Radical Alignment in 10 Questions



This post is inspired by a stranger who kindly shared his 14 hour work schedule with me a few days ago.

His job consists of 4–6 hours of meetings per day — meetings with the team, clients, board meetings, and 1:1’s to ensure all his reports have time to meet with him to align their goals & direction. Or even just for them to just complain. He manages a team of 24, and meets with each employee either weekly or biweekly.

I was deeply shocked by the number of hours he devoted to meetings — what about his brainstorming time, work time, preparation time, learning time?

Inspired by his story, I have assembled some of the most effective and insightful questions I’ve asked (and encouraged my colleagues & clients to ask) over the years. The purpose of these questions is to elicit feedback that establishes a long-term foundation for trust, openness, and alignment.


A Task for Managers

I once read an article suggesting managers to prepare for 1:1’s by asking their reports to make a list of all the tasks and projects he/she is working on. The manager should then make the same list and use it as a basis for communication & alignment. I’ve personally tried this method and found it very effective, and was surprised to see what was being missed in the 1:1 discussions. Over the course of the past few years, I’ve shared this method with dozens of other managers, who have mirrored my results and fascination.

Continuously fascinated by cultures with open communication, I’ve spent the last years studying feedback, and which types of questions generate the most growth. Getting honest and helpful feedback isn’t always easy. And oftentimes, the feedback we hear only confirms what we already know or want to hear. It takes a great leader to create a culture of open feedback, and the right questions to learn what you didn’t know you didn’t know. Examples of what executives & managers have uncovered from these questions are: employees who were planning to leave, a new product/service, poor use of technology, inadequate leaders…etc.


Questions To Ask New Hires

1. Aside from your current manager, is there someone in particular within the company you would like learn from?

This question uncovers not only which mentors are most admired, but more surprisingly, employees’ learning styles. According to our studies, the mentors who employees choose are those with teaching styles that align with the individual’s learning style. This is especially important when examining the employee’s potential for growth under his/her manager relationship.

Furthermore, this exercise forces employees to examine their future and also research the leaders of their company.

At When Toys Age, we use questions like these to help develop & shape your mentorship program. Employees have found powerful advantages in having mentors outside of their department, as they feel more personally connected to the company as a whole, as well as their personal growth.

2. Other than your current department/role, what other departments or roles interest you?

I personally love this question because there’s unlimited potential in what you do with it and where it could lead you.

  1. Discover Their Passions: When you ask why, watch their eyes light up. This is passion speaking, so remember what it looks like. Know what your employees are good at, and learn what they love doing. Then create a role around it. I’ll never forget what my last boss said to me, “Be excellent at everything you do, and unmatched at what you love to do.”
  2. Establish a Joint Project: Let your employees explore their passions and goals. Give them an opportunity to test their fit by initiating a joint project between two departments. Oftentimes, employees are happy to take on the project in addition to their roles. Plus, you never know what you might learn. This is a chance for two departments to collaborate.
3. Are there things about the company that you feel you should know?

I used to ask a variation of this question, but especially like how Claire Lew, CEO of Know Your Company phrased it.

Asking this question allows you to assess what type of communication your company is missing, as well as areas of expansion. Companies have taken this question further to discover what employees want to learn about, and then restructure their onboarding & ongoing training programs. When you ask this question, examples of what you might find are:

  1. Your employees struggle with the software your company is using
  2. Employees outside of sales/product don’t understand your product all that well
  3. Your vision lacks clarity or requires revision
  4. Certain policies are outdated and no longer apply
4. Describe your ideal lifestyle.

This question says so much about an individual — what they value, what their long-term goals are, where work/the company fits into their priorities. If you ask this, you’ll have solid grasp on how to motivate and reward them.

Motivation and rewards are an integral focus of our work. At When Toys Age, we study the effectiveness of a company’s reward system to enable the proper employee incentives for growth. Far too often do employers rewards employees without understanding what they value. An $100 gift card & lunch with the boss might not be what your employee wants. And carelessness with reward systems can cause heightened expectations and therefore, dissatisfaction.

If you’d like to share your incentive program success story or learn more about our method for assessing proper incentives and building an effective reward system, we’d love to hear from you!


Continuous Alignment

1. Is there a part of your job that makes you nervous? Are you afraid of anything at work?

This could range anywhere from a personal insecurity around the responsibilities of the position to a negative work-life balance, to a poor relationship with his/her manager, and even reservations about the direction of the company. Answering this question requires a great deal of honesty and vulnerability, so managers, please treat these answers with respect & an open mind.

And don’t disregard the answer to this question. This question is remarkably powerful because what you decide to do with it can make or break your relationship. If you choose to ignore your employee’s fears, you’re pushing him/her to find someone who won’t.

2. Do you believe you’ll be able to reach your full potential here?

This is a simple yes or no question, and self-explanatory. Holds immense weight nonetheless.

3. If you could hire a personal assistant, what kind of work would you delegate?

This is a two-part assessment:

  1. Did they consider the aspirations and skills of the hire? Did they describe the ideal candidate?
  2. This answer reveals the parts of the job that aren’t as high in priority, and is an opportunity to delegate or automate! It also tells how fit they are for their role.
  3. An insightful follow-up question is: Hypothetically, if you were to quit tomorrow, what would your reason be?
4. Is there something our company should measure that we currently do not?

Answers span from employee recognition to investment proposals. The answers to this question are all things that employees notice, things that they see that you may not. These answers will help grow your company, business, or both.

When conducting our preliminary evaluation of a company’s culture/innovation capacity, this is one of the most telling questions. In the past, we’ve transformed this question into Quarterly Company Shark Tank Sessions for our clients, who now keep a far more open mind on what they measure.

5. Have you seen great work go unnoticed in the office?

This is a powerful question for many reasons.

  1. It allows the employee to think beyond themselves and their desires
  2. It establishes connection and builds support within the company
  3. Studies show that standing up for someone empowers individual confidence and places individuals in their natural state of comfort
6. What have you recently learned outside of work that you have applied in the workplace?

This question digs into what is happening in the employee’s life outside of work. Whether the employee reveals a recent life experience or something they learned while taking a course, this question is crucial because it prioritizes the employee’s growth, and also shows that your interest in the employee’s well-being expands beyond the workplace.

A variation and perhaps potential follow-up question is Have you seen something recently and wished that it could be done here? Boom — potential project.


Over the years, we’ve assembled a database of hundreds of questions & strategies that dive deep into individual aspirations, goals, and barriers, and weaved the responses into the company’s mentality, culture, and overall identity. Whether in management mentality, culture innovation, or employee expansion, these questions are there to serve one mission: To eradicate barriers & unlock potential.

At When Toys Age, that’s our job, our pride, and our deepest gratification.

To learn more about our offerings or invite us to your company, please email hillary@whentoysage.com.

Thank you for learning with us,


Oh and P.S. In addition to consistent 1:1’s, look into establishing a system that promotes consistent feedback. Create a process that belongs solely to your company & team. The purpose is to cut back on meeting time and still continue robust & honest communication.