5 Questions You Must Ask Your Employees Each Day

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One of the questions our team often gets asked during interviews, particularly for other leadership positions, is, “How much time will I get to spend with Adam.” Our leadership team knows, it’s not much! But that’s okay. I spend my time pouring into the right leadership people. Let me explain.

My days are scheduled down to the minute, which doesn’t leave much time for the “drive-by conversation.” That’s not my style anyway. I like purposeful and productive interaction. The quicker and more decisive, the better. That doesn’t work for everyone and it is often an adjustment period for higher maintenance staff members who want or need constant interaction. I’m pretty (okay, very) blunt about the fact that I am more concerned with who my employees become, than being their friend. So again, very purposeful.

I actually spend quite a bit of time with my team. We have a weekly Wildy Important Goal meeting, as well as individual company meetings. I run a very autonomous organization and the people who are the right fit for our company and our culture are the ones who are able to take our decisions from the various meetings and execute throughout the week.

But there is one critical piece that makes all of this work, and that is the five daily questions  I have each of my leadership team members email me at the end of every day. They in-turn have their staff email these questions to them, and so on, throughout the organization.

Here are the 5 daily questions you must ask your employees each day:

  1. What successes did you or your team have today?
  2. What struggles did you have today?
  3. How did you overcome them?
  4. Where is your mindset on a scale of 1-10? (1 being terrible. Be honest here. I don’t care if it’s a 1, but if there is something preventing you from being at the top of your game, we need to know and fix it.)
  5. Who is your replacement? (Ultimately, there should be 5 people – inside or outside of the organization. If you don’t have anyone, use the next 30 days to start filling the gap.)
Why these questions?
Primarily because they are fast and effective for both you and your staff. As we’ve heard, it’s hard to have contact with the CEO, Director, or supervisor every day. These questions serve as a daily touch-point for the leader and employee. People often open up more on email, too, which begins to build trust. More often than not, the answers I receive to these questions have much less to do with the day to day operations of the business, and more to do with where the employee’s mindset is or what is going on in their personal life. Your employee’s personal life does bleed into their work life, even if they don’t talk about. Be aware and show that you genuinely care about what they learned, what they failed at, how they are feeling, and how they are coping with it (at home and at the office).
These questions help you keep a great pulse on the people who report to you, especially when you are traveling, in all-day trainings, or simply aren’t able to spend time walking around to feel the energy in the office. These daily questions are a system to ensure that you have a pulse on the energy of the office, even if you aren’t physically there. From there, you are able to direct the energy of your team.
The last question always gets the most questions! It’s designed to get your team to be thinking about future opportunities for their growth. If they are searching for their replacement (either inside or outside of the organization), then they are focused on their growth, the growth of the company, as well as who they are grooming and pouring into. It’s a model for internal growth.
More than anything, these questions are a tool for your team. Yes, it is a quick way to gauge your team member’s mindset, pain points, and progress, but it’s an even better tool for them to increase their self awareness. This daily reflection focuses your employees on what they learned and what they could do better tomorrow… every day. It’s a forced journaling model for them to follow and growth for them is simply inevitable! Which is exactly what I’m after as a leader.
A couple of things to note:
  • Start these questions on day one with new employees. Set the precedent that their growth is valuable to you and to the organization.
  • If you are implementing this with existing team members, please explain to them the reason behind why you are asking these questions and make sure you are replying. Take this seriously. Your employees are taking the time to answer these questions daily and you’re going to hear some very personal (and professional) business struggles. This is exactly what you want! It’s impossible for the two not to go hand-in-hand. Be prepared to respond with care and candor and allow your employee the space to be honest and vulnerable.
  • Be very specific about explaining question #5. We implement these questions immediately with new staff, so it’s no surprise. However, if you are implementing these questions after an employee has been with you for three years, they may think their job is in jeopardy. Let them know it is a growth-based question and that as they continue to grow, they will need to find others to take over pieces of their position (or their entire role!) in order for them to move into a different opportunity.
  • You are not looking for any specific answers here, but rather for patterns of behavior and problems that you need to help resolve. For example, if one of your staff members mindset is always at an 8 (they’ll never be a ten), then when you see them drop to a 5, you know something is up. Conversely, you’ll have team members who are always at a 10, so dropping to an 8 or even a 9 could be a red flag. Other questions you might ask yourself as you are reviewing their responses, are: Where they able to solve their own challenges or did they blame others? Are they taking responsiblity for missed deadlines? Are they learning and progressing each week? All of these questions (and the patterns that emerge) are simply a model to help you be a better leader.

These are powerful and valuable questions whether you travel three weeks out of the month or are in an office with just one other employee. Add these into your cadence of accountability with your team and watch your relationships grow and your team members flourish, no water cooler conversation necessary.

What questions would you add to this daily check-in?

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