is always a product of an unmet expectation. These questions will help you set a realistic course for your new managers and understand what they think they need from you.  If their expectations are out of alignment with what you’re prepared to provide then is a golden opportunity for you to reconsider your training approach, or simply use it as a teachable moment. There is simply no downside. The upside is that your new leaders will become as effective as possible as quickly as possible (thus, making your life SO much easier).

So without further ado, here are the 5 things you should be regularly asking your new leaders:

·      What do you need to know about the company goals that would help you motivate your team and be as productive as possible?

·      How much of my time do you feel like you need each week?

·      During that time, what do you need more of? Less of?

·      What conversations with your team or your colleagues have you not had that you should have? (and vice versa)

·      What about the (department/organization) processes do you feel like you need to know more about to be more effective (and why)?

Lest you think this list too simplistic, I’ll explain the method to my madness. The first and last questions are directly tied to management systems. New managers need to be aware of the goals of not only the company, but their department and they need to be aware of what productive means. They also need to know the internal processes related to output and to maneuver through the infrastructure. This is the heart of performance and without a solid understanding they will be unable to manage the performance of their subordinates.  If your new managers are not confidently dialed in to what it takes to produce (whatever it is your produce) then that is the first thing you need to address.

The middle three questions will all give you insight into emotional intelligence, self-awareness, and expectations. If their expectation of time with you is radically different than yours, this needs to be addressed promptly, as it will erode your relationship. If you’re not giving them ANY time, it’s going to be very difficult to build a healthy reporting relationship – especially when they’re new. If they want 10 hours a week, that’s probably not feasible and you’ll need to work with them on reasonable expectations.

It’s good to get an idea of their tolerance and willingness to engage in conflict and constructive dialogue. Asking what conversations they’ve had that they shouldn’t should also give you a good read on their judgment and ability to manage their emotions.

It probably goes without saying that you’re not going to get good answers to these questions if you haven’t built a relationship yet, so if that’s the case you can explain that you’re starting a new one-on-one format and keep any negative feedback at a bare minimum to start with. (Practice neutral expressions in the mirror to help deal with unexpected or disappointing answers).

This is just the tip of the iceberg, but your life as a senior leader or company owner is directly impacted by the performance of your team. If you can get in the habit of asking these, you’ll be amazed at the useful information you’ll find out!

Carrie Maldonado is the founder of Today’s Leadership Solutions, a Seattle-based consulting firm focused on helping organizations, leaders and job seekers to identify workplace solutions that work.  As a certified executive coach, organizational development expert and resume writer, Carrie consults with small to medium sized businesses on OD, human resources and recruiting solutions in addition to providing career coaching to managers and executives in transition. Carrie can be reached for consultation at



By Carrie Maldonado

Carrie Maldonado, is an organizational development consultant, author, and speaker. Carrie's eclectic mix of professional interests include writing, speaking, coaching, and consulting on topics ranging from organizational behavior management to spiritual transformation in and out of the workplace. Carrie lives in the beautiful Pacific Northwest with her patient and long-suffering husband and their three children.

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