365 Books: The First 90 Days by Michael Watkins

I discovered this book and started applying it in my work a number of years ago. When I first read it, I wasn’t starting at a new company, I was moving to a new role within the organization where I had grown up, and I wanted to be strategic about how I approached the relationships with my new employees and my new boss.

Later, when I did get a new job at another organization, it came in handy again, even though that organization was a start-up. I used it again at the next organization, and it has never let me down.

It provides a solid blueprint for how to approach your transition: assessing the organization that you are joining or the department that you are transferring into and determining your strategy; building credibility with those around you; quickly learn what you need to know; demonstrating competence with quick wins; getting your boss to trust you and give you the rope you need to get things done; how to persuade your boss to buy into your proposed changes1; planning changes to make with your team; building cross-functional collaboration; and keeping your balance.

I think back to one reorganization when I started working for a new boss. I had the things I was working on, things my colleagues brought me, and – increasingly – the things he assigned me, sometimes in email, sometimes he dropped them on my desk as he passed, and some he handed me in meetings with others. At first, I couldn’t figure out how to gain his trust. Finally, I set up a weekly 1:1 with him and, every week I’d come to sit with him, bringing a list: status of things he had asked me to work on; reports on regular business; and updates on topics that he was interested in that I had gleaned during my normal interactions with colleagues outside his department. He liked the list; so I formatted it in a way that would appeal to him, too, and started handing him a copy when we met. He loved it. The list earned me his trust and persuaded him that I was competent. He began to trust me with increasing responsibility and we were off to the races.

The book organizes the chapters to make things easy to take action, providing – for example – five conversations you should have with your new boss:

  • The situational diagnosis conversation… understanding how your new boss sees the business situation.
  • The expectations conversation… understanding and negotiating expectations
  • The style conversation… how you and your new boss can best interact on an ongoing basis
  • The resources conversation… a negotiation for critical resources.
  • The personal development conversation… how your tenure in this job will contribute to your personal development.

Each conversation is structured for you, with prompts and objectives that you can refer to. It makes it easy!

I still go back to this book when I am working with new organizations or departments. It helps me build a mental map of the organization, build alliances, understand motivations and objectives, draw connections between departments, and influence change. I gift this book to friends when they get promoted or start new jobs.

  1. Hmm, I seem to have dog-eared a lot of pages in this section. ↩︎

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