5 questions team leaders must ask their agents (and staff) every day

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If you are anything like me, your 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. 

But don’t confuse purposeful and productive with dismissive, impatient or apathetic. I actually spend quite a bit of time with my team. We have a weekly Wildy Important Goal meeting, a weekly CEO training and check-in, Monday morning power-ups, and 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 can take our decisions from the various meetings and execute them throughout the week.

But there is one critical piece that makes all of this work: It’s the five daily questions I have each of my leadership team members email me the answers to at the end of each day.

They’ve already had their staff email the answers to them, and those staff members have already had their agents send them the answers, and so on throughout the organization.

Here are the five daily questions you must ask your agents or 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 something is preventing you from being at the top of your game, we need to know and fix it.)

Question 5 varies depending on whether you are connecting with an employee or an agent on your team: 

1. For employees: Who is your replacement? (Ultimately, there should be five people — inside or outside of the organization. If you don’t have anyone, use the next 30 days to start filling the gap.)
2. For agents: What is your next opportunity for growth? 

What is so powerful about these questions is that they allow me to quickly get insight into what’s happening throughout the organization at all levels daily. The information flows upward. Additionally, they show me where teams are focused so I can redirect if necessary and make sure that we are all moving together at full force as an organization. 

These questions also alert me early on if there is an issue that a team needs support with and provide employees with regular feedback and coaching from their leaders. 

These questions serve as a daily touch point for the leader and employee or agent. It’s fast and effective for both you and your team. It’s a system designed to ensure that you keep a finger on the pulse of projects “at the office” and the energy of the team. From there, you can direct the energy of your team as needed. 

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), they are focused on their growth, the company’s growth, and who they are grooming and pouring into.

It’s a model for internal growth. Agents don’t always have “replacements,” which is why we sometimes use the other question. However, both options can work for either your employees or agents. 

More than anything, these questions are a tool for your team. Yes, it’s a quick way to gauge your team member’s mindset, pain points and progress, but it’s an even better tool to increase their self-awareness.

This daily reflection focuses your employees and agents on what they learned and what they could do better tomorrow — and every day. It’s a forced journaling model for them to follow. If completed consistently, growth for them is simply inevitable! Which is exactly what I’m after as a leader.

A couple of additional things to note as you begin to implement these daily questions:

• Start these questions on Day One with new employees or new agents. Set the precedent that their growth is valuable to you and the organization.
• If you are implementing these questions with existing team members, please explain to them the reason 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 employees and agents the space to be honest and vulnerable.
• Be very specific about explaining question No. 5 to employees. We implement these questions immediately with new staff, so it’s no surprise. However, if you are implementing these questions after employees have been with you for three years, they might think their jobs are 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!) for them to move into a different opportunity.
• For question No. 4, you are not looking for any specific answers here, but rather for patterns of behavior and problems you need to resolve. For example, if one of your staff members’ mindset is always at an 8 (they’ll never be a 10), 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: Were they able to solve their own challenges, or did they blame others? Are they taking responsibility 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. And because we are a growth organization — we want our team growing both in business and their personal life — and this one of our most effective and efficient tools for pouring into our employees and agents while also providing us with visibility into the entire organization.

These are powerful and valuable questions whether you travel three weeks out of the month or work 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. 

What questions would you add to this daily check-in? Please share in the comments section below.

Adam Hergenrother is the founder and CEO of Adam Hergenrother Companies, the author of The Founder & The Force Multiplier, and the host of the podcast, Business Meets Spirituality. Learn more about Adam’s holistic approach to business here.