A Leader’s Shadow; The 4 Steps to Evolving & Preparing Your Right-Hand Person!

I’m a BIG believer in three things when you’re in a position of leadership… putting people in the right seat; especially your Right-Hand Person, being willing and able to have tough conversations with your people… up to and including letting them go, and that it should never come as a surprise to an employee if they are demoted or let go. However, there are many things in between your leadership, their ability, and possibly letting someone go!

I don’t promote my 1-on-1 Leadership Training Sessions, however from time to time I’m honored to have people reach out to request services and it’s a blast to meet so many extraordinary leaders around the world. One leader shared that every time he left the building for vacation or business trips, his Right-Hand failed miserably to meet metrics, created a muck of things, and he spent as much time fixing issues as he did on vacation. I asked if this was an isolated incident or was the pattern consistent… and he quickly responded, “My Right-Hand is 5 for 5!”. We laughed, as the way he said it was funny, but I quickly hit him with my World’s Famous Preface Statement, “Remember the time when I said I might have to say something that’s hard to hear or ask some tough questions, but I wouldn’t be doing my job if I didn’t? Are you ready?”. Again, we snickered as he braced for impact! I shared that he hired someone he knew was ill-prepared, has not improved, and has failed five times in a row, my client had not had the tough conversation with his Right-Hand to address concerns and find out “The Why”, and apparently his Right-Hand would be shocked if he was suddenly demoted or let go because a plan of action and improvement deadline hasn’t been discussed… That’s poor leadership!

The leader of the organization accepted full responsibility and we moved forward to the Role Play portion and delved into “The Why” for both him and his Right-Hand; settling on a plan of The Leader’s Shadow! This concept and activity can be used promptly after a promotion or hire, in training situations, or last straws. The point is for you to shadow them instead of them shadowing you! You are still on the job, announcing to your team even though you’re present… all things go through ____(Your Right-Hand)___, and you’ll be there to listen, observe, and later reflect! So, how to do it?

Tough Conversation!

Tough conversations are an art form in delivery and your ability to listen! Imagine how shocking it would be to be demoted or fired out of the blue; thinking you were doing a great job! Or, constantly told you failed, but never knowing why, what to do better, or how to do it better.

Therefore, as a leader, be sure to verbalize what your employee is doing great, ask them to help you understand what’s going on in the drop-off areas, their thoughts on why it’s occurring, and their suggested plan to fix it. Their plan may be just what’s needed, may benefit from being fine-tuned, or you may realize they have no clue and really need an answer and a plan from you.

The tough Conversation may sound like, “Hi _________. Do you have a second? You remember the time when I said I may have to ask you some questions or say something that’s hard to hear but I wouldn’t be doing my job if I didn’t? Ready? When I’m here, you’ve done a great job and I can tell the team really enjoys you. However, when I’m not here you seem to struggle quite a bit; as metrics haven’t been met ____etc.____ and it’s happened several times in a row. I know you mentioned Advancement is important to you; it’s going to be hard to advance or even continue in this position with this continuously happening. Can you help me to understand what’s going on with that?”. After discussing the issue… A Leader’s Shadow may be a great plan of action!

Give the Keys!

Many leaders wait to leave their Right-Hand in charge when it’s time for that well-earned vacation or meeting they must travel for. How ideal it would be for all things to work out seamlessly… that’s not always the case!

When your Right-Hand expresses anxiety preparing for your absence, or they’ve failed multiple times in your absence… Instead of waiting for vacation or meetings to leave them in charge… give them the keys to run things for a week (or two depending) while you’re still there. Explain they’ll run things as if you were away; however you’ll be present and by their side. Explain to your team the dynamics as well. All questions, concerns, complaints, and suggestions go to your Right-Hand and you are observing. Finally, explain to your Right-Hand you will both sit to debrief twice per day… once in the am and another time before day’s end. This leads us to Step 3!

The 3 Questions!

During my Master’s Program for Counseling Psychology, I had to write a transcript. It was the most painful, tedious, and yet most powerful assignment I’ve ever engaged in. We were to record a therapy session and type a 10 min portion of the recording… typing every question I asked, my client’s response, my response, and an alternative response for myself. The assignment was life-impacting for two reasons:

  1. It’s amazing how many words two people can say in 10 minutes. Therefore, I was mindful only to say what was needed and thought-provoking.


  1. Coming up with an alternative response to my initial response was game-changing. The alternative response was ALWAYS better, more profound, and what I wish I’d said the first time. I’ve not always done this perfectly in my life, professionally and personally… but what a skill to practice and have in your Leader’s Toolbox!

Inevitably, as you Shadow, you’ll witness your Right-Hand lead through many issues big and small and with many different people. You’ll be able to see where they excel and why… as well as where and when they shrink and why. Instead of simply giving feedback, ask these questions when you debrief:

  1. What were you most proud of this am/pm and why?
  2. Where do you feel you could have done better… simply have him/her say the situation; not explain it!
  3. Now go back… one situation/issue at a time and ask… What would you have done or said instead? Why? When their answer is on point, great! If not or they don’t know; provide an answer and your reasoning for it!


At the beginning of this article, I shared about the Right-Hand that struggled to follow through and lead the team in their boss’s absence… five times in a row. When my client implements A Leader’s Shadow, has the Tough Conversation, Gives the Keys, and asks The 3 Questions twice per day for a week… both he and The Right-Hand will know if improvement has occurred or not. If not, then a demotion or let go more easily makes sense to them both. If your Right-Hand has improved, great! Is the improvement enough for them to remain in their position, be on a probation period, keep their job and be effectively trained for the next time you exit the building? Either way, it’s time for YOU to make a decision, a plan, and follow-through!

I hope you enjoyed a Leader’s Shadow as it would seem to add more to your day and to your leadership; however, your job is still getting done, you’re enhancing your leadership skills and theirs, and it’s preparing you for better vacations and time off. Enjoy!

“Tough conversations are an art form in delivery and your ability to listen!”   – Andre Young

Written by: Andre Young

Click www.youevolvingnow.com to connect, chat, and to find out more about Andre Young’s Leadership & Work/Life Harmony Trainings, Speaking Engagements, Books, and more; evolving your organization, your leaders, employees, and teams!

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