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Should I Buy Monday.com?

Should I Buy Monday.com?

How one senior executive discovered that accountability isn’t a technology problem, it’s a communication problem.

The chat in our webinar was fairly steady, so it was difficult to keep up and try to sound intelligent in my presentation at the same time. But, this one question stuck out to me for some reason.

“Would you recommend I buy Monday.com for my team to increase accountability and transparency?”

On the surface, this question was reasonable.  Her team was missing deadlines.  Projects were falling through the cracks.  Nobody seemed to own anything.  

So, naturally, she did what most high-performers tend to do: she put everything on her shoulders and now she was looking for a tool to take some of that weight.

I’ve learned a lot over 30+years in my career.  Mostly by making mistakes.  As a coach, I have the opportunity to learn, and delve into, dozens of other’s mistakes and I’ve come to learn that when a team isn’t accountable, the problem is never solved by stacking on new technology.

Insight After The Webinar

The senior executive and I connected after the webinar and I could feel the desperation in her voice as she explained her rationale behind seeking a project management software.  “…I figured having everything in one place would make it more difficult for my team to hide…”

That led me to ask her a simple question, “When you hand-off a project to someone on your team, how do you know they are clear about what success looks like?”

Her pause told me everything.

To paint this picture clear, this CEO I was speaking with has a brilliant resume, inspiring accomplishments, and knew her industry better than most.  She has vision, drive, and very high standards for herself, and her team. But somewhere her message was getting lost.  

Projects weren’t failing because her people lacked effort or talent.  Projects were failing because there was not one unified definition of what success looks like.

She wasn’t facing a project management problem.

She was facing a collaboration and delegation problem.

A Common Problem for Leaders: Delegating Properly

High-achievers have a common challenge as leaders.  They believe that everyone on their team has the same ability to see problems and map out solutions the same way they do.

And like most accomplished leaders, this executive wasn’t making this error because of a shortcut. She assumed her team “got it”. She trusted her team was smart and would make it work like she would.  This blind trust led to common delegation errors.

Trust is key in leadership.

But trust without structure isn’t leadership.  It’s hope.

And as we’ve all heard, hope is not a strategy.  And it’s certainly not going to build healthy accountability on a team.

What We Built Together

Instead of stacking a new technology platform on top of a broken system, we went to work on the foundation.

And the results were, and still are, amazing.

  • Defining the Destination:
    We reestablished her core values and built mission pillars, giving the entire organization a North Star.  These weren’t the kind of core values that look good on a website, we’re talking non-negotiables that were the crux of every decision made throughout the year.

  • Structuring for Success:
    We mapped out every department and every role to a clear number.  Not an org chart that shows who reports to whom, but rather who OWNS what. 

    We were looking to build pride, not compliance.

  • Measuring What Matters:
    We built role-specific scorecards for every team on the senior leadership team, and they did the same for their team.

    Clear, measurable leading and lagging indicators tied to the week, the month, and the quarter. Goals went from vague, to a crystal clear vision of what success looks like for their role and their department.

  • Building a Rhythm:
    We restructured the meeting framework to ensure consistent communication that would clear roadblocks and build alignment.  The kind of alignment that eliminates the need for micromanaging.

  • Speaking the Same Language:
    We also introduced DISC Assessment teamwide. By understanding each other’s communication styles, behavioral drives, and blind spots, the team learned how to collaborate and resolve friction fast.

What Happened Next

In under 90 days, the executive reported something she hadn’t experienced in years.

She was no longer the bottleneck.

Her team went from having a difficult time completing tasks, to anticipating problems early, and bringing solutions instead of excuses.  They collaborated with each other.  Without dragging her into it.  

Her team said to her, and I quote, “…we’re so glad we’ve made these changes, working together is actually fun and makes us proud to be part of this team…”

These steps are how leaders go from policing and micromanaging to coaching.  It’s the moment when accountability stops being something a leader enforces to something that is owned by the entire team–with pride.

Typically, it doesn’t start with stacking software.  It starts with clarity in the leader’s communication.

Is your team missing deadlines? The fix isn’t a new software—it’s a unified definition of success.

Stop being the bottleneck for your organization. Let’s partner to build a structured framework that drives autonomous, high-performing teams.

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