1. Give an example of a time you managed a difficult employee, and how you overcame it.
Effective leaders build strong teams by communicating openly and
fostering a sense of connection and belonging, as mentioned in the
HBR study. This unity can be disrupted by an employee who is
troublesome, doesn't perform well, or causes conflicts among team
members. Ask candidates about their experience dealing with
difficult employees to assess their ability to handle conflicts
within their team.
Their answer should demonstrate their conflict resolution skills, as
well as their ability to communicate and compromise. While their
solution for dealing with a difficult employee may have ended in
termination, that should have been their last resort. You want to
learn the steps they took to resolve their issues before it came to
You're also looking into how they manage their own behavior around
difficult people. Take note of how they perceive the person they
were in conflict with. Are they hostile or empathetic? Do they have
the ability to look at things from more than one perspective and
find common ground?
Follow-up question: How do you deal with people who disagree with you?
2. How do you motivate your team?
This question is meant to get your candidate talking about their
philosophy on people management. Remember that good leaders are able
to nurture growth and empower their team by creating a safe and
Listen for well-developed strategies for encouraging career growth
and strong performance from their employees. Do they use a carrot
(positive motivation) or stick (negative motivation) approach? Do
they create a feeling of succeeding — or failing — together for their
team? Are they able to provide concrete examples of how they have
motivated teams in the past, or does the candidate mostly speak in
You are also looking to see if they are realistic in their
expectations for employee performance. Use follow-up questions to
learn how they get under-performing employees back on track.
Follow-up question: How would you approach a team member who
3. How do you set priorities for the different projects you manage?
Prioritization and self-organization are very important skills for
senior-level staff. Misplaced priorities, or an inability to rank
projects by urgency and importance, can lead to inefficiency and
missed deadlines that cause trickle-down effects throughout the
The candidate should be able to demonstrate a method for
prioritizing their own and their team's tasks. Do they have a mental
model for making decisions, and are they able to communicate their
strategy well? Can they regulate their time and delegate important
tasks to other people when necessary, or do they try to do
Follow-up question: How do you decide what tasks to assign to
4. Walk me through a time you managed a complex team project. What was your approach to the work, and how did you delegate tasks?
Great leaders foster a collaborative environment by optimizing
individual employee's strengths. They encourage employees to
“self-organize” by providing encouragement and direction, and by
allowing them to achieve their own goals. Leaders who try to control
every part of each process will smother employees and burn out.
Look for people who are able to assign tasks based on the abilities
of team members. Are they able to delegate tasks, and are they
comfortable giving employees the autonomy to self-direct? Kerrie
Juels, Technical Recruiter at Formlabs,
uses this question to assess whether a candidate's leadership style
aligns with their organization: “We are a company that emphasizes
lack of micromanagement; does [your] leadership align with that
Follow-up question: How do you deal with team members who fall
behind schedule or can't keep up their part of the plan?
5. How do you give feedback to employees?
Communicating your evaluation of an employee's performance is a huge
part of being a leader. The candidate must be able to give both
positive and negative feedback in a way that nurtures employee
growth. Leah Ward, Chief of Staff at Teampay, often asks interviewees how they give
feedback because “they'll constantly be required to direct their
team and communicate their strategies to other leaders in the
The candidate should be able to give feedback that helps employees
learn and improve their performance going forward. They should have
established methods for doing so often and openly.
In the follow-up discussion, probe their ability not just to give
feedback, but to receive it — from their peers and those they manage.
Have they established ways for employees to give feedback
anonymously, for example?
Follow-up question: How do you like to receive feedback?
6. What’s the most difficult decision you’ve had to make recently, and why?
Leaders need to be decisive. While it's important to fairly examine
all options and hear everyone's perspectives, too much back and
forth can look wishy-washy and be ineffective. A leader who can
quickly and fairly make decisions inspires the trust of their
In the candidate's answer, you are looking for a few key pieces of
information. First, why was this decision difficult for them? Was
their greatest worry the impact on the customer? Was it their ego
and looking good to others? Was it the well-being of their
Then, you want to hear how they attacked the problem and came to a
resolution. Were they flexible in their thinking? Did they consider
new ideas or approaches to the problem? How was their solution
Follow-up question: How did you communicate your decision to
those that might disagree with you?
7. How do you help employees grow and develop in their careers?
The best managers nurture growth among their team members to help
create the next generation of leaders. Employees who feel challenged
and encouraged often respond with higher-quality work.
The candidate should show a commitment towards helping their
employees grow within the organization. Do they expect employees to
be internally driven, or do they provide opportunities for training
and learning new skills? Do they allow room for trial and error and
a safe environment for failure?
Follow-up question: Can you give me a specific example of an
employee who you helped take on new responsibilities?
8. Tell me about a time you had to think outside the box to complete a task.
Being open to new ideas and approaches are key components of
encouraging organizational learning. With this question, you're
asking about the candidate's flexibility and their ability to
approach problems in new ways and come up with novel solutions.
Their answer should give you a window into their creativity and
problem-solving abilities. First, they should be able to articulate
a good example of a time they approached a solution in an unorthodox
way. Second, they should be able to walk you through their
decision-making process, explaining what choices they made and why.
In the follow-up, ask them to explain how they were able to get
buy-in on their new ideas. Novel solutions are great, but can also
be opposed by others precisely because they are untested. A good
leader should be able to influence others and receive buy-in on
their ideas, or they may never be able to act on them.
Follow-up question: How do you get people on board with a