How to Start and Succeed in a Senior Role - Part One

A practical guide to nailing your first 90 days

Over my 22-year career, I’ve worked at five companies in 13 roles. At Amazon, I held five senior managerial positions, leading teams and managing other managers.

I’ve always been drawn to general management because it offers endless opportunities to learn. Early in my career, a mentor advised me that to become a general manager I need to try a variety of roles, so I took his advice to heart. Over the years, I have worked in Sales, Marketing, Tech, Strategy, Operations, Product Management, Category Management, Supply Chain, and General Management. I have succeeded in some roles and failed in others.

Over time, I have developed a set of best practices for starting a new role. I revisit them each time before I start, in order to create a tailored plan of action. I break them into three broad categories: Context, People and Execution. I wanted to write about all of them in one post, but it ended up being too long and my husband said “are we gonna see you today or tomorrow?” so I will publish it in three parts instead. Part one is about Context: Preparing before you start, Understanding the business and Diagnosing its current state. Part two is about People: Building trust with your boss, Establishing relationships with stakeholders and Growing your new team. Part three is about Execution: Negotiating expectations, Delivering early wins, and Accelerating beyond 90 days. Subscribe if you don’t want to miss parts two and three.

As I am writing this, I am standing on the shoulders of giants. Among the many resources I explored on the subject, the single best one for senior leaders has been The First 90 Days by Michael Watkins, a professor at IMD. I’ve drawn from his structure and frameworks while adding my own experience and insights. Watkins’ book dives deeper into case studies, key questions, and practical frameworks for success in a new role, so I recommend it for a thorough deep dive.

1. Start before you start

Whenever you start a new role, the first 90 days are critical — they set the stage for your long-term success. You’ll feel like you’re drinking from a firehose, with more tasks than time. That’s why starting strong begins before day one.

First, make sure you are fully rested and energized. Tie up loose ends in your personal life — family, health, home — so you can focus on the challenges ahead. Jumping straight from one demanding role into another without recovery is like running a marathon two days after finishing the last one. Give yourself time to recharge so you can show up as your best self.

Next, arm yourself with knowledge. Ask your future boss for specific materials: the latest strategy document, your predecessor’s contact information, names of one or two key stakeholders, and a couple of customers they recommend you meet. If you simply ask, “What should I do before I start?” they’ll likely respond with something vague like, “Just come in refreshed and ready.” Be specific in your requests.

Your predecessor can be an invaluable resource. If they failed in the role, you’ll learn what pitfalls to avoid. If they succeeded and remain with the company, they might become an early ally — they will want to see their legacy endure.

Seek internal documents: strategic plans, performance reports, and team documents. Explore external information like shareholder reports, press releases, and industry analyses. When I joined Amazon in 2011, there was only one book about the company (Amazonia by James Marcus). So, I read Sam Walton: Made in America. The parallels between Walmart and Amazon’s customer-centric cultures were striking.

If your new company is a B2B, reach out to customers. It’s astonishing how few leaders actually talk to clients. Doing so early can deliver immediate value and set you apart. Remember to do it when you are in the job too. If it’s a B2C company, become a customer yourself. Sign up, use the service, test the helpdesk, and see how the experience feels. After a month, ask yourself: On a scale of 1 to 10, how likely would I recommend this company to a friend?

Finally, before your first day, write down your initial hypotheses about the business and draft a list of key questions. These will accelerate your learning curve as you get in.

For a deeper dive into this phase, check out The New Leader’s 100-Day Action Plan by George Bradt et al., where it’s aptly named the “Fuzzy Front End”.

2. Learn the business and the culture

When you start, the first 30 days are about listening, observing, and asking thoughtful questions—even if you’ve held similar roles elsewhere.

In 2011, Doug Gurr joined Amazon UK as a VP. Before his arrival, the UK Country Manager sent an email introducing Doug: triple Ironman, former professor, ex-McKinsey partner, successful entrepreneur, and Asda board director. On paper, he seemed superhuman, and many of us were both impressed and slightly intimidated.

When Doug arrived — a few weeks before his official start date — he wasn’t the commanding presence we had envisioned. He was unassuming, quiet, and thoughtful. In meetings, he’d often say, “Go ahead, ignore me, I’m just here to listen”.

When he officially started, he held an introductory meeting with his org. He spoke about his career with humility and said he was taking time to learn about the company and its business. I don’t recall the details of his speech, but I remember emailing him afterward with a question. Despite leading hundreds of people, he took the time to respond.

During the first weeks, he held a number of roundtables with employees at all levels, gathering insights about what was working, what wasn’t, and where opportunities lay. Two months later, he shared his findings and a clear five-step plan. I don’t know how much of this plan aligned with the original hypothesis he had, but it felt authentic and relevant for the org because he took time to learn.

During this phase, ask questions that unlock insight:

• What are the biggest challenges the business is facing, and why?

• How did we get here?

• What are the most promising opportunities?

• If you were me, what would you focus on?

• Who else should I talk to?

These conversations should span frontline employees, senior leaders, and customers. The connection between leadership and the frontline often reveals gaps—frequently larger than leaders expect.

Understanding the business also means understanding how it’s measured. Amazon has a practice of business reviews (weekly, monthly and quarterly). Senior leaders recommend doing a couple of “slow” weekly business reviews in the beginning, instead of 30 minutes, spending 90 minutes for the first couple of weeks with your team. Ask for metric definitions, ask why each one matters, and challenge outdated processes. Here, your prior customer research will come in handy - you may have an idea of things that are broke, but the business is unaware about it.

Equally important is understanding the company’s culture. Even if you are moving internally, cultural dynamics can vary widely between business units. Ask:

• How are big decisions made?

• Who holds influence?

• What gets rewarded: results, collaboration, innovation?

• How is conflict managed—head-on, avoided, or escalated?

• How do company values show up in day-to-day work?

Observation is as important as inquiry. Walk the floor, visit a warehouse, and a customer service center. You’ll learn more from casual interactions than polished presentations.

If you are transitioning internally, don’t underestimate the adjustment. Internal transitions are 70% as difficult as being hired from the outside. You’ll have an advantage from institutional knowledge, but support structures like onboarding and training may be absent unless you specifically request them. Expectations for quick results will also be higher.

3. Diagnose the Situation You Are In

Once you have begun learning and observing, it’s time to update the hypotheses about your business’s challenges and opportunities. Michael Watkins offers a powerful tool for this: the STARS framework. It categorizes business situations into five types:

• Start-Up: Building something new from scratch.

• Turnaround: Repairing a struggling business or project.

• Accelerated Growth: Scaling up a promising initiative that’s already gaining traction.

• Realignment: Addressing emerging issues in a once-successful business before they escalate.

• Sustaining Success: Taking an already-thriving business to the next level.

Each scenario demands a unique strategy and mindset. Explore these further in Michael Watkins' Harvard Business Review article.

Earlier in my career, I misdiagnosed a situation. I assumed (and was told) that I stepped into a Sustaining Success role and began planning growth initiatives, only to realise - too late - that the business needed Realignment. There were hidden structural issues that required urgent attention. It took me longer than 90 days to identify the core problems, and by then, they had become my problems.

Misdiagnosis sets you on the wrong path from day one.

Steps for Diagnosing Your Situation:

1. Start with Your Boss’s Perspective: Ask your boss about her view of the business. If she’s familiar with the STARS framework, great. If not, ask thoughtful questions:

   • What changes are you expecting in the next six months?

   • What would success in this role look like?

   • Are there any immediate fires I should focus on?

   However, don’t take her assessment as gospel. She may have a bird’s eye view and may not be aware of ground-level realities.

2. Conduct Your Own Assessment: Speak with your team, key stakeholders, and customers. Cross-reference their feedback with your boss’s perspective. If your findings differ from your boss’s expectations, address the gap early. Misaligned expectations can derail your efforts, even if your diagnosis is correct.

3. Look for Patterns: Pay attention to recurring themes. Are people consistently flagging the same problems or opportunities? Are there disconnects between leadership goals and frontline realities?

At this stage, clarity is your most powerful tool. An accurate diagnosis enables you to build a credible plan and align your team behind it.

That’s all for today! In Part Two, I’ll cover the key people in your onboarding journey: your boss, stakeholders, and team. Stay tuned.

If you have your own tips or strategies for starting a new role, please share them in the comments!

Additional Resources:

📚 Michael Watkins – The First 90 Days The definitive guide for leaders stepping into a new role. Good frameworks, essential questions, case studies, and actionable advice. If you can only read one book, read this one.

📝 Ian McAllister – When Starting a Senior Mid-Level Role: What Should Your Priorities Be? A concise answer that distills the most important focus areas for the first weeks and months in a new role.

🚀 Dave Anderson – Hit the Ground Running Dave shares his approach as a senior tech leader to ramp up effectively in the first three weeks. Half of the article is free, and the rest is behind a paywall—but his newsletter is well worth subscribing to. I often share this one with the new Product Managers.

🛠️ George Bradt, Jayme Check, Jorge Pedraza – The New Leader’s 100-Day Action Plan A detailed guide with extensive checklists and frameworks (perhaps too detailed and thus overwhelming). Excellent as a reference - especially the “Leverage the Fuzzy Front End before Day One” section, which complements The First 90 Days.