How to Help That Annoying “Stuck” Person: Part 2

In part one of this post series, we talked about what team members need when they get stuck moving from conscious incompetence (i.e. they know what they don’t know) to conscious competence (i.g. they know what to do, but they still need your help.) Today, in part two, here’s what you need to do help a stuck team member climb out of the Pit of Despair:

Think back throughout your leadership journey. How many individuals would you say that you have intentionally developed? Who would you point to and say that you have passed on your knowledge, skills, and expertise into their life? Apprenticeship is rare.


As leaders, we often underestimate what it takes to apprentice just one person. To bring someone along and intentionally raise their capacity is an incredibly rewarding and also challenging experience. It exposes our own insecurities by showing us how effective we are really being at developing others.

One of the foundational skills needed to effectively apprentice others is the capacity to help someone out of what we call the Pit of Despair. In my last post, I suggested that it may very well be your fault that your annoying stuck person remains stuck. If all you are doing is giving information, telling them what to do and expecting them to miraculously figure it out without an ongoing connection to someone who will walk with them, you’re sadly mistaken.

When team members fall into the Pit of Despair, leaders can — and should — function as the ladder to help them climb out.

Pit of Despair

Here are three key skills that you need to function as the ladder to help people out of what we refer to as the pit of despair.

  1. Own it: This is a pretty significant shift for most of us. You have to take primary responsibility for getting the person out of the pit. They need to know this, so communicate it to them daily!
  2. Schedule it: Schedule short and extended times with the person: The goal here is frequency. Let’s be honest, no one really does the 1-minute manager.  Have you ever managed someone well in 1 minute? Really? It’s amazing what you can get done in a 15-minute check in. Figure out the best rhythm for the person you are committing to. Is it 10 minutes daily, and one 30 minute block weekly?
  3. Invite and Involve: This person must be able to observe you (or someone) functioning with the skill set or solutions that they need. Invite them to shadow you. The second part of this is that you involve them in something you are doing. Have them do something with you to boost their confidence and capacity to do it on their own.    

These are things I have learned and not done perfectly over the past 10 years of my leadership journey. What challenges or input do you have in relation to serving that stuck person?

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