Pieces of Wisdom From Failing More Than Once at My New Jobs

2-min. read

Recently, I had a fascinating conversation with a middle manager considering a new role in general management.  We talked at length about how to best prepare for it. 

This reminded me how both exciting and challenging any new responsibility is and how critical the first ninety days are.

Looking back, I can count more than 20 times I found myself with a new role in my hands and limited guidance. In most cases, my boss would congratulate me on the new job, ask me not to mess things up, and request my “master plan” in the next thirty days.

Like many new leaders, I sought advice from various sources: my own boss, my peers, my team, my friends…

But after a few epic failures, I felt the need for a more structured framework that would leave no stone unturned. I wasn’t sure how to find the best coach or mentor, but I eventually discovered a book that saved me more than once: The First 90 Days from Michael Watkins.

I have recommended and gifted this book to countless team members and friends who were getting started with a new job.

The book itself is “just” a reference framework and doesn’t replace self-discipline or accountability partners. But it helps cover all the critical aspects of any transition.

Without a solid framework, the reality is that it usually takes closer to six months for a new leader to be up and running. So how to shorten that period to just ninety days?

The first concept of the book is that you need to avoid the typical transition traps that sabotage your credibility. Here are the top seven:

  • Assuming past success factors will work in the new role.
  • Rushing to act before learning the essentials of the new context.
  • Trying to accomplish too much at once and diluting effort.
  • Jumping to premature conclusions without due diligence.
  • Focusing on the technicalities instead of culture, relationships.
  • Neglecting horizontal relationships (peers and other stakeholders).
  • Failing to clarify goals and imperatives.

Once you are aware of these traps, the author recommends you focus on ten strategies that will help you build momentum. No need to list them all, but here are the ones I found the most impactful in my experience:

1. Be prepared in advance

Take a break if needed before the transition and set up a plan that will help accelerate your learning. Meaning, identifying all the key stakeholders and preparing for discovery conversations with them in the first few weeks on the job.

2. Understand your situation and adjust accordingly

There’s no “one-size-fits-all” approach that works. You need to understand if the business is in a startup, turnaround, accelerated-growth, or continued success mode and adapt your strategy to it.

3. Look for alignment across the board

Identify potential misalignments and develop a plan early to address them, including your team. Also, make sure you properly manage expectations with your boss and align on the definition of success and the required resources.

4. Build alliances and seek early wins

Establish some relationship capital inside and outside of your team. As you build alliances, look for the most impactful early wins you can get. They don’t have to be big, but they’ll matter in establishing your credibility.

5. Take care of yourself

Transitions can quickly become overwhelming as you have to combine intense discovery and the need to promptly deliver. Keep your personal balance in check and regularly assess your own progress with the essential traps and success factors in mind.

That’s it! 

It’s a robust framework, and I recommend you to read The First 90 Days if you haven’t yet.

As importantly, don’t go alone. Seek a mentor, a coach who can act as a sounding board. And if you ever get stuck, reach out to The Product Sherpa. I’ll be glad to assist.

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