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The First 90 Days:

Leaders in Transition Share Lessons Learned

Mature smiling female executive doing her work

Michael D. Watkins’ enduring book “The First 90 Days: Proven Strategies for Getting Up to Speed Faster and Smarter” was first published in 2003, expanded and updated ten years later, and today remains an international bestseller and proven guide for leaders changing jobs or careers. Watkins' book acknowledges that expectations are steep when walking into a new role. He challenges leaders to think, assess and plan from (before) day one to the end of three months, and beyond.

The Alexander Group is such a firm believer in the strategies outlined in the book that we send a copy to every executive we recruit on behalf of our clients. We thought it would be helpful to reach out to some of these executives and ask what advice they have for leaders moving into a new company, role or industry.

Repeat guiding principles until they roll their eyes

Kelly Young, Chief Executive Officer at the nonprofit organization Career and Recovery Resources, Inc., recommends, “Go in with the intent to listen, talk about change all the time, and repeat key guiding principles or messages until people start to roll their eyes.”

“To bridge between the old and the new, I insert new messaging into established routines. For example, I keep all-staff meetings on the same schedule as they were prior to my arrival to maintain the ‘rhythm’ of the day-to-day, but insert my work philosophy, discuss my pet peeves, and focus on the aspects of an organization that I hold important (such as data, quality and communication).

This is my third chief executive position, and what I continue to learn is that it is best to be yourself and to know yourself, specifically your weaknesses.

“During the first couple months—depending on how established the organizational design and processes are—I have people spell out on sticky notes what they believe their job duties are and then have them place those duties under a department heading. I then build out a matrix showing how items will shift based on structural changes that I might make. This allows for them to communicate to me what they think they are supposed to be doing, and it allows me to show them where I might place those duties.”

“My door is always open for the first six months. I spend most of that time in informal discussions, learning the pace and focus of work through observation, while quietly working out changes behind the scenes. I time the rollout of changes based on times of the year when the workload and general work environment is flowing easily.’

"These are generalizations,” Ms. Young says, “but I have been successful in retaining those who buy into my leadership, and helping those who will not, to leave successfully. That way within the first year I have a team, goals, and expectations aligned and driving towards a common goal. The focus is on who we serve, what difference do we want to make, and how will we know when we get there.”

Regarding lessons learned, Ms. Young says, “I always wish I had listened more, asked more questions and trusted my instincts. Leadership requires you to hold yourself to account. Knowing your own decision-making process tends to be what you depend on in the end.”

Be the enlightened monk, not the samurai

A strategy officer for an Am Law 100 firm shares the advice she received on her second day in a new role. The advice was, “Be the enlightened monk, not the samurai.”

“As a former consultant, I was trained to be a samurai,” she says. “This advice, in many ways, freed me from past expectations and gave me the luxury to listen and learn before jumping too quickly to advise.”

“I spent my first few weeks meeting all of the leaders from the business, asking questions to understand the culture and the history, developing my opinions and testing my thinking. Because of this, I built credibility as someone who was looking to come in, understand and ‘get it’—not someone looking to shake things up unnecessarily.”

“Within the first 90 days, I had created a solid group of partners who were happy to give me input on my ideas and also wanted my opinions on their roles.”

A Chief Technology Officer agrees, “There’s no shortcut for learning and adjusting to a new culture. I spent my first month getting to know people. I met leaders in various organizations and participated in their business meetings. This allowed me to identify and confirm many issues and learn their challenges. Ask someone to arrange these meetings for you as part of your on-boarding.”

Problems and opportunities aren’t always what they appear to be

A senior finance executive with a professional services firm, recommends looking at problems as possible symptoms of a deeper issue: “Problems and opportunities aren’t always what they appear to be. Keep an open mind to that possibility. Asking probing questions and garnering a deeper understanding of the issues will often lead to the identification of different challenges—ones that weren’t as readily apparent as the symptoms.”

A few quick wins will help build momentum.

“Prioritizing these issues and creating a one-year plan can help bring a team together while demonstrating your leadership skills. Ensuring that the plan reflects the input and analysis you’ve gathered during the first 90 days from all the constituents will increase the likelihood that you get you off to a fast and strong start.”

Build trust, especially in a matrix structure

A business unit leader with an oil and gas services company, says: “One of my early lessons had to do with navigation of the matrix structure. I was coming from an organization with a mature matrix structure, whereas this organization was less than a year removed from the direct-line reporting model. Many of the leaders were still getting comfortable with the new structure and I found that I needed to provide more in-depth and frequent communication when crossing boundaries.”

I found that I needed to provide more in-depth and frequent communication when crossing boundaries.

“Building trust in the early days is critical for any new executive. However, this situation required building trust not only in me, but also in the matrix structure itself.”

In a crisis, be positive and be accessible

One pharmaceutical executive was recruited to assist the company during a crisis. In a crisis situation, she recommends: “Get a quick lay of the land to identify the things that need your immediate attention. Once you have a pulse on the most critical things that have to be done or started immediately, then go back and do a deeper dive.”

A quick overview of the situation allowed me to highlight the critical success factors to management.

“Listen to people, and communicate even more than you think that you need to. Be positive and be accessible. People are attracted to people who are positive, and you want people rallying around you—and with you—in a crisis. You want your team to know that they can talk to you if something goes wrong.”

Regarding lessons learned, she says, “I thought I only had time and energy to focus on getting to know my immediate group well. But it would have been helpful to forge relationships at the peer level as well. Those peer relationships can make for strong allies—in and out of a crisis.”

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