The "Vacation Test": Are You Essential... or an Obstacle?
tldr; It has been suggested that I type... a lot. So, here is the short version! If you stepped away for a month, would your team thrive or dive? We often blame our teams for bottlenecks, but the hard truth is that the bottleneck is usually us. This week's post offers a simple 4-step "Coaching Challenge" to help you identify where you are hoarding control and how to empower your team to win without you.
It’s been nice to have some time off for the holidays.
I hope you all were able to disconnect, recharge, and spend quality time with loved ones. For me, the quiet moments away from work are always the most fertile ground for reflection. I spent some time thinking on my own career journey—the wins, the losses, and the messy middle parts.
During one of these quiet moments, a question popped into my head. It’s a scary one, but I want you to sit with it for a moment:
"What would happen if you had to take a month off starting tomorrow—no email, no messaging, no phone?"
Your immediate reaction might be panic. But push past that. If you truly vanished for 30 days, which parts of your organization would thrive? And which parts would fall apart?
The Hard Truth in the Mirror
When we look at the "weak" parts of our organization—the teams that miss deadlines, the projects that stall, the decisions that get stuck—our instinct is to look at them. We blame the process, the market, or the team's capability.
But here is a hard pill to swallow: Weakness within an organization is often reinforced by the behaviors of the people who lead them.
Successful leaders are often blind to the things that are holding them and their organization back. We confuse "being involved" with "being effective." We confuse "helping" with "controlling." If a department fails because you aren't there, that isn't a sign of your importance; it's a sign of a fragility you have created.
Identifying these blind spots is difficult. It requires us to look in the mirror.
Coach's Challenge: The 4-Block Reflection
Challenge yourself to try something over the next two weeks. It won't take much time, but it requires honesty. Schedule yourself four 10-minute blocks of time. Put away the phone. Close the email. Just you and a notebook.
Here is the approach:
Block 1: The Assessment
In your first 10 minutes, consider that "month off" question again.
"If I had to take a month off with no contact unexpectedly, what parts of my organization would fail, and what parts would thrive?"
Be specific.
Example: "Department X would fail because they need weekly approval to move forward."
Example: "Department Z would thrive because they have a clear roadmap and execute well."
Write down your answers and put them aside.
Block 2: The "I" Shift
In your second block, take those answers and rewrite them from an 'I' perspective. This is where the magic (and the pain) happens.
Change: "Department X would fail because they need approval..."
To: "Department X would fail because I am not there to approve decisions."
Change: "Department Z would thrive because they execute well..."
To: "Department Z would thrive because I’ve already approved their roadmap and trusted them to work."
See the difference? Write them down and step away.
Block 3: The Patterns
Review your "I" statements. What patterns do you see?
Is there a consistent theme across your "I" statements?
Are there any actions that you are doing that may be hindering teams to innovate and thrive?
What are the things you never considered before regarding your impact on the team's speed? Write down your observations.
Block 4: The Action
Read your observations. Now, we move to action.
Identify ONE change you will make over the next quarter to address these observations. Maybe it's delegating approval authority for Department X. Maybe it's not giving specific answers, but instead challenging team members to solution themselves. Maybe it's stepping back from operational decisions. Maybe it's setting outcome goals, instead of specific functional directions.
List your accountability partners. Who will you ask to hold you accountable? (This will take some vulnerability, so you may need to be specific as to "why" you're asking for help.)
What is your hypothesis? What changes in the organization are you expecting to see after you change your behaviors?
Reflect. Come quarter-end, did you genuinely adjust your behaviors and approach? Did you see a resulting change in the way your organization is working? Will you have a different answer to your "What if I'm out for a month..." question? (In fact, why not run the exercise again and see where you may want to focus next.)
Making change is hard. It’s even harder when you are unaware of the behaviors that are holding you and your organization back. But once you see them, you can begin to fix them fix them.
We all win together!
Coach Dan
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